Executive Resume October 2026

David A. Olk

New York, NY davidolk@gmail.com LinkedIn

Founder, operator and investor with more than 20 years of experience building and financing technology businesses. Operating Partner at Interplay Ventures, helping source, diligence and incubate potential investments. Co-founded ShopKeep, founded and led Voray and SaySo through exits, and co-founded Junction Venture Partners. Combines company building and founder relationships with venture investing, financial diligence and M&A execution. Currently leads investor coverage in New York for Stifel Venture Banking.

20+ Years building and financing technology businesses
$440M ShopKeep acquisition by Lightspeed, as announced
$200M+ Equity and debt raised across 3 venture-backed companies

Founder and Investment Leadership

Interplay Ventures

Current

Operating Partner

New York based investment and company building platform

  • Source, diligence and incubate potential investment opportunities, bringing founding and operating experience to investment evaluation and company development.
  • Interplay’s venture strategy targets North American technology-enabled companies from seed through Series B, with a focus on Series A, application-layer AI and marketplaces.

ShopKeep

Acquired 2020

Co-Founder, COO and CFO

Company acquired by Lightspeed in 2020

  • Co-founded and helped build a cloud commerce business for independent retailers and restaurants; led operations, finance, go to market and fundraising.
  • Helped raise more than $100 million in capital. ShopKeep was acquired in a transaction announced at approximately $440 million, with $7 billion in annual gross transaction volume.

Junction Venture Partners

2021 to 2025

Co-Founder and General Partner

  • Co-founded an early stage venture fund making investments of $250,000 to $2 million in SaaS and B2B marketplace businesses.
  • Sourced and evaluated opportunities and supported founders on product market fit, growth strategy, operations and capital planning.

SaySo

2024 to 2025

CEO and Co-Founder

  • Founded a software platform using Dutch auctions to help retailers recover value from excess inventory.
  • Raised a $4 million seed round, secured an anchor partnership with Ashley Canada and led enterprise sales, operations and strategy.

Voray

2015 to 2023

Chairman, CEO and Co-Founder

  • Built a professional network business, scaled it to $4.2 million in annual recurring revenue and led an exit in 2023.
  • Led fundraising and developed workflow software supporting events and community engagement.

Current Venture Ecosystem Role

Stifel Venture Banking

Current 2025 to Present

Managing Director, Venture Banking

  • Lead investor coverage in New York, developing venture firm relationships and working with portfolio companies on banking, deposits and venture debt.

Mergers and Acquisitions

RK Equity Capital

2010 to 2011

Co-Founder and Managing Director

  • Led an iron ore producer sale process and structured offtake agreements with Chinese steel buyers.

IAC

2007 to 2010

Director, Mergers and Acquisitions

Publicly traded holding company chaired by Barry Diller.

  • Led deal structuring, diligence and execution for acquisitions and venture investments; worked across internal teams and external counterparties.

PwC

2000 to 2007

Transaction Services

  • Led financial due diligence for private equity and strategic buyers in New York and Hong Kong, including work supporting IBM’s sale of its PC division to Lenovo.
  • Promoted to director at age 27; received the firm’s Chairman’s Award in 2006.

Arthur Andersen

1998 to 2000

Associate, Audit

  • Conducted commercial client audits before transitioning to transaction advisory.

Selected Investments

Junction

Kontango Ingest.ai The Many Company ePallet Helios Solar

Earlier personal and GP investments

Kickstarter Jellysmack Headspace Hungryroot Shelf Simplebet Morty Bookkeep Wagmo Mable Sensa Padel Confetti Olive

Board and Advisory

Kickstarter Simon Quick Advisors ShopKeep Voray Vengo Gooten Amper Music

Education and Credentials

MBA, Columbia Business School, 2011

BSM, Accounting, Tulane University, 1998

CPA FINRA Series 79 FINRA Series 66

Harvard Business School case. Subject of Time-Driven Activity-Based Costing at Voray (Ethan Rouen, 2018), required in Harvard cost accounting coursework. Occasionally visits Harvard to teach the case.

Writing and Community

Failing Forward

Wrote a weekly Inc. column on venture-backed entrepreneurship, covering fundraising, leadership, and the mistakes founders repeat. Read the columns.

Columbia Business School

Former Adjunct and Entrepreneur in Residence. Taught the Lean Launchpad with Steve Blank and Venturing to Change the World with Jenny Fielding.

Lang Entrepreneurship Center

Former board member of the Eugene M. Lang Entrepreneurship Center. The advisory board shapes programming, curricula, and resources for students and alumni.

Tulane University

Innovator in Residence at the Albert Lepage Center for Entrepreneurship and Innovation, mentoring and investing in students interested in becoming entrepreneurs. Innovators in Residence.

Mentoring

Mentors founders through Techstars in New York.

Team Fox

Triathlete with Team Fox, the community fundraising program of the Michael J. Fox Foundation for Parkinson’s Research.