Head of Engineering (Ruby on Rails)

Role

Can be a purely management role or a hands-on engineering + management hybrid. Lead and be accountable for technical architecture, code quality, team performance, and developer workflows for a Ruby on Rails and React codebase.

Key Responsibilities

• Lead and manage a team of developers building on Ruby on Rails and React.
• Drive AI enablement across product, engineering workflows, and non-technical processes to increase output and efficiency.
• Establish and track performance metrics for individuals and the team; implement systems for accountability, velocity tracking, and continuous improvement.
• Be accountable for technical architecture decisions and code quality at scale (responsibility may be delegated to an architect/CTO).
• Conduct regular 1:1s, performance reviews, sprint retrospectives, and coaching with actionable outcomes.
• Collaborate with product and design to translate business requirements into technical deliverables.
• Build and refine hiring, onboarding, and developer growth processes; identify and remove technical, process, or people blockers.

Requirements

• Deep technical expertise in Ruby on Rails and React and related stacks (explicitly mentions PostgreSQL, Redis, Sidekiq).
• Hands-on experience integrating AI tooling into products, developer workflows, and/or business processes.
• Prior experience as a Technical Manager, Engineering Director, VP of Engineering, or CTO at a venture-backed company.
• Demonstrated ability to drive developer performance using metrics and processes.
• Comfortable operating in a fast-moving startup environment with ambiguity and rapid iteration.
• Strong communication skills and expectation management; track record building high-performing engineering teams.

Success in 30 Days

• Establish yourself as the technical leader and run regular 1:1s with each developer.
• Establish a positive engineering culture and enforce standards developers want to be part of.
• Put in place processes that ensure AI is used to compound output while maintaining high-quality results.
• Hold the team accountable to established standards and velocity expectations.

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).

Working Arrangements

• Flexible title and time: full-time, part-time, side-gig (off-hours), or fractional (contract).
• Flexible commitment: short-term, long-term, or intermittent.
• Remote-first environment.