Hilary Headlee

Executive Vice President
Assistant: Kayla Saunders

Hilary Headlee

Hilary is the Advisory Leader for Insight Partners’ Early and Growth Segment, where she partners with founders and executives to build scalable, high-performing go-to-market (GTM) organizations. With over 20 years of GTM operating experience, she specializes in aligning strategies, teams, and programs to fuel growth across B2B SaaS organizations.

Throughout her career, Hilary has collaborated extensively with Product, Marketing, Sales, Finance, and IT departments, contributing to five successful exits, including IPOs for high-growth companies such as Zoom (ZM) and Alteryx (AYX), as well as M&A support for Mindbody (PE), Lynda.com (now LinkedIn Learning), and Iconoculture (now Gartner).

In her leadership roles, Hilary has focused on bridging the gap between product development and sales, overseeing GTM Operations, Enablement, and Customer Success teams to ensure that customers receive the support they need. Her global experience includes managing teams across North America, EMEA, APAC, and LATAM, supporting sales motions from SMB to Enterprise, and guiding organizations through growth stages ranging from $0 to $4B in revenue.

Hilary graduated from Augustan College with a focus on Business, Communications, and Psychology. Outside of work, she begins each day with a Dolly Parton sized "cup of ambition" and a commitment to helping others achieve their goals.