Plan 03 · Leadership
Executive IT leadership,
scaled to your stage.
The role that behaves like a CIO: strategy, governance, and compliance leadership across IT, security, and AI tooling — sitting in your leadership meetings, answering your investors' questions, and accountable for the roadmap. Without the executive salary.
The decisions, and the accountability for them.
Where the environment goes next, sequenced against your headcount plan and runway.
Vulnerability scans, penetration tests, and the remediation governance behind them.
SOC 2, HIPAA, ISO 27001, PCI-DSS: what applies, what doesn't yet, and what the audit will ask.
When regulation requires a name, ours goes on it. Details →
The person in the room when diligence questionnaires, enterprise security reviews, and board questions arrive.
Access policy, vendor risk, AI tooling policy, and the judgment calls in between.
The questions that create this role.
An enterprise customer sends a 200-line security questionnaire. An investor's diligence list has an IT section nobody owns. Your team is adopting AI tools faster than anyone is setting policy. A framework audit is twelve months out and nobody knows the distance. These are Leadership-shaped problems — they don't need a full-time CIO, they need one accountable senior person with the context.
$6.5k – $12k flat monthly — or $2.5k – $6k as an add-on.
A full-time equivalent runs $11.7k – $17.5k fully loaded — and at early stage, rarely has a full-time job's worth of work. As an add-on to Support or Administration engagements, Leadership starts at $2.5k/mo.
Frequently asked
How is this different from a fractional CTO?
A fractional CTO owns product and engineering. This role owns the company's internal technology: IT, security, compliance, and the systems your team runs on. Growing companies often have both; they answer different questions.
Does Leadership include hands-on implementation?
Leadership sets direction and governs; implementation is the Administration role. They're priced separately so you only buy the altitude you need — and combined engagements are how most Leadership clients run.
Can you represent us in customer security reviews and audits?
Yes — that's a core function. Questionnaires, live security reviews, auditor interviews: the role shows up as your IT leadership, with the documentation to back the answers.
Do you set AI usage policy?
Yes. Tool evaluation, data-handling boundaries, and a written policy your team can actually follow — treated as governance work like any other platform decision, not a moral panic or a free-for-all.
What does the first quarter look like?
Assessment of current state, a prioritized roadmap reviewed with your leadership, and the standing cadence established: leadership syncs, quarterly reviews, and the governance calendar. From there the role runs like any executive function — against the plan.
Let's see if we're a match.
30-minute discovery call. We'll come prepared with a few questions.