[Hiring] Head of Engineering @59 Pines

Role Description

We're hiring a Head of Engineering!

• 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 end of Q1 2026. That gives us just 3 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.

Qualifications

• Deep technical expertise in Ruby on Rails, React, and related stacks (PostgreSQL, Redis, Sidekiq, etc.)
• Hands-on experience with AI enablement
• Prior experience as a Technical Manager, Engineering Director, VP of Engineering, or CTO at a venture-backed company
• Demonstrated ability to drive developer performance through metrics, not just vibes
• Comfortable operating in a startup environment with ambiguity and rapid iteration
• Strong communicator who excels at expectation management
• Track record of building high-performing engineering teams from the ground up

Requirements

• Lead and manage a team of developers building on Ruby on Rails and React
• Drive AI enablement across the organization
• Establish and track performance metrics for individual contributors and the team as a whole
• Implement systems for accountability, velocity tracking, and continuous improvement
• Be accountable for technical architecture decisions and code quality at scale
• Conduct regular 1:1s, performance reviews, and sprint retrospectives with actionable outcomes
• Collaborate with product and design to translate business requirements into technical deliverables
• Coach developers and create training materials that raise the bar across the team
• Build and refine hiring, onboarding, and developer growth processes
• Identify and remove blockers — whether technical, process, or people-related

Benefits

• Up to $400,000 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.