About the RoleThis is a rare, high-trust opportunity to serve as the right hand to the CEO at a fast-growing, early-stage insurtech marketplace that is reimagining how consumers compare and purchase insurance. The company connects users with real, bindable quotes from dozens of top carriers - combining technology with personalized advisory to eliminate friction and spam from the insurance-buying experience.
As
Chief of Staff, you will operate at the center of the business - owning cross-functional initiatives, supporting fundraising execution, helping scale the go-to-market motion, and ensuring the CEO's highest priorities move forward with urgency and precision. This role is ideal for a high-agency operator who thrives in ambiguity, ships before things are perfect, and is energized by building from zero to one.
This is a fully on-site role in San Francisco, CA, requiring in-person availability 6 days per week including Saturday. No visa sponsorship is available - candidates must be legally authorized to work in the United States.What You'll Do- Act as the CEO's operational partner - systematize work, track priorities, and ensure end-to-end project ownership across the business
- Support fundraising activities, including investor communications, deck preparation, data room management, and relationship tracking
- Help recruit, onboard, and scale sales and go-to-market teams
- Build and maintain financial models, business analyses, and dashboards to inform strategic decisions
- Draft and refine investor emails, internal memos, partner communications, and executive-level documents
- Collaborate across GTM, operations, product, and marketing to drive alignment and remove blockers
- Identify operational inefficiencies and design lightweight systems and processes to address them
- Manage special projects from scoping through completion with minimal direction
What We're Looking forRequired
- 1-3 years of professional experience in consulting, investment banking, startup operations, strategy, or a similarly high-intensity environment - strong new graduates with exceptional signals will be considered
- Strong analytical skills: advanced spreadsheet proficiency, financial modeling, and the ability to synthesize data into clear recommendations
- Excellent written and verbal communication skills; comfortable producing polished external and internal documents
- Proven ability to own projects end-to-end with minimal supervision in a fast-paced, ambiguous environment
- Entrepreneurial mindset - high agency, bias toward action, comfort operating without a playbook
- Experience with or strong interest in fundraising and investor relations
- Experience supporting the hiring or scaling of sales or GTM teams
- Proficiency with Google Workspace, Excel, and CRM or analytics tools
- High integrity and discretion - this is a trust-foundational role with direct exposure to sensitive business information
- Located in San Francisco or genuinely committed to relocating before the start date
- Must be legally authorized to work in the United States without visa sponsorship
Nice to Have
- Familiarity with investor communications, pitch decks, and fundraising processes
- Background from a top-tier firm or elite institution (e.g., McKinsey, JPMorgan, or equivalent)
- Prior experience at a high-growth startup, insurtech, or fintech company
Compensation & Benefits- Salary: $130,000 - $180,000 per year, depending on experience
- Early-stage equity participation
- Direct exposure to company leadership and fundraising at the ground floor
Location- On-site in San Francisco, CA - 6 days per week including Saturday
- Visa sponsorship is not available; candidates must be authorized to work in the United States
