SSG
SpecialSituationsGroup

Fractional CTO Services

Experienced technology leadership for RIAs and growth-stage fintechs — strategic architecture decisions, vendor evaluation, and technology roadmap development without the cost and commitment of a full-time executive hire.

When you need one

Strategic technology leadership at a critical inflection point

Most RIA firms and growth-stage fintechs reach a point where technology decisions become business-critical — but hiring a full-time CTO is premature, expensive, or impractical. You need someone who can evaluate vendors, design system architecture, assess technical talent, and guide build-vs-buy decisions without the overhead of a permanent C-suite role.

That is where a fractional CTO engagement makes sense. Common scenarios include:

  • PE-backed RIA needing a technology strategy roadmap as part of growth planning or pre-exit preparation
  • Growth-stage fintech evaluating critical architecture decisions — monolith vs. microservices, cloud migration, vendor consolidation
  • Firm evaluating build-vs-buy for a core platform and needing independent technical assessment of vendor capabilities
  • Post-acquisition technology integration planning — assessing acquired systems, planning data migration, evaluating team structure

What the engagement covers

Strategic and tactical technology leadership

A fractional CTO engagement is scoped to your specific needs — from a one-time architecture review to ongoing strategic advisory over several months. Typical areas of focus include:

Technology Strategy & Roadmap

  • Architecture decisions aligned with business growth plans
  • Vendor evaluation and selection guidance
  • Build-vs-buy analysis for core platform decisions
  • Technology budgeting and ROI modeling for proposed projects

Architecture Review & Modernization

  • Legacy system assessment and modernization planning
  • Cloud migration strategy and cost-benefit analysis
  • Security architecture review and compliance posture assessment
  • Scalability analysis and performance bottleneck identification

Team & Vendor Management

  • Engineering team structure and capability assessment
  • Vendor evaluation, contract review, and SLA negotiation
  • Technical hiring strategy and interview process design
  • Offshore and nearshore development team guidance

Due Diligence & M&A Support

  • Pre-acquisition technology assessment and risk evaluation
  • Post-merger technology integration planning and execution
  • Technology debt quantification and remediation roadmap
  • Intellectual property and system architecture documentation

Our background

Built and exited fintech companies

SSG principals have held CTO and VP Engineering roles at fintech companies from early-stage through exit. We have built trading platforms, portfolio management systems, and compliance infrastructure that institutional clients relied on daily. We understand both the technology and the business constraints of regulated financial services — the regulatory overhead, the vendor lock-in risks, the compliance audit cycles, the cost structure of scaling a financial services firm.

When you work with SSG as your fractional CTO, you are not getting generic technology consulting. You are getting seasoned leadership from people who have made these decisions under real business pressure — and lived with the consequences.

SOC 2 Type II Certified

Let's work together

Schedule a complimentary consultation

Whether you need a one-time architecture review, vendor evaluation, or ongoing strategic technology leadership — we bring founder-level experience and fintech domain expertise to every engagement. No sales pitch. No boilerplate recommendations. Just candid, practical guidance from people who have built and scaled fintech companies in regulated environments.