Head of Engineering

About the role

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.