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Roy Mathew

Investor

Advisor at Diagram Collective

New York, New York

Writes $100K – $5M checks · typically $1.5M

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About

Roy Mathew is Head of Sales at Gumloop. He brings over 15 years of experience in sales leadership, go-to-market strategy, and scaling high-growth companies, with previous roles including VP of Sales at Recurrency, early employee at Airtable, and founder and CEO of uQuote. He has also held positions at public companies including Elastic and Box.

Experience

  1. GumloopHead of Salescurrent2026 — presentSan Francisco, California, United States
  2. Diagram CollectiveInvestor / Advisorcurrent2022 — present
  3. RecurrencyVP of Sales2025 — 2026
  4. RecurrencyHead Of Sales2022 — 2025New York, United States
  5. AirtableSales Leader, Strategic Accounts2017 — 2021New York, United States
  6. First Round CapitalMentor2021
  7. uQuoteCo-Founder & CEO2014 — 2017San Francisco
  8. ElasticHead of Growth2014
  9. BoxManager, Strategic Planning & Analysis2013 — 2014
  10. BoxProduct Marketing Manager, Pricing2011 — 2013
  11. Jefferies & CompanySpecial Situations Derivatives Trader2009 — 2011
  12. Results Tutoring GroupFounder / Tutor2004 — 2006Danville, California

Skills & more

Analytics36Product Marketing32Data Analysis32Marketing Strategy19Pricing Strategy8Cloud Computing15Entrepreneurship6Competitive Analysis6Statistical Modeling4Eloqua4MicrostrategyOptions Strategies2
+12 moreSalesforce AdministratorHedgingEquitiesStart-upsFinancial ModelingStrategic PartnershipsBusiness DevelopmentStrategyStataPythonVBAMicrosoft Excel
  • Command of the Message — Force Management

From Roy's professional profile.

Colleagues at Diagram Collective

Allison Tan
Investor at Diagram Collective
Benjamin Clark
General Partner at Diagram Collective
Joey Brown
Investor at Diagram Collective
Joshua Steinberg
Managing Partner at Diagram Collective
Matthew Yalowitz
General Partner at Diagram Collective
Nakul Patel
Managing Partner at Diagram Collective
Richard Allen Farmer
General Partner at Diagram Collective
Thai Bui
Investor at Diagram Collective

Frequently asked questions

Who is Roy Mathew?
Roy Mathew is Head of Sales at Gumloop. He brings over 15 years of experience in sales leadership, go-to-market strategy, and scaling high-growth companies, with previous roles including VP of Sales at Recurrency, early employee at Airtable, and founder and CEO of uQuote. He has also held positions at public companies including Elastic and Box.
Where does Roy Mathew work?
Roy Mathew is Advisor at Diagram Collective.
What check size does Roy Mathew write?
Roy Mathew typically writes checks of $100K – $5M.
Where did Roy Mathew go to school?
Roy Mathew studied at Harvard University (AB Honors (Cum Laude), Economics); The Wharton School (Joseph A. Wharton Fellow, MBA); Monte Vista High School.

Same school

Shared employers