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Not sure which one fits? We built a quick diagnostic. Five questions, two minutes, an honest read on which engagement matches your situation — or whether a free call is the better starting point. Or browse all seven below.
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How the pricing works. Each engagement is a flat monthly fee × 3 months, set by the time intensity the work actually requires. Lighter engagements (Tech Hire, Engineering Baseline) cost less than the retainer; heavier ones (Discovery Sprint, Agile Transformation, AI Strategy) cost more. The $4,500/mo retainer sits in the middle as the ongoing-judgment option for after the project lands. No setup fees, no hidden hours, no scope creep without a conversation.

Engagement · Hiring & evaluation

Tech Hire

"We need our first dedicated tech person, and we don't know how to hire one well."

Best fit · Any size company hiring their first dedicated tech lead — from 5-person teams to 100+
$2,500 / month
$7,500 over 3 months
M1
Scope the role
  • Diagnostic interviews with founders and key stakeholders
  • Role definition: title, responsibilities, success metrics
  • Lancaster / mid-Atlantic market-rate analysis
  • Job description drafted
M2
Structure the search
  • Interview kit: technical, behavioral, leadership stages
  • Scoring rubric for candidate evaluation
  • Reference check protocol
  • Compensation package design
M3
Run the search
  • Joining 4–6 candidate interviews to calibrate scoring across the panel
  • Reference checks reviewed and patterns surfaced
  • Final candidate recommendation with written rationale
  • 30-60-90 onboarding plan handoff
By 90 days
You've hired (or you know you need to keep looking, with a clear written reason why), with a defensible structure and a rubric you'll re-use the next time.
After 90 days: optional retainer if you want continued support. Start with this →
Engagement · Culture & leadership

Org Culture Engagement

"Strategy keeps not happening. Retros are vent sessions. Retention is soft. The leadership team isn't aligned on the values they're modeling."

Best fit · Leadership teams who've felt the truth of Drucker's line: culture eats strategy for breakfast
$7,000 / month
$21,000 over 3 months
M1
Diagnose the lived culture
  • Leadership team interviews on values, behaviors, blockers
  • Skip-level interviews across the organization
  • Team Health Scorecard run formally with each leader
  • The gap between stated values and lived ones, named
M2
Reset the operating values
  • Facilitated leadership team sessions to articulate operating values
  • Specific leadership behaviors expected, written down
  • Unwritten rules working against strategy, surfaced
  • Decision authority and disagreement norms established
M3
Embed and coach
  • Coach the leadership team through the first 30–60 days
  • Reflection rhythm installed at the leadership level
  • Cascade rituals: how the new behaviors show up in standups, reviews, hiring
  • Measurement: what gets tracked to know it's working
By 90 days
A leadership team aligned on what the culture actually is and how to model it. New rituals running. Specific behaviors changed. The gap between strategy and what gets done starts closing because the team finally has the operating values to make it close.
Often the first engagement when nothing else is sticking — culture is upstream of operating model and execution. Start with this →
Engagement · Process excellence

Engineering Baseline

"We have an engineering team and we don't know how it's actually performing."

Best fit · Any company with an existing engineering team and no experienced outside read on it
$3,000 / month
$9,000 over 3 months
M1
Diagnostic
  • 1:1 interviews with engineering and adjacent leadership
  • Code, deploy, and ticket sample review
  • Four-lens scoring: health, compliance, AI, deploy
  • First-pass narrative on what's working
M2
Map the gaps
  • Detailed gap analysis by lens
  • Tech debt inventory with cost estimates
  • Process gaps: review, deploy, incident, planning
  • Stakeholder alignment session
M3
Roadmap
  • 90-day improvement roadmap with named owners
  • Baseline metrics for next-quarter measurement
  • Final readout to leadership
  • Optional: continuing baseline refresh on retainer
By 90 days
A measured posture, a written gap roadmap, and baseline metrics to track improvement against next quarter.
After 90 days: quarterly refresh on retainer ($4,500/mo) is the natural follow-on. Start with this →
Engagement · Compliance

Compliance Push

"A customer (or auditor, or regulator) asked for SOC2, HIPAA, or AI governance evidence and we're not ready."

Best fit · Any company facing a customer or audit-driven compliance ask in the next 6–12 months
$4,500 / month
$13,500 over 3 months
M1
Gap analysis
  • Current-state diagnostic across applicable trust criteria
  • Vendor inventory and security review status
  • Policy and evidence gap inventory
  • Pre-audit risk assessment
M2
Remediation plan
  • Prioritized remediation roadmap
  • Policy templates: AUP, IR, change mgmt, vendor mgmt
  • Evidence collection structure
  • Internal compliance owner identified and trained
M3
Pre-audit readiness
  • Mock audit dry run
  • Evidence package review
  • Auditor selection support if applicable
  • Auditor coordination handoff
By 90 days
Audit-ready, with policy in place, evidence collection running, and an internal owner who can sustain it.
Auditor fees and SaaS tooling (Vanta, Drata, etc.) billed separately by the vendor. Start with this →
Engagement · Strategy + facilitation

Discovery Sprint

"We have an idea, or a stalled product, and we don't know what to actually build."

Best fit · Founders pre-build, or any team whose product needs a hard reset
$5,500 / month
$16,500 over 3 months
M1
Frame the problem
  • Kickoff workshop with leadership and stakeholders
  • Problem statement, success definition, in/out scope
  • Customer / user discovery interview structure
  • Hypothesis canvas drafted with the team
M2
Customer discovery (facilitated)
  • 8–12 customer interviews — your team conducts, we facilitate the structure and the debrief
  • Journey mapping workshop
  • Jobs-to-be-done synthesis
  • Hypothesis validation against findings
M3
MVP definition
  • Zero-based design workshop with the team
  • MVP scope with feasibility annotations
  • Sequenced backlog with dependencies
  • 90-day build readiness handoff
By 90 days
You know what to build, what NOT to build, and your team owns the decisions. The discovery brief is theirs — not a deck you delivered.
After 90 days: build phase typically follows; FCTO retainer can run alongside it. Start with this →
Engagement · Transformation + coaching

Agile / Operating Model Transformation

"We tried agile and it became standup theater. The work isn't getting better."

Best fit · Any team running ceremonies that aren't producing outcomes — or starting their first agile rollout
$6,000 / month
$18,000 over 3 months
M1
Operating model design
  • Diagnostic of current ceremonies, planning, and delivery patterns
  • Quarterly outcomes and decision authority defined
  • Operating rhythm: weekly pulse, monthly review, quarterly planning
  • Cascade from outcomes to team commitments
M2
Coach the team running it
  • Scrum master, PO, and lead coaching: first retros and refinement
  • First story mapping and refinement sessions facilitated by us; the team takes over from there
  • Leadership pulse meetings designed and run with the leadership team in the room
  • Standups stop being status theater
M3
Hand off and measure
  • Team running their own ceremonies with coaching observation
  • Operating metrics baseline established
  • Leadership team running the rhythm independently
  • Retainer transition discussion if relevant
By 90 days
A sustainable operating model the team is running themselves, with a real leadership rhythm and the people who run it coached through it.
Evening / weekend coaching sessions available when that fits the team's reality. Start with this →
Engagement · AI strategy

AI Strategy & Pilot Scoping

"We need to do something with AI and we don't know where to start."

Best fit · Any company feeling AI pressure (customers, competitors, board) without a clear strategy
$7,000 / month
$21,000 over 3 months
M1
Roadmap
  • Workflow audit: where AI actually pays back vs. where it doesn't
  • Prioritized opportunity list ranked by ROI and feasibility
  • Vendor landscape briefing — Claude, GPT, embedded SaaS AI, custom
  • Shadow-AI inventory across the company
M2
Governance + pilot scope
  • AI acceptable-use policy drafted
  • Vendor evaluation and selection
  • One pilot scoped end-to-end: workflow, success metrics, owner, timeline
  • Data readiness assessment
M3
Pilot kickoff
  • Pilot launched with documented success criteria
  • Internal owner trained
  • Governance running: review cadence, output checks
  • Quarterly review structure established
By 90 days
A prioritized AI roadmap, a written governance policy, and one pilot live with a clear way to measure whether it worked.

Note: ongoing AI tooling costs — API tokens, vendor subscriptions, embedded SaaS AI features — are billed by the vendor and remain the client's responsibility. Engagement fee covers the experience, scoping, and coaching only.

After 90 days: ongoing AI governance and pilot oversight on retainer is the typical next step. Start with this →
When engagements chain together

The transformation arc most companies actually need.

"Culture eats strategy for breakfast."

— Peter Drucker

Most companies pick one engagement and stop. Some run several in sequence — this is the most common shape when they do. Each one builds on the last: culture upstream of operating model, operating model upstream of execution, execution upstream of building the right thing.

12 months
Guided transformation arc
$64,500
Total program investment
4 deliverables
One per 3-month phase

For context: a full-time CTO loaded at $250K–$400K/year. The full arc is roughly 15–25% of one year of that — with a defined endpoint, named deliverables at each step, and the option to stop after any phase.

Each step is its own 3-month engagement. Companies typically run them with a beat in between to absorb the change — sometimes on retainer to hold the new ground while the next engagement scopes up.

Don't see the right shape? The retainer is the open-ended option.

If your situation doesn't slot cleanly into one of these six, the $4,500/mo Fractional CTO retainer is the same experience without the named-engagement scope. ~10 hours/month, 90-day initial commitment, then month-to-month. Some clients start there because the work doesn't fit a single named project — multiple pillars need attention concurrently.

See retainer details →

Common questions about engagements

What if we want more than one engagement?
Common pattern. Discovery Sprint → Engineering Baseline → ongoing retainer is one shape we see frequently. Each engagement is priced independently; we'd talk through sequencing on the discovery call so the second one builds on the first instead of duplicating work.
Can we extend an engagement past 90 days?
Yes — either by extending the engagement at the same monthly rate (typically a month or two if the work is genuinely longer) or by converting to the $4,500/mo retainer for ongoing experienced support. Most engagements end at 90 days as scoped; the retainer transition is the more common pattern when there's a continuing need.
How does this compare to just signing the retainer for 3 months?
Three months of retainer at $4,500 is $13,500 of experienced support with flexible scope. An engagement gives you a named outcome and a written deliverable for that period. If you want a clear deliverable at day 90, pick the engagement. If you want flexibility and an experienced outside voice on whatever surfaces, pick the retainer. The lighter engagements (Tech Hire, Engineering Baseline) cost less than retainer because they're less time. The heavier ones (Discovery Sprint, Agile Transformation, AI Strategy) cost more because they require more hours per month.
What about software, SaaS, or AI vendor costs during the engagement?
Engagement fees cover the experience, scoping, facilitation, and coaching only. Software you buy — SaaS tools, AI vendor subscriptions, API tokens, audit tooling, recruiting platforms — is billed by the vendor directly to you and is your decision to make. We'll evaluate options with you and advise on selection; we don't take referral fees from any vendor.
Can we cancel mid-engagement?
If the engagement isn't working for either side, we have the conversation early rather than letting it drift. Practically: 30 days written notice ends the engagement; you pay for the month in progress. We'd rather end cleanly than complete a project that isn't producing value.
Are evening or weekend sessions available?
Yes — especially for Agile / Operating Model Transformation, where the team often can only carve out time outside business hours. The engagement adapts to your team's reality, not the other way around. Same fee.

Talk through which one fits.

30 minutes, free, no pitch. We'll walk through what's actually slowing you down and tell you honestly which engagement (or retainer) is the right next move — or whether the answer is something else entirely.

Book a Discovery Call →