Fractional CTO

Michael O'Boyle
oboyle.co · michael@oboyle.co
Architecture decisions, technical strategy, and engineering leadership for startups that need a CTO's judgment without a full-time hire. Fixed monthly retainer + equity. Pre-seed through Series A.
Equity-First $3,000 – $6,000 /mo + 1.0–2.0% equity
8–15 hours/week · Best for: pre-seed, cash-constrained, high-conviction bets

For ventures where cash is tight but the opportunity is strong. Lower retainer compensated by higher equity. I'm betting on the outcome alongside you.

IncludedDetails
Architecture ownershipTechnology decisions, stack selection, infrastructure design. I own the technical direction.
Sprint planningPrioritize the backlog, define sprint goals, translate product vision into engineering tasks.
Dev team interfaceDirect communication with your engineering team or agency. Review PRs, unblock decisions, maintain quality standards.
Weekly sync30-minute founder alignment call. Async updates between syncs.
Fundraising supportTechnical narrative for investor decks. Architecture documentation that demonstrates execution readiness.
Advisory $5,000 – $8,000 /mo + 0.25–0.5% equity
4–8 hours/week · Best for: funded startups needing architecture guidance, not daily execution

Strategic technology oversight. You have a team that can execute — you need someone to make sure they're building the right thing the right way.

IncludedDetails
Architecture reviewEvaluate current system, identify risks, recommend improvements. Written assessment with prioritized action items.
Technology strategyBuild vs. buy decisions, vendor evaluation, technical debt prioritization. Opinionated guidance, not generic frameworks.
Bi-weekly sync60-minute deep dive every two weeks. Async availability for urgent questions between sessions.
Hiring supportTechnical interview design, candidate evaluation, team structure recommendations.
Board/investor readinessTechnical sections of board decks. Due diligence preparation. Architecture documentation.
Embedded $15,000 – $25,000 /mo + 0.1–0.5% equity
20–30 hours/week · Best for: growth-stage needing near full-time CTO capacity

Near full-time engagement for companies in critical phases — pre-launch push, fundraising, M&A technical due diligence, or scaling past the first engineering team.

IncludedDetails
Everything in StandardArchitecture, hands-on leadership, engineering process, vendor management.
Executive team participationAttend leadership meetings, contribute to company strategy, represent technology in board discussions.
Team buildingRecruit, interview, and onboard engineering hires. Define roles, levels, and compensation benchmarks.
On-call availabilityAvailable for urgent technical decisions and incident response. Priority response within 2 hours during business hours.
Transition planningWhen ready for a full-time CTO: define the role, lead the search, onboard the successor, ensure clean handoff.

Side-by-Side

CapabilityEquity-FirstAdvisoryStandardEmbedded
Architecture decisions
Sprint planning
Dev team interface
Fundraising / investor docs
Technology strategy
Hiring support
Code reviews / hands-on
Engineering process (CI/CD, testing)
Performance + security review
Executive team participation
Team building + recruiting
On-call availability
Successor transition
Monthly retainer$3K–$6K$5K–$8K$8K–$15K$15K–$25K
Equity1.0–2.0%0.25–0.5%0.5–1.0%0.1–0.5%
Hours/week8–154–810–2020–30

Equity ranges based on Carta advisor data (2024), FAST agreement benchmarks, and TopStartups.io CTO compensation database. Retainer ranges reflect 2025–2026 market rates for independent fractional CTOs.

What Drives the Price

FactorLower endUpper end
Company stagePre-seed, bootstrappedSeries A, funded
Team sizeSolo founder + outsourced dev5+ engineers needing leadership
Technical complexityStandard web/mobile stackAI/ML, real-time systems, compliance-heavy
Hours neededAdvisory cadence (weekly call + async)Daily standups, sprint planning, code reviews
Cash vs. equity preferenceHigher equity, lower cashHigher cash, lower equity
The cash-equity tradeoff: Less cash = more equity. If you're paying $3K/month instead of $15K, the equity compensates for the discount. This is standard in the fractional CTO market — the specific ratio is negotiated per engagement based on company valuation and funding stage.

Communication

ChannelCostNotes
EmailIncludedUnlimited. Primary channel for non-urgent items.
Slack / TeamsIncludedAsync daily. Response within same business day.
Scheduled meetingsIncludedWeekly or bi-weekly sync included in each tier. Additional meetings as needed.
Loom / async videoIncludedArchitecture walkthroughs, decision explanations, code review summaries.

How It Works

StepWhatDetails
1DiscoveryOne call to understand your product, team, stage, and technical challenges. Free, no obligation.
2AssessmentI review your codebase, architecture, and team structure. You review my background and references. Mutual fit check.
3TermsTier selection, retainer amount, equity percentage, vesting schedule. Written agreement before the first week.
4OnboardWeek 1: access to repos, Slack, project management. Architecture assessment delivered by end of week 2.
5OngoingMonthly retainer, weekly/bi-weekly syncs, async availability. Month-to-month after initial 3-month commitment.

What This Is Not