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Sarah McCrary

Sarah McCrary

CEO/COO- B2C & B2B Fintech & Fintech-Enabled Businesses, Payments, Subscription, SaaS

Boston, Massachusetts

My first leadership experience was leading a girl gang. I organized six fellow kindergarten pals to take-down a sixth-grade playground bully. We succeeded and I was hooked on the power of teamwork to accomplish ambitious outcomes.

As a CEO/COO of tech-enabled businesses, I have launched, grown, turned around, and stabilized several early-stage companies during periods of organizational change and market disruption to put them on a path to profitability and position them for successful exits.

My expertise encompasses technology-product leadership; payments technology; executive management of finance, marketing, sales, engineering, and business development teams; stream lining of business operations; and M&A strategy.

I have developed and executed successful roadmaps to support digital transformation as well as go-to-market and monetization strategies for B2C and B2B mobile, subscription, and SaaS (data insights, point-of-sale) platforms.

It gives me energy to connect teams to a shared mission and nurture a work community of belonging and purpose. Results invariably follow strong, aligned teams.


  • Senior Technology Project Manager (Alliance Data Systems (Network Services division acquired by Heartland Payment Systems May 2008))
  • Strategic Planning Director (Heartland Payment Systems)
  • Director, Product Management End-to-End Encryption Program (Heartland Payment Systems)
  • CEO & Board Member (Leaf)
  • CEO & Board Member / COO (GasBuddy)
  • COO (Leaf)
  • VP, Digital Strategy (Heartland Payment Systems (Acquired by Global Payments))


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