Chief of Staff

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).

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 Founders 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) thats 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 isnt 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.

• 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
  

• 13 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 its 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
  

• 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
  

Employment: Full-Time Location: New York NY In-person Experience: 13 years
Compensation: $130000$180000 / year meaningful early-stage equity direct founder mentorship. No visa sponsorship.