Trailhead Strategy Co.
Mountain trail at golden hour

Business Strategy & Finance

Getting lost is easy. Finding the trailhead is everything.

Trailhead exists to help businesses find their way again. Not by forcing change, but by providing direction grounded in truth, structure, and wisdom.

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Summer view from Breckenridge mountain overlooking the town

Our Story

Built With Intentional Provision.

Trailhead was founded in 2025 by David Ireland, a C-suite executive who had seen too many good businesses struggle because of bad advice, poor decisions, and financial data that leadership couldn't trust.

The vision was to build something different.

Trailhead brought together experienced executives who shared a desire to serve business owners, especially those who had been burned by consultants before or simply found themselves unsure of the path forward. The idea behind the name became the model for the company itself. When you've lost your way on the trail, sometimes you need a guide. Other times, you know exactly where you're going but need the right tools and supplies to make the climb.

That's where Trailhead comes in: providing the guidance, tools, and experience businesses need for the climb ahead.

At the center of it all is our faith. The question that shaped Trailhead from the beginning was simple: How can we use the gifts God gave us to serve others?

That calling became the foundation of how we operate and the mission we continue to build around today:

God First. Others Second. Us Third.

About Trailhead Strategy Co.

01

Our Mission

Our mission is to steward businesses with integrity and wisdom, bringing structure, accountability, and truth to finance and operations so leaders can make better decisions and move forward with confidence.

02

Our Team

We are not career consultants. We are executives and operators who have sat in the seat and understand what it takes to lead a business through uncertainty. Our relationships with clients are built on trust, accountability, and a shared commitment to doing what is right, even when the right decision is difficult.

03

Our Results

When a business finds its footing again, the difference is obvious. What was once reactive becomes structured. What felt uncertain becomes measurable. Leaders stop guessing and start operating with direction. The result is a stronger business with a clear understanding of where it's going and what it will take to get there.

04

Our Approach

We don't sit on the sidelines and hand over recommendations. We step into the business, identify what's working, uncover what isn't, and help fix what needs to change. Our work is hands-on, grounded in real executive experience, and focused on building the financial and operational structure leaders need to make better decisions and build for the long term.

What We Do

Experienced leadership, where your business needs it most.

Not every business needs another consultant. Sometimes it needs someone who can step into the seat, understand the problem, and help lead the way forward.

Trailhead provides experienced fractional executives across the core functions of a business. We work alongside owners and leadership teams to solve problems, strengthen operations, and build the financial and organizational structure needed for what comes next.

Finance & Strategy

From financial reporting and cash flow management to forecasting, capital strategy, and executive decision support, our CFO leadership turns financial data into information you can actually use.

Operations

Our COO leadership brings structure to growing or struggling organizations by improving processes, accountability, systems, team alignment, and execution across the business.

Technology

Technology should support the business, not become another problem to manage. Our technology leadership helps companies evaluate systems, improve infrastructure, manage implementation, and make better technology decisions.

Revenue & Growth

Growth without direction can create as many problems as it solves. Our revenue leadership helps businesses strengthen sales strategy, identify opportunities, improve execution, and build a more intentional path to growth.

One team. Different expertise. One direction.

Our clients don't have to solve every problem with a different consultant. Trailhead brings experienced leaders together under one roof, giving businesses access to the expertise they need without the cost or commitment of building a full-time executive team.

Meet Your Guides

Meet Your Guides

Trailhead brings together experienced executives who have spent their careers making decisions, solving problems, and leading organizations from inside the business.

Trailhead Leadership
David Ireland

David Ireland

Founder & CEO

David leads Trailhead Strategy Co. and its vision of bringing experienced executive leadership to businesses that need a better path forward.

Dr. Kendrick Brunson

Dr. Kendrick Brunson

Vice President, Strategic Partnerships

Dr. Brunson leads strategic partnerships and relationship development for Trailhead, helping connect business owners and organizations with the resources and leadership they need to grow.

Executive Network

Our executive network allows Trailhead to build the right leadership team around each engagement. Clients gain access to experienced operators based on the needs of their business without having to build an entire C-suite internally.

David Ireland

David Ireland

Fractional CFO | Finance & Strategy

Financial leadership, forecasting, risk management, executive decision support, and financial strategy.

Jordan Agee

Jordan Agee

Fractional COO | Operations & Strategic Advisory

Operational leadership, organizational strategy, process improvement, execution, and strategic advisory.

Brian Smith

Brian Smith

Technology & Software Systems Strategic Advisory

Technology strategy, software systems, infrastructure, implementation, and executive technology leadership.

Different expertise. One team. One direction.

Now in Development

The Future of Strategic Intelligence
is Almost Here

We're building an AI-powered platform that delivers the strategic clarity and operational intelligence your business needs to move with confidence. Be first in line.

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Operational Intelligence
Strategic Clarity

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