Customer Service Representative

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.

Plenty of people can tell a customer what their policy says. You're licensed to change it.

The Thesis

A business owner calls because they just won a job and the contract demands an additional insured endorsement by Friday. Or they bought a truck. Or they opened a second location. At most brokerages that starts a week of voicemail. Here it takes a licensed person who knows the product, can read the contract, and can make the change today.

That's the difference this role makes, and it's why this is the largest and most important group in our service organization. AI is taking the repetitive work off your plate—status lookups, standard certificates, document retrieval—so the licensed judgment is what's left. That's the part worth doing.

It's also the bench. Our specialists—the people who own carrier relationships and handle our most complex accounts—come from this team. We'll get you licensed in every state you need and back you to grow.

The Role

You do the licensed service work: endorsements, certificates with real wording requirements, binding, coverage questions answered from the policy itself, cancellations and reinstatements, renewal preparation, audit intake, and billing corrections. When the front line can't resolve something without a license, it comes to you—and you finish it.

You work directly with carriers and wholesalers on routine service, and you'll learn their people and their portals quickly. You have genuine authority here: policy changes inside appetite, governed payment actions, reinstatement requests, and closing an issue once the work is actually done.

The pace is the real thing to know. Certificate wording and endorsements turn around inside a business day. A bind request goes out the day validation passes. A reinstatement request goes out the day the notice lands. When something needs coverage judgment or a different market, you pass it to a specialist with the history and evidence already assembled—a clean handoff, never a shrug.

What You'll Do

• Keep policies current with the business — Endorsements for new vehicles, drivers, locations and equipment, plus limit changes inside appetite; a customer's coverage should never lag behind their growth

• Get certificates exactly right — Additional insured, waiver of subrogation, primary and non-contributory, loss payee, notice of cancellation; read what the customer's contract actually requires and issue to match

• Carry new business across the line — Validation, chasing subjectivities, bind requests, DocuSign and premium finance packets, policy delivery, and the binder-to-policy check that confirms it's real

• Answer coverage questions from the policy — Open the form, read it, and explain in plain language what a business is and isn't covered for

• Keep coverage in force — Cancellation notices, payment cures, reinstatement requests and autopay enrollment; a lapse is the worst thing that can happen to a customer

• Prepare renewals properly — Exposure updates, loss runs, and flagging the accounts a specialist should remarket for better terms

• Run audits and inspections at intake — Payroll and sales records, photographs, affidavits, scheduling and carrier-portal submission, so nothing stalls on a missing document

• Fix billing — Refunds and corrections inside your authority, resolved rather than explained

• Hand off complete, never half-done — When a case needs market or coverage judgment, the specialist gets the full timeline and evidence pack from you

• Make the tooling better — You'll live in our service workbench; tell Product and Engineering what should be one click instead of twenty

You Might Be a Fit If...

• You're licensed in property & casualty, or you're ready to get licensed fast

• You'd rather resolve the thing than route the thing

• You can follow a playbook and speak up when the playbook is wrong

• You're comfortable picking up the phone to an underwriter

• You're accurate at speed—volume doesn't make you sloppy

• You like knowing the product deeply, not just the process

• You want to grow into a specialist who owns carrier relationships and the hardest accounts

• You're curious about AI tools and want a say in what gets automated

Requirements

• 2+ years in commercial lines service, account management, or brokerage operations

• Active property & casualty license, or the ability to obtain one quickly—we handle resident, non-resident and reciprocal licensing across all 50 states

• Working knowledge of certificates, endorsements, and binding documentation

• Ability to talk, type and navigate multiple systems at once without losing accuracy

• Comfort with technology and genuine interest in working alongside AI tools

• Based in New York City or San Francisco, or willing to relocate; this role is in-office

Nice to Have

• E&S and surplus lines exposure: filings, surplus lines tax, binding packets

• Premium finance familiarity: PFAs, reconciliation, finance-company coordination

• Workers' comp and class-code knowledge

• Wholesaler, MGA, or high-volume commercial lines background

• Bilingual (Spanish)

• Experience at an insurtech or tech-forward brokerage

Compensation

• Pay: $75,000 - $95,000, depending on experience and licensing

• Type: Full-time, exempt

• Sign-on bonus: Available for strong candidates

• Location: San Francisco, Atlanta, or New York City, in-office

• Schedule: Monday–Friday, 8 AM – 8 PM ET. The hours are long. The learning curve is steep. The people who thrive here wouldn't have it any other way.

• Start date: Immediate

Benefits

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

The Process

1. Team lead screen — Skills and culture fit

2. Manager screen — Alignment on pace and expectations

3. On-site day — Meet the team, see the operation, work through real scenarios

To Apply

If you've spent a few years doing commercial lines service well and you're tired of a queue that never empties and a system that fights you, come do the same work with better tools and real authority. Send your resume and tell us about a customer you got covered when the deadline was tight.