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The Trailhead Group, LLCThe Trailhead Group, LLC
The Trailhead Group, LLC
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The Trailhead Group LLC Purpose Guides Action


The Trailhead Group helps business leaders build and execute strategies that drive revenue, earn customer loyalty, and strengthen their teams.

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We deliver value in four distinct areas:

Pragmatic Objectivity

Thoughtful observation, genuine curiosity, and relentless inquiry optimizes 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

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

Fractional Leadership

Experienced leadership to guide the team through challenging times. We bring the clarity, focus, and discipline necessary to execute on the priorities and deliver on the company goals.

Talent Optimization

Your people are one of your most valuable assets. We identify where your team is prepared to support your objective and where improvements are necessary to succeed.

Our Services

Retained Services

Focus and experience yields quality deliverables

Engagements rooted in strategic practicality bring tested experience to construct and execute plans with reliability and clear deliverables. These commitments are crafted for the executive team that requires ongoing access to an objective advisor who brings a fresh and experienced perspective to tackle critical initiatives.

Fractional Executive

Leadership capacity to bridge the gap

Short-term support for the CEO who needs a critical seat during crucial growth periods. Extend your management team’s capacity and accelerate your path to success with a trusted, seasoned executive.

Guide Services

Direct questions shape crucial decisions

A time and cost-efficient subscription model for Founder / CEOs who want access to honest and objective counsel that advances company growth and success. Guide Service focuses on the discrete, high-impact conversations and assignments a CEO wants and needs to perform most effectively. The engagement is supported by the same integrity, strategic thinking, market knowledge, and operational expertise from The Trailhead Group’s traditional retainer structure.

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What People Say

  • 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

Our Clients

About The Trailhead Group

The Trailhead Group, led by seasoned ed-tech executive Matt Doherty, helps founders and leadership teams navigate complex challenges, scale effectively, and achieve meaningful exits. With 20+ years of building, running, and selling successful companies, we bring objective insight, proven strategies, and hands-on leadership to help your business thrive.

Whether you’re planning your next stage of growth—or facing an unexpected challenge that puts your company or leadership under pressure—we step in with clarity, focus, and experience to guide you through the moments that matter most.

Matt Doherty, Founder & Principal

Matt Doherty, Principal
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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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