KEITH KOSTRZEWSKI
Partner
Keith is a growth-focused operator with 20+ years leading revenue and commercial strategy across B2B SaaS, services, and education technology, with additional experience in commercial real estate development and sports/community ventures. He sets clear commercial direction, builds high-trust teams, and installs an operating rhythm that connects strategy, markets, and execution to results.
His enterprise and high-growth background includes leadership roles at LEGO Education and Pearson, and he served as CEO of Curriki. Earlier, he spent eight years at SchoolNet, leading sales operations and later overseeing the company’s largest enterprise SaaS client prior to its acquisition by Pearson. These roles sharpened how he aligns Product, Marketing, Finance, and Customer Success, pairing commercial judgment with disciplined management.
Keith founded and built Sidekick Group, partnering with CEOs, investors, and boards to turn strategy into execution via market definition and entry strategy, positioning and offer architecture, partner ecosystems, pricing and monetization, and the operating cadence that unites Sales, Marketing, Product, and Customer Success. He is co-founder of Abode Development in Hilton Head, leading commercial real estate strategy, capital and stakeholder partnerships, joint-venture structuring, and government relations. He holds an MBA from Northwestern’s Kellogg School of Management.
GET TO KNOW KEITH
Keith is the proud father of three girls and has fully embraced the “girl dad” motto. After chapters in Boston, New York, and Chicago, his family settled in Hilton Head; most weekends are on the beach or the boat, and many evenings are on the soccer field where he coaches his daughters.
A Buffalo native and lifelong Bills fan, he started his career with the Buffalo Bills as a graduate assistant and played college soccer at Providence College. He serves on the Board of Fighting Pretty, helped start a men’s group at his church, advises several nonprofits, and enjoys writing narrative essays on brand, sport, and community.