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.

You’ll be the first voice customers hear when they come to Harper.

The Thesis

Every customer conversation you have becomes data that makes our AI smarter. Every detail you capture correctly means a business gets the coverage they actually need. This role is the front line of a company transforming how millions of businesses get insured—and the foundation for what comes next.

The Role

High-volume, high-intensity phone work. You’ll talk with business owners all day—contractors, restaurant owners, consultants, trucking companies—learning about their operations and capturing the information that powers everything downstream.

You’re the critical top of funnel—the first voice of the company. Your job is to quickly and accurately understand all types of businesses, identify their potential risks, and ask the right questions so we can get quotes faster with more accurate coverage. You work closely with Sales and Customer Service, and everything you capture feeds directly into our AI training pipeline.

What You’ll Do

• Handle back-to-back customer calls — Continuous engagement throughout your shift; every call matters

• Capture information with precision — Type while talking, listen while entering data, maintain accuracy at speed

• Be the face of Harper — Professional, confident, helpful—hour after hour, call after call

• Feed the AI system — Your documentation becomes training data; patterns you flag improve the product

• Flag edge cases — Identify exceptions and escalate when needed

You Might Be a Fit If…

• You’ve done high-volume customer work before (call center, sales floor, customer service)

• You’re comfortable with technology and AI tools

• You have business acumen and can quickly understand how different businesses operate

• You can type fast while talking—simultaneously, not sequentially

• You stay organized under pressure with strict protocols and shifting priorities

• You genuinely enjoy talking to people—it energizes you, not depletes you

• You have stamina for 12-hour shifts and maintain quality from first call to last

Requirements

• Prior experience in high-volume phone or customer-facing roles

• Strong typing speed and multitasking ability

• Professional communication skills

• Reliable internet and quiet home environment

• Availability for Monday–Friday, ET and PT

Nice to Have

• Experience in insurance, financial services, or regulated industries

• Bilingual (Spanish)

• CRM or call center software experience

Compensation

• Salary: $22.00-$26.00/hour + performance bonuses

• Variable/Commission: Performance bonuses based on volume and quality

• Location: Remote

• Schedule: Monday–Friday, overtime eligible

Benefits

• Health, dental, and vision insurance

The Process

1. Application questions

2. AI assessment — Mock intake call with an AI agent

3. Team lead screen — Skills and culture fit

4. Manager screen — Alignment on pace and expectations

5. Founder call

To Apply

This is a great first tech job. We’re rapidly growing, and for the right person, this is a foot in the door to a career at one of the fastest-moving companies in the industry. If you thrive under pressure and get energy from customer interaction—apply.