Menu
Request a Consultation
Executive Technical Leadership
Fractional CTO · Private Equity

Diligence before close.
A CTO after it.

Technical due diligence that tells you what you're actually buying, and fractional CTO leadership that delivers the value-creation plan afterward — from operators who have run engineering inside a healthcare investment portfolio.

Book a Leadership Session
Proven Across a Portfolio

The technical arm of a
healthcare investment portfolio.

We've served as embedded technical leadership across the Greenleaf Ventures portfolio of healthcare and Medicare operating companies — assessing inherited systems, modernizing billing and integrations, and shipping roadmaps that had stalled.

That is the same lifecycle a deal runs on: understand what the technology can and cannot do, price the work to fix it, then own the delivery that turns the thesis into a release cadence the board can plan around.

Portfolio 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

From diligence
to value creation.

The same work a fractional CTO owns, read through the deal lifecycle — a clear technical read before you close, then embedded leadership to deliver the plan afterward.

Technical Due Diligence

A clear-eyed read on a target's systems, team, and roadmap before you close — architecture risk, key-person exposure, security posture, and the real cost to get the technology where the thesis needs it.

Post-Close Value Creation

We unblock stalled roadmaps in the portfolio: tightening scope, restructuring teams, and modernizing delivery so releases ship on a cadence the board can plan around.

Portfolio CTO Coverage

Fractional executive technical leadership across one or several portfolio companies — senior judgement and accountability where a full-time CTO is not yet justified.

Integration & Carve-Out Support

Technical leadership through integrations and carve-outs — separating or combining systems, teams, and data without stalling the operating business.

AI & Automation Strategy

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

Compliance-Aware Diligence

In regulated targets, HIPAA and CMS/Medicare exposure is a diligence input — surfaced before close, with a remediation plan, rather than discovered after an audit finding.

Scoping a deal?

Start with the CTO Readiness Assessment.

Twelve questions we ask in every first engagement — a fast frame for the architecture, delivery, and key-person risk you want surfaced before you commit.

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.

Private Equity CTO FAQ

What people ask
before they start.

A clear-eyed read on the target's systems, team, and roadmap: architecture and scalability risk, security and compliance posture, key-person and single-point-of-failure exposure, delivery capability, and the realistic cost and timeline to get the technology where the investment thesis needs it. You get a prioritized findings and remediation plan, not just a deck.
Yes — that is the intended arc. The team that ran diligence already understands the systems and the risks, so it can step straight into embedded fractional CTO leadership to deliver the value-creation plan rather than handing off to someone starting from zero.
Either. We provide fractional CTO coverage for one operating company or spread senior technical leadership across several portfolio companies — sized to where the judgement is needed and scaled up around a specific deal or integration.
Because in a regulated target, HIPAA and CMS/Medicare exposure is a real diligence risk with a real remediation cost. We have run engineering inside Medicare and healthcare operating companies, so we surface that exposure before close rather than letting it show up as a post-close surprise.
We scope to the deal timeline. A focused technical read can be delivered inside a typical diligence window; a deeper architecture and delivery review takes longer but still lands against the milestones the transaction is running on.
A consultant hands you a recommendation and leaves. We own the outcome. We can run the diligence and then stay on as the CTO who delivers the plan — accountable for whether the roadmap actually ships, not just for the findings.

Still have questions?

Talk to Us

A technical read you can
underwrite a decision on.

Tell us about the target or the portfolio company. We'll show you how we've assessed and delivered inside healthcare operators before — and what it would take here.

No pitch deck. A working conversation about your roadmap.

Rather look around first? See all services.