A marketplace CTO with GigEasy two-sided MVP experience
Architecture that scales per funding round, payments strategy, trust and safety, first engineering hires. $4,500/mo Advisory, $8,500/mo full.
Who this is for
Marketplace founder pre-Series A, non-technical, with trust & safety, scale, and payments decisions piling up and investors asking for CTO presence.
The pain today
- Trust & safety, scale, and payments decisions piling up
- No CTO yet and investors asking
- Current tech team is junior and making big architectural decisions alone
- Scaling architecture is unclear for next funding round
- First engineering hires pending but no one to interview them
The outcome you get
- Fractional marketplace CTO at $4,500 to $8,500/mo
- Architecture scaling plan through Series A
- Payments (Stripe Connect), trust & safety posture defined
- Hiring plan for first 3 to 5 engineers
- Investor-facing technical story from GigEasy track record
Marketplace-specific CTO topics
Four topics dominate pre-Series A marketplace CTO work. Supply and demand — architecture decisions that affect both sides. Trust — moderation strategy, identity verification, user reputation. Payments — Stripe Connect vs custom, escrow patterns, 1099 reporting. Hiring — first engineering hires with clear levelling and onboarding. Each is CTO territory. Fractional CTO at $4,500 to $8,500/mo delivers all four without the cost of full-time CTO hire ($300k+ loaded) that is typically premature pre-Series A.
Architecture that scales to each funding round
Seed-stage marketplace architecture differs from Series A, which differs from Series B. Pre-seed: simplest thing that works — Next.js, Postgres, Stripe Connect, basic search. Seed: dedicated search (Algolia, Meilisearch), improved moderation, observability. Series A: scalability hardening, cost optimisation, growth-engineering tooling. Over-engineering early kills runway; under-engineering creates Series A technical debt. I help phase architecture investment to match runway and growth.
Hiring the first 3 to 5 engineers
First engineering hire for most marketplaces is a full-stack senior who becomes tech lead. Second and third hires typically: one senior specialist (payments, search, mobile) plus one mid-level full-stack. Fourth and fifth depend on growth pressure. Compensation ranges calibrated to market, levelling aligned with impact expectations. Interview loops designed to assess technical judgement plus values fit. I have hired at W2O (led 15 engineers) and at Imohub — hiring marketplace engineers is familiar territory.
Pricing tiers
CTO Advisory $4,500/mo — 1 to 2 days per week. Strategic input, architecture, hiring, investor support. For founders with existing tech lead needing senior guidance. Fractional CTO $8,500/mo — 3 days per week. Deep CTO role — architecture, execution, hiring, investor prep. For founders without senior engineer. 14-day money-back guarantee. Cancel anytime. NDA standard. US LLC invoicing. Typically 6 to 18 months through Series A.
Case: GigEasy — two-sided marketplace playbook
GigEasy: 3-week investor-ready MVP for Barclays and Bain Capital-backed founders — a two-sided gig-worker financial services platform. Stack: Laravel, React, AWS, PostgreSQL, Redis, Docker, Pulumi. 70 percent faster than typical 10-week industry cycle. Zero post-launch fires. Investor demo on schedule. The two-sided marketplace complexity (supply and demand, payments, moderation) shipped cleanly through disciplined scope and senior engineering. Same playbook applies to marketplace MVPs across categories.
When to hire full-time instead
Hire full-time CTO post-Series A once the company has committed to a specific strategic direction (expansion, international, vertical integration) requiring dedicated leadership. Fractional CTO bridges pre-seed through Series A effectively. I help with the full-time CTO search — interview loops, levelling, onboarding — as part of the engagement. For marketplace founders who raise, I often stay as technical advisor post-handoff at reduced rate. Continuity of architectural decisions without full-time commitment.
Recent proof
A comparable engagement, delivered and documented.
Built and shipped an investor-ready MVP from scratch
Built the entire technological base and delivered MVP in just 3 weeks, enabling a successful rapid launch and investor demo.
Frequently asked questions
The questions prospects ask before they book.
- Stripe Connect or something else?
- Stripe Connect is the default for marketplace MVPs — clean developer experience, wide market coverage, KYC and 1099 reporting handled. Express accounts for simpler onboarding; Custom accounts when marketplace needs full seller experience control. For international marketplaces, Adyen is an alternative with deeper local payment method coverage in specific regions. For some verticals (adult content, cannabis, firearms), neither Stripe nor Adyen serves — specialist providers.
- How do you handle trust and safety pre-Series A?
- Minimal automated moderation pre-Series A — not worth the investment until volume justifies. Manual review queue for listings and user reports. Basic rate limiting on signup and messaging. Identity verification via Persona or Stripe Identity for sensitive categories. As volume grows post-seed, layer in automated flagging, better tooling, dedicated T&S staff. I help phase T&S investment to match volume.
- Can you attend investor meetings?
- Yes. For marketplace founders raising, I attend technical DD calls, architecture walkthroughs, and pitch meetings where tech is a topic. Preparation beforehand on expected questions. GigEasy track record helps with investor calibration — proven two-sided marketplace at unicorn-backed scale. Typically 2 to 4 meetings across a fundraise cycle.
- What about international expansion?
- International marketplace launches have layers — payments per market, compliance per market, language, customer support. I help sequence markets based on market-fit evidence and regulatory complexity. For marketplaces entering EU, VAT and local payment methods. For entering LATAM or APAC, local payment methods and fulfillment. bolttech experience with 40+ payment providers across Asia and Europe transfers.
- How do you handle scaling architecture?
- Pre-Series A: simplest stack that ships — Next.js, Postgres, Algolia, Stripe Connect, Vercel. Post-Series A: dedicated search, database read-replicas, background job workers, observability stack, cost optimisation. Series B: regional deployment, advanced caching, ML infrastructure for matching and moderation. Each phase has natural breakpoints; I help you see them coming and invest ahead of blocker.
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