Head of Engineering (Ruby on Rails)

Were hiring a Head of Engineering!

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 Were 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. Were also interested in long term side gig relationships if thats what youre into - in our experience a few expert hours often beat full-time learning-curve hours.

About Us

Were 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.

Learn more about our founder team and comp structures at .

About The Role

Can be a purely management role or a hands-on coding management hybrid. Either way you must be deeply fluent in Rails and React strong enough to spot-check code quality and call BS on padded estimates or sandbagged velocity.

Compensation

Up to $400000 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

Many devs are currently using AI to achieve the same outcome with 70% less work. We want you to achieve the opposite: same effort higher velocity.

• Youve established yourself as the alpha nerd and are running regular 1:1s with each developer
• Youve established a positive culture that devs WANT to be part of
• Youve established processes that ensure AI is being used to compound output
• Youre holding the team accountable to the standard youve set

What Youll Do

• Lead and manage a team of developers building on Ruby on Rails and React
• Drive AI enablement across the organization integrate AI into the product engineering workflows and non-technical processes to maximize output and efficiency
• 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 (responsibility can be delegated to an architect or CTO)
• 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

What Were Looking For

• Deep technical expertise in Ruby on Rails React and related stacks (PostgreSQL Redis Sidekiq etc.) strong enough to spot-check PRs validate estimates and know when velocity numbers are bullshit
• Hands-on experience with AI enablement youve integrated AI tooling into products dev 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 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