Sales Development 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.

The Role

High-volume, high-intensity phone work — outbound and inbound, all day, every day.

You’ll prospect and cold call business owners, and you’ll handle inbound leads as they come in. Either way, your job is the same: get on the phone, qualify fast, capture accurately, and move to the next one. You’re the first voice of Harper — the person who turns a cold contact or a curious inbound into a real opportunity for our sales team to close.

There’s no ambiguity about what this job is. You’re on the phones. That’s the work, and it’s the whole work.

What You’ll Do

• Run outbound prospecting calls — You’re dialing cold leads, warming them up fast, and identifying businesses that need coverage. Rejection is part of the rhythm; you don’t let it slow you down.

• Handle inbound intake calls — When business owners come to us, you’re the first voice they hear. You learn their operation quickly, ask the right questions, and capture everything needed to get them a quote.

• Qualify fast and accurately — You figure out what a business does, what risks they carry, and whether we can help them — in minutes, not hours.

• Capture information with precision — You type while you talk. Your notes are complete, accurate, and fast. A clean intake means a faster quote and better coverage.

• Hit daily volume and quality targets — You’re measured on both. You don’t sacrifice accuracy for speed or speed for accuracy.

• Hand off cleanly to Sales — You set the table. Sales closes. Your handoff quality directly affects conversion.

You Might Be a Fit If…

• You’ve worked a high-volume phone role before — outbound sales, call center, SDR, customer service — and you were good at it

• Cold calling doesn’t faze you; you’ve been hung up on and called back

• You’re energized by talking to people all day, not worn down by it

• You can type while talking — simultaneously, not sequentially

• You stay sharp and professional on call 50 the same as call 1

• You want a real foot in the door at a fast-growing company and you know you have to earn it

Requirements

• Prior experience in a high-volume outbound or inbound phone role

• Strong typing speed and multitasking ability — talk, listen, and log at the same time

• Professional, confident, and clear on the phone

• Based in San Francisco, in-office

Nice to Have

• Experience in insurance, fintech, or financial services

• Bilingual (Spanish)

• CRM or call center software experience (Salesforce, HubSpot, Five9, etc.)

Compensation

• Salary: $85,000–$125,000 DOE + performance bonuses

• Location: San Francisco, in-office

• Schedule: Monday–Friday, 5 AM–8 PM. This is not a typo. The hours are long. 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

1. People screen — Initial fit and alignment

2. Lead screen — Skills and culture fit

3. Super day — Case exercise and hands-on work with the team

To Apply

This is the fastest way into tech—and the best one. If you want to learn an entire industry, work at an AI company that's actually shipping, and grind your way into a real career—apply.