Harper is nearing $5M ARR with clear line of sight to $10M ARR by Q1. We started in August of 2024 and were only at $400k of ARR in January. We're an AI-native insurance brokerage that's proven AI can work in traditional industries by building the systems ourselves first.
We've been trying to put people with traditional backgrounds into operational roles, and they never scale themselves - they only grow linearly. We keep needing to add more of them. We realized we need a different type of operator to create the leverage we need, where theoretically one person can handle 10,000 customers.
The best person to do this is someone who's scrappy and looking to ultimately build a workflow automation or AI-type company. So we decided to post a job for future AI founders. There'll be a lot of hard work, but you'll learn how to actually do AI automation directly and learn about insurance - a massive field you might want to start a business in. Because you'll be bought in, I can also teach you about being a founder and give you exposure to running a company.
- Handle customer calls, gather documents (licenses, photos, financials), coordinate with carriers in excess and surplus markets
- Process complex, unstructured data requests that create bottlenecks limiting our quote volume
- Work on automations that directly unlock more quotes = more revenue
- Experience firsthand where customer implementation challenges actually happen
- Work directly with our forward-deployed engineers to automate the pain points you experienced
- Become the technical PM for automating your own job
- Daily syncs with engineering about what broke, what's inefficient, what could be automated
- Build systems that eliminate the manual work you just completed
- See why 95% of AI implementations fail and learn to build the 5% that succeed
- Build learning systems with direct customer feedback loops, not static workflows
- Understand what prevents customer adoption - the gap that kills most AI startups
- Want to start an AI company within 2-3 years
- Technical literacy and systematic thinking about automation (insurance experience not required)
- Basic technical knowledge - strongly preferred to have a highly technical background (most successful applicants will currently be SWEs)
- Willing to commit minimum 1 year to this role
- Can handle dual-shift work: operations during business hours, automation work evenings/weekends
- Are scrappy and can handle hard operational work while thinking strategically
- Think differently than traditional operators (who just execute tasks vs. identifying automation opportunities)
- Want direct customer feedback loops before building your own AI company
- Are fascinated by where the 95% pilot-to-5% adoption gap actually happens
- Work directly with the founders on AI automation and company building
- Real experience with AI automation that actually works in production
- Deep exposure to insurance industry and potential business opportunities
- Technical PM experience working with forward-deployed engineers
- After 1 year: Y Combinator recommendations and our network connections
- Direct access to founders who've solved implementation challenges you'll face
- Experience with the customer implementation challenges that kill most AI startups
- $100K-150K based on experience
- Significant equity in fast-growing company
- Real impact on scaling from $3.5M to $10M ARR
This isn't glamorous work. You'll handle frustrated customers, chase down missing documents, and coordinate between carriers. But you'll systematically automate each process while learning why AI implementation is harder than anyone expects and how to make it actually work.
You'll work hard, but you'll learn how to build AI systems that customers actually adopt - knowledge that will make you one of the 5% of AI founders who succeed.
Ready to learn AI implementation from the inside? This role gives you the experience most AI founders never get: seeing why customers resist automation and learning how to build systems they actually want to use.