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The Trailhead Group, LLCThe Trailhead Group, LLC
The Trailhead Group, LLC
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The Trailhead Story

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.

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Matt’s Story

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.

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Testimonials

  • Matt is a constant idea generator and one of the most nimble thinkers of anyone I’ve worked with. He has the uncanny ability to take seemingly unrelated concepts and synthesize them into something meaningful and relevant. Although Matt has an exceptional ability to think in the abstract, he also has a keen understanding of pragmatic action. This balance of seemingly competing concepts formed the cultural foundation of our small company and contributed significantly to its success.

    Shane Foster
    Chief Product Officer (Former Colleague)
  • Matt is the perfect balance of a person who draws upon his vast experience while looking towards the future in a creative way. He is able to present a clear vision of where a product or company can evolve while managing the larger strategic goals and inevitable tactical demands. On numerous topics, I have relied on Matt’s sage advice to help me forge a path forward with more confidence.

    Steve Shapiro
    CEO, FineTune
  • Matt brings the uncanny ability to observe teams at work, assess their dynamics and work collaboratively with them to make them better, through coaching, strategic hiring and, at times, gentle redirection. I always appreciated his thoughtful approach and found his guidance invaluable. If you find your team or company struggling to adapt or achieve the next stage of growth, Matt might be just the guy to unstick you, by identifying skill or personnel gaps, suggesting small adjustments to team structure and determining a path forward.

    Sarah Newlin
    Vice President, Marketing (Former Colleague)
  • After years working in the Digital Media world, I am now set to launch my own business, but have struggled with how to get the process in motion. I turned to Matt, who helped me to articulate my unique value proposition more effectively and to adjust my business plan accordingly. Matt is a quick study with a knack for asking the insightful questions that reveal perspectives that will surely set me on the right path ahead. Matt is good at this.

    James Williams
    Principal, Digital Video Strategies
  • Matt is an outstanding leader who cannot only create a compelling vision, but sell that vision to the organization, the market, and the investment community. Matt’s knowledge of the education industry combined with his investment and strategic business development background come together in a package that is rarely found in this space. Matt is on my short list of those who create opportunities for growth at an executive level.

    Ramsey Chambers
    Senior Vice President, Product (Former Colleague)
  • As we explored strategic alternatives for our portfolio companies, Matt came highly recommended. His insightful questions challenged our perspective and led to the generation of a set of options with related benefits and risks. Matt does his homework, listens, and adapts. Matt has earned the respect of the MRR Soft executives and investors. We would work with him again.

    Shajan John
    Head, Corporate Development & Board Director

Matt Doherty

Founder & Principal

Matt Doherty, Principal

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The Trailhead Group, LLC

The Trailhead Group

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  • info@thetrailheadgroup.com
  • www.thetrailheadgroup.com

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