Harper
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
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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
#J-18808-Ljbffr