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.
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.
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.
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’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
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
Experience in insurance, financial services, or regulated industries
Bilingual (Spanish)
CRM or call center software experience
Salary: $22.00-$26.00/hour + performance bonuses
Variable/Commission: Performance bonuses based on volume and quality
Location: Remote
Schedule: Monday–Friday, overtime eligible
Health, dental, and vision insurance
Application questions
AI assessment — Mock intake call with an AI agent
Team lead screen — Skills and culture fit
Manager screen — Alignment on pace and expectations
Founder call
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.
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