Head of Engineering

What You’ll Do

Accelerate Building with AI

• Drive adoption of AI-powered development tools (AI-assisted coding, automated testing, code review, agentic systems) to multiply engineering velocity.
• Partner with Product and ML to embed AI into core product experiences — search, matching, personalization, and pricing.
• Foster a culture of experimentation; ensure frontier capabilities show up in shipped products, not slide decks.

Define Technical Vision and Strategy

• Lead a clear engineering vision aligned to our product, personalization, and marketplace strategy.
• Ensure architecture enables rapid iteration, scalability, and reliability at scale.
• Partner with the executive team to set strategic priorities through the lens of engineering capability.

Build and Lead a High-Performing Org

• Set a clear performance bar. Run rigorous calibration. Act decisively on underperformance.
• Develop engineering managers and identify future leaders early; invest in succession planning.
• Own recruiting strategy to attract and retain top engineering talent.
• Create systems and rituals that drive velocity, collaboration, and accountability.

Elevate Quality, Velocity, and Individual Growth

• Champion best practices: code quality, testing, CI/CD, observability, incident response, and architectural review.
• Ship fast, fix fast, raise the bar every sprint. Foundations earn their seat by enabling speed, not by slowing it down.
• Evolve our platform and infrastructure for scalable, reliable, performant experiences.
• Build clear career ladders and invest deeply in coaching, mentorship, and skill development across all levels.

Strengthen Cross-Functional Alignment

• Serve as a strategic thought partner to Product, Design, Data, and ML leaders.
• Bring technical feasibility and opportunity into every decision-making conversation.
• Bring genuine appreciation for craft, interaction quality, and the details that create user delight.

What You’ll Bring

• 8+ years leading engineering teams, including managing managers and scaling orgs of 40+ engineers in fast-paced, high-growth environments.
• Strong technical foundation: modern web technologies, iOS & Android apps, distributed systems, cloud infrastructure, data-intensive applications.
• AI-native track record: shipped AI-native products to production at consumer scale; drove measurable productivity gains from AI tooling.
• Performance management track record: raised the bar, made hard calls.
• Marketplace or consumer product experience: built and scaled two-sided marketplaces or high-traffic consumer products.
• People-first leadership: built cultures where ICs thrive, grow, and retain.
• Business-minded: connects engineering investment to business outcomes.
• Deep design partnership experience.

Compensation

• Zone 1: $300,000 - $350,000 TTC (including $255,000 - $297,000 base salary) + equity
• Zone 2: $278,000 - $323,000 TTC (including $236,000 - $275,000 base salary) + equity
• Zone 3: $255,000 - $297,000 TTC (including $217,000 - $252,000 base salary) + equity