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Episode 11: Kyle York and Tom Wentworth
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Kyle York is co-founder, CEO and managing partner at York IE™ where he sets the vision and leads the vertically integrated strategic growth and investment firm. Kyle works closely with entrepreneurs, operators and investors to help them realize their shared ambition to build good companies, create new jobs, grow generational wealth and impact the world.

Advising and investing in over 100+ startups, primarily in B2B SaaS, Kyle is a board member for several portfolio companies. Current York IE portfolio highlights include Cyberhaven, Flywheel, Metadata and Vetro. York IE touts advisory services clients Linksquares, Shoobx, Stavvy, and dozens more. He is also co-founder of 3rd generation family business, YORK Athletics MFG., within the York Creative Collective, and Managing Partner of York Real Estate.

Kyle was CRO at Dyn from 2008 until it’s acquisition by Oracle in 2016 for $600M. He spearheaded strategy and go-to-market to $100M ARR, 5,000 enterprises, 1M paid users, $100M raised, 500 global employees and 11 executed M&As. For three years, he was VP Product Strategy for Oracle Cloud Infrastructure ($1B+) and GM of Oracle Dyn ($150M P&L). Founders and operators from acquisitions DataScience, Renesys, StackEngine, Wercker and Zenedge reported into Kyle. Prior to joining Dyn, Kyle spent six years in EdTech at vertical SaaS company WhippleHill, acquired by Blackbaud.

Kyle has committed his career to the enterprise software industry driving growth for subscription, recurring revenue business models. He past served as an independent board member for Datanyze (ZoomInfo), Assent (Vista), Forcivity (Jolt) and Flowtraq (Riverbed). Kyle’s most successful startup engagement to date, Fastly, IPO’d in 2019 peaking at $13B.

An expert in software, infrastructure and technology markets and trends, Kyle has been featured in the Wall Street Journal, Entrepreneur, the New York Times, TechCrunch, USA Today, and Wired, and broadcasts such as NPR’s All Tech Considered, NBC’s Today Show and PBS’s Frontline. He has been a guest speaker at many conferences worldwide.

The York Family Foundation and York IE provide non-profit support and board work to Boston Children’s Hospital, NH Tech Alliance, Manchester Historic Association, Stay Work Play NH, Manchester Boys & Girls Club and Joe Yukica NH Chapter of the National Football Foundation, among others, all focused on inspiring the next generation. He was named Entrepreneur of the Year in 2021 by the NH Tech Alliance. Kyle has a BS in marketing from Bentley University and is chairman of the Entrepreneurship Executive Council.

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