The Trailhead Group advises senior executive teams who seek to identify and execute on new market opportunities.
A new business unit or revenue stream has the potential to drive sustained growth and attract inspired talent. We understand how these strategic conversations can transform the trajectory of a company in the eyes of customers and employees. We embrace the moment in the organization’s growth and commit ourselves to delivering objective, direct, and informed decision support for the company’s leadership.
Two decades in Executive leadership, Operations, Sales, and Partnerships bring a diverse, practical, and pragmatic perspective to our advisory work. These experiences inform the process in which we plan for sustainable business success built on engaged employees, happy customers, and thriving communities.
If you find your company at a juncture where a market shift or expansion may be needed, we invite you to connect.
Matt’s professional career includes executive, revenue generation, operational and partnership leadership roles in the education and workforce sectors. Most recently, Matt was COO at LearnPlatform, a venture-backed company that delivers product efficacy insights to K-12 education district leaders. LearnPlatform was acquired by Instructure (INST) in December 2022. For almost 10 years, Matt was President at Academic Benchmarks, a self-funded data service, and successfully built the company leading to its acquisition by Certica Solutions, a private equity-backed technology platform, in 2016. Matt has also served in strategic business development and sales roles at companies such as Blackboard, The Princeton Review, and Spectrum K12.
Early in his career, Matt helped develop a School/Work program in Washington, D.C. and taught in the Boston Public Schools as well as a parochial high school in San Francisco. Matt received his Bachelors degree in American Studies from Georgetown University and a Masters in Secondary Education from Boston College.
Matt lives in Washington, D.C. with his wife, soccer ball, bicycle, BBQ smoker, and mandolin. The couple’s two children attend college, currently.