Head of Engineering at Highlightai

Highlight is building a shared intelligence layer for the modern workforce. Highlight unifies context across every person and tool on your team, seamlessly bridging information silos. It evolves with your organization to proactively route knowledge and reliably automate workflows. The Role We're seeking a Head of Engineering to lead our technical team as we scale the intelligent OS for the agentic age. You'll play a role in architecting Highlight's core infrastructure, building and mentoring a world-class engineering team, and shipping high-craft AI experiences that users trust. You'll value extreme ownership of technical decisions, the opportunity to shape product direction from the ground up, and working directly with founders in a fast-paced, high-trust environment. Note: this is an on-site role, requiring five days a week in our office. Job Responsibilities - Own technical architecture and engineering roadmap as we scale from Series A to product-market fit and beyond - Build, mentor, and retain a senior engineering team that ships fast without compromising on craft or user experience - Drive execution across the stack—from real-time context capture to agentic workflows—while maintaining system performance and reliability - Partner closely across the org to define how AI-native experiences should work, not just what they should do - Establish engineering culture, processes, and standards that support rapid iteration while scaling team size and complexity Profile We’re looking for someone who is interested in building the AI user experience for the future. We punch above our weight so we value extreme ownership, accountability, and proactiveness. You are a good fit if you have: - 8+ years engineering experience with 3+ years leading technical teams at high-growth startups or product-focused companies - Track record of shipping complex, user-facing products from 0→1 and scaling them to millions of users - Deep technical expertise across frontend, backend, and systems engineering—you've built (or rebuilt) core infrastructure under pressure - Comfort with ambiguity and bias toward action; you thrive in early-stage environments where priorities shift weekly - Passion for AI/ML product experiences and conviction about how agents will reshape knowledge work - Ownership mentality (no task is too small for you) – it’s all hands on deck here and we need everyone rowing the boat. - Excellent communication skills and a collaborative mindset – we’re extremely lean so we’re looking for a team player who works well with others. - Type-A tendencies: maybe you’re extremely detail-oriented. Or maybe you take pride in shipping high-quality products. Whatever it is you do, you give it your all. - Must be based in or willing to relocate to SF – although we’re flexible with days off & schedules, we have a 100% in-office culture during the week. And even if you don’t fall neatly into any of these buckets, we’re looking for scrappy and motivated self-starters above all. Hustle is expected, grit is required. Perks - Competitive salary and generous equity package - Health, dental, and vision insurance - Flexible PTO and parental leave - Paid team lunches and dinners during the week - Relocation package