Fractional CTO for Series A+ and Scaling Stage

Build a mature engineering organization. Scale from 15-20+ engineers to 50+. Establish processes, metrics, culture, and leadership that enable sustainable hypergrowth.

Challenge

Challenges startups face at this stage

  • Engineering team of 15-20+ people and growing fast
  • Need management layer (leads, managers)
  • Processes that worked for 10 people break at 20+
  • Multiple teams, unclear ownership and poor coordination
  • Technical decisions taking too long
  • Inconsistent engineering quality across teams
  • Hiring 2-3+ engineers per month
  • Preparing for Series B/C or scaling after fundraising
  • Need metrics and data-driven engineering culture
  • Incident response and management becoming critical

Common mistakes at this stage

Promoting people to management without training
Copying big company processes without adaptation
No clear team structure or ownership
Metrics theater (tracking for the sake of tracking)
Too much process, slowing everything down
Too little process, creating chaos
No investment in engineering enablement
Ignoring engineering culture/morale

What I do

Engineering organization design
Team structure and management
  • Team structure: squad/pod design, clear ownership
  • Engineering management: building management layer (leads → managers → directors)
  • Career ladders: engineer and manager tracks with clear expectations
  • Compensation framework: levels, ranges, equity
  • Organizational scaling: from 20 to 50 to 100+ engineers
  • Cross-team coordination: architecture review boards, tech councils
Processes and operational excellence
Mature engineering practices
  • Engineering metrics: DORA, velocity, quality KPIs
  • Incident management: on-call rotation, blameless postmortems
  • Change management: feature flags, gradual rollouts, A/B testing
  • Technical standards: RFCs, ADRs, design reviews
  • Planning rhythms: quarterly planning, roadmap alignment
  • Tech debt management: systematic approach with dedicated capacity
Technical strategy and architecture
Long-term technical vision
  • Long-term technical vision: 2-3 year roadmap
  • Platform engineering: internal tools and platforms
  • Microservices transition: if and when to decompose the monolith
  • Multi-region strategy: infrastructure for global expansion
  • Data architecture: analytics, ML pipelines, data governance
  • Security and compliance: SOC2, GDPR, HIPAA as needed
Leadership and culture
People and team development
  • Engineering culture playbook: values, principles, behaviors
  • Leadership development: coaching for managers and leads
  • Hiring and onboarding: scalable processes for high-volume hiring
  • Retention programs: career development, recognition
  • Internal communication: all-hands, RFCs, documentation culture
  • Performance management: reviews, feedback, PIPs
Board and executive engagement
Strategic alignment
  • Engineering reporting: dashboards, OKRs, board updates
  • Strategic planning: align technical and business roadmaps
  • Fundraising support: technical pitch, due diligence prep
  • Budget management: engineering spend optimization
  • Vendor negotiations: AWS, third-party services at scale
  • M&A technical integration: when acquiring or merging companies

How it works

Recommended package: Scale CTO

1

Month 1-2: Assessment and organization design

Weeks 1-8

Comprehensive organizational assessment. Design team structure. Identify management talent. Quick wins in processes and tooling. Establish baseline metrics.

2

Month 3-6: Building management and processes

Weeks 9-24

Hire/promote engineering managers. Train and coach managers. Implement processes (planning, reviews, incidents). Engineering metrics and dashboards. Define culture and values.

3

Month 7-12: Scaling and maturity

Weeks 25-48

Scale team to target size. Refine org structure as needed. Advanced practices (platform engineering, SRE). Leadership development. Fundraising preparation. Succession planning (transition to full-time CTO if desired).

Results You'll Achieve

What success looks like after 6-12 months

Clear engineering organization structure (teams, leads, managers)
Engineering management layer functioning well
Team scaled from 20 to 30-50+ engineers
DORA metrics in top quartile
Engineering culture playbook and values defined
Predictable delivery and velocity
Low attrition (<10% annually)
Effective incident response (<1h MTTR)
Engineering brand attracts top talent
Successful Series B/C due diligence

Success metrics

Deploy frequency: multiple times per day
Lead time for changes: <1 day
Change failure rate: <5%
MTTR: <1 hour
Engineer satisfaction score: 8+/10
Hiring: <30 days time-to-fill
Retention: >90% annually
Team velocity: predictable sprint-over-sprint

Pricing

Scale CTO for Series A+ and scaling companies

Contract Length:

Scale CTO

≈3 days per week, 80 hours per month

Series A+ startups with 15-20+ engineers preparing for the next funding round.

  • Everything from Growth CTO package
  • Participation in executive meetings and investor discussions
  • Building engineering management team (leads, engineering managers)
  • Due diligence support for fundraising
  • Organizational design: team structure, processes, rituals
  • Technical debt strategy and refactoring roadmap
  • Vendor and partner negotiations (AWS, third-party services, contractors)

Package price

$12,000per month

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Frequently asked questions

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Fractional CTO for Series A+ and Scaling Stage - Anton Golosnichenko - Fractional CTO