🦾 Head of Engineering

What you’ll do

• Build and lead a high-performing engineering organization that can ship ambitious product and infra work with speed, quality, and accountability
• 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 40+ 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 here
• Hold a high bar for performance: celebrate wins and exceptional outcomes; 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
• 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

Anticipated annual salary: $250,000 - $300,000, plus a generous equity package.