Field Growth & Engagement 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.

Computational distribution still needs fuel—real customer insight and GTM motions that feed the machine.

The Thesis

The best GTM strategies are built on the ground, not in slides. You’ll own vertical go-to-market execution in the real world, pressure-test messaging with real customers, and turn human insight into scalable workflows. In 6-12 months, you’ll have built repeatable playbooks for multiple verticals that become company assets.

The Role

You’ll own go-to-market execution in the field. Embedded with sales, product, and engineering—working directly with customers in verticals like construction, med spas, and manufacturing while expanding into new segments.

You work directly with founders. 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 in construction, med spas, manufacturing, and new verticals

• Be in the market — Customer site visits, industry events, roundtables, partnerships

• Close the feedback loop — Translate field insights into better messaging, landing pages, and automation

• Experiment and iterate fast — Run GTM experiments; measure results; double down or kill quickly

You Might Be a Fit If…

• You’re an operator, not a planner—you think in systems: insight → playbook → automation → scale

• Being close to customers isn’t a chore—it’s where you do your best work

• You’ve built GTM from scratch (5+ years in new markets, verticals, or regions)

• You ship fast and thrive in ambiguity

• You translate field insight into clear action—then execute

Requirements

• 5+ years launching or scaling new markets, verticals, or regions

• B2B, SMB, or services-heavy industry experience

• Track record of creating demand through events, partnerships, or direct engagement—tied to pipeline

• Strong written and verbal communication

• Based in San Francisco or willing to relocate

Nice to Have

• Insurance, fintech, or regulated industry experience

• Experience with marketing automation and CRM systems

• Prior startup or high-growth company experience

Compensation

• Salary: $100,000–$140,000 + performance bonuses

• Location: San Francisco, in-office (expect regular field travel)

Benefits

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

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

If you want to build GTM motions that feed a machine that’s never existed and work directly with customers in industries most people ignore—send your resume and tell us about a market you’ve cracked.