

Should I Work for a Startup or a Big Company?
I get asked all the time about what it’s like to work for a startup vs. a big company. They are very different worlds, and
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 York IE portfolio companies. Current York IE portfolio highlights include Cyberhaven, Flywheel, Metadata and Vetro. York IE also touts advisory services clients including Linksquares, Shoobx, Stavvy and dozens more. Kyle is also co-founder of third-generation family business YORK Athletics MFG., within the York Creative Collective, and managing partner of York Real Estate.
Kyle was chief revenue officer at Dyn from 2008 until its acquisition by Oracle in 2016 for $600 million. He spearheaded strategy and scaled go-to-market to $100 million annual recurring revenue, with 5,000 enterprise customers, 1 million paid users, $100 million raised, 500 global employees and 11 executed mergers and acquisitions. For three years, he was vice president of product Strategy for Oracle Cloud Infrastructure (a $1 billion-plus business) and general manager of Oracle Dyn ($150 million P&L). Founders and operators from acquisitions DataScience.com, Renesys, StackEngine, Wercker and Zenedge reported into Kyle. Prior to joining Dyn, Kyle spent six years in EdTech at vertical SaaS company WhippleHill, which was acquired by Blackbaud.
Kyle has committed his career to the enterprise software industry, driving growth for subscription-based recurring-revenue business models. He in the past served as an independent board member for Assent Compliance (Vista), Datanyze (ZoomInfo), Flowtraq (Riverbed) and Forcivity (Apps Associates). Kyle’s most successful startup engagement to date, Fastly, IPO’d in 2019 peaking at $13 billion.
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 on broadcasts such as NPR’s All Tech Considered, NBC’s Today Show and PBS’s Frontline. He has been a guest speaker at conferences worldwide.
The York Family Foundation and York IE provide nonprofit support and board work to Boston Children’s Hospital, the New Hampshire Tech Alliance, Manchester Historic Association, Stay Work Play New Hampshire, Manchester Boys and Girls Club and Joe Yukica New Hampshire Chapter of the National Football Foundation, among others, all focused on inspiring the next generation. Kyle was named Entrepreneur of the Year in 2021 by the New Hampshire Tech Alliance. He has a BS in marketing from Bentley University and is chairman of the Entrepreneurship Executive Council.
Follow Kyle York on Twitter and connect with him on LinkedIn.
I get asked all the time about what it’s like to work for a startup vs. a big company. They are very different worlds, and
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