Sean Flynn is a global sales and P&L leader with extensive experience in fast-growth start-ups and established technology companies. Strategic, data-driven, and customer-focused, he builds scalable go-to-market engines and delivers sustainable growth. He has helped lead new ventures to $1B+ valuations, executed complex turnarounds, and integrated 5 software acquisitions, driving profitable results.

In a career spanning the military, IBM, and PE-backed firms, Sean’s teams deliver through an intentional approach to building culture, skills, and resilience. As a leader, he is laser-focused on delivering results while taking care of the people around him. Boards, executives, and clients value his integrity, consistency, and candor.

Notable experience includes:

PE SaaS GTM Leadership: Led a global sales team of 900+ sellers for Vista Equity’s largest SaaS acquisition at Avalara, growing bookings from $900M to $1.4B+ in three years while becoming a Rule of 50 company. Designed and implemented sales transformations including Go-Global, Seller Certification + Career Maps, Customer Experience 360, and an award-winning AI-for-Sales program.

Fast-Growth Start-Ups: Scaled InStride programs to support over 52,000 learners across 30+ Fortune 1000 companies, helping learners avoid $520M of student debt. Led Gympass US (now Wellhub) to 96 corporate clients, 700,000 eligible members, and 8,726 fitness partners in 16 months.

Complex Turnarounds: Delivered 21% year-over-year growth leading 900+ sellers in highly competitive segments of IBM’s Collaboration and Talent Management portfolio.

Business Transformation: Deployed new go-to-market models transforming North America sales of a $1.1B Commerce brand with 500+ sellers transitioning to SaaS.

Collaboration & Teaming: Worked closely with InStride’s CEO Advisory Board, which included former CEOs from HP, Ford, Michaels, and Citi NA, to build go-to-market engines for target client segments.

Sean combines operational excellence with board-level insight, helping organizations navigate growth, transformation, and strategic challenges while building resilient, high-performing teams.