AI Product Manager

We're Rebuilding Professional Services from First Principles

Commercial insurance is broken not because of insufficient capital or demand—it's broken because distribution scales linearly. Traditional brokers need more people, more training, more locations. We're replacing that model with computational systems.

We're not building a better brokerage. We're building the model that makes traditional brokerages obsolete. We've proven the thesis: our sales reps generate 30x industry average revenue per head by moving everything except closing conversations to AI systems. This isn't productivity improvement—it's structural transformation.

Professional services represent a $12 trillion market in the US. Insurance is our entry point to proving that AI-native models can replace human-centric expertise with computational systems that scale exponentially. If we win here, we change how every knowledge work industry operates.

The Role: Own a Critical Product Domain

You'll own one of three high-impact modules in our AI-native commercial insurance platform:

Intake → Submissions

Transform how we collect customer information and route it to underwriters. Build product-led experiences that replace manual data gathering with intelligent automation. Drive submission quality, underwriter acceptance rates, and time-to-bind improvements.

Sales

Own the end-to-end sales product experience. Design tools and workflows that amplify rep productivity. Ship features that compress sales cycles, improve conversion, and enable reps to close deals while AI handles everything else.

Service & Retention

Build customer service and renewal experiences that maximize retention and expansion. Create tools that reduce handle time while improving satisfaction. Make renewals self-service and predictive.

What You'll Do

Discovery & Strategy

• Embed with agents, operators, and end users to understand workflows

• Define product strategy, roadmap, and success metrics for your domain

• Translate operational pain into product requirements

Execution & Delivery

• Write crisp PRDs and user stories that engineering can ship immediately

• Partner with data engineers, core engineers, and AI application engineers to deliver features

• Ship weekly, iterate based on metrics, kill what doesn't work

Measurement & Iteration

• Instrument everything: conversion rates, cycle times, adoption, CSAT

• Design and run experiments to validate hypotheses

• Use data to drive prioritization and prove impact

Cross-Functional Leadership

• Work with Operations to embed AI agents across workflows

• Manage dependencies across pods and engineering teams

• Create release plans and enablement materials

• Communicate tradeoffs clearly to stakeholders and founders

Success Looks Like

30 Days:

• Shipped 2-3 high-impact features in your domain

• Built dashboard tracking core metrics

• Earned trust of ops team and engineers through execution

60 Days:

• Demonstrable improvement in key metrics (conversion, cycle time, or retention)

• Running weekly experiments with clear hypotheses

• Product roadmap aligned with business priorities

6 Months:

• Your domain operating measurably more efficiently than before you arrived

• AI agents embedded in production workflows

• Product-led experience replacing manual processes

• You're the go-to expert for your domain across the company

What We're Looking For

Required

• 4-7+ years shipping production software as a PM

• Demonstrated ownership of complex workflows or multi-step funnels

• Technical fluency: build dashboards, design experiments, deep understanding of AI

• Worked closely with engineers in fast-paced, ambiguous environments

• Familiarity with AI-enabled products or operational AI systems

• Bias to action: Ship 80% solutions fast, iterate to 95% with data

Preferred

• Experience in insurance, Insurtech, or regulated domains

• Domain expertise matching your module:

  • Intake → Submissions: Back-office operations, workflow automation

  • Sales: CRM systems, sales funnels, rep enablement tools

  • Service & Retention: Customer service platforms, retention tooling

• Track record integrating AI agents into operational workflows

• Previous startup or high-growth company experience

Critical Attributes (These Matter More Than Resume)

Ownership

You take responsibility for outcomes, not deliverables. If something breaks, you fix it. You think like an owner, not a passenger.

Pace

You ship in days, not weeks. You're comfortable with "good enough for now, will iterate." You'd rather launch three imperfect solutions than one perfect solution.

Taste

You know when simplicity wins and when complexity is necessary. You see the 80/20 immediately. You're ruthless about cutting unnecessary work.

Day Zero Mindset

You'll throw away your work if data proves it wrong. No ego about past decisions. Status quo bias is your enemy.

How We Operate

"There is no try, there is just do"

Ship fast, measure, iterate. Analysis paralysis is failure. Better an 80% solution today than perfection in two weeks.

"Actions lead to information"

The fastest way to learn is to ship and measure. Don't wait for perfect data—start with what you have.

"Strong opinions, loosely held"

Form viewpoints backed by data. Argue passionately. But when new data emerges, pivot completely. We're always at day zero.

"Software updates, not training updates"

When you discover an insight, it should improve the system automatically for everyone—not require retraining humans.

What You're Getting

Compensation

• Base: $110K - $150K (depending on experience)

• Equity: 0.01% - 0.05%

Real Learning

• See how AI works in production at scale (not pilots that never launch)

• Learn company building from founders executing a 100x growth trajectory

• Pattern recognition for what makes AI systems succeed vs. fail

• Knowledge most founders spend years and their capital learning

Career Acceleration

• 12 months here = 3-5 years of learning anywhere else

• Work with exceptional operators pushing you to improve daily

• Front-row seat to transforming a trillion-dollar industry

Benefits

• Full health, dental, vision

• Relocation assistance to SF if needed

• Learning & development budget

• Work with founders who will make you a better operator

Location: Hybrid/remote acceptable with core hours overlap. In-person collaboration strongly preferred.

The Mission

We're building the first professional services factory. For centuries, professional services have been human-centric. We're making them computational.

The data you generate, the products you ship, the workflows you transform—they don't just improve margins. They prove that computational systems can replace expert judgment at scale. That professional services can be a software update, not a hiring plan.

If you want to own outcomes, ship AI-powered products that matter, and help transform how knowledge work operates—we should talk.

Harper is an equal opportunity employer. We believe diverse teams build better products and create competitive advantages. We encourage applications from people of all backgrounds, experiences, and perspectives.

Learn more: harperinsure.com