How I work

Fractional CTO, technical due diligence, and AI workflow-risk engagements.

Two speeds, one identity. Lane A (fast, weeks): fractional AI/Tech CTO retainer, advisory days, technical due diligence, and Workflow Risk Snapshots. Lane B (durable, 6–12 mo): Decision Memo and Hardening Sprint for AI workflows facing funding, customer, enterprise, audit-prep, or agent/API exposure events. A 30-minute scoping call confirms fit before any paid step.

See Proof

Investment ladder

Two speeds. One named senior expert.

Engagements are sized to the decision in front of you. Start with a scoping call, then the smallest useful step — an advisory day or a bounded snapshot. Deeper written work follows only when a real event needs it: funding diligence, an enterprise or payer security review, audit-prep, or agent and API exposure.

$2.5–5k flat

Workflow Risk Snapshot

Use as the first paid step in a warm conversation: fast, bounded, proves judgment.

Lowest-friction entry at $2.5–5k flat. Converts naturally to an advisory day or retainer relationship.

$2.5–5k/day

Day-Rate Advisory

Use for episodic senior judgment: architecture review, security check, diligence day, or board prep.

$2.5–5k/day (AI/senior specialist rate). Converts to fractional CTO retainer when ongoing leadership is warranted.

$15–40k per deal

Technical Due Diligence

Use when evaluating an AI or SaaS build for investment, acquisition, or major partnership — need a clear technical read before committing.

$15–40k per engagement depending on scope and depth. 1–3 weeks.

$8–15k/mo

Fractional AI/Tech CTO Retainer

Use when you need ongoing senior AI/tech leadership: architecture direction, security posture, and board-ready judgment on a retainer basis.

$8–15k/mo retainer (~2–4 days/month). Enter via a Workflow Risk Snapshot or advisory day; anchor with a monthly retainer.

$45k fixed

Hulbon Decision Memo

Use when a funding, enterprise, customer-review, audit-prep, or agent/API exposure event creates a budget event for written technical judgment.

Fixed-scope paid decision artifact; typically seeded inside a fractional or diligence relationship.

$125k follow-on

Hulbon Hardening Sprint

Use when blockers are known and the highest-risk boundaries need implementation before an enterprise review, audit-prep conversation, or customer handoff.

Follow-on sprint after scope is confirmed by memo, evidence, or a narrow intake. Highest-ceiling durable engagement.

Proposal-only after assessment

Portfolio / Agency Handoff Program

Use when several client builds, portfolio companies, or workflows need the same review pattern.

Proposal-only path until repeat-risk proof validates a fixed public program price.

Custom after assessment

Founder-Assessed Custom Scope

Use only when known scope crosses teams, systems, regulated constraints, or launch support.

Requires founder review and written custom scope before any investment number is confirmed.

Lane B — durable decision artifact

Hulbon Decision Memo

In 5–7 days, Hulbon delivers a full-workflow assessment — codebase, boundaries, and dependency map — with a written proceed, proceed-after-hardening, or pause decision artifact for technical, investor, customer, enterprise-review, or audit-prep conversations. Sold inside an advisory relationship, not as a cold first contact.

Use when:Funding diligence, enterprise security review, customer review, audit-prep, or acquisition review creates a defined budget event.Investment:See the fixed-scope investment ladder above.Output:
  • Proceed, proceed after hardening, or pause investment/handoff
  • Top 3 risks blocking the next funding, customer, launch, acquisition review, or handoff event
  • Fixed-scope remediation recommendation with what to fix now, defer, or exclude
  • Evidence plan for investors, enterprise buyers, customer reviewers, or agency clients
Not required:Production credentials, live customer data, or an unpaid deep audit before scope.

Low-friction entry: one workflow, one to two days

Workflow Risk Snapshot

You need a clear-eyed read on one AI or agent workflow — top risks, what is a blocker, and what to fix — without committing to a full codebase review.

First paid step inside a warm conversation; proves method and judgment fast.

Buyer

Founders, CTOs, and senior engineers who need a fast, structured read on one AI workflow before a decision, launch, or investor conversation.

Trigger

Early diligence, pre-engagement trust-builder, or first paid step inside a warm conversation.

Timeline

1–2 days.

  • One AI/agent workflow reviewed read-only
  • Top-5 risks identified and ranked (critical, high, medium)
  • Go, proceed-after-hardening, or pause call
  • Effort estimate to clear the blockers

Senior judgment by the day

Day-Rate Advisory

You need senior expert judgment for one specific decision or review — an architecture call, a security posture question, a diligence conversation — fast, without a long-term commitment.

Episodic entry that converts naturally into the fractional CTO retainer when ongoing leadership is a fit.

Buyer

Founders, CTOs, and technical leads who need senior AI/tech judgment for a specific decision, review, or hard call — without a long-term commitment.

Trigger

Episodic senior judgment: architecture review, security posture check, hard build-vs-buy call, or board-ready opinion.

Timeline

Booked by the day; typically 1–4 days per month.

  • Senior-level review, assessment, or working session on the agreed topic
  • Written notes or decision artifact from the day
  • Recommendation and next-step framing

For investors, PE/VC, and acquirers

Technical Due Diligence

A deal depends on understanding whether an AI or SaaS build is architecturally sound, secure, scalable, and run by a team capable of executing. You need a clear-eyed technical assessment, not a checkbox.

Per-deal diligence engagement: written report and debrief call for investment or acquisition decisions.

Buyer

Investors, PE/VC funds, acquirers, and founders preparing for technical diligence on an AI or SaaS build.

Trigger

Investor, PE/VC, or acquirer evaluating an AI/SaaS build; founder preparing for technical diligence before funding or M&A.

Timeline

1–3 weeks per engagement.

  • Architecture review: structure, scalability, and technical debt assessment
  • Security and access-control evaluation
  • AI-specific risk assessment: agent boundaries, data handling, model dependencies
  • Team and execution capability assessment
  • Written diligence report with clear findings and recommendations
  • Debrief call to walk through findings and answer questions

The anchor engagement — ongoing senior AI/tech leadership

Fractional AI/Tech CTO Retainer

Your AI-powered product needs senior technical leadership that combines deep AI/ML expertise with production-at-scale judgment and regulated-systems experience — but a full-time CTO is premature or unavailable.

The ongoing anchor engagement: fractional AI/Tech CTO for teams that need senior AI/tech leadership roughly 2–4 days per month.

Buyer

Founders, CEOs, and technical leads who need ongoing senior AI/tech leadership: AI architecture direction, security and compliance posture, hiring and code review, and board-ready judgment.

Trigger

Founder or CEO who needs ongoing senior AI/tech leadership without a full-time CTO; team that needs AI architecture direction, security posture, or board-ready judgment on an ongoing basis.

Timeline

Ongoing monthly retainer; typically 2–4 days/month.

  • AI and technology architecture direction and review
  • Security and compliance posture oversight
  • Hiring, code review, and technical team guidance
  • Board-ready technical judgment and communication
  • AI risk, vendor selection, and build-vs-buy decisions
  • Ongoing availability for hard calls and urgent reviews

Lane B — durable: for funding, enterprise, and audit-prep review events

Hulbon Decision Memo

You are entering a funding round, customer review, enterprise review, audit-prep conversation, or agent/API exposure moment that requires clarity on AI workflow risk, boundaries, and evidence gaps.

Durable Lane-B entry — full-workflow decision artifact, sold inside an advisory or diligence relationship.

Buyer

Enterprise AI teams, funded founders, CTOs, and portfolio operators whose AI workflow needs a written technical decision artifact before funding diligence, customer review, enterprise review, audit-prep, or agent/API exposure.

Trigger

Funding diligence, enterprise security review, acquisition review, customer review, audit-prep conversation, or agent/API exposure where written technical risk clarity is required.

Timeline

5–7 days for the memo.

  • Proceed, proceed-after-hardening, or pause recommendation
  • Workflow, codebase, and dependency map
  • Auth, tenant, payment, data, and agent/API boundary review
  • Test, CI/CD, release, and observability gap map
  • Prioritized remediation path with fix/defer/exclude decisions

Lane B — durable: implement the review-blockers, not just advise

Hulbon Hardening Sprint

The highest-risk workflow boundaries are known, and the product needs focused implementation — tenant isolation, approval gates, audit evidence — before the next enterprise review, audit-prep conversation, or customer handoff.

Implementation path when the blocker set is specific enough to fund focused hardening — build, not just advise.

Buyer

Enterprise AI teams, PE/VC portfolio operators, regulated-workflow CTOs, and founders with known workflow blockers before an enterprise review, audit-prep conversation, or customer handoff.

Trigger

A paid memo, tightly scoped evidence review, enterprise review, audit-prep question, or known urgent blocker shows implementation funding is warranted.

Timeline

10 business days for the sprint.

  • Permission, approval, and safe-write boundary implementation
  • Auth, tenant, payment, data, and agent/API scope hardening
  • Tests, CI, deployment, rollback, and observability improvements
  • Audit logs, rate limits, abuse controls, and secrets handling
  • Handoff evidence for enterprise reviewers, clients, operators, or future builders

For PE/VC portfolios, studios, and agencies with repeat AI workflow risk

Portfolio / Agency Handoff Program

Multiple AI-built products, portfolio companies, or regulated workflows need a repeatable review and handoff pattern before customer handoff, enterprise review, audit-prep, or agent/API expansion.

Proposal-only review path when one-off triage is not enough for a portfolio or agency queue.

Buyer

PE/VC portfolio operators, venture studios, accelerators, AI-MVP agencies, and enterprise teams with multiple AI workflows or products needing repeatable review discipline.

Trigger

Several client builds, portfolio companies, or agent/API workflows carry repeat workflow, codebase, handoff, or exposure risk.

Timeline

Program scope and sequence agreed in writing.

  • Portfolio or agency handoff risk map
  • Repeatable memo pattern across products or client builds
  • Workflow hardening recommendations by priority and buyer trigger
  • Operating recommendations for review, handoff, and implementation discipline
  • Escalation path for any build that needs a focused sprint

Do you need access to production data or credentials?

No. A Workflow Risk Snapshot or Decision Memo uses source code, implementation notes, test environments, anonymized logs, and guided walkthroughs. Production credentials are not required for a first pass.

How is this different from generic AI consulting?

The judgment comes from running AI and money-movement at $2B+ regulated scale and personally building a production agentic-AI platform — not a slide deck. Work is tied to concrete implementation: workflow boundaries, agent permissions, audit evidence, and real remediation.

What is the fastest way to start?

A 30-minute scoping call, then either a Workflow Risk Snapshot ($2.5–5k, 1–2 days), an advisory day, or a fractional CTO scoping conversation — whichever fits the urgency. Cold $45k memos are not the first contact; they are seeded inside an advisory relationship.

Technical resources

Practical reference for AI trust, agent boundaries, and workflow evidence.

Browse the full resource cluster, or jump directly into the guide that matches your current review, audit, diligence, or hardening pressure.

View all technical resources

AI-built codebase decision checklist

Review generated or AI-assisted products across architecture, auth, tenant boundaries, payments, tests, deployment, and agent/API exposure.

Read the decision checklist

Agent/API workflow boundaries

Design scoped agent tools, OAuth or restricted-key access, read/write separation, audit logs, rate limits, and prompt-injection-aware boundaries.

Read the agent/API launch checklist

AI-generated workflow risk

Prioritize trust-boundary drift, auth and data access gaps, payment-state errors, dependency exposure, test illusions, and agent blast radius.

Read the workflow risk taxonomy

Agent-exposed SaaS architecture

Shape AI agent access around scoped tools, delegated identity, read/write separation, approval gates, audit trails, and operational controls.

Read the architecture patterns

AI feature and MVP hardening

Turn demo-ready AI-assisted products into customer-ready systems with ownership, trust-boundary, testing, payment, deployment, and observability hardening.

Read the workflow hardening checklist

Next step

Bring the codebase, diligence question, or ongoing AI/tech leadership need.

A free 30-minute scoping call confirms fit before any paid step. Hulbon will check whether the situation warrants a Snapshot, an advisory day, a diligence engagement, or an ongoing fractional CTO relationship.