Wayne Easterwood
Your technology is a black box. Your spend is out of control.
And nobody owns it.
Wayne Easterwood brings senior technology leadership to founder-led and PE-backed B2B services companies, aligning your technology spend with your business goals and building a clear, secure roadmap for growth.
SOUND FAMILIAR?
You're writing a big check to a technology service provider every month. Each department is buying its own software. You've had a few cybersecurity scares that made you uncomfortable. And when you ask your team how it's all holding together, the answer isn't reassuring.
You're not sure what you're getting for what you're spending. And nobody in the building owns the answer.
- Technology is supposed to support your business goals, but it creates friction instead
- There's no identified owner of the technology strategy. Tactical tasks get handled, but no one is steering
- Cybersecurity feels like a gap you haven't filled yet, and that keeps you up at night
- Every department is buying its own software, leading to isolated data, no visibility, and runaway spend
- IT projects run late, go over budget, or quietly stall
- Regulation adds complexity that your team isn't equipped to manage
- You've handed the problem to a managed service provider and still feel stalled
"I just need someone who can get more out of what we're spending and get our technology strategy out of the black box."
What a fractional CIO actually does for you
A managed service provider keeps the lights on. A consultant writes a report. A fractional CIO owns the strategy, is embedded in your leadership team, is accountable to your business goals, and is responsible for making technology a competitive advantage rather than a recurring headache.
Wayne Easterwood brings nearly 30 years of technology leadership across healthcare technology, enterprise business systems, and administrative services. He's led technology through acquisitions, growth stages, and complex regulatory environments. He knows what good looks like and how to get you there.
Strategic Alignment & Leadership Clarity
Technology that directly supports business goals, backed by a clear roadmap your leadership team can understand, trust, and plan around.
Operational Efficiency & Financial Control
Streamlined systems that eliminate IT sprawl, improve coordination, ensure projects are delivered on time and on budget, and give you full visibility into costs.
Risk Management & Execution Ownership
A proactive cybersecurity and regulatory strategy paired with embedded leadership that doesn’t just recommend solutions, but owns and drives execution.
This is built for a specific kind of company
Wayne works with B2B services companies at a specific inflection point:
- $5M–$50M in revenue, founder-led or PE-backed
- Business services, healthcare services, manufacturing, or industrial
- Technology is a growing liability, spend is up, clarity is down
- No internal technology leader with both strategic and operational authority
- Leadership has tried managed service providers and still feels exposed
- Not yet ready or able to justify a full-time CIO at $250K+
If that's you, you don't need another vendor. You need a technology leader who owns the outcome.
What You Can Expect
After 30 Days
We identify the root causes of your technology challenges, risk, inefficiencies, and missed opportunities, then deliver a clear action plan and initial roadmap aligned to your business goals.
After 60 Days
We refine priorities, build a structured technology roadmap, and ensure alignment between your systems, gaps, and growth objectives, creating clarity your leadership team can act on.
90 - 180 Days
With embedded leadership, we drive execution in real time, reducing risk, improving efficiency, completing projects, and transforming technology into a transparent, strategic asset.
Why not just keep your managed service provider?
Managed service providers keep the lights on. That's what they're paid to do.
What they don't do is sit in your leadership meetings, align your technology spend to your growth goals, hold your vendors accountable, or build a cybersecurity posture that keeps pace with your business. They react. A fractional CIO leads.
Wayne brings something no provider can - embedded ownership. He's not managing a ticket queue. He's accountable to your outcomes.
need quote
need quote
Choose the level of leadership your business needs right now
Whether you need clarity before you commit or ongoing senior technology leadership embedded in your team, there's an engagement built for your stage.
Technology Audit & Strategy Sprint
30-day engagementThis sprint identifies the root causes of your technology tension, the friction, the risk, the wasted spend, and the missed opportunities. You'll finish with a clear picture and an actionable plan, not a stack of slides you'll never open again.
What you get
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Root cause analysis of your technology friction and pain points
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Identification of your top technology opportunities for growth and efficiency
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A cybersecurity and regulatory risk assessment
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Alignment of your technology gaps with your current business goals
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A prioritized action plan tied to real outcomes
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A drafted technology roadmap framework
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A plain-language summary of gaps, needs, and next steps
Fractional CIO
1 day per weekFor companies ready to move from technology chaos to a system. One dedicated day per week of senior technology leadership embedded in your business, driving your action plan forward, reducing risk, and executing against your technology roadmap. You finally have an identified owner of the technology strategy.
What you get
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An identified owner of technology strategy inside your leadership team
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Consistent progress against your action plan and technology roadmap
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Cybersecurity and regulatory risk reduction, steady and measurable
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Management of your technology vendors and managed service providers
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Reduction of technology tension and day-to-day IT friction
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Monthly leadership update: what moved, what's next, what it means for the business
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Alignment between technology decisions and your business goals
Fractional CIO
2 days per weekFor companies that need to move faster, where multiple teams must work together, where projects are stalled, or where a PE growth mandate requires full operational integration of technology leadership. Two days per week means Wayne is embedded as a true operational leader, not a part-time advisor.
What you get
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Full operational integration. Wayne owns technology strategy and day-to-day IT leadership
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Embedded presence across senior leadership team meetings and relevant operational decisions
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All technology tension, risk, and sprawl addressed, not just managed
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IT projects completed on time and on budget, with full leadership visibility
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IT spend consolidated, coordinated, and aligned with business goals
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Proactive cybersecurity posture improvement with a clear maturity roadmap
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Bi-weekly leadership updates tied to business outcomes
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Full vendor accountability. Your managed service providers work for your goals, not theirs
Ready to get your technology working for your business?
Start with a 30-minute discovery call. No pitch, no pressure, just a clear picture of where your technology stands and what it would take to align it with where you're going.