Founding GTM Engineer

Working pattern: Five days per week in the office ABOUT OPEN INSURANCE We are a venture-backed technology company disrupting a multi-trillion-dollar industry that has remained largely unchanged for decades. Our platform uses modern infrastructure and AI to bring greater transparency, efficiency, and better decision-making to a highly fragmented market, starting with commercial real estate. We closed the largest pre-seed in insurtech history, backed by Tier 1 VCs and the largest strategics in the space. We have strong early market traction, a differentiated product, and a founding team with a proven track record of building and scaling category-defining companies. We are building toward a $100B+ outcome and investing in the people, systems, and technology that will get us there. We are currently operating in extreme stealth ahead of launch. We can share much more upon connecting. WHY THIS ROLE We are hiring our first GTM Engineer to build the systems that power Open Insurance's commercial engine. Working directly with the founder, you'll sit at the intersection of go-to-market strategy, AI, and automation, designing the infrastructure that enables smarter outreach, better qualification, and a more scalable sales process. Our north star is simple: generate a near-infinite supply of quality meetings through quality outbound. You'll build the workflows, automations, and systems that make that possible, helping the commercial team operate more efficiently and creating the foundation for long-term growth. If you enjoy building from zero to one and using technology and AI to solve complex operational challenges, you'll have significant ownership and impact from day one. WHAT YOU WILL BUILD End-to-end outbound infrastructure: enrichment pipelines, signal-based triggers, multi-channel sequencing, and AI-powered personalization at scale, built to run intelligently without requiring manual intervention at every step. The data layer that makes our outbound smarter: identify the right signals, pull from the right sources, keep records clean, and ensure every rep interaction is backed by accurate, real-time context on each prospect. AI tooling and automation that power GTM: deploy AI agents, LLM-driven personalization, and workflow automation (e.g. Clay, n8n, Zapier, or similar) to streamline segmentation, content generation, and campaign operations. Systems that multiply rep capacity: the goal is that a single rep working our stack can run more tailored, high-quality conversations in a day than a traditional team runs in a week. The GTM tech stack, owned end-to-end: evaluate tools, build integrations where needed, eliminate waste, and ensure the stack compounds in value as the team scales. Feedback loops from market conversations into product and positioning: structured pipelines from conversation data into the decisions that shape how we grow. The playbook: document everything you build, then hire and develop the team that runs what you created as the organization scales beyond the founding stage. WHAT WE ARE LOOKING FOR We are looking for someone who is obsessed with leverage. Someone who looks at a manual process and instinctively thinks about how to eliminate it. Someone who lives in the communities where modern GTM is being invented, has strong opinions about the right tools and workflows, and has built revenue infrastructure from scratch before. Active practitioner in the modern GTM engineering community: you are in the conversations where the best operators share what is actually working, and you bring that intelligence into your daily work. Deep fluency with the tools that define the modern outbound stack: enrichment, orchestration, sequencing, AI-powered personalization, and the integrations that tie them together. Engineering or technical fluency sufficient to build and maintain integrations, write scripts, work with APIs, and extend what off-the-shelf tools cannot do on their own. Strong opinions on what a well-supported rep motion looks like: you understand the difference between a rep grinding through raw call volume and a rep spending their day in tailored, high-context conversations, and you know how to build the system that produces the latter. Track record of building outbound or revenue infrastructure that measurably moved a number, at a company that had not already figured it all out. Comfortable operating without a playbook, without a team, and without a finished product: you are energized by being first, not slowed down by it. Exceptional systems thinking: you design for scale, not just for what works this quarter. HOW WE WORK & WHO WE ARE In-office in New York City, five days a week. Building in person is how we move. Working hard and working sustainably are not in tension here: teammates regularly take time to work from abroad, go off the grid, and do what they need to stay at 100%. Low process, high context, flat by design. We organize around the belief that category-defining companies are built by people with chips on their shoulders and a hunger to own outcomes of increasing scope. Autonomy by default. The best cultures are built on intrinsic motivation, not management. We hire people we do not have to manage and give them room to operate. Best idea wins. We want people who generate sharp ideas, defend them well, and update fast when evidence moves. We are obsessed with ground truth. COMPENSATION Aggressive base aligned with experience Founding-team equity; top of band given the scale of the round 100% health insurance covered; top-of-market benefits #J-18808-Ljbffr Open Insurance