Chief of Staff — Truvo

New York

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.