Nick Wakefield
Founder and Principal
Built in the field, not in the classroom.
I have spent 34 years working in operations, human resources, safety, and recruiting. Not talking about it or studying it, but doing it.
I have run frontline operations and P&Ls, built HR functions from scratch, navigated acquisitions, fixed turnover crises, and developed managers who went on to lead at the highest levels.
Trailhead Results was built on a simple premise: most transportation and HR problems are not mysteries. They are execution problems. And execution gets fixed when the right expertise meets the right team with the right support.
I work with your team to grow their skills and develop consistency over time.
I measure success based upon your team being prepared to perform with confidence and competence when the work is done.
Founder Story:
Built by an operator who became a Chief Human Resources Officer.
The founder, Nick Wakefield, spent 15 years in frontline retail and operations leadership before moving into human resources, ultimately rising to Chief People Officer at the enterprise level.
That operator foundation is what makes Trailhead Results different.
Most HR consultants come from HR.
Nick came from running operations in labor-intensive businesses. Leading multiple locations & service centers, owning a P&L, and managing dispersed field teams.
Every recommendation is filtered through a simple question:
Will this actually work for the people running the business?
Why
To be of good service to others.
Vision
Help companies align strategy, structure, and people systems to achieve better business outcomes.
Mission
To be the trusted advisor to small and mid-sized businesses with labor-intensive, operationally complex, or geographically dispersed workforces.
Values
Integrity
We say what we will do, then we do it. No spin. No fine print.
Trust
Earned through the work. Reinforced by transparency, consistency, and showing up.
Accountability
Owners of outcomes — not authors of explanations.
Inquiry
Ask first. Diagnose before we prescribe. Curiosity over assumption.
Service
The work is in service of the client's people and the client's business. Always.
Why are we different:
EXPERTISE
Trailhead Results brings earned and applied expertise to every engagement.
Most consulting firms sell theory. We sell what we have actually done. Trailhead Results is built on 34 years of combined operations and human resources experience, 15 years running frontline operations and P&Ls, and 19 years across recruiting, employee relations, HR technology, and Chief People Officer leadership at publicly traded and private companies. Our experience includes scaling enterprises from launch to $200M+ in revenue, driving culture change and results in a $700M organization, integrating four acquisitions, and modernizing the workforce systems that make growth possible. This is not expertise we read about. It is expertise we built in the field.
TRANSPORTATION FLUENCY
We know trucking from the dispatch board to the boardroom.
Most HR firms do not understand transportation and logistics. We do. Trailhead Results has spent two decades inside trucking and logistics running operations, human resources, solving driver recruiting & retention at multiple carriers, building safety and compliance systems, redesigning driver-manager routines, and leading workforce strategy.
We bring scope and scale serving having served start-up carriers to scaling $700M+ publicly traded carriers. We understand why drivers leave, why driver managers burn out, and what it takes to fix both. When other consultants need to learn the business, we already speak it.
HANDS-ON
We do not consult from a distance. We work next to your team.
The traditional consulting model is broken: drop a strategy deck, send an invoice, disappear.
Trailhead Results is the deliberate opposite.
We embed with leadership, walk the floors with operations managers, sit through difficult employee conversations, and build a long-term relationship with the company. We become an extension of your leadership team.
We believe the true measure of success for our clients is not a binder on a shelf. It is a team that operates better long after we are gone, with capability and confidence in how to deliver results.
FRACTIONAL LEVERAGE
C-suite impact at a fraction of the cost.
A full-time CHRO costs $300K+ in base salary plus benefits, equity, and onboarding risk. Many growing companies, particularly transportation carriers in the 50 to 500 truck range, need that level of thinking but cannot justify the full investment.
Trailhead Results
The trail metaphor in our name is not accidental: the company is built on the belief that great work begins by meeting people where they are and walking the path with them.
The market and business landscape will change, but if we keep moving forward, we can reach new, amazing destinations.