CTO Advisory for Founders Navigating 0 → PMF → Scale

I help early-stage teams make the right technical and product decisions before they become expensive, irreversible mistakes.

Clarity on what to build, how to build it, and what actually matters right now.

Craig M. Booth

The Problem

You're moving fast—but you're not sure you're moving right

Most teams don't fail because they move too slowly. They fail because they make a handful of early decisions that quietly compound into constraints.

You might be feeling it already:

  • The roadmap is full, but not clearly prioritized
  • The product vision exists, but execution feels scattered
  • You're making technical decisions without enough signal
  • Your team is busy, but progress doesn't feel linear
  • Security and compliance are looming, but unclear
  • You don't know what will break as you scale—and when

None of these are catastrophic on their own. But together, they create drag that's hard to unwind later.

Outcomes

What changes when we work together

A clear, defensible product direction

A technical foundation that won't require a rewrite in 6 months

A roadmap aligned to learning, not just output

Faster iteration with less wasted effort

Confidence in your security and compliance posture

A team that understands what matters—and why

The goal isn't more activity. It's fewer, better decisions.

Services

How I work with teams

CTO Coaching

High-leverage support for founders and early CTOs

  • Ongoing decision support
  • Product and technical tradeoff guidance
  • Founder ↔ technical alignment
  • Lightweight, fast feedback loops

Technical & Product Audit

A focused, time-boxed deep dive

  • Architecture and system review
  • Roadmap and execution analysis
  • Risk identification (technical, product, security)
  • Clear, prioritized action plan

You walk away with a concrete plan—not just observations.

Ongoing Advisory

A consistent thought partner as you build

  • Embedded strategic support
  • Quarterly recalibration of roadmap and architecture
  • Ongoing review of major decisions
  • Support through key transitions (funding, hiring, scaling)

Security & Compliance (Integrated)

Security and compliance aren't separate projects. They're part of how the system is designed from the start.

  • Practical, right-sized security posture
  • Early alignment with compliance expectations
  • Avoiding late-stage “rewrite for compliance” scenarios

Who This Is For

Good Fit

  • Early-stage companies (pre-seed → Series A/B)
  • Founders making high-stakes product and technical decisions
  • Teams moving quickly in uncertain environments
  • Situations where clarity matters more than process

Not a Fit

  • Large enterprises with rigid procurement cycles
  • Teams looking to outsource execution entirely
  • Situations where decisions are already locked and unlikely to change

Trusted by teams at

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Start With a Working Session

We'll look at your current situation, identify the highest-leverage decisions in front of you, and determine whether it makes sense to work together.

No pitch. Just clarity.

Book a 30-Minute Session