Chief of Staff

About The RoleJoin a well-backed, AI-native consumer insurtech startup as Chief of Staff — a high-leverage generalist seat sitting directly next to the CEO. This is not a coordination role. You will be the closest operational extension of the CEO, touching fundraising, operations, GTM, analytics, partnerships, product strategy, and whatever the highest-priority problem is that week.The company is an AI-powered consumer insurance broker operating at real scale — partnering with 40 of the largest US carriers, expanding nationally across all 50 states, and launching new product lines. Backed by seed-stage funding with top-tier angel investors, this is a rare opportunity to see the full architecture of building a company in real time.What You'll DoServe as the right hand to the CEO across every functional area of the businessOwn discrete high-priority projects end-to-end — solve them, systematize them, automate or hand them offSupport and drive fundraising processes including investor communications and financial modelingBuild and maintain operational infrastructure across GTM, hiring, and partnershipsConduct analytical deep-dives and synthesize insights to inform strategic decisionsDraft high-quality written communications for investors, partners, and internal stakeholdersJump between contexts fluidly — one day might span recruiting, marketing optimization, carrier onboarding, and financial modelingWhat We're Looking For1–3 years of experience in consulting, investment banking, startups, or a similarly high-intensity environment (exceptional new grads considered)Strong analytical skills including spreadsheet proficiency, financial modeling, and data interpretationExcellent written communication — crisp, clear, and professional across investor emails, internal docs, and partner notesHigh agency and a bias toward action — you ship before it's perfect and move without waiting to be unblockedHigh integrity — this is a trust-based, right-hand role; integrity is foundationalBased in San Francisco or genuinely committed to relocating (role is in-person 6 days/week including Saturdays)Comfort operating in ambiguity with a blank-canvas mindset and genuine ownership mentalityNice to HaveBackground in fintech, insurtech, or a similarly regulated consumer-facing industryExperience at a top-tier strategy consulting firm or investment bank (e.g. McKinsey, JPMorgan)Prior exposure to early-stage startup environmentsCompensation & BenefitsSalary: $130,000 – $180,000 USD annuallyEquity participation in a fast-growing seed-stage companyVisa sponsorship is not available for this roleLocationSan Francisco, CA — on-site, 6 days per week (including Saturdays). Candidates must be local or committed to relocating.