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Executive Technical Leadership
Fractional CTO · Healthcare

A CTO who already knows
HIPAA, CMS, and Medicare.

Executive technical leadership for healthcare and Medicare operating companies — from operators who have run engineering inside them. Compliance is a design input from day one, not an audit-driven retrofit.

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Proven in Healthcare

Delivery accelerated inside
Medicare & healthcare operators.

We've served as embedded technical leadership across the Greenleaf Ventures portfolio of healthcare and Medicare operating companies — modernizing billing systems, standing up compliant integrations, and shipping roadmaps that had stalled under audit and regulatory pressure.

Because we come from inside these businesses, HIPAA and CMS/Medicare requirements shape the architecture from the first decision — so the technology holds up to an audit rather than being reworked after a finding.

Healthcare Companies Served

  • Access Medical
  • Arriva Medical
  • Comfort Medical
  • Aptiva Medical
  • AptivaRx

Greenleaf Ventures healthcare & Medicare operating companies, spanning medical supply, pharmacy, and billing operations.

What You Get

Everything a CTO owns,
with compliance built in.

Engagements flex from a few days a month of strategic advisory to embedded, hands-on leadership of your engineering organization — with HIPAA, CMS/Medicare, and audit requirements treated as design inputs throughout.

Technical Roadmapping

A concrete, sequenced technology plan tied to your business objectives — what to build, what to buy, and in what order.

Delivery Acceleration

We unblock stalled roadmaps: tightening scope, restructuring teams, and modernizing engineering workflows so releases ship on a cadence you can plan around.

Architecture & Platform Reviews

Deep reviews of your systems for scale, security, and future-readiness — with a prioritized remediation plan, not just a findings deck.

Engineering Leadership & Mentorship

Hands-on leadership for your existing team: hiring plans, career ladders, code review culture, and the operating rhythm of a high-performing org.

AI & Automation Strategy

Where agentic AI actually pays off in your operation — and where it doesn't. Honest build-vs-buy guidance grounded in production experience.

Compliance-Aware Engineering

Technology decisions made with HIPAA, CMS/Medicare, and audit requirements as design inputs from day one — not retrofits.

Not ready to talk?

Run the CTO Readiness Assessment first.

Twelve questions we ask in every first engagement — covering roadmap, delivery, architecture, compliance, and team. Built from work inside regulated healthcare environments.

Get the Assessment
How It Works

From first assessment
to a running engine.

01

Assess

We review your systems, team, and delivery pipeline to find what's actually slowing you down.

02

Roadmap

You get a sequenced technical plan aligned to business milestones — with clear owners and timelines.

03

Embed

We operate as your CTO: running the engineering org, driving delivery, and reporting to leadership.

04

Scale & Transition

As you grow, we help hire and onboard permanent leadership — or stay on in an advisory capacity.

Healthcare CTO FAQ

What people ask
before they start.

Yes — that is the environment we come from. We have run engineering inside Medicare and healthcare operating companies, so compliance shapes the architecture from day one rather than being retrofitted after an audit finding. That covers HIPAA, CMS/Medicare billing rules, and the audit trail an assessor expects to see.
The same job a full-time CTO does, sized to what you need: owning the technical roadmap, making build-versus-buy calls, running or rebuilding the engineering org, and reporting to leadership on delivery — with compliance and auditability treated as first-class requirements rather than afterthoughts.
Yes. We integrate with the systems you already run rather than proposing a rip-and-replace — standing up compliant integrations across billing platforms, clearinghouses, and the operational systems a Medicare or healthcare business depends on.
A consultant hands you a recommendation. We own the outcome. We sit inside your leadership team, make the decisions a CTO makes, and stay accountable for whether the roadmap actually ships — through audits, integrations, and scale.
We usually start with a short assessment of your systems, team, and delivery pipeline, which gives you a sequenced roadmap regardless of whether we continue. From there most engagements run for several quarters, tapering as we help hire and onboard permanent leadership.
That is the intended ending, not a failure. We help write the role, screen candidates, and hand over the roadmap and team — and we can stay on in an advisory capacity through the transition.

Still have questions?

Talk to Us

Technical leadership that has
shipped in regulated healthcare.

Tell us where your roadmap is stuck. We'll show you how we've unstuck it before inside Medicare and healthcare operators — and what it would take in your organization.

No pitch deck. A working conversation about your roadmap.

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