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Ryan Schaffer
ResearchedAngel Investors

Ryan Schaffer

Angel InvestorsSeed Round
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At a glance

Full Name
Ryan Schaffer
Title
Chief Financial Officer & Board Member, Expensify (angel investor in a personal capacity)
Firm
Expensify, Inc. (day job); invests personally as an angel
Firm Type
Angel Investor (individual)
Investment Stage
Seed / Angel round
Sector Focus
No formal thesis published; sole disclosed deal is in consumer/e-commerce (fashion rental)
Geographic Focus
United States
Location
Maui, Hawaii

Background

Ryan Schaffer is the Chief Financial Officer and a member of the board of directors of Expensify, Inc. (NASDAQ: EXFY), the expense-management and payments company. He has held the CFO and board role since 2017, and before that served as Expensify's Director of Marketing and Strategy from 2013, when he first joined the company. As CFO he oversees all major financial activities at the business — he has led multiple equity buybacks from early shareholders, raised debt financing for the company, and acted as the primary liaison between Expensify and its investors. He was part of the leadership team that took Expensify public via IPO in November 2021.

In his earlier marketing-and-strategy role, Schaffer spearheaded brand-marketing campaigns that raised Expensify's profile in the accounting and finance world, including a Super Bowl television commercial. Prior to Expensify he worked in marketing roles elsewhere, including directing marketing at Alerstallings Law Firm and managing online marketing at The Michelson Organization.

Schaffer holds a Bachelor of Science in Business from the University of Dayton, with a specialization in Marketing and Sales Management (graduating in 2009). He is based in Maui, Hawaii, where he lives with his wife (and their cat, Cornpop), and lists scuba diving and gardening among his interests.

It is worth flagging that Schaffer is primarily an operating executive rather than a professional investor. The "Angel Investor" label reflects occasional personal investments; public databases record only a single disclosed deal, so his angel activity appears light and opportunistic rather than programmatic.

Investment Thesis & Focus

  • Invests personal capital as an individual angel, not through a fund — there is no published thesis, target check size, or stated investment criteria.
  • Disclosed activity is at the angel/seed stage, consistent with the "Seed Round" stub.
  • The one documented deal is in consumer e-commerce / subscription commerce, but a single data point is not enough to define a firm sector preference.
  • Given his background, founders should assume any value-add would center on his operating expertise — finance, marketing/brand, and scaling a SaaS/fintech company through late-stage financing and IPO — rather than large or frequent checks.

Notable Investments

  • Armoire — Seattle-based women's clothing-rental subscription service; Schaffer participated in the company's ~$3M angel round on October 24, 2018, alongside a group of co-investors that reportedly included Jesse Draper and Dawn Lepore.

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