The Trailhead Group helps business leaders build and execute strategies that drive revenue, earn customer loyalty, and strengthen their teams.
Let's Talk!We deliver value in four distinct areas:

Our 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.
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.
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.
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














