Jason Kaplan

Jason is a seasoned technology executive with over 28 years of leadership experience in tech startups and enterprises, specializing in scaling early-stage businesses.

As CEO of SixMap, Inc., Jason was brought in by lead investors to grow this Series A company. His strategic initiatives—refining messaging, focusing the product roadmap, and repositioning go-to-market strategy—led to a successful $7 million funding round and significant growth in both commercial and federal revenue.

Previously, Jason served as CEO of CyTwist (Israeli advanced attack detection) and CRO at RocketDocs, where his team increased ARR bookings by over 450% in one year. His early career includes serving as the first Director of Sales at Akamai Technologies in 1999, where he built the first sales organization.

As founder and CEO, Jason built Milestone Sports from inception to successful acquisition by Zwift in 2018, developing innovative wearable devices and data analytics platforms for athletic retailers.

Jason remains active as a consultant, advisor, and mentor. He is currently advising companies including Netmaker and Avelo, and participating in TEDCO's Venture Mentor Services program. He holds a Bachelor's degree in Business Administration from Emory University.