Jessy Paull is a strategic leader and growth operator with deep expertise in digital health, employer-sponsored benefits, and go-to-market execution. With 20+ years of experience spanning sales, product strategy, and revenue enablement, she has consistently driven innovation and commercial impact across high-growth health tech organizations.

A trusted advisor to C-level executives and consultants, Jessy has built and scaled solutions that sit at the intersection of technology and human care—delivering outcomes-driven programs that improve access to high-quality, affordable healthcare. She played a pivotal role in launching Headspace’s EAP product, generating over $32M in revenue and capturing a significant share of the late-stage pipeline within two years.

Throughout her career, Jessy has been known for her ability to lead cross-functional teams, shape product vision, and architect scalable GTM strategies. She excels at identifying friction points, aligning stakeholders, and translating complex market dynamics into actionable growth plans. Currently, Jessy is thrilled to serve on the board of Pietential, helping employers better understand and support holistic well-being through data-driven insights, and also leads independent consulting engagements focused on market strategy, growth, and product innovation.

When she’s not working, Jessy enjoys spending time with her husband and two daughters, cheering on Philadelphia sports teams, and tackling new skills and household projects big and small. A naturally curious builder, she loves learning and finding creative ways to bring new ideas to life.

Jessy is now focused on formal leadership roles where she can lead teams, mentor talent, and continue to influence the future of healthcare and benefits through strategic innovation and commercial excellence.