🦾 Head of Engineering

The Role

We’re looking for a Head of Engineering to build and lead a high-performing engineering org that can ship ambitious product outcomes with speed and quality as we scale.

You’ll own the health, output, and growth of the engineering team - making sure the right people are in the right roles, the management layer is strong, and recruiting, culture, and execution all reinforce each other. You set the pace by example - willing to dive into the work, do what it takes during critical moments, and hold the bar high for yourself and the team. This is not a “headcount first” role - you should be obsessed with motivating and getting maximum leverage out of a small team, using AI as a force-multiplier and preparing engineers for a world where the work of software engineering is fundamentally shifting.

What you’ll do

• Build and lead a high-performing engineering organization that can ship ambitious product and infra work with speed and quality

• Partner closely with the CTO on technical strategy, architecture, and roadmap prioritization; balance short-term product goals with long-term scalability and reliability

• Partner closely with the CEO & CTO to communicate company vision and strategy, ensuring the entire engineering team is highly motivated to achieve ambitious goals

• Own engineering execution and deadlines: ensure every project has clear goals, scope, owner, and deadlines - and that they’re consistently hit

• Introduce lightweight, effective systems for ownership, accountability, and visibility (planning, status, reviews) without weighing the team down in process

• Systematically identify bottlenecks and friction in team workflows - from planning and handoffs to QA and releases - and simplify or redesign processes so engineers spend more time on deep work and shipping

• Assess and develop existing leads; build a strong middle-management layer (EMs / Leads / Staff ICs) that can scale us from 15 to 30+ engineers

• Define, roll out, and maintain a clear career ladder and performance framework for engineers and managers

• Build a culture where high performers are energized - people feel real ownership, are recognized and rewarded for impact, and are motivated to do the best work of their careers

• Hold a high bar for performance - celebrate wins and exceptional outcomes, and ensure underperformance is identified early and addressed directly (whether via coaching, role changes, or exits)

• Own engineering recruiting end-to-end with the CTO and People team: set the bar, refine the process, and personally help source, interview, and close top talent

• Codify and enforce engineering culture and standards (speed, craftsmanship, ownership, resilience); make excellence the default via code review norms, postmortems, documentation, and technical design practices

• Strengthen cross-functional collaboration with Product, Design, and Ops so engineering effort is tightly aligned to company goals

• Establish and track key metrics for engineering velocity, quality, and recruiting pipeline health, and use them to guide decisions

• Design AI-powered systems, tools, workflows, and processes that accelerate productivity and shipping speed

• Work "in the trenches" with the team: we're in the office 3 days a week, with occasional late nights to get the job done

What you’ll bring

• 10+ years of software engineering experience, with proven leadership of 15–40+ engineers in a fast-paced startup or high-growth environment

• Direct experience building and scaling an engineering org: hiring, org design, management systems, and performance management

• A track record of driving operational excellence in engineering - predictable delivery, clear ownership, and high-quality output

• Strong people leadership skills: you’ve hired, leveled, developed, and retained high-performing engineers and managers

• Comfort making and executing on hard people decisions with clarity and empathy

• Deep experience partnering with a founder/CTO and product leaders on roadmap, architecture, and tradeoffs

• Strong recruiting instincts: you’re personally effective at sourcing, assessing, and closing top talent

• Clear and concise communication; you create alignment, set context, motivate teams, and make decisions in the face of ambiguity

• You’re energized by high-intensity, hands-on building - you’re willing to roll up your sleeves, live close to the work, and model the pace and standards you expect from the team

• Nice-to-haves (but not required):

  • Background in consumer or highly product-centric engineering

  • Experience managing both product and infra/platform teams

  • Experience scaling teams in hybrid or in-office environments

What we offer

• Competitive salary and meaningful equity

• 401(k) with company matching

• Comprehensive health, dental, and vision insurance for you and your dependents

• OneMedical membership, telehealth, and virtual mental health support

• Commuter benefits & contributions towards fitness / wellness (e.g., ClassPass, Citibike)

• Flexible PTO and ~14 paid holidays per year

• Quarterly stipend to plan your own party and dogfood the product, plus semiannual team offsites

• Parental leave

• A front-row seat at an early, fast-growing company that cares deeply about product quality, culture, and building something people love

The anticipated annual salary for this position is $250,000 - $300,000, plus a generous equity package. This range does not include any other compensation components or other benefits for which an individual may be eligible (other benefits listed above). The actual salary offered depends on a variety of factors, which may include as applicable, the qualifications of the individual applicant for the position, years of relevant experience, specific and unique skills, level of education attained, certifications or other professional licenses held, and the location in which the applicant lives and/or from which they will be performing the job.