Chief of Staff — Truvo

Chief of Staff — Confidential (AI-Native Insurtech Startup) Location: New York City, NY (Onsite) Compensation: $130,000 – $180,000 base + 0.1% – 0.3% equity Visa Sponsorship: None available Experience Level: 1–3+ years Employment Type: Full-Time About the Company A seed-stage AI-native consumer insurance platform automating quoting, binding, servicing, and policy management using AI agents — attacking a trillion-dollar legacy insurance market still dependent on manual workflows, legacy carrier systems, and fragmented infrastructure. The company works with 40 major U.S. insurance carriers and is preparing a nationwide rollout across all 50 states. Backed and advised by an elite network including co-founders of Indeed and Wave, Octopus leadership, and talent from Google, Meta, Pinterest, Coinbase, and Trade Desk. The founding team includes elite engineers, research-driven technical talent, and sales leadership recruited from top digital insurance brokerage competitors. About the Role This is a direct CEO right-hand role with broad ownership across company-critical initiatives. This is not an operations coordinator role. This is not a project manager role. This is a high-agency startup operator seat with aggressive ownership across changing priorities. Core ownership includes: • Fundraising support — investor research, deck iteration, data room management, and follow-up coordination • Operational project ownership — vendor evaluation, hiring pipeline buildout, and process design • Analytics — unit economics, lead conversion, and carrier performance analysis • GTM strategy support — lead generation, partnership outreach, and carrier relationship support • Investor and external partner communications • Systems building and automation • Special projects based on founder priorities Requirements • 1–3 years of top-tier professional experience (exceptional new grads considered) • Top-tier backgrounds strongly preferred — Goldman Sachs, McKinsey, Bain, BCG, or comparable elite firms • Strong spreadsheet and financial modeling capability • Excellent written communication and analytical decision-making • High agency, bias for action, and self-directed execution • High integrity and trustworthiness in a founder-facing role • NYC-based or committed to relocation • Comfort with intense startup pace Nice to Have • Startup, fintech, or insurtech experience • AI-native company exposure • Multi-stakeholder project ownership • External partnership experience Target Backgrounds Highest signals: Goldman/MBB pedigree, candidates who have multiple strong options but are intentionally choosing a startup, end-to-end project ownership, and strong startup intensity. Behavioral fit: blank canvas comfort, high urgency, low ego, strong ownership mentality, and fast execution. This Role Is NOT For • 10+ year corporate consultants • Candidates who need heavy direction or highly structured environments • Frequent short tenure instability • Low agency candidates Benefits • Meaningful early equity (0.1% – 0.3%) • Founder mentorship and significant ownership • Front-row seat to AI transformation of insurance Interview Process • Initial screen • First round • Second round • Work trial • Offer Logistics • Role is fully onsite in New York City — please only apply if you can commit to this • No visa sponsorship available Shortlisted candidates will be contacted by David Joseph & Co., the recruiting partner managing this search.