[Hiring] Staff Engineer / Team Lead (Ruby on Rails) @59 Pines

Role Description

We're hiring a Staff Engineer / Team Lead (Ruby on Rails)! This is a high-velocity individual contributor role with product ownership — not a people-management position. You set the bar for how fast great Rails code ships, and you do it by being the person who's best at directing AI to multiply output.

• 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.

We believe working with AI is a lot like working with a brilliant but inexperienced junior developer: it can produce enormous volume, but only if you know how to define the work, decompose it into right-sized pieces, and review output with a critical eye. If you've ever been the senior who made a team of juniors wildly productive — not by doing their work, but by giving them crystal-clear specs and fast feedback — this role is built for you.

This is also a product-forward role. We're not hiring a separate product manager for this team. You'll work directly with stakeholders to figure out what needs to be built, not just how to build it. You should genuinely enjoy that part — talking to users, unpacking requirements, making scope calls, and translating business problems into shippable slices.

Qualifications

• Deep Ruby on Rails expertise — you've built and shipped production Rails applications and you know the framework inside and out (PostgreSQL, Redis, Sidekiq, Active Job, etc.).
• 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.
• Product instincts — you genuinely enjoy talking to stakeholders, understanding user problems, and making calls about what to build and what to cut.
• Velocity as a value — you care about shipping. You find ways to move fast without cutting corners.
• Strong decomposition skills — you can take a large, ambiguous objective and break it into concrete, well-scoped pieces of work.
• 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.

Requirements

• 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've taken ownership of at least one product area: you know the stakeholders, you understand what they need, and you're making scope and prioritization calls confidently.
• You're decomposing work 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.

Benefits

• Up to $375,000 max total compensation in Tier 1 cities; cash and equity components to be negotiated.

Company Description

We're a credible, funded, remote-first startup led by a serial technical founder, and backed by a 20-person team. The product is live in private alpha.

• The First Team to Execute Captures Everything.
• Multi-Trillion Dollar TAM: Global market opportunity across multiple high-value sectors.
• Category Creation: Not disrupting existing markets, creating entirely new infrastructure category.
• Macro-Resilient Model: Business grows during recessions, job displacement, and AI automation cycles.
• Experienced Founder: 25-year serial entrepreneur and former CTO with proven track record.
• Established Team: 13 experienced professionals committed with equity-only compensation.
• Stealth Mode Advantage: Currently operating under the radar to build competitive moat.
• Network Effects Day One: Winner-takes-all dynamics with immediate compounding effects.
• Ultra Low CAC: Efficient customer acquisition through network-driven growth model.
• AI-Native Organization: Built from day one with advanced AI capabilities and no legacy baggage.