Sales Development Representative
Sales Development Representative
Harper is an AI-native commercial insurance company in San Francisco. We're not bolting AI onto insurance — we're rebuilding the entire business as software, on a simple bet: turning expert human judgment into compute is one of the largest transitions left to make, and a trillion-dollar industry still run 90% by hand is the place to prove it. We've grown ~100x in the last year and we move at that speed — on-site, in person, long days, very high standards. Almost no one joins Harper for insurance; they join to build the company that replaces how it works.
The role
You're the first human voice in a business we're rebuilding as software. Outbound and inbound, all day, every day. You dial cold business owners, work the inbound leads as they land, qualify fast, capture the details cleanly, and hand a real opportunity to the team that closes it.
There's no ambiguity about what this job is. You're on the phones. That's the work, and it's the whole work. It's also the most direct way into an AI-native company that's actually shipping: the best performers here don't stay SDRs. This is a deliberate first step, not a ceiling — but you earn the next step by being undeniable at this one.
What you'll do
Run outbound at volume. Dial cold leads, warm them up fast, find the businesses that need coverage. Rejection is part of the rhythm. You hear "no," and you dial the next one.
Work inbound the moment it lands. When a business owner comes to us, you're the first voice they hear. Learn their operation quickly, ask the right questions, capture what's needed to move a quote.
Qualify fast and accurately. Figure out what a business does, what risk it carries, and whether we can help — in minutes, not hours.
Capture with precision. Type while you talk. Your notes are complete, accurate, and fast, because a clean intake means a faster quote and better coverage.
Hit volume and quality targets — both. You're measured on each. You don't trade accuracy for speed or speed for accuracy.
Hand off clean. You set the table; Sales closes. Your handoff quality moves their conversion directly.
Who you are
You've worked a high-volume phone role and you were good at it — or you haven't, but everyone who knows you is sure you would be.
Cold calls don't rattle you. You've been hung up on, and you called the next one without flinching.
Talking to people all day energizes you. It doesn't wear you down.
You can type while you talk — at the same time, not one after the other.
Call 50 gets the same energy as call 1.
You want a real foot in the door at a fast-growing company, and you know you have to earn it. You don't need hand-holding; you need a shot.
You get that high standards and high growth come together, and you want it that way.
The reality — read this before you apply
This is high-volume, high-rejection phone work, on-site in San Francisco, ~5am–7pm, Monday–Friday, in the building with the team. Most of your day is dialing, getting told no, and dialing again. The volume is the job; the rejection is the job. If that drains you, you'll be miserable here and it'll show by call 30.
But if you're the kind of person who gets sharper as the count climbs, this is one of the fastest and most honest paths into tech: you'll learn an entire industry from the inside, work at an AI-native company that's actually shipping product, and prove yourself somewhere the next step is real and earned. Almost no one takes this job for insurance. They take it for the door it opens.
Compensation & logistics
Salary: $80,000–$125,000 OTE depending on experience; higher for top performers. Plus bonus and commission.
Equity: Yes.
Location: On-site, San Francisco. Full-time, in-office.
Schedule: Monday–Friday, very early morning start, in-office 5 days a week.
Benefits
Uber commuter benefits
Meals provided — breakfast, lunch, and dinner
Snacks, drinks, and coffee stocked daily
Free gym membership
Health, dental, and vision insurance
Nice to have
Insurance, fintech, or financial-services background
Bilingual+
High-volume SaaS outbound experience (SDR/BDR roles running Salesloft, Outreach, ZoomInfo, Apollo, or similar)
Experience at a SaaS or AI company in an outbound or customer-facing role
Process
We run a tight, no-fluff process and move fast.
Fit and alignment call — who you are, what drives you, whether this is the right environment for you to do your best work.
Super day — 3–4 hours on-site: case exercises, hands-on work with the team, and a real look at the job. As much for you as for us.
To apply
Send your resume and tell us about the highest-rejection stretch of work you've ever pushed through — and why you kept dialing.
