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person · Reporting owner

McIlwain Matthew S

Disclosed activity across 3 companies

Tapewire entity
36351
SEC CIK
0001381752

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
Nautilus Biotechnology, Inc.NAUT · Entity 6679DirectorJune 18, 2026June 22, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

Nautilus Biotechnology, Inc.

Report date June 18, 2026 · Filed June 22, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Stock Option (Right to Buy)SEC Table II · derivative / convertible security · Conversion / exercise price $2.28 · Expires 2036-06-18Direct45,000 Reported balance After 2026-06-18 transaction · row 1 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 1 · 2026-06-18 · Grant · Acquired 45,000 · Balance 45,000

F1: Subject to reporting person's continuous status as a "Service Provider" (as defined in the the Issuer's 2021 Equity Incentive Plan) through each applicable vesting date, one-twelfth (1/12th) of the shares subject to the Option shall vest on a monthly basis following the date of grant on the same day of the month as such grant date (or on the last day of the month, if there is no corresponding day in such month).

Filing footnotes · ownership attribution and instrument terms

F1: Subject to reporting person's continuous status as a "Service Provider" (as defined in the the Issuer's 2021 Equity Incentive Plan) through each applicable vesting date, one-twelfth (1/12th) of the shares subject to the Option shall vest on a monthly basis following the date of grant on the same day of the month as such grant date (or on the last day of the month, if there is no corresponding day in such month).

Past disclosures · reporting ended (2)

No longer tracked through insider filings. These historical balances do not imply present ownership or a zero position.

Apptio Inc

Report date January 10, 2019 · Filed January 11, 2019

Section 16 reporting ended · disclosed 2019-01-11. Current position is not established by this disclosure.

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Class A Common StockSEC Table I · non-derivativeDirect0 Ending reported balance After 2019-01-10 transaction · row 5
4 source rows · reconciled sequence

Row 1 · 2018-12-13 · Gift · Disposed 3,600 · Balance 58,584

Row 2 · 2018-12-21 · Gift · Disposed 3,000 · Balance 55,584

Row 3 · 2018-12-21 · Gift · Disposed 14,971 · Balance 40,613

Row 5 · 2019-01-10 · Disposition to issuer · Disposed 40,613 · Balance 0

F3: Includes 4,652 restricted stock units which vested solely as a result of the consummation of the Merger Agreement, which were cancelled and automatically converted into the right to receive a cash payment of $38.00 per share.

F1: Disposed of pursuant to the merger agreement between Apptio, Inc., Bellevue Parent, LLC, and Bellevue Merger Sub, Inc. (the "Merger Agreement") in exchange for a cash payment of $38.00 per share.

Class A Common StockSEC Table I · non-derivativeIndirectSee Footnote0 Reported balance After 2019-01-10 transaction · row 4 Account identity is unresolved; indirect or unspecified ownership is not merged.
1 source row

Row 4 · 2019-01-10 · Disposition to issuer · Disposed 23,916 · Balance 0

F1: Disposed of pursuant to the merger agreement between Apptio, Inc., Bellevue Parent, LLC, and Bellevue Merger Sub, Inc. (the "Merger Agreement") in exchange for a cash payment of $38.00 per share.

F2: Shares held by the McIlwain Family GST Trust.

Stock Option (right to buy)SEC Table II · derivative / convertible security · Conversion / exercise price $14.31 · Expires 2025-11-05Direct0 Reported balance After 2019-01-10 transaction · row 6 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 6 · 2019-01-10 · Disposition to issuer · Disposed 30,000 · Balance 0

F4: Includes 7,545 options which vested solely as a result of the consummation of the Merger Agreement, which were cancelled and automatically converted into the right to receive a cash payment of $38.00 per share, less the applicable exercise price of the option, subject to any required withholding of taxes.

F5: Includes 22,455 vested options which were cancelled and automatically converted into the right to receive $38.00 per share, less the applicable per share exercise price and subject to any applicable withholding taxes.

F6: 1/3rd of the shares subject to the option shall become vested on September 29, 2017 and 1/36th of the shares subject to the option shall vest monthly thereafter for the next 24 months. The option is subject to an early exercise right and may be exercised in full prior to the vesting of the shares underlying the option, subject to the issuer's right of repurchase.

Filing footnotes · ownership attribution and instrument terms

F1: Disposed of pursuant to the merger agreement between Apptio, Inc., Bellevue Parent, LLC, and Bellevue Merger Sub, Inc. (the "Merger Agreement") in exchange for a cash payment of $38.00 per share.

F2: Shares held by the McIlwain Family GST Trust.

F3: Includes 4,652 restricted stock units which vested solely as a result of the consummation of the Merger Agreement, which were cancelled and automatically converted into the right to receive a cash payment of $38.00 per share.

F4: Includes 7,545 options which vested solely as a result of the consummation of the Merger Agreement, which were cancelled and automatically converted into the right to receive a cash payment of $38.00 per share, less the applicable exercise price of the option, subject to any required withholding of taxes.

F5: Includes 22,455 vested options which were cancelled and automatically converted into the right to receive $38.00 per share, less the applicable per share exercise price and subject to any applicable withholding taxes.

F6: 1/3rd of the shares subject to the option shall become vested on September 29, 2017 and 1/36th of the shares subject to the option shall vest monthly thereafter for the next 24 months. The option is subject to an early exercise right and may be exercised in full prior to the vesting of the shares underlying the option, subject to the issuer's right of repurchase.

SMARTSHEET INC

Report date January 22, 2025 · Filed January 24, 2025

Section 16 reporting ended · disclosed 2025-01-24. Current position is not established by this disclosure.

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Class A Common StockSEC Table I · non-derivativeDirect0 Reported balance After 2025-01-22 transaction · row 1
1 source row

Row 1 · 2025-01-22 · Disposition to issuer · Disposed 131,122 · Balance 0

F1: The shares were disposed of pursuant to the Agreement and Plan of Merger, dated September 24, 2024 (the "Merger Agreement"), by and among Smartsheet Inc. (the "Company"), Einstein Parent, Inc. ("Parent"), and Einstein Merger Sub, Inc., a wholly owned subsidiary of Parent ("Merger Sub"). Pursuant to the terms of the Merger Agreement, Merger Sub merged with and into the Company (the "Merger"), with the Company surviving the Merger as a wholly owned subsidiary of Parent. At the effective time of the Merger (the "Effective Time"), each share of the Company's Class A common stock, no par value per share ("Common Stock"), was canceled and automatically converted into the right to receive $56.50 in cash, without interest and less any applicable withholding taxes (the "Merger Consideration").

Restricted Stock Units (RSU) (Class A)SEC Table II · derivative / convertible security · Expires 2034-06-18Direct0 Reported balance After 2025-01-22 transaction · row 2 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 2 · 2025-01-22 · Disposition to issuer · Disposed 4,864 · Balance 0

F2: Each RSU represents a contingent right to receive 1 share of the issuer's Class A Common Stock upon settlement.

F3: Pursuant to the Merger Agreement, at the Effective Time, each RSU that vested solely on the basis of time that was outstanding as of immediately prior to the Effective Time and was either (i) held by a non-employee member of the Board of Directors (whether vested or unvested) or (ii) vested in accordance with its terms but not yet settled as of the Effective Time (each, a "Vested RSU") was canceled and converted into the right to receive an amount in cash obtained by multiplying (A) the total number of shares of Common Stock underlying such Vested RSU, by (B) the Merger Consideration, subject to any required withholding of taxes.

F4: Pursuant to the Merger Agreement, at the Effective Time, each RSU that was outstanding as of immediately prior to the Effective Time and that was not a Vested RSU (each, an "Unvested RSU") was canceled and automatically converted into the contingent right to receive an aggregate amount in cash equal to the product obtained by multiplying (i) the total number of shares of Common Stock underlying such Unvested RSU, by (ii) the Merger Consideration (the "Unvested RSU Consideration"), subject to any required withholding of taxes. The Unvested RSU Consideration will vest and become payable on substantially the same terms and conditions that applied to the Unvested RSU immediately prior to the Effective Time.

F5: The RSUs shall fully vest on the earlier of (a) the date of the 2025 annual meeting of the issuer's shareholders and (b) June 18, 2025, subject to continued service through the vesting date.

Filing footnotes · ownership attribution and instrument terms

F1: The shares were disposed of pursuant to the Agreement and Plan of Merger, dated September 24, 2024 (the "Merger Agreement"), by and among Smartsheet Inc. (the "Company"), Einstein Parent, Inc. ("Parent"), and Einstein Merger Sub, Inc., a wholly owned subsidiary of Parent ("Merger Sub"). Pursuant to the terms of the Merger Agreement, Merger Sub merged with and into the Company (the "Merger"), with the Company surviving the Merger as a wholly owned subsidiary of Parent. At the effective time of the Merger (the "Effective Time"), each share of the Company's Class A common stock, no par value per share ("Common Stock"), was canceled and automatically converted into the right to receive $56.50 in cash, without interest and less any applicable withholding taxes (the "Merger Consideration").

F2: Each RSU represents a contingent right to receive 1 share of the issuer's Class A Common Stock upon settlement.

F3: Pursuant to the Merger Agreement, at the Effective Time, each RSU that vested solely on the basis of time that was outstanding as of immediately prior to the Effective Time and was either (i) held by a non-employee member of the Board of Directors (whether vested or unvested) or (ii) vested in accordance with its terms but not yet settled as of the Effective Time (each, a "Vested RSU") was canceled and converted into the right to receive an amount in cash obtained by multiplying (A) the total number of shares of Common Stock underlying such Vested RSU, by (B) the Merger Consideration, subject to any required withholding of taxes.

F4: Pursuant to the Merger Agreement, at the Effective Time, each RSU that was outstanding as of immediately prior to the Effective Time and that was not a Vested RSU (each, an "Unvested RSU") was canceled and automatically converted into the contingent right to receive an aggregate amount in cash equal to the product obtained by multiplying (i) the total number of shares of Common Stock underlying such Unvested RSU, by (ii) the Merger Consideration (the "Unvested RSU Consideration"), subject to any required withholding of taxes. The Unvested RSU Consideration will vest and become payable on substantially the same terms and conditions that applied to the Unvested RSU immediately prior to the Effective Time.

F5: The RSUs shall fully vest on the earlier of (a) the date of the 2025 annual meeting of the issuer's shareholders and (b) June 18, 2025, subject to continued service through the vesting date.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
June 14, 2019 Filed Jun 18, 2019 20:48 UTC SMARTSHEET INC SMAR · Entity 83899 SaleClass A Common Stock 863,001 $43.50 $37,540,543.50
Disclosure

SEC source: 0001381752-19-000017 · wf-form4_156090530865742.xml · nonDerivative · entry 6

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV, L.P.

Disclosed balance after: 0

F3 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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June 14, 2019 Filed Jun 18, 2019 20:48 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 863,001 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000017 · wf-form4_156090530865742.xml · nonDerivative · entry 5

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV, L.P.

Disclosed balance after: 863,001

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F3 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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June 14, 2019 Filed Jun 18, 2019 20:48 UTC SMARTSHEET INC SMAR · Entity 83899 SaleClass A Common Stock 164,797 $43.50 $7,168,669.50
Disclosure

SEC source: 0001381752-19-000017 · wf-form4_156090530865742.xml · nonDerivative · entry 4

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III-A, L.P.

Disclosed balance after: 0

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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June 14, 2019 Filed Jun 18, 2019 20:48 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 164,797 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000017 · wf-form4_156090530865742.xml · nonDerivative · entry 3

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III-A, L.P.

Disclosed balance after: 164,797

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
June 14, 2019 Filed Jun 18, 2019 20:48 UTC SMARTSHEET INC SMAR · Entity 83899 SaleClass A Common Stock 4,125,207 $43.50 $179,446,504.50
Disclosure

SEC source: 0001381752-19-000017 · wf-form4_156090530865742.xml · nonDerivative · entry 2

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III, L.P.

Disclosed balance after: 0

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
June 14, 2019 Filed Jun 18, 2019 20:48 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 4,125,207 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000017 · wf-form4_156090530865742.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III, L.P.

Disclosed balance after: 4,125,207

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
June 12, 2019 Filed Jun 14, 2019 21:17 UTC SMARTSHEET INC SMAR · Entity 83899 GrantRestricted Stock Units (RSU) (Class A) · Derivative 3,159 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000015 · wf-form4_156056141287224.xml · derivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,159

Underlying: Class A Common Stock · 3,159 shares

Expires 2029-06-12

F1 · derivative.exercise_price: Each RSU represents a contingent right to receive 1 share of the issuer's Class A Common Stock upon settlement.

F2 · derivative.exercise_date: The RSUs shall fully vest on the earlier of (a) the date of the next annual meeting of the issuer's shareholders and (b) the date that is one year following the effective date of the award of the RSUs, subject to continued service through the vesting date.

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June 12, 2019 Filed Aug 26, 2019 18:21 UTC Amendment SMARTSHEET INC SMAR · Entity 83899 GrantRestricted Stock Units (RSU) (Class A) · Derivative 3,519 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000019 · wf-form4a_156685809395405.xml · derivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 3,519

Underlying: Class A Common Stock · 3,519 shares

Expires 2029-06-12

F1 · derivative.exercise_price: Each RSU represents a contingent right to receive 1 share of the issuer's Class A Common Stock upon settlement.

F2 · shares: This amended Form 4 is being filed solely to correct an inadvertent error that transposed the number of RSUs granted to the reporting holder in the original filing. No other changes are reflected.

F3 · derivative.exercise_date: The RSUs shall fully vest on the earlier of (a) the date of the next annual meeting of the issuer's shareholders and (b) the date that is one year following the effective date of the award of the RSUs, subject to continued service through the vesting date.

F2 · balance_after: This amended Form 4 is being filed solely to correct an inadvertent error that transposed the number of RSUs granted to the reporting holder in the original filing. No other changes are reflected.

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May 29, 2019 Filed May 30, 2019 18:36 UTC SMARTSHEET INC SMAR · Entity 83899 SaleClass A Common Stock 18,388 $44.01 $809,300.01
Disclosure

SEC source: 0001381752-19-000013 · wf-form4_155925580387138.xml · nonDerivative · entry 2

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 216,818

F1 · kind: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the holder.

F2 · price: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $44.00 to $44.05 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

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May 28, 2019 Filed May 30, 2019 18:36 UTC SMARTSHEET INC SMAR · Entity 83899 SaleClass A Common Stock 81,612 $44.01 $3,591,638.02
Disclosure

SEC source: 0001381752-19-000013 · wf-form4_155925580387138.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 235,206

F1 · kind: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the holder.

F2 · price: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $44.00 to $44.05 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

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May 07, 2019 Filed May 7, 2019 20:42 UTC SMARTSHEET INC SMAR · Entity 83899 SaleClass A Common Stock 13,265 $42.01 $557,285.20
Disclosure

SEC source: 0001381752-19-000011 · wf-form4_155727611063134.xml · nonDerivative · entry 2

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 316,818

F1 · kind: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the holder.

F3 · price: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $42.00 to $42.06 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

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May 06, 2019 Filed May 7, 2019 20:42 UTC SMARTSHEET INC SMAR · Entity 83899 SaleClass A Common Stock 86,735 $42.00 $3,643,199.59
Disclosure

SEC source: 0001381752-19-000011 · wf-form4_155727611063134.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 330,083

F1 · kind: The sales reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the holder.

F2 · price: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $42.00 to $42.075 per share, inclusive. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

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April 26, 2019 Filed Apr 30, 2019 18:09 UTC SMARTSHEET INC SMAR · Entity 83899 Exercise / conversionRestricted Stock Units (RSU) (Class A) · Derivative 10,000 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000009 · wf-form4_155666217061480.xml · derivative · entry 2

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock · 10,000 shares

Expires 2028-04-26

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each RSU represents a contingent right to receive 1 share of the issuer's Class A Common Stock upon settlement.

F2 · derivative.exercise_date: The RSUs vested on April 26, 2019, the date that is one year following the effective date of the RSU award.

Read SEC document
April 26, 2019 Filed Apr 30, 2019 18:09 UTC SMARTSHEET INC SMAR · Entity 83899 Exercise / conversionClass A Common Stock 10,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001381752-19-000009 · wf-form4_155666217061480.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 416,818

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each RSU represents a contingent right to receive 1 share of the issuer's Class A Common Stock upon settlement.

Read SEC document
March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass B Common Stock · Derivative 31,876 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · derivative · entry 13

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV-A, L.P.

Disclosed balance after: 54,687

Underlying: Class A Common Stock · 31,876 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_price: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.expiration_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass B Common Stock · Derivative 1,250,728 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · derivative · entry 12

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV, L.P.

Disclosed balance after: 2,145,836

Underlying: Class A Common Stock · 1,250,728 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_price: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.expiration_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass B Common Stock · Derivative 238,836 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · derivative · entry 11

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III-A, L.P.

Disclosed balance after: 409,756

Underlying: Class A Common Stock · 238,836 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_price: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.expiration_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass B Common Stock · Derivative 5,978,560 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · derivative · entry 10

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III, L.P.

Disclosed balance after: 10,257,237

Underlying: Class A Common Stock · 5,978,560 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_price: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.expiration_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 285,572 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 9

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 406,818

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

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March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 31,876 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 8

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV-A, L.P.

Disclosed balance after: 0

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 31,876 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 7

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV-A, L.P.

Disclosed balance after: 31,876

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 1,250,728 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 6

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV, L.P.

Disclosed balance after: 0

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 1,250,728 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 5

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV, L.P.

Disclosed balance after: 1,250,728

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 238,836 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 4

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III-A, L.P.

Disclosed balance after: 0

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 238,836 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 3

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III-A, L.P.

Disclosed balance after: 238,836

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 5,978,560 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 2

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III, L.P.

Disclosed balance after: 0

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
March 21, 2019 Filed Mar 25, 2019 20:23 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 5,978,560 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000007 · wf-form4_155355980552281.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III, L.P.

Disclosed balance after: 5,978,560

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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January 10, 2019 Filed Jan 11, 2019 21:30 UTC Apptio Inc APTI · Entity 161106 Disposition to issuerStock Option (right to buy) · Derivative 30,000 Not disclosed Strike: $14.31 Not disclosed
Disclosure

SEC source: 0000899243-19-001075 · doc4.xml · derivative · entry 6

McIlwain Matthew S · CIK 0001381752 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 30,000 shares

Expires 2025-11-05

F4 · shares: Includes 7,545 options which vested solely as a result of the consummation of the Merger Agreement, which were cancelled and automatically converted into the right to receive a cash payment of $38.00 per share, less the applicable exercise price of the option, subject to any required withholding of taxes.

F5 · shares: Includes 22,455 vested options which were cancelled and automatically converted into the right to receive $38.00 per share, less the applicable per share exercise price and subject to any applicable withholding taxes.

F4 · price: Includes 7,545 options which vested solely as a result of the consummation of the Merger Agreement, which were cancelled and automatically converted into the right to receive a cash payment of $38.00 per share, less the applicable exercise price of the option, subject to any required withholding of taxes.

F5 · price: Includes 22,455 vested options which were cancelled and automatically converted into the right to receive $38.00 per share, less the applicable per share exercise price and subject to any applicable withholding taxes.

F6 · derivative.exercise_date: 1/3rd of the shares subject to the option shall become vested on September 29, 2017 and 1/36th of the shares subject to the option shall vest monthly thereafter for the next 24 months. The option is subject to an early exercise right and may be exercised in full prior to the vesting of the shares underlying the option, subject to the issuer's right of repurchase.

F4 · derivative.underlying_shares: Includes 7,545 options which vested solely as a result of the consummation of the Merger Agreement, which were cancelled and automatically converted into the right to receive a cash payment of $38.00 per share, less the applicable exercise price of the option, subject to any required withholding of taxes.

F5 · derivative.underlying_shares: Includes 22,455 vested options which were cancelled and automatically converted into the right to receive $38.00 per share, less the applicable per share exercise price and subject to any applicable withholding taxes.

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January 10, 2019 Filed Jan 11, 2019 21:30 UTC Apptio Inc APTI · Entity 161106 Disposition to issuerClass A Common Stock 40,613 Not disclosed Not disclosed
Disclosure

SEC source: 0000899243-19-001075 · doc4.xml · nonDerivative · entry 5

McIlwain Matthew S · CIK 0001381752 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F3 · shares: Includes 4,652 restricted stock units which vested solely as a result of the consummation of the Merger Agreement, which were cancelled and automatically converted into the right to receive a cash payment of $38.00 per share.

F1 · price: Disposed of pursuant to the merger agreement between Apptio, Inc., Bellevue Parent, LLC, and Bellevue Merger Sub, Inc. (the "Merger Agreement") in exchange for a cash payment of $38.00 per share.

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January 10, 2019 Filed Jan 11, 2019 21:30 UTC Apptio Inc APTI · Entity 161106 Disposition to issuerClass A Common Stock 23,916 Not disclosed Not disclosed
Disclosure

SEC source: 0000899243-19-001075 · doc4.xml · nonDerivative · entry 4

McIlwain Matthew S · CIK 0001381752 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · See Footnote

Disclosed balance after: 0

F1 · price: Disposed of pursuant to the merger agreement between Apptio, Inc., Bellevue Parent, LLC, and Bellevue Merger Sub, Inc. (the "Merger Agreement") in exchange for a cash payment of $38.00 per share.

F2 · ownership.nature: Shares held by the McIlwain Family GST Trust.

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December 28, 2018 Filed Feb 14, 2019 17:31 UTC SMARTSHEET INC SMAR · Entity 83899 GiftClass A Common Stock 5,000 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000003 · wf-form5_155018347211288.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 117,681

F1 · shares: Represents shares of the issuer's Class A Common Stock that the reporting person donated as a gift.

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December 21, 2018 Filed Jan 11, 2019 21:30 UTC Apptio Inc APTI · Entity 161106 GiftClass A Common Stock 14,971 $0.00 $0.00
Disclosure

SEC source: 0000899243-19-001075 · doc4.xml · nonDerivative · entry 3

McIlwain Matthew S · CIK 0001381752 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 40,613

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December 21, 2018 Filed Jan 11, 2019 21:30 UTC Apptio Inc APTI · Entity 161106 GiftClass A Common Stock 3,000 $0.00 $0.00
Disclosure

SEC source: 0000899243-19-001075 · doc4.xml · nonDerivative · entry 2

McIlwain Matthew S · CIK 0001381752 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 55,584

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December 13, 2018 Filed Jan 11, 2019 21:30 UTC Apptio Inc APTI · Entity 161106 GiftClass A Common Stock 3,600 $0.00 $0.00
Disclosure

SEC source: 0000899243-19-001075 · doc4.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 58,584

Read SEC document
December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass B Common Stock · Derivative 21,251 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · derivative · entry 13

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV-A, L.P.

Disclosed balance after: 86,563

Underlying: Class A Common Stock · 21,251 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_price: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.expiration_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass B Common Stock · Derivative 833,818 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · derivative · entry 12

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV, L.P.

Disclosed balance after: 3,396,564

Underlying: Class A Common Stock · 833,818 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_price: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.expiration_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass B Common Stock · Derivative 159,224 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · derivative · entry 11

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III-A, L.P.

Disclosed balance after: 648,592

Underlying: Class A Common Stock · 159,224 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_price: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.expiration_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass B Common Stock · Derivative 3,985,708 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · derivative · entry 10

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III, L.P.

Disclosed balance after: 16,235,797

Underlying: Class A Common Stock · 3,985,708 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_price: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.exercise_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F5 · derivative.expiration_date: The Class B Common Stock is convertible into the issuer's Class A Common Stock on a 1-for-1 basis (a) at the option of the holder or (b) automatically upon (i) any transfer, except for certain permitted transfers, or (ii) the date that is the earliest of (x) the date specified by a vote of the holders of not less than a majority of the outstanding shares of Class B Common Stock, (y) April 26, 2025 and (z) the date that the total number of shares of outstanding Class B Common Stock ceases to represent at least 15% of all outstanding shares of the issuer's common stock, and has no expiration date.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 122,681 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 9

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 122,681

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

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December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 21,251 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 8

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV-A, L.P.

Disclosed balance after: 0

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 21,251 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 7

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV-A, L.P.

Disclosed balance after: 21,251

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 833,818 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 6

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV, L.P.

Disclosed balance after: 0

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

Read SEC document
December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 833,818 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 5

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund IV, L.P.

Disclosed balance after: 833,818

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F4 · ownership.nature: These securities are held of record by Madrona Venture Fund IV, L.P. ("Madrona IV") and Madrona Venture Fund IV-A, L.P. ("Madrona IV-A"), as applicable. Madrona Investment Partners IV, L.P. ("Madrona Partners IV") is the general partner of Madrona IV and Madrona IV-A, and Madrona IV General Partner, LLC ("Madrona IV LLC") is the general partner of Madrona Partners IV. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona IV LLC, and each may be deemed to share voting and investment power over the securities held by Madrona IV and Madrona IV-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 159,224 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 4

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III-A, L.P.

Disclosed balance after: 0

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 159,224 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 3

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III-A, L.P.

Disclosed balance after: 159,224

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 3,985,708 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 2

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III, L.P.

Disclosed balance after: 0

F3 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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December 07, 2018 Filed Dec 11, 2018 21:15 UTC SMARTSHEET INC SMAR · Entity 83899 ConversionClass A Common Stock 3,985,708 $0.00 $0.00
Disclosure

SEC source: 0001381752-18-000006 · wf-form4_154458090290346.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Indirect · By Madrona Venture Fund III, L.P.

Disclosed balance after: 3,985,708

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: Represents the number of shares that were acquired upon conversion of Class B Common Stock to Class A Common Stock.

F2 · ownership.nature: These securities are held of record by Madrona Venture Fund III, L.P ("Madrona III") and Madrona Venture Fund III-A, L.P. ("Madrona III-A"), as applicable. Madrona Investment Partners III, L.P. ("Madrona Partners III") is the general partner of Madrona III and Madrona III-A, and Madrona III General Partner, LLC ("Madrona III LLC") is the general partner of Madrona Partners III. Matthew McIlwain, a member of the issuer's board of directors, together with Tom Alberg, Paul Goodrich, Scott Jacobson, Len Jordon, and Tim Porter, are the managing members of Madrona III LLC, and each may be deemed to share voting and investment power over the securities held by Madrona III and Madrona III-A. The reporting person disclaims beneficial ownership over such securities except to the extent of his pecuniary interest therein, and such securities' inclusion herein shall not be deemed an admission of beneficial ownership of the reported securities for purposes of Section 16 or any other purposes.

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December 07, 2018 Filed Mar 11, 2019 20:27 UTC Amendment SMARTSHEET INC SMAR · Entity 83899 OtherClass A Common Stock 126,246 $0.00 $0.00
Disclosure

SEC source: 0001381752-19-000005 · wf-form4a_155235041163226.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 126,246

F1 · kind: The shares reported on this form represent pro rata distributions, and not sales or purchases, of securities by the reporting entity to its partners or members or the funds for which it acts as nominee without consideration.

F2 · balance_after: This amended Form 4 is being filed solely to correct an inadvertent error regarding the number of shares of Class A Common Stock distributed to the reporting holder. No other changes are reflected.

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November 07, 2018 Filed Nov 9, 2018 18:18 UTC Apptio Inc APTI · Entity 161106 SaleClass A Common Stock 2,500 $26.00 $65,000.00
Disclosure

SEC source: 0001209191-18-058016 · doc4.xml · nonDerivative · entry 1

McIlwain Matthew S · CIK 0001381752 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 23,916

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on February 26, 2018.

F2 · ownership.nature: Shares held by the McIlwain Family GST Trust.

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August 08, 2018 Filed Aug 9, 2018 20:54 UTC Apptio Inc APTI · Entity 161106 OtherClass A Common Stock 10,225 $0.00 $0.00
Disclosure

SEC source: 0001209191-18-046106 · doc4.xml · nonDerivative · entry 6

McIlwain Matthew S · CIK 0001381752 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 26,416

F10 · kind: Acquisition by the McIlwain Family GST Trust, pursuant to the Distribution.

F6 · ownership.nature: Shares held by the McIlwain Family GST Trust.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.