Fractional CTO Engagements

Senior tech leadership.
Structured for scale.

I work with a small number of retainer clients as their embedded Fractional CTO, supplemented by selective ad hoc engagements. Most relationships start with a fixed-scope Tech Audit.

Retainer Engagement

What ongoing CTO support looks like

  • Weekly strategic alignment sessions with the CEO/founder
  • Technology roadmap development and quarterly planning
  • Oversight of internal tech staff and outsourced IT/dev partners: accountability, performance, fit
  • Systems and architecture review: ERP, CRM, operational software, integrations, data
  • Board and investor-facing technology reporting
  • Vendor evaluation and contract negotiation support (software, MSPs, implementation partners)
  • On-call availability for urgent decisions (SLA defined in contract)

Two tiers: Strategic (4 to 6 hrs/wk) for companies with an IT manager or outsourced provider in place who need senior technology leadership above them, and Embedded (8 to 10 hrs/wk) for companies where I'm effectively acting as their full CTO.

Who I Work With

Companies that fit

  • Founder- or family-led: the person I work with is the person running the business
  • $5M to $30M in revenue, profitable or near-profitable
  • Non-tech industries: professional services, construction, manufacturing, distribution, healthcare, specialty retail, and similar
  • Strong at sales and delivery, underperforming on systems and technology leverage
  • At an inflection point: scale, AI adoption, capital event, or mounting complexity
  • Willing to think architecturally, not just tactically

Most companies I work with are exceptional at what they do and have grown because of founder-driven execution. The question is whether the architecture, the systems, the technology, the organizational structure, can support the next phase.

That's the work. A sustained strategic relationship with someone who has built, scaled, and navigated the transitions you're facing.

Tech Audit Package

The natural starting point

A fixed-fee, fixed-scope assessment over 2 to 3 weeks. Most engagements start here.

  • Full assessment of current systems, infrastructure, and data: how the business actually runs on technology today
  • Evaluation of internal tech staff and outsourced IT/dev partners: accountability, responsiveness, fit
  • Security posture and risk overview
  • Vendor and tooling review: what you're paying for, what's working, what's redundant
  • AI and automation opportunity scan: where technology could remove cost or unlock growth
  • Written Tech Health Report with prioritized recommendations and a 90-day roadmap
  • 60-minute executive readout with leadership
Ad Hoc Engagements

Scoped, time-boxed work

For companies that don't need (or aren't ready for) a full retainer. Fixed scope, fixed estimate, no ongoing commitment.

  • Technology due diligence for acquisitions or investment rounds
  • Technology audit and assessment of current systems, team/partners, and processes
  • Systems migration planning: ERP replacement, platform consolidation, cloud transitions
  • Crisis response: outages, security breaches, failed implementations, key-person departures
  • Vendor selection and RFP processes (software, MSPs, implementation firms)
  • AI and automation opportunity assessments

Process

How an engagement begins

  1. Discovery call. 30 minutes, no pitch. We talk about where your company is and whether there's alignment.
  2. Tech Audit. A fixed-scope assessment over 2 to 3 weeks, delivering a written Tech Health Report and executive readout.
  3. Retainer proposal. Based on what the audit surfaces, I recommend a retainer tier with a clear scope tied to the roadmap we just built.
  4. Onboarding. First 30 days: stakeholder interviews, systems and vendor walkthrough, current-state documentation, and operating rhythm.
  5. Ongoing delivery. Weekly 1:1 with the CEO, monthly status reports, quarterly roadmap reviews. 60-day notice clause on either side.
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Guardrails

What this is not

I cap retainer engagements at a deliberately small number. Not because I can't take on more, but because the work requires genuine attention, and I'm not willing to dilute it.

I'm not a hands-on implementer. I don't run your helpdesk, administer your systems day-to-day, or implement the changes we design together. I bring senior leadership, architecture, and judgement. Your internal staff, MSP, or implementation partners carry the execution.

No pricing on this page. No urgency. If it's the right fit, we'll both know after a conversation.

Relationships are limited.
Conversations are open.

If you're a founder navigating complexity, scale, or optionality, reach out.

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