Digital & AI transformation
Fractional Chief Transformation Officer.
Grayhill Strategic gives your digital and AI transformation a single, steady hand - clear strategic direction from the first assessment through to adoption, with the oversight that keeps complex, high-stakes change on course. One trusted advisor, vendor-neutral throughout, thinking several moves ahead on your behalf.
Digital transformation rarely fails due to lack of a plan. It fails in the long stretch between the plan and adoption - which is where I stay with you.
How an engagement works
One strategy, followed through four phases.
Strategy
Discovery, a data-readiness scan, and an opportunity roadmap that narrows to one clear direction - so you invest in what is genuinely worth doing, and know why.
Selection & procurement support
Turning the strategy into clear requirements and helping you evaluate and choose the right vendors with confidence. Vendor-neutral throughout, so the advice serves only you.
Implementation oversight
A steady eye on the implementation partner's execution against strategy, with milestone checkpoints that catch risk and drift early - protecting the budget, the timeline, and the outcome you set out to achieve.
Adoption & change management
Guiding leadership and teams through the change and defining how success is measured, so the investment is genuinely used and the results last well beyond go-live.
A right-sized option
Have just one thing in mind?
Not every business needs a full transformation. If you already know the one thing you want - an AI tool or an automation - the Focused AI & Software Sprint scopes it, chooses how to build it, and sees it through cleanly in under three months, at a fixed fee. The same independent judgment, right-sized to a single goal.
About
Strategy that works.
My name is Carrie Hayes, Fractional Chief Transformation Officer and Principal at Grayhill Strategic. Grayhill Strategic exists because the most useful strategic advice comes from people who have actually built the thing, sold the thing, and delivered it under pressure - not from a framework rented for the engagement.
I have personally led over 30 digital transformation projects from mid-market through to public sector and enterprise scale. My strategic guidance has helped organizations select the right ERP, CRM, database software, lead gen engine, accounting program, CPQ, and many other solutions.
My work in has been informed by a master of Digital Media and over 25 years in business, most of it in direct-to-CEO and intrapreneurial roles. That experience - what it takes to choose the right system, survive contact with procurement, and actually get a transformation adopted - is what I bring to clients now.
The thing I most want clients to feel is that durable results come from patient, systematic work, not hope. I think in systems, read people closely, and spot project risks quickly. I am most useful when I can focus those abilities on a client's hardest problem.
What I bring
- End-to-end transformation ownership
- Vendor-neutral software selection
- Far-reaching sight & risk reduction
- Systems & methodology design
- Strategic reading of people & dynamics
Durable results come from patient, systematic work - not hope.
Services
Data Readiness, Software Selection & AI Implementation.
A single, senior advisor giving your digital and AI transformation clear direction from end to end - the steady strategic hand that decides what to do, keeps the work on course, and sees it through to adoption. Each engagement follows one strategy from start to finish, because the work is sequential: every phase sets up the next.
Automation Strategy
It starts with discovery and a data-readiness scan, then an opportunity roadmap, narrowing to a single strategy deliverable. That deliverable takes one of three forms, each scoped around one problem - assessed broadly, narrowed to one implementation.
Selection & procurement support
Turning the chosen strategy into clear requirements, then evaluating the options and guiding you to a confident selection. Always vendor-neutral, so the recommendation reflects what is genuinely right for you - independent advice that protects the decision and keeps procurement clean.
Implementation oversight
A steady, experienced eye on the build, measured against the strategy at every milestone - catching risk and drift early, while there is still time and budget to course-correct. The oversight that keeps a complex, high-stakes project moving toward the outcome you set.
Adoption & change management
Guiding leadership and teams through the change, defining how success is measured, and shaping the training and support that turn a new system into everyday practice - so the investment delivers lasting value, not just a launch.
Standing advisory
Once the arc is complete, a lighter ongoing seat for the decisions that follow - next-cycle planning, roadmap refresh, and vetting future proposals. If a second priority emerges, it becomes a new arc that begins the same way.
The three strategy types
Phase one delivers one of three strategies;
Scoped AI pilot
A clear-eyed look across three candidate use cases, narrowing to the one with the strongest case so effort goes where it pays off. You come away with a focused strategy and a scoped pilot plan, carried into a carefully overseen build.
Software assessment
Evaluating the leading options to solve one problem class - the CRM, say, or the ERP - and narrowing to a single, well-reasoned recommendation you can act on with confidence. Where the assessment surfaces a deeper issue, you hear about it early, before it becomes a costly surprise.
Data strategy
Governance documentation plus a cleanup plan and oversight for one bounded data domain - for example, customer data ahead of a CRM migration, not the whole organization at once. Often the foundational first arc that enables a later software or AI initiative.
How I work
The same standard in every engagement.
Every engagement starts with one clearly defined problem, so effort and budget stay focused on what matters most. The advice is always independent and centred on your interests. And the thinking is captured in writing throughout - clear direction, decisions, and risk flags on the record - so you always know where things stand and why, and have a sound basis for the choices ahead.
Always true
- One clearly defined problem, in focus
- Clear direction at every stage
- Independent, in your interest
- Risk and drift caught early
- Decisions documented in writing
A right-sized option
Focused AI & Software Sprint
For a small business that already has one specific thing in mind - an AI tool or an automation - and wants it scoped, chosen, and delivered cleanly from start to finish. The same advisory judgment as the full practice, focused on a single goal and delivered at a fixed fee in under three months.
Diagnostic & scope
A fast, honest read on whether the one thing is the right thing - confirming your data and process can actually support it before any money goes into building. You leave with clear requirements, success metrics, and a short neutral shortlist of how to build it.
Build
The vendor does the building while I stay close as oversight - measuring against the scope, catching drift early, and keeping everything pointed at the goal you set.
Launch & adoption
Making sure it lands: confirming it works against the success metrics, advising on rollout, and supporting the change so your team genuinely uses it.
Stages can be taken together as one fixed package, or the diagnostic alone - a low-commitment way to get the scoping right before deciding on the build. And if that diagnostic reveals the one thing is really several, or the groundwork needs more than a sprint, you'll hear it honestly - the natural bridge into the full Fractional Chief Transformation Officer engagement above.
Engagements typically begin with a scoping conversation
Not sure where your transformation should start? That's the first conversation.
Get in touchCase Studies
Coming soon.
Client stories are on the way. In the meantime, I'm glad to talk through relevant experience directly.
Contact
Let's find out if there's a fit.
The best first step is a short conversation about what you're working on. No pitch - just whether I'm the right person for it.
Find a time directly
Grab a 30-minute scoping call at whatever time works for you.
Schedule a call →Send a note
Tell me a little about what you're working on, and I'll reply within a business day.
info@carriehayes.com →