The enterprise deal isn't stuck. It's waiting for proof.
Security questionnaires, SOC 2, ISO 27001, HIPAA. Somebody has to build the infrastructure behind the answers. I'm a fractional CIO who has done exactly that inside 4Catalyzer, Redesign Health, Qualio, and Bilt, and I do it for one company at a time: yours.
A fractional CIO is an experienced Chief Information Officer who works part-time so a startup gets senior technology and security leadership without a full-time executive salary. For health-tech, fintech, and SaaS companies, that means one person who owns the roadmap and builds the infrastructure behind SOC 2, ISO 27001, and HIPAA, so enterprise deals stop stalling in security review.
Three moments where IT and security suddenly become the whole ballgame.
The deal blockerEnterprise buyers won't sign without evidence: SSO, managed devices, a certification or a credible path to one. I build the infrastructure behind the answers, then help you answer.
The compliance clockFrom zero to audit-ready: the tooling, the ISMS policies, the evidence, and the auditor relationship. I've run this end to end, including first audits with zero major findings.
The scaling debtEvery startup accrues it. I replace it with identity, device management, and offboarding automation that scales from 15 people to 500, before an incident or an auditor finds it first.
Three ways to work together. Every one starts small.
No six-month proposals, no discovery theater. Each engagement is scoped around a concrete outcome, and most clients start with the Sprint.
Security & Compliance Sprint
A fixed-scope engagement that takes you from where you are to audit-ready on the framework you're targeting.
- Gap assessment against SOC 2, ISO 27001, or HIPAA
- Identity, MDM, and EDR stack built and hardened
- Compliance platform wired up, evidence flowing
- ISMS policies, access reviews, IR & DR plans
- Auditor selection and audit support
Fractional CIO
Part-time, ongoing ownership of your technology and security function, strategy through execution.
- Roadmap, budget, and vendor ownership
- Security reviews answered as they arrive
- Quarterly access reviews and vendor risk
- Onboarding/offboarding that runs itself
- Board- and buyer-ready reporting
Diligence & Scale Events
Focused engagements when the stakes spike and the technical answers have to be right.
- Technical diligence prep for fundraising or M&A
- IPO/SPAC readiness, done through multiple events
- Audit rescue when findings are piling up
- Office build-outs and infrastructure moves
You have four other options. Here's the honest comparison.
Option 01Hire a full-time CIO or Head of IT
The right call eventually, and I'll tell you when you're there. Until then it's a $250k+ salary line for a function that needs senior judgment weekly, not daily. Several clients have had me build the function, then hire and hand off to their first full-time leader.
Option 02Sign with a generalist MSP
MSPs are built for tickets: reset the password, fix the printer, close the queue. They don't sit in your board meeting, own your audit, or answer an enterprise prospect's security review. You'd still need someone senior directing them, which is the role I fill, and I bring the hands too.
Option 03Rely on your compliance platform alone
Vanta, Drata, and Secureframe are excellent, and I implement them constantly. But they're monitoring layers: they tell you which controls are failing. Someone still has to build the Okta, Jamf, and CrowdStrike infrastructure underneath so the checks turn green, and write the policies auditors actually read.
Option 04Bring in a big consultancy
You'll get a polished readiness assessment and a roadmap, priced at multiples of a full engagement with me, and the implementation will still be your problem. I deliver the assessment in week one, then stay to do the work.
Fifteen years of owning the outcome, not just the ticket.
The first conversation is a working session, not a sales call.
Tell me what's in front of you: the framework you're targeting, the questionnaire on your desk, the deal that's stalling. I'll tell you exactly what it takes to get through it, whether or not that involves me.
You'll leave with a clear picture of your gaps and priorities either way. If we're a fit, I'll follow up with a scoped proposal within days, not weeks.
Book a working session- Your situation. The deal, the deadline, the framework, the board pressure. Fifteen minutes.
- Rapid gap read. We walk your stack: identity, devices, cloud, vendors, against the target framework.
- The path. What audit-ready takes from where you stand: sequence, effort, and honest timeline.
- Fit, or not. If I'm not the right shape for it, I'll say so and point you somewhere better.
I've been the first and only IT hire. I know what the job actually needs.
For fifteen years I've built technology and security functions from scratch, inside venture studios like 4Catalyzer and Redesign Health, genomics companies like Color, analytics platforms like Looker, and fintech scale-ups like Bilt. I've carried companies through SPACs, IPOs, first audits, and 300% growth years, usually as the most senior technical operator in the room.
Before any of that I taught IT at the college level, which turns out to be the most useful credential for this work: I can make an ISMS policy, a zero-trust rollout, or an auditor's finding make sense to a founder who has nine other fires burning. You get the judgment of a CIO and the hands of an engineer, at a fraction of either salary line.
The questions founders actually ask.
What is a fractional CIO?
A fractional CIO is an experienced Chief Information Officer who works part-time, on a retainer or project basis, giving a startup senior technology and security leadership without the cost of a full-time executive. For regulated startups, a fractional CIO typically owns the technology roadmap, builds the identity, device, and security infrastructure, and leads SOC 2, ISO 27001, or HIPAA readiness. Read the full explainer →
How much of your time do we actually get?
It depends on the engagement. A compliance sprint is front-loaded and intensive; a fractional CIO retainer typically means a consistent weekly commitment, with more during audits, incidents, and scale events. We set the shape in the scoping conversation, and it flexes when reality demands it.
We already have an IT person. Do you replace them?
Usually the opposite. If you have a capable admin or support engineer, I give them direction, architecture, and air cover, the senior layer they've been missing. Several engagements have ended with me hiring my own full-time replacement, which I consider a success.
We already bought Vanta. Isn't that enough?
Vanta (or Drata, or Secureframe) is the monitoring layer, and I'll happily work with whichever you chose. But the platform reports on infrastructure; it doesn't build it. The SSO, device management, EDR, and policies underneath are what make the checks turn green, and that's the work I do.
SOC 2 or ISO 27001, which one do we need?
Short version: if your buyers are mostly US enterprises, SOC 2 Type II is usually the ask; if you sell into Europe or into quality-driven industries, ISO 27001 often carries more weight, and health-tech frequently ends up needing HIPAA alignment regardless. The real answer depends on who's asking you for proof. See the full comparison →
What does it cost?
Less than a full-time hire, more than a helpdesk contract, and always scoped to a concrete outcome before we start. I'll give you a specific number after the working session, when I know the size of the gap, and you'll never get an open-ended invoice.
Have a deal in security review, or an audit on the calendar?
Bring me the questionnaire, the framework, or the mess. One working session and you'll know the path, whether or not it includes me.
Book a working session