Special Projects Lead

Harper•San Francisco, CA

8d•$140,000 - $160,000•Onsite

About The Position

36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We’re building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We’re adding ~1,000 customers per month. We’ve grown 100x since last year. We’re looking to do even more this year—and that’s why we’re hiring. We just closed our $36M Series A. We’re at an inflection point where the systems we build now determine whether we scale from $30M in premiums to $300M—and eventually to billions. The Thesis This role is custom-built for someone who can operate as a future founder inside Harper. Someone who thinks holistically about the business, understands the customer deeply, and solves first-principles challenges across product, operations, growth, and automation. This is not a job with a fixed scope. The company is changing fast. What we need is someone who can flex across the business and tackle whatever becomes most urgent. Week to week, it will shift. The work you do will meaningfully shape the company’s trajectory. The Role You’ll work directly with the CEO on the hardest problems in the business—with inclusion in everything substantive. Biz ops, growth, strategic projects, investor materials, M&A diligence, and whatever else becomes urgent. The goal is for you to see every part of this business, deeply. If you perform the way we think you can, this role evolves into whatever makes sense—running a function, becoming a true right-hand, or using what you learn here to go build your own thing. You’ll understand how to build a company, start a company, and run a team.

Requirements

2-5 years in high-intensity analytical or operational roles (investment banking, private equity, management consulting, or equivalent startup experience)
Exceptional analytical skills—comfortable with complex data, financial modeling, and ambiguous problem sets
Strong written and verbal communication
Ability to operate autonomously and context-switch rapidly
Track record of delivering under pressure with high standards
Based in San Francisco or willing to relocate immediately

Nice To Haves

Experience in insurance, fintech, or regulated industries
Background working directly with founders or C-suite
Familiarity with AI/automation tools and workflows
Prior startup or 0→1 experience

Responsibilities

Tackle the CEO’s hardest problems — Direct access to everything substantive; scope shifts week to week based on what’s most critical
Build 0→1 systems — Across underwriting operations, customer experience, and risk evaluation; leverage AI to replace historically manual brokerage workflows
Run deep analysis — Customer interactions, underwriting requirements, operational workflows; uncover patterns, improve conversion, increase throughput
Bridge engineering, operations, and growth — Translate customer needs and market realities into product requirements and iterative improvements
Own mission-critical problems end-to-end — Gather data, map the system, identify constraints, propose solutions, run experiments, drive to completion
Manage cross-functional initiatives — Coordinate across engineering, carriers, underwriters, and customers with speed, clarity, and high quality
Build the intelligence layer — Dashboards, metrics, and reporting structures that surface truth and drive clarity on throughput and efficiency