Chief of Staff

About the Company

A seed-stage, AI-native consumer insurance broker (founded 2025) on a mission to rewire a trillion-dollar industry that still runs on phone calls, fax machines, and legacy carrier systems. Its platform uses AI agents to quote, bind, and service policies autonomously — saving the average household hundreds of dollars while delivering better protection at the moments that matter most. Works with 40 of the largest US insurance carriers, prepping to go live across all 50 states, and launching life insurance as a new product line. Backed by top-tier funds and angels (including co-founders of Indeed, Wave, and Octopus, early team members from Google and Meta, and board members from Pinterest, Coinbase, and TTD).

About the Role

A high-leverage generalist role sitting directly next to the CEO. The Chief of Staff owns whatever is most important that week — fundraising, operations, GTM, analytics, partnerships, or product strategy. The scope is intentionally broad and constantly changing. The previous Founder's Associate ran five different projects in a single day (hiring sales agents, optimizing marketing campaigns, finding a branding agency, building financial models, bringing on new carriers) — that's the pace.

The CEO ramps you closely through the first few projects; from there the expectation is high agency fast: own a project, solve it yourself first, then systematize, automate, or hand it off. If you need to be told exactly what to do, this role isn't for you. Culture runs on three pillars: customer obsession, high integrity, and working hard while having fun. This person is the closest representation of the CEO on the team and must be someone he can trust completely. Candidates from top-tier firms and institutions (Goldman Sachs, McKinsey, Bain, BCG, and comparable) are strong signals; exceptional new grads welcome.

Key Responsibilities

• Support fundraising end-to-end: investor research, deck iterations, data room management, follow-up coordination
• Own operational projects start to finish: vendor evaluation, hiring pipeline buildout, process design
• Analyze data to surface insights across lead conversion, unit economics, and carrier performance
• Support GTM strategy: lead generation, partnership outreach, carrier relationship management
• Draft investor updates, internal documentation, and external communications without hand-holding
• Build early-stage projects yourself first, then systematize/automate and hand off to future hires
• Jump into whatever is most on fire that week
  

Must-Have

• 1–3 years at a top-tier firm (Goldman, McKinsey, Bain, BCG, or comparable); exceptional new grads considered
• Strong analytical ability: comfortable in spreadsheets, can build a model, finds signal in data without being directed
• Excellent written communication: can draft an investor email, internal brief, or partner note without oversight
• High agency and bias toward action: figures things out before asking, ships before it's perfect
• High integrity — this is a right-hand role and trust is the single most important thing being hired for
• Based in NYC or genuinely committed to relocating; in-person
  

Nice-to-Have

• Prior experience at a startup, fintech, or insurtech company
• Exposure to insurance, financial services, or AI-native products
• Experience managing multi-stakeholder projects or external partnerships
• Comfortable with light financial modeling and operational analysis
  

Details

Employment: Full-Time  |  Location: New York, NY — In-person  |  Experience: 1–3+ years
Compensation: $130,000–$180,000 / year + meaningful early-stage equity, direct founder mentorship. No visa sponsorship.