Chief of Staff

Location: New York City, NY
Work Type: In-person
Employment: Full-Time
Experience: 1–3+ years
Salary: $130,000–$180,000 per year
Visa Sponsorship: None Available

About the Role

This is a high-leverage generalist role working directly alongside the CEO. The Chief of Staff owns whatever is most important that week, whether that is fundraising, operations, GTM, analytics, partnerships, or product strategy. The scope is intentionally broad and constantly changing.

The role demands strong judgment, analytical ability, exceptional execution, and a high degree of ownership. You will move rapidly across projects, solve problems independently, and build toward increasing agency from day one.

Early projects may span hiring sales agents, optimizing marketing campaigns, evaluating vendors, building financial models, developing partnerships, and bringing on new insurance carriers.

The expectation is that you build toward high agency quickly: own a project, solve it yourself first, then systematize, automate, or hand it off to new hires.

This is a role for someone who thrives on a blank canvas, operates with urgency, and is comfortable being accountable for whatever is most important at the time.

The culture is built around customer obsession, high integrity, and working hard while having a lot of fun. This is a right-hand role where trust, judgment, and execution are critical.

Key Responsibilities

• Support fundraising end-to-end, including investor research, deck iterations, data room management, and follow-up coordination

• Own operational projects from start to finish, including vendor evaluation, hiring pipeline buildout, and process design

• Analyze data to surface insights and inform decisions across lead conversion, unit economics, and carrier performance

• Support GTM strategy through lead generation, partnership outreach, and carrier relationship management

• Draft investor updates, internal documentation, and external communications independently

• Build out early-stage projects yourself first, then systematize or automate them and hand them off to future hires

• Jump into whatever is most critical each week

Requirements

• 1–3 years of experience at a top-tier firm such as Goldman Sachs, McKinsey, Bain, BCG, or comparable; exceptional new graduates considered

• Strong analytical ability with the ability to work comfortably in spreadsheets and build models

• Ability to identify meaningful signals in data without being directed

• Excellent written communication skills, with the ability to independently draft investor emails, internal briefs, and external partner communications

• High agency and bias toward action; figures things out before asking, ships before it is perfect, and does not wait to be unblocked

• High integrity and strong judgment; this is a right-hand role where trust is critical

• Based in NYC or genuinely committed to relocating

• Willingness to work 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

• Comfort with light financial modeling and operational analysis

Benefits & Perks

• Meaningful equity in an early-stage company

• Direct mentorship from the founder

• Autonomy and ownership from day one

• Front-row seat to AI transformation of a $2T industry

Interview Process

1. Pending Approval

2. Initial Screen

3. First Round

4. Second Round

5. Work Trial

6. Offer

7. Hired