The Problem
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.
What You’ll Do
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
You Might Be a Fit If…
You have raw analytical horsepower and think in systems
You have a bias toward action—you move toward execution, not away from it
You’re not afraid to engage with complexity; you’re energized by it
You care deeply about getting things done with excellence
You’re eager to learn and constantly pursuing improvement
You’ve worked in high-intensity environments (banking, consulting, PE, high-growth startups) and thrived
You want exposure to every part of building a company—and you’re willing to work for it
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 Have
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
Compensation
Salary: $140,000 - $160,000 + performance bonuses & equity
Location: San Francisco, in-office
Schedule: Monday–Friday, 5 AM – 8 PM. The hours are long. The learning curve is steep. The people who thrive here wouldn't have it any other way.
Benefits
Health, dental, and vision insurance
Commuter benefits
Team meals and snacks
The Process
Founder screen — Initial fit and alignment
On-site day — Meet the team, work through real scenarios
To Apply
We want to be direct: this will be hard. We start early and run late. The intensity is comparable to being a banking analyst, except the stakes are higher because it’s real. If you’re up for that—if you’re okay with ambiguity, okay with the scope changing constantly, okay with this potentially being the hardest you’ve ever worked—then the ceiling is limitless.
If you want exposure to everything, trust to execute, and a path that accelerates faster than anywhere else—send your resume and tell us about a time you owned something ambiguous and drove it to completion.