Head of Engineering

Your Role

Head of Engineering – Build, Lead, Ship

We're at an inflection point. The home-building industry is being transformed by AI, and we're positioned to lead that change. As Head of Engineering, you'll drive how we leverage these new tools and technologies—not just in our product, but in how your team builds software. LLMs, AI-assisted development, automated testing, new paradigms—you'll decide what matters and what's hype, then bring meaningful change to our engineering organization.

But here's what makes it different:
This isn't a pure management role. You'll write code, review PRs, debug production issues, and architect systems—while leading a team of senior engineers who expect you to stay technical. If you've been itching to get back into the code while still shaping technical direction, this role bridges both worlds.

We're past the MVP phase but still moving fast. You'll inherit working Django/Python applications, a revenue-generating product, and a team that ships weekly. Your job is to scale what works, fix what doesn't, and push the boundaries of what's possible—both in what we build and how we build it.

WHAT YOU'LL ACTUALLY DO

Code & Architecture (40-50% of your time)

• Write Python/Django backend code regularly—this isn't symbolic; it's expected
• Lead by example in code reviews, setting standards for quality, performance, and maintainability
• Make architectural decisions with production trade-offs in mind: when to refactor, when to ship fast, when to pay down tech debt
• Debug gnarly production issues alongside the team when things break

Technical Leadership & Innovation (30-40%)

• Own the technical roadmap—translating business goals into concrete engineering initiatives
• Drive AI transformation across two dimensions: (1) AI/ML features that create real product value, and (2) how AI changes how we build software (dev tooling, workflows, automation)
• Make build‑vs‑buy decisions on infrastructure, tools, and third‑party integrations
• Lead the charge on modern development practices—from AI‑assisted coding to automated testing—and bring meaningful tooling changes to the engineering org
• Drive security, scalability, and performance improvements as the user base grows

People & Team (20-30%)

• Lead a senior engineering team (Frontend, Backend, Data, QA) who value autonomy and clarity over micromanagement
• Mentor engineers through code, architecture discussions, and career development—including helping them adapt to new AI‑powered workflows
• Own hiring, compensation decisions, promotions, and performance management—you'll shape not just the team's future but their growth
• Build lightweight processes that enable speed, not bureaucracy
• Partner cross‑functionally with Product, Business, and Operations teams

Technical Depth (Non‑Negotiable)

• 8+ years building production web applications, with significant hands‑on Python experience
• Deep Django/DRF expertise preferred—you should be comfortable jumping into our codebase on day one
• Strong system design skills: APIs, Postgre
  
  SQL, caching, scalability patterns, performance optimization
• Production mindset: monitoring, logging, incident response, security best practices
• Solid grasp of GDPR, authentication/authorization, and secure coding practices

Leadership Experience

• 3+ years leading engineering teams, ideally in high‑growth or startup environments
• Track record of mentoring senior engineers and shipping high‑impact products
• Proven ability to make technical trade‑offs that balance speed with sustainability
• Comfortable making decisions with incomplete information and adapting as you learn

Startup DNA

• You thrive in environments where priorities shift, resources are lean, and shipping matters
• You're equally comfortable debugging CSS, optimizing database queries, or discussing business strategy
• You default to action over analysis paralysis
• You've worked in scale‑up environments (Series A to
  
  C) and know the difference between startup chaos and productive iteration

Communication & Collaboration

• You can explain technical concepts to non‑technical stakeholders without dumbing things down
• You translate business requirements into technical solutions and technical constraints into business…