SideGuy Operator Match · Fractional CTO / Tech Leadership · San Diego, CA
San Diego Fractional CTO · Cloud · SaaS · AI · Platform Scaling
VP-level product + technology leadership for funded startups scaling cloud + SaaS + AI infrastructure beyond the founder's first build
✓ Vetted by PJ
Operator: identity protected until Text-PJ intro · same way StubHub holds reseller info
How this works: SideGuy is the operator-honest matching layer. Like tickets without the holding broker info — you see the service + region + specialty + my vetting; the operator's identity stays held until you Text PJ for the intro. I vet the match, route the conversation, and step out. No fee for the intro; if you engage the operator, they may pay SideGuy a referral. The honesty stays the same regardless.
What they offer
Concrete services. No buzzwords. What buyers actually pay them for.
- Fractional CTO engagements (8-20 hrs/week) for seed → Series B SaaS + AI startups
- Cloud architecture review + redesign (AWS / GCP / Azure / multi-cloud)
- Engineering org design + first-VP-of-Eng hiring + leveling/comp framework
- AI integration strategy (which models, which platforms, build vs. buy, on-prem vs. API)
- Product → engineering handoff process design for scaling beyond founder-coded MVP
- Technical due diligence for VC investors evaluating SaaS/AI deals
Who they typically help
The operator's ICP — what kind of buyer fits this match best.
- Non-technical founders post-Seed who need a 'pre-CTO' partner to scale infra
- VC-backed seed → Series B startups in San Diego's deeptech ecosystem
- PE-funded acquisitions integrating multiple SaaS stacks
- Founders preparing for Series A who need engineering org chart for the deck
- AI/ML companies past prototype, entering enterprise sales (need cloud + security maturity)
Where this is the wrong fit
The operator-honest moat. If any of these apply, this is the wrong match — Text PJ for a different intro.
- Pre-seed / pre-funding companies that can't afford fractional executive rates ($8K-25K/mo typical)
- Companies needing a hands-on senior IC engineer to write code daily (this is a leadership role, not implementation)
- Pure agency/services businesses without a real product platform
- Hardware / electronics / robotics startups (this operator is software-focused)
How they work
Engagement model. Project / fractional / advisory / referral — what to expect.
- Monthly fractional retainer (8-20 hrs/week, structured around weekly sprints)
- 3-month minimum engagement (anything shorter doesn't compound)
- Project-based engineering audit + roadmap as a starter package ($10-25K, 4-week deliverable)
- Advisory equity available for early-stage companies in lieu of partial cash
PJ's vetting note
Multi-cycle product+tech leader I've watched publish on cloud + SaaS + AI scaling for years. The combination of cloud-architecture depth + AI-integration savvy + founder-org-design experience is rare — most fractional CTOs pick one of those three and call it good. This operator is the one I'd send a funded SaaS founder to who needs all three layers at once.
Related SideGuy reads
Comparison pages + sibling matches the buyer should also see.