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.
Behind every AI system is a business that needs to actually run. Someone has to make all of it work—and make it work better every week.
The Thesis
Underwriters need answers. Carriers need data. Sales needs enablement. Customers need follow-ups. Right now, a lot of that runs on people keeping track of things in their heads. Someone has to learn the entire operation—not one slice of it—and turn tribal knowledge into systems that scale. The patterns you spot become the specs that engineering builds next. The people who learn this business inside out become the ones who run it.
The Role
One day you're following up with underwriters on a stalled quote. The next you're building a process to make sure no quote ever stalls again. The day after that you're on a call with a customer, then feeding what you learned into a product spec.
No two weeks look the same. That's the point. You'll rotate across sales enablement, underwriting operations, customer service, and carrier relations—owning real work in each, not observing. The scope is wide because the company moves fast and the problems don't respect org charts.
What You'll Do
Run the operation — Tackle underwriter follow-ups, manage carrier communications, keep deals moving through the pipeline
Build systems that scale — Create processes, workflows, and organizational structures that make the entire team more effective; make manual work obsolete
Own customer and underwriter relationships — Be the person who ensures nothing falls through the cracks on either side
Enable sales — Arm the sales team with what they need to close: data, materials, process improvements, feedback loops
Touch every stage of the insurance lifecycle — Intake, onboarding, servicing, renewals; you'll see how the entire business works, not just one slice
Shape what engineering builds — Work directly with engineering teams to translate operational pain points into product requirements
Jump between roles — Move fluidly across functions based on what's most urgent; comfort with ambiguity isn't optional, it's the job
You Might Be a Fit If...
You've been the best at something before—top of your class, captain of the team, first in your cohort—and you're looking for the next thing to pour that into
At every previous job, you ended up doing way more than your title suggested
You get energy from moving fast across lots of different problems, not sitting in one lane
You'd rather own a messy problem end-to-end than execute a clean task someone handed you
You context-switch without losing intensity
You care about outcomes, not job descriptions
You want to understand how an entire company works, not just your corner of it
Requirements
1–3 years of experience in a high-pace environment (startup, consulting, banking, operations, or equivalent)
Strong communication skills—written and verbal—with customers, underwriters, and internal teams
Comfort with data: you don't need to be a data scientist, but you should be able to pull insights from a spreadsheet and make a decision
Bias toward action over analysis
Based in San Francisco or willing to relocate immediately
Nice to Have
Previous startup or founder experience
Insurance, fintech, or regulated industry exposure
Familiarity with CRM tools, workflow automation, or AI-assisted tooling
Background in sales, customer success, or account management
Compensation
Salary: $110,000–$140,000 + performance bonuses & equity
Location: San Francisco, in-office
Schedule: Monday–Friday, 5 AM – 8 PM. The hours are long. The learning curve is steep. The people who thrive here wouldn't have it any other way.
Benefits
Health, dental, and vision insurance
Commuter benefits
Team meals and snacks
The Process
People screen — Initial fit and alignment
Lead screen — Skills and culture fit
Super day — Case exercise and hands-on work with the team
To Apply
This role is a launching pad. People who thrive here go on to run functions, lead teams, or start companies—because they've seen every part of how a business actually works. 12 months here compresses years of learning into one.
If you've been waiting for the opportunity that finally matches your ability—send your resume and tell us about a time you owned something messy and made it work.