[Hiring] Startup CTO @59 Pines

Role Description

You've been a 0→1 startup CTO, you write Rails, and you ship products (not people; not features). If your last few years were management, that's fine — as long as you want to write Rails again. The MVP is live. The stack is chosen. The CEO is technical. We have 2 additional X-CTOs. We want one more.

Summary

• Flexible Title: Can tailor to reflect your skills & experience.
• Flexible Time: Can do full-time, part-time, side-gig (off-hours), or fractional (contract).
• Flexible Commitment: Can do short-term, long-term, or intermittent.

Why so flexible? We're a FUNDED startup racing to launch in 60 days. That gives us less than 2 months to stack features while raising additional working capital. Feel free to jump in, help us ship, then bounce >> or stick around. A successful launch translates into lots of permanent jobs for those that want them. We're also interested in long term "side gig" relationships, if that's what you're into - in our experience, a few expert hours often beat full-time learning-curve hours.

About The Role

This is not a traditional software developer role. We're hiring product developers — people we can hand a large initiative and trust to own the whole arc: figure out the requirements, shape the UI/UX, break the work into shippable chunks, and deliver at AI pace.

• You set the bar for how fast great product ships on Rails, and you do it by being the person who's best at directing AI to multiply output.
• We deliberately do not have product managers on staff. You'll act as a technical product owner for your initiatives — deciding what to build, designing the experience, delegating the build to AI (and collaborators), and reviewing the result for both correctness and solid engineering.

Compensation

Up to $400,000 max total compensation in Tier 1 cities; cash and equity components to be negotiated (amount reflects combined cash and equity components).

What Success Looks Like in 30 Days

• You've taken ownership of at least one meaningful initiative: you know the problem space, the stakeholders, and you're making scope and prioritization calls confidently.
• You're shipping production Rails features at a pace that makes the rest of the team recalibrate what "fast" means.
• You've established a personal workflow for AI-assisted development that demonstrably multiplies your output — and you're sharing what works.
• You're decomposing initiatives into well-specified, right-sized tickets that AI (and other developers) can execute against cleanly.
• The code you're shipping and reviewing is clean, well-tested, and production-ready — velocity without quality doesn't count.

What You'll Do

• Own initiatives end-to-end — from ambiguous business problem to shipped product: research, requirements, UX judgment, decomposition, build, and launch.
• Ship features fast — own the full cycle from stakeholder conversation to production deployment, using AI tooling to maximize throughput.
• Define and decompose work — break large initiatives into well-specified, right-sized tickets that serve as both alignment artifacts and AI prompts.
• Decide what to build — work directly with stakeholders (no PM intermediary); make scope calls; cut ruthlessly so what ships actually solves the problem.
• Set the velocity standard — demonstrate what's possible when a senior builder combines product judgment, deep Rails expertise, and disciplined AI-assisted workflows.
• Review and elevate — review PRs, validate AI-generated output, and raise the quality bar across the codebase.
• Collaborate on architecture — contribute to technical decisions on Rails, PostgreSQL, Redis, Sidekiq, and related infrastructure.

What We're Looking For

• You've been a 0→1 startup CTO — you were the technical leader of a company at 0→1 (shipped product, users, revenue, a raise, or an exit). Not a title. The job you already did.
• You write Rails — or you want to again — you've built and shipped production Rails (PostgreSQL, Redis, Sidekiq, Active Job, etc.). If it's been a while, you want back in the codebase.
• Product instincts — you genuinely enjoy figuring out what to build: talking to users/stakeholders, unpacking requirements, shaping UX, and making calls about what to cut. You've done this without a dedicated PM.
• Proven AI-assisted development chops — you're already using AI tooling (Cursor, Copilot, or similar) to ship meaningfully faster, and you have opinions about what works and what doesn't.
• The "senior who makes juniors productive" skillset — you know how to specify work clearly enough that someone (or something) less experienced can execute it well. You give great direction, catch issues early in review, and don't waste cycles on rework.
• Strong decomposition skills — you can take a large, ambiguous initiative and break it into concrete, well-scoped pieces of work. You think in dependency trees, not to-do lists.
• Velocity as a value — you care about shipping. You find ways to move fast without cutting corners. You're allergic to unnecessary process and drawn to approaches that compress cycle time.
• Comfort with startup ambiguity — you thrive when things aren't fully figured out, and you're energized (not paralyzed) by the need to make decisions with incomplete information.

Nice to Have

• You still merge; or you miss it.
• Background shipping marketplace, SaaS, or consumer-facing products end-to-end.
• Familiarity with spec-driven workflows.
• Experience integrating via APIs, browser automation, or Chrome extensions when clean integrations aren't available.
• Experience building or contributing to AI-augmented development workflows at an organizational level.

Who This Is Not For

• People looking for a manager's chair — this is a writing-Rails seat.
• Staff / Principal ICs who have not been the 0→1 technical leader of a company.
• Engineers who prefer well-groomed tickets handed down by a product manager.
• Specialists who only want to write code and leave requirements, UX, and scope to someone else.
• People who think "AI-assisted" means autocomplete, not owning the full define → decompose → review loop.