We're on the frontier of building an AI-native professional services company. We're building the best AI commercial insurance distribution engine for scale.

The Problem

36 million businesses in America need insurance. It's not optional—regulations require it, contracts demand it, landlords won't lease without it. Yet the industry is broken.

77% of small businesses are underinsured. 40% have no coverage at all. Most don't even understand what their policies cover. They're running with risk because the distribution system failed them—too slow, too opaque, too confusing to navigate.

Over 90% of commercial insurance distribution is still human-led. The same manual process as 30 years ago—just with email instead of fax. Brokers playing phone tag with underwriters. Customers chasing quotes for weeks. Everyone hoping someone gets it right.

We're building the inverse: 90%+ AI-led, inching toward the higher 90s. Not by automating tasks, but by capturing the decision traces—the exceptions, precedents, and cross-system context—that let AI make the same judgment calls humans do.

The Thesis

Every industry with human-bounded distribution consolidates rapidly once someone makes it computational. Search had thousands of engines until Google made ranking computational. Ride-hailing was fragmented until Uber made dispatch computational.

When distribution becomes computational, Jevons Paradox kicks in: increased efficiency leads to increased consumption. Better search didn't mean less searching—it meant vastly more. Cheaper rides didn't mean fewer trips—it meant transportation for use cases that never existed.

Insurance will follow the same pattern. When getting the right coverage becomes fast and frictionless, the 77% of underinsured businesses will finally get properly protected. The market expands, not contracts.

We're building the engine that makes that happen. But computational distribution still needs fuel—real customer insight, vertical-specific knowledge, and GTM motions that feed the machine.

The Role

You'll own go-to-market execution in the real world. Not "supporting" marketing—creating demand, pressure-testing messaging, and turning human insight into scalable workflows.

You'll be embedded with sales, product, and engineering, working directly with customers in core verticals like construction, med spas, and manufacturing while helping Harper expand rapidly into new segments. The best GTM strategies are built on the ground, not in slides.

We're looking for an operator who learns by doing and thrives in motion. You'll work directly with the founders. There's no committee. No approval chain. You run it, you measure it, you own the outcome.

What You'll Do

Own vertical GTM execution. Launch and scale field marketing efforts across construction, med spas, manufacturing, and new verticals. Develop deep understanding of buyer behavior, decision cycles, and objections in each segment. Build repeatable vertical-specific GTM playbooks that become company assets.

Be in the market. Meet customers on-site, attend industry events, host roundtables, and build partnerships. Identify conferences, associations, and offline channels worth investing in. Act as a direct extension of Harper's brand in the field—not behind a desk, but in front of the people we serve.

Close the GTM feedback loop. Translate field insights into better messaging, landing pages, and demand gen strategies. Work closely with sales and engineering to turn insights into automation and tooling. When something works in one vertical, systematize and scale it across the org.

Experiment and iterate fast. Run fast GTM experiments—events, partnerships, outbound plays, localized campaigns. Measure results, double down on what converts, kill what doesn't. Optimize for learning speed and impact, not perfection.

You Might Be a Fit If…

You're an operator, not a planner. You like owning outcomes, not decks. You think in systems: insight → playbook → automation → scale. You'd rather run an experiment today than perfect a strategy next quarter.

You're energized by the field. Being close to customers isn't a chore—it's where you do your best work. Events, site visits, partner meetings—that's where you learn what actually matters.

You've built GTM from scratch. 5+ years launching or scaling new markets, verticals, or regions. B2B, SMB, or services-heavy industries. You've created demand through events, partnerships, local campaigns, or direct customer engagement—and tied it to pipeline, not vanity metrics.

You ship fast and iterate. You thrive in fast, noisy, high-velocity environments. Priorities change. Ambiguity is constant. You don't wait for permission or perfect information.

You translate insight into action. Strong written and verbal communication. You can synthesize what you're seeing in the field and clearly articulate what to do next—then actually do it.

Compensation

Salary: $100,000 - $140,000

Location: San Francisco, in-office. We build together. Expect to be in the market regularly—events, customer visits, partner meetings.

The Process

1. People screen — Initial fit and alignment

2. Case study — GTM prioritization and field experiment design

3. Lead screen — Skills and culture fit

4. Work trial — See how you operate in real time

To Apply

We're building a vertically integrated AI platform that connects go-to-market, sales operations, customer service, and retention under one architectural roof. That integration creates compounding through feedback loops—every interaction makes the system smarter. Thousands of businesses already trust us.

If you want to build GTM motions that feed a machine that's never existed, work directly with customers in industries most people ignore, and move with people who show up with the same intensity every day—send your resume and tell us about a market you've cracked.

We're a championship-minded team. We push each other. We move fast. We care about craft. If that sounds like where you belong, let's talk.