Special Projects Lead

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

Benefits

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

The Process

1. Founder screen — Initial fit and alignment

2. 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.