Chief of Staff

About the Role

This 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 for

Required

• 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