Chief of Staff

New York City, NY · On-site · Full-time
Compensation: $130,000 – $180,000 + 0.1%–0.3% equity

About the Company

An AI-native consumer insurance broker rewiring a trillion-dollar industry that still runs on phone calls, fax machines, and legacy carrier systems. The platform uses AI agents to quote, bind, and service policies autonomously, saving households money while delivering better protection. The company partners with dozens of the largest US insurance carriers, is preparing to operate across all 50 states, and is launching a new life insurance product line.
Founded 2025 · 1–10 people (seed stage) · Industry: FinTech

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. Expect to own a project, solve it yourself first, then systematize, automate, or hand it off as the team grows.

What you'll be doing

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

Nice to have: prior experience at a startup, fintech, or insurtech; exposure to insurance, financial services, or AI-native products; experience managing multi-stakeholder projects or external partnerships; comfort with light financial modeling and operational analysis.

Tech stack: Not specified.

Requirements

• 1 to 3 years at a top-tier firm (Goldman, McKinsey, Bain, BCG, or comparable); strong new grads considered
• Strong analytical skills including spreadsheet proficiency, financial modeling, and data interpretation
• Excellent written communication for investor emails, internal docs, and external partner notes
• High agency and bias toward action, ships before it is perfect, moves without waiting to be unblocked
• Based in NYC or genuinely committed to relocating
• High integrity, this is a right-hand role and trust is the foundation of the hire

Green Flags

• Background from a top-tier firm or program (Goldman, McKinsey, Bain, BCG, or equivalent)
• Has multiple strong offers or optionality, and is choosing startups anyway
• Can point to a project they owned end-to-end and drove from start to finish
• Scrappy and fast execution mindset
• Genuinely excited about building from the ground floor
• Eyes light up when talking about the work, not the title or the comp

Red Flags

• 10+ years at a large consulting or corporate firm, wrong pace and wrong expectations for this stage
• Needs heavy direction or structured processes to execute
• Changing jobs every 3 months or less
• Motivated primarily by title or structured career ladders over ownership and impact
• Any integrity concerns, this is an immediate disqualifier
• Tier-two firm background without clear evidence they were performing at a tier-one level
• Primary background in venture capital (e.g., VC analyst, scouts, associate, investor roles)

Why Join

• Right-hand seat to the CEO with direct founder mentorship
• Genuine ownership and autonomy from day one
• Meaningful equity and a front-row seat to the AI transformation of a $2T industry