Founding Enterprise Account Executive - Insurance

WHO ARE WE We're a tight-knit, collaborative team on a mission to make knowledge accessible to everyone in an organization — building the durable layer where decisions, context, and institutional know-how live so no one is left hunting through Slack or piecing together what happened. If you love working where curiosity is contagious, ideas travel fast, and the work you ship tangibly changes how teams think and build, you'll fit right in. IN THIS ROLE, YOU WILL - 🤝 Use your existing relationships across carriers, MGAs, TPAs, insurtechs, and industry partners to open senior-level conversations, develop opportunities, and close enterprise deals - 🚀 Work alongside the founders on high-profile insurance accounts, from discovery to close - 📬 Learn the founder-led playbook (already working and producing revenue), then run it and improve it - 🎯 Build target-account lists and buyer maps across carriers and claims organizations, and run outbound and follow-up - 🎤 Choose the right insurance conferences and events, then prepare, start conversations, and follow up fast - 🧩 Run discovery and demos, and turn messy claims and operations problems into a clear business case and next step - 🛡️ Work through carrier security reviews, legal, and procurement with founder support - 🧭 Know when to bring in founders, product, or engineering, and stay the quarterback on your deals - 🌱 Build your own book: source, open, close, and expand carrier and partner accounts you own - 🔁 Feed what you hear from claims, operations, and technology leaders into ICP, messaging, demos, and product - 🗂️ Keep CRM, follow-up, and the forecast clean and current We're looking for a hands-on builder-seller who knows insurance, is hungry, resourceful, and quick to learn, with a record of owning deals. You keep a high operating tempo, you are comfortable doing the unglamorous work, and you want to take over more and more of a working founder-led motion. This is a hands-on individual contributor role. This is a chance to learn enterprise insurance selling at close range with the founders and help land important carriers. You start alongside them, take on more of the cycle as you ramp, then apply the same proven playbook to build a book of your own.   YOU MAY BE A GOOD FIT IF YOU - Education: Bachelor's degree in a related field, or equivalent practical experience. - Experience: 4–12 years of professional experience in B2B sales, including time carrying a number selling to insurance carriers, MGAs, TPAs, or into insurance at a software or technology company. - Insurance network: You bring an established, active network in the insurance industry, particularly with Claims, Operations, Technology, and Transformation leaders. You have turned those relationships into qualified opportunities and revenue. - Sales skills: You have sourced, advanced, and closed real deals with long carrier buying cycles. Time selling into regulated, technical, or enterprise categories is a plus. - Outbound and events: You start from a blank list: research, messages, calls, insurance events, follow-through. - Product fluency: You learn an AI or enterprise product fast, run a solid first conversation with a claims or operations leader, and know when to bring in specialists. - Ownership and communication: You are self-directed, write clearly, and keep accountability after a handoff. - Mindset: You value hunger, learning speed, and ownership over title, and you value different perspectives.   OUR MOTION - Channels: Targeted outbound • Insurance events • Referrals • Carrier and insurtech partners - Sales path: Discovery • Tailored demo • Scoped evaluation or pilot • Production • Expansion - Working model: Own your pipeline • Involve the founders and team deliberately • Never drop accountability at a handoff - Tools: Apollo (prospecting) • Lightfield (CRM) • Devin and Lovable (demos)   LOCATION & WORK AUTHORIZATION - Location: Hybrid - we’re in the office in Palo Alto, CA near the Caltrain station from Tuesday to Thursday, with Mondays and Fridays remote. - Work Authorization: At this time, we are unable to sponsor new visas, but we encourage you to check back soon, as this may change.