The Ledger ResearchPrivate

The Front Office

Scouting report · DOCN

W. Matthew Steinfort

  • Chief Financial Officer, DOCN since 2023-01src

DigitalOcean CFO since January 2023; formerly CFO of Zayo Group

B72 / 100

Ranked #16 of 23

Scouting sheet

as of 24 Sep 2026
Delivers guidance685 beat · 0 met · 2 missed · 1 withdrawn
Answers the question881 dodge in 14 answers on 2 calls
Capital allocation60company five-year record: neutral
Pay design73revenue, fcf, time only · 97.8% for · 1.85% of net income
Skin in the game74stake worth $42.8m, 9× last year's pay
Age
56src
In the role
4 yr
Promises scored
8
Hit rate
62%
Dodges / 100 answers
7.1
Airtime on calls
23%
Every promise, oldest firstBBBBBXWX

What to weigh

Red flag 1

  • Answered both logged dodges on all-in free cash flow including lease payments (Q1 and Q2 2026, same analyst). The dossier credits him by name for Q1; the Q2 answer is also his in the transcript but the dossier text does not name him, so only Q1 is credited heresrc

Watch 3

  • Seven months into his tenure, the Audit Committee found the Q1 2023 10-Q unreliable over an income-tax (Section 174) error that overstated tax expense by about $18m. The company declared a tax-accounting material weakness, and EY's opinion on 2022 internal control was reissued as adversesrc
  • Sold 25,000 shares at $152.50 on 2026-05-15, ten days after the Q1 call, in a Form 4 not marked as a 10b5-1 trade. His other 2026 sales were under a plansrc
  • The 2025 bonus and PSUs were paid partly on adjusted FCF margin: 18.6% met the 18% target. The FY2026 guide for the same measure was then cut from 15-17% to 11-13% (dossier S8 row 6)src

In their favour 1

  • 65% of his annual equity is performance-conditioned (PSUs on ARR and adjusted FCF margin; 2025 earned 89% of target); hedging and pledging are banned; the CFO ownership guideline was raised to 8x salary in February 2026src

Career

  1. 2023 – now
    DigitalOcean Holdingssrc
    Chief Financial Officer
  2. 2017 – 2022
    Zayo Group Holdingssrc
    Chief Financial Officer
    CFO from 2017-09-15 (ZAYO-DEF14A-2018); Zayo's last public year was 2019, revenue $2.6bn per the DigitalOcean release
  3. 2016 – 2017
    Zayo Group Holdingssrc
    EVP, Corporate Strategy, Development and Administration
  4. 2006 – 2016
    Envysion, Inc.src
    Co-founder and CEO; director 2013-2021
    Video intelligence SaaS company, privately held; merged with Motorola Solutions in November 2021

Undated in the sources

  • ICG Communicationssrc, SVP, Corporate Strategy
  • Level 3 Communicationssrc, Vice president roles in Consumer Voice, Corporate Strategy and Development, and Softswitch Strategy and Finance
  • Bain & Company; Cambridge Technology Partnerssrc, Consultant positions early in career

Not located: Ten years are fully covered by filings (2006 onward). The years at ICG, Level 3, Bain and Cambridge Technology Partners before February 2006 are undated in every source read

Achievements

  • CFO of Zayo Group from September 2017 through its time as a public company, overseeing finance, strategy and M&Asrc
  • Co-founded Envysion, a video intelligence SaaS company, and ran it as CEO for ten years (2006-2016); it later merged into Motorola Solutionssrc
  • DigitalOcean's GAAP net income went from a $27.8m loss (FY2022, restated) to $259.3m profit (FY2025) during his tenure as CFOsrc
  • Took the 2025 cash bonus at 98% of target and the 2025 PSUs at 89%, on revenue, run-rate revenue and adjusted FCF marginsrc

Education

  • Princeton University, BSE Civil Engineering and Operations Researchsrc
  • MIT Sloan School of Management, MBA Businesssrc

Background

  • Family The appointment 8-K states there are no family relationships between him and any director or executive officer and no Item 404(a) related-party transactionsrc
  • Boards Director of Envysion from January 2013 until its merger with Motorola Solutions in November 2021src
  • Other Hired with a $14m time-vested RSU award and a $252,000 sign-on bonus. In September 2023 salary went to $540,000, target bonus to 80%, plus a $2.6m RSU and two years of enhanced severancesrc

The promise ledger

8 scored · 0 open
ResultWhat was promisedWhere it is scoredHow
B BeatQ1 2026 revenue $249–250mDOCN row 1said it
B BeatQ1 2026 adj. EBITDA margin 36–37%; non-GAAP EPS $0.22–0.27DOCN row 2written outlook
B BeatQ2 2026 revenue $272–274mDOCN row 3written outlook
B BeatQ2 2026 adj. EBITDA margin 37–38%; non-GAAP EPS $0.20–0.23DOCN row 4written outlook
B BeatFY2026 revenue $1.075–1.105bn (21% growth)DOCN row 5written outlook
X Missed❗ FY2026 adjusted free-cash-flow margin 15–17% of revenueDOCN row 6written outlook
W Withdrawn❗ FY2026 unlevered adjusted FCF margin 18–20% of revenueDOCN row 7written outlook
X Missed❗ FY2026 fully diluted weighted average shares ~111–112mDOCN row 8written outlook

Questions dodged

7.1 per 100 answers

  1. Q1 2026 · free cash flow including lease payments · Jason Ader (William Blair). Asked: "for 2027, you talked about adjusted free cash flow margin in the mid- to high teens, I believe. Could you give us a sense of what it would be, including lease payments?" Matt Steinfort: "It's hard to answer, though, because it will depend entirely on the lease terms that we have… That's why we're not guiding to that at this…

    from DOCN · dossier-2026-09-23.md

Calls reviewed

  • FY2026-Q1.roic.json — 6 answers, 19% of the words
  • FY2026-Q2.roic.json — 8 answers, 27% of the words

Sources

14
  1. Filing DigitalOcean Holdings DEF 14A (accession 0001582961-26-000029) · 2026-04-24
  2. Filing DigitalOcean Holdings 8-K Item 5.07, 2026 annual meeting results (0001582961-26-000051) · 2026-06-17
  3. Filing DigitalOcean Holdings 8-K Item 5.02, CFO employment agreement (0001582961-22-000054) · 2022-11-17
  4. Filing Ex-99.1 to the 8-K of 2022-11-17, 'DigitalOcean Names Matt Steinfort Chief Financial Officer' · 2022-11-17
  5. Filing DigitalOcean Holdings 8-K Item 5.02, amendment to CFO employment agreement (0001582961-23-000052) · 2023-09-19
  6. Filing DigitalOcean Holdings 8-K Item 4.02, non-reliance on Q1 2023 financial statements (0001582961-23-000028) · 2023-08-03
  7. Filing Zayo Group Holdings DEF 14A (accession 0001047469-18-006457), executive officer biographies · 2018-09-27
  8. Filing SEC XBRL companyconcept us-gaap/NetIncomeLoss, CIK 1582961 (FY2025 10-K, 0001582961-26-000019) · 2026-02-24
  9. Filing Form 4, Matt Steinfort (reporting CIK 1717324), PSU vesting 2026-02-27, tax withholding 2026-03-01, 10b5-1 sale 2026-03-03 (0001717324-26-000002) · 2026-03-03
  10. Filing Form 4, Matt Steinfort, sale of 2026-05-15, not marked as a 10b5-1 trade (0001717324-26-000006) · 2026-05-19
  11. Filing Form 4, Matt Steinfort, tax withholding 2026-06-01 and 10b5-1 sale 2026-06-02 (0001717324-26-000010) · 2026-06-03
  12. Filing Form 4, Matt Steinfort, tax withholding 2026-09-01 and 10b5-1 sale 2026-09-03 (0001717324-26-000012) · 2026-09-03
  13. Call transcript DOCN Q1 2026 earnings call (2026-05-05), ROIC.ai
  14. Call transcript DOCN Q2 2026 earnings call (2026-08-04), ROIC.ai