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