Strategic experience. Systems thinking. A navigator’s instinct.
Cheryl Detrick is the Founder and Strategic Navigator of Detrick Strategy and the creator of The Detrick Compass™.
For more than four decades, she has helped organizations, leaders, and communities make sense of complexity, see the larger system, and move toward a clear destination. Her career has crossed construction, real estate, business brokerage, chambers of commerce, community development, nonprofit leadership, public policy, and political work. The settings have changed. The work beneath them has remained remarkably consistent: understand the terrain, clarify what matters, assemble the right people and resources, and build a practical path forward.
The landscape changes. True North doesn’t.
A career built at the intersections
Cheryl’s perspective was shaped long before she entered the nonprofit sector. Her early work in construction, real estate, and business brokerage taught her to understand how enterprises actually operate—how decisions affect people, how resources move, how plans meet physical and financial reality, and why execution matters as much as vision.
She later brought that practical foundation into chambers of commerce, community organizations, policy environments, and executive leadership. Most recently, as CEO of a complex regional nonprofit enterprise, she led an organization serving ten counties through more than fifty programs, with approximately 150 employees and a budget that grew from $9 million to $25 million. Her work included organizational transformation, integrated service design, housing development, public and private capital, cross-sector partnerships, and the alignment of programs, people, systems, and funding around measurable community outcomes.
That chapter is important evidence of her work. It is not the boundary of it.
How Cheryl works
Cheryl does not arrive with a prepackaged answer and impose it on an organization. She begins by listening, studying the landscape, and helping leaders see what is already present: the purpose, strengths, tensions, patterns, constraints, and possibilities that can be difficult to see from inside the work.
Depending on what the moment requires, she may serve as:
- Architect — designing the structure, strategy, systems, and path that can support the destination
- Navigator — helping leaders read changing conditions, make sound decisions, and remain oriented toward True North
- Orchestrator — bringing the right people, perspectives, and expertise together so the work can move as a coordinated whole
- Steward — protecting the purpose, integrity, and long-term capacity of the enterprise while meaningful change is underway
She believes ownership and expertise are not the same thing. The organization belongs to its leaders, board, employees, and community—not to the advisor. Her responsibility is to bring disciplined thinking, honest counsel, practical imagination, and the right expertise to the table without pretending to possess every answer.
Preparation is an act of respect
Cheryl’s political background continues to shape how she approaches strategy and leadership. Good campaign fieldwork prepares a candidate not merely with talking points, but with a deep understanding of the person, the history, the environment, the difficult questions, and the central purpose of the campaign.
She brings that same rigor to organizations and leaders. She believes people deserve a real answer to the question in front of them—not an evasive pivot. The work is to answer honestly, then connect the answer to the larger direction and the central message. Preparation is not performance. It is how leaders avoid being caught flat-footed and how organizations build the confidence to move with clarity.
The work now
Detrick Strategy grew from Cheryl’s recognition that she was no longer searching only for a next role. She was building a next chapter around the work she has been doing throughout her career.
Through executive advisory, fractional strategy and transformation leadership, focused strategic intensives, and leadership and stakeholder alignment, she helps organizations:
- Discover direction when the path forward is unclear
- Design practical strategies grounded in organizational reality
- Align leadership, people, systems, operations, and resources
- Navigate growth, transition, and meaningful transformation
- Turn strategy into coordinated movement and measurable impact
The Detrick Compass™ gives that work a disciplined framework
Orient → Envision → Design → Align → Navigate → Measure
What Cheryl believes
Organizations usually hold more wisdom, courage, and possibility than they can see when the fog descends. A trusted guide does not seize the wheel. She helps leaders recover their bearings, understand the terrain, and move forward with greater clarity, conviction, and purpose.
Cheryl’s work is grounded in a simple promise:
When the fog descends, we help leaders find the path to their True North again—reminding them they already have the courage to lead with clarity, conviction, and purpose.
Let’s start a conversation
If your organization is navigating complexity, transition, or a strategy that is not yet moving in practice, let’s talk about what is happening and what would help.
