Head of Engineering

About the Role

We're building an AI-native platform for the insurance industry - a $7T market still largely powered by manual workflows and legacy software. Our product is live, trusted by a rapidly growing customer base, and now entering its next phase of scale. We're looking for a Head of Engineering to own the engineering function end-to-end: execution, architecture, quality, and the team.

This is a builder-leader role - you'll report directly to the technical founder (CTO/CPO) and serve as the person who turns product direction into shipped, reliable software. The founder is moving increasingly toward customers, product strategy, and the hardest technical problems; you own everything in between. There's a clear path to VP Engineering as the team grows.

You're not starting from scratch. You inherit a working product, paying customers, a real data asset, and a team to grow. What's yours to build is the engineering organisation: team structure, pod model, tech-lead layer, engineering culture, and the processes that let us ship fast without breaking things.
What You'll Do

• Own engineering output. Drive architecture, technical decisions, and day-to-day shipping. Hands-on enough to design hard systems and review critical code - not a purely hands-off manager.
• Build and lead the team. Hire, manage, and coach engineers. Organize the org into focused pods (e.g., Voice/AI, Campaigns & Integrations, Platform/Reliability) with strong tech leads.
• Make reliability boring. Own the release gate, on-call rotation, and incident response. Drive the team from firefighting mode to a stable, predictable operational baseline - this is the #1 success metric for the role.
• Ship the core platform. Lead engineering on a real-time voice platform, an agent/skills layer, omnichannel messaging (voice, email, SMS), and deep integrations with insurance-industry systems (AMS, CRMs, carrier portals).
• Run an AI-native engineering org. You and your team use AI coding tools (e.g., Claude Code, Codex) as a daily force-multiplier - orchestrating agents rather than hand-typing everything - and raise the team's leverage without sacrificing quality.
• Collaborate with leadership. Partner closely with the CTO/CPO, product, design, and customer success to translate strategy into prioritised, shipped features.
• Set the quality bar. Define engineering standards, testing practices, and the cultural expectation that speed and quality are not trade-offs.

What We're Looking For

Required

• Proven experience leading an engineering team to ship end-to-end products in a fast-moving startup environment, including direct hiring and people development
• Strong ownership of system architecture and production-quality software - you set the technical direction, standards, and quality bar
• Hands-on experience building and shipping real-time voice platforms , omnichannel messaging systems, and deep integrations with external APIs or industry-specific systems
• Ability to operate effectively in a fully remote, globally distributed team with asynchronous communication across multiple time zones
• Proven track record collaborating with executive stakeholders (CTO, CPO, product, design, CS) to translate strategy into concrete engineering deliverables

Nice to Have

• Background in AI/ML product engineering or experience deploying LLM-based features in production
• Familiarity with the insurtech or broader fintech landscape
• Experience at a high-growth B2B SaaS company (e.g., sales engagement, conversational AI, CRM, or revenue intelligence tools)
• Prior experience building and scaling an engineering org from ~5 to 20+ engineers

Compensation & Benefits

• Salary: $120,000 - $144,000 USD annually
• Early-stage equity participation
• Fully remote work environment
• Visa sponsorship: Not available - candidates must be authorised to work in the US

Location

This role is fully remote . The company is headquartered in San Francisco, CA. Candidates based in the US are preferred, but the team is internationally distributed and operates across multiple time zones.