Fractional CTO + Hands-On EngineeringStrategy Meets Execution

Strategic technology leadership combined with senior engineering execution. Get the architecture, roadmap, and team leadership of a CTO - plus the hands-on delivery of battle-tested senior engineers.

4 Pillars of Fractional CTO Leadership

Strategic technology guidance combined with hands-on engineering execution—not just advice

Technical Strategy & Roadmap

Multi-year technical roadmap aligned with business goals. Make confident build vs. buy decisions.

What You Get:

  • Technology roadmap creation (3-12 month plans)
  • Architecture decisions & technical standards
  • Build vs. buy analysis & vendor evaluation
  • Team scaling strategy & hiring roadmaps
  • Technology stack evaluation & modernization planning

Team Leadership & Mentorship

Elevate your engineering team through code reviews, standards, and performance frameworks.

What You Get:

  • Engineering team leadership & guidance
  • Code review & quality assurance
  • Engineering hiring support & interviewing
  • Performance frameworks & career development
  • Engineering best practices & documentation standards

Hands-On Engineering Execution

We don't just advise—we roll up our sleeves and ship production code alongside your team.

What You Get:

  • Sprint participation & delivery accountability
  • POC & prototype development
  • Infrastructure automation & DevOps
  • Technical debt reduction & refactoring
  • Critical bug fixes & production firefighting

Business-Aligned Technical Decisions

Technology decisions grounded in ROI, timelines, and business outcomes—not technical vanity.

What You Get:

  • ROI analysis for technical investments
  • Stakeholder communication & alignment
  • Risk assessment & mitigation planning
  • Cost optimization & resource allocation
  • Executive reporting & technical translation

How Fractional CTO Engagements Work

From discovery to ongoing strategic partnership—here's our proven process

1

Discovery & Technical Audit

Week 1-2

Comprehensive assessment of your current technical landscape, team capabilities, and business goals. Identify gaps, risks, and opportunities.

Deliverables:

  • Current state technical assessment
  • Team capability analysis
  • Technology stack evaluation
  • Security & infrastructure audit
  • Priority recommendations report
2

Strategic Roadmap & Execution Plan

Week 3-4

Develop a clear, actionable technology roadmap aligned with business objectives. Define architecture, team structure, and execution priorities.

Deliverables:

  • 3-12 month technology roadmap
  • Architecture design & documentation
  • Team scaling plan & hiring priorities
  • Technology investment recommendations
  • Sprint planning & milestone definition
3

Ongoing Advisory + Hands-On Execution

Monthly retainer

Continuous strategic guidance combined with hands-on engineering support. Weekly check-ins, sprint participation, and execution accountability.

Deliverables:

  • 10-20 hours/month strategic advisory
  • Weekly technical check-ins
  • Architecture reviews & code reviews
  • Hands-on engineering (billed separately)
  • Unlimited async communication (Slack/Email)
4

Quarterly Reviews & Roadmap Updates

Every 90 days

Formal quarterly business reviews to assess progress, refine strategy, and adjust priorities based on business evolution and market changes.

Deliverables:

  • Quarterly progress review
  • Roadmap updates & reprioritization
  • Team performance evaluation
  • Technology investment review
  • Strategic planning for next quarter

Why Choose RegainFlow for Fractional CTO Services

U.S.-based senior engineering leadership with a proven track record of architecting production AI systems and leading technical teams.

7+ Years Enterprise Architecture Experience

Battle-tested technical leadership across AI/ML systems, data pipelines, full-stack platforms, and DevOps automation.

15+ Production AI Systems Architected

From multi-agent automation to RAG pipelines serving 6,000+ daily users, we've shipped production AI at scale.

Hands-On Execution, Not Just Slides

We don't just create roadmaps and disappear. We participate in sprints, ship code, and deliver production systems.

U.S.-Based Senior Engineers

Premium boutique consultancy with senior-level engineers (P4/P5 equivalent), not offshore junior devs.

Business Outcomes, Not Just Technical Deliverables

We measure success by business impact—faster time-to-market, reduced costs, and technical decisions that accelerate growth

Accelerate Time-to-Market

Ship features 2-3× faster with clear technical direction, reduced decision paralysis, and expert architectural guidance.

De-Risk Technical Decisions

Avoid costly technical mistakes with battle-tested architecture patterns, vendor evaluation, and strategic build vs. buy analysis.

Scale Engineering Team

Build a high-performing engineering culture with hiring support, performance frameworks, and technical mentorship.

Maximize ROI on Technology

Optimize technology investments with cost-benefit analysis, vendor negotiation support, and strategic resource allocation.

Reduce Technical Debt

Proactively manage tech debt with code quality standards, refactoring strategies, and architecture modernization.

Deploy AI & Automation

Implement production AI systems (RAG, multi-agent, LLM integrations) and business process automation with hands-on execution.

Who Benefits from Fractional CTO Services

Whether you're scaling fast or building from scratch, we meet you where you are

1

Series A/B Startups

Scaling teams that need CTO-level leadership but can't afford a $300k+ full-time executive.

Common Challenges:

  • Can't afford a full-time CTO ($300k+ salary + equity)
  • Technical decisions slowing down growth
  • Struggling to scale engineering team effectively
  • Architecture decisions causing tech debt
  • Need to build vs. buy guidance for AI/ML systems

Outcomes You'll Achieve:

  • Strategic technology roadmap without executive salary
  • Confident technical decisions aligned with business goals
  • Team scaling strategy & hiring support
  • Production-ready AI/ML systems & data pipelines
  • Reduced technical debt & improved code quality
2

SMBs Building Internal Tools

Small and mid-sized businesses building custom software but lacking in-house technical leadership.

Common Challenges:

  • Lack of technical leadership for internal projects
  • Vendor selection paralysis (build vs. buy)
  • Unclear technology strategy & roadmap
  • Struggling to modernize legacy systems
  • Need AI/automation but don't know where to start

Outcomes You'll Achieve:

  • Clear technology roadmap for internal tools
  • Expert guidance on build vs. buy decisions
  • Legacy system modernization & data migration
  • AI-powered automation for business processes
  • Cost-effective technology investments with proven ROI
3

Mid-Market Companies

Established companies with engineering teams that need strategic guidance and architectural oversight.

Common Challenges:

  • Have developers, but no technical leadership
  • Engineering team lacks direction & standards
  • Code quality & technical debt accumulating
  • Need architectural guidance for complex systems
  • Struggling to implement AI/ML capabilities

Outcomes You'll Achieve:

  • Technical leadership & team mentorship
  • Engineering standards & best practices
  • Architecture reviews & technical debt reduction
  • AI/ML strategy & hands-on implementation
  • Improved team velocity & code quality

Frequently Asked Questions

Common questions about Fractional CTO services, engagement models, and pricing

A Fractional CTO provides strategic technology leadership on a part-time, retainer basis—typically 10-20 hours per month. You get the same expertise and accountability as a full-time CTO (technology roadmaps, architecture decisions, team leadership) without the $300k+ salary and equity commitment. We combine strategic advisory with hands-on engineering execution, so you get both guidance and delivery.
Senior contractors execute on tasks you define. A Fractional CTO defines the strategy and then executes it. We provide technology roadmaps, make architecture decisions, lead your team, evaluate vendors, and align technology with business goals—then roll up our sleeves and ship code alongside your team. It's strategic leadership + hands-on execution, not just labor.
Both. The monthly retainer covers strategic advisory (10-20 hours/month): roadmaps, architecture decisions, code reviews, team mentorship. Hands-on engineering is billed separately as project work. We don't just create PowerPoint decks—we participate in sprints, ship production code, and fix critical bugs. Strategy meets execution.
Most Fractional CTO engagements are 6-12 months minimum, with many clients retaining us for years. The first 1-2 months focus on discovery and roadmap creation. Months 3+ are ongoing advisory and hands-on execution. We recommend a minimum 3-month commitment to allow time for meaningful impact (strategy + execution).
Fractional CTO retainers range from $8,000 to $14,000 per month depending on team size, complexity, and hours required. This covers strategic advisory (10-20 hours/month). Hands-on engineering is billed separately: hourly ($115-$155/hr) or fixed-price projects ($25k-$180k). Most clients invest $12k-$30k/month total (retainer + hands-on work).
Absolutely. We integrate seamlessly with your existing team—whether you have 2 developers or 25. We lead through collaboration, not command-and-control. Expect regular code reviews, architecture discussions, sprint planning, and mentorship. We elevate your team's capabilities while shipping production code alongside them.
Not necessarily. If you have a clear, scoped project (e.g., "Build a RAG chatbot for customer support"), our AI Discovery Sprint ($18k, 2 weeks) or fixed-price project work ($25k-$80k) may be a better fit. Fractional CTO makes sense when you need ongoing strategic guidance, team leadership, and long-term technology roadmap—not just a one-off build.
Most engagements start within 2-4 weeks. We begin with a free 45-minute strategy session to understand your needs, followed by a custom proposal. Once signed, we kick off with discovery and technical audit (Week 1-2), then strategic roadmap creation (Week 3-4), followed by ongoing advisory and execution.

Ready to Lead with Strategic Technology?

Book a free 45-minute CTO strategy session. We'll discuss your technical challenges, business goals, and create a custom roadmap—with honest guidance on whether Fractional CTO services are the right fit.

  • Free 45-minute strategy call with a Fractional CTO
  • Honest technical assessment of your current state
  • Custom roadmap recommendation
  • Transparent pricing in 24 hours
  • No obligation, no sales pressure