$130,000–$180,000 Per Year
Analysis Skills, Artificial Intelligence (AI), Artificial Intelligence (AI) Agents, Brokerage, Canvas, Data Management, Economics, Financial Modeling, Fundraising, Home Automation, Insurance, Lead Generation, Leadership, Mentoring, Organizational Skills, Performance Analysis, Project/Program Management, Spreadsheets, Startup, Technical Research, Technical Sales, Vendor/Supplier Evaluation, Writing Skills
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.