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The Trailhead Group, LLCThe Trailhead Group, LLC
The Trailhead Group, LLC
  • Home
  • What We Do
  • About
  • Outfitter
  • Contact Us

The Trailhead Group LLC Purpose Guides Action What We Do What We Do

The Trailhead Group advises business leaders to construct and execute the business strategies that maximize revenue generation, customer loyalty, and employee retention.

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We deliver value in four distinct areas:

Pragmatic Objectivity

We bring thoughtful observation, genuine curiosity, and relentless inquiry into our work as we assess how to optimize your business opportunity. We identify costly organizational blind spots. We help you create a plan that will serve your purpose, customers, and business goals.

Go To Market Strategy

We assess the current market landscape to determine where shifts or new paths might unleash additional opportunities. We partner with you to refine the value propositions, business models, and product strategies that deepen customer adoption.

Partner Identification

The right partnership can accelerate growth and focus your team. Bad partnerships waste time and scatter critical resources. Based on your desired path, we help you define the partner profile then move to execute on the plan.

Talent Optimization

Your team is one of your most valuable assets. We take inventory of your team’s strengths. We identify where your team is prepared to support your objective and where improvements are needed to succeed.

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Our Services

What People Say

Interim Executive Support

Strategic Assessment

Retained Services

  • 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

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The Trailhead Group, LLC

The Trailhead Group

Purpose Guides Action

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  • The Trailhead Group, LLC
  • Washington, D.C.
  • info@thetrailheadgroup.com
  • www.thetrailheadgroup.com

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