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.

You're the first human voice in a business we're rebuilding as software — but this isn't your traditional SDR seat. On top of high-volume calls, emails, and LinkedIn follow-ups, you'll work shoulder-to-shoulder with the account executive (AE) and intake teams on real deals, helping close 50+ a month. You prospect and cold-call business owners, work inbound leads as they land, and support intake by gathering the business details needed to get a quote moving. Either way the job is the same: get on the phone, qualify fast, capture accurately, and move to the next one.

You're the person who turns a cold contact or a curious inbound into a real opportunity the AE team can close. There's no ambiguity about what this job is — and 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.

• Run outbound at volume. Outbound calls, email campaigns, and LinkedIn follow-ups — you're the first voice of Harper. Cold-prospect leads, warm them up fast, and 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 an interested business owner is on the line, you're the first voice they hear. Learn their operation quickly, ask the right questions, and capture everything needed to get them 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.

• Use AI habitually. Stay highly detail-oriented, but know when to lean on AI to turbocharge your efficiency.

• 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; the AE closes. Your handoff quality moves their conversion directly.

• You're excited to join the sales team at a hyper-growth AI startup disrupting the insurance industry.

• 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, stayed unfazed, and called the next one.

• Talking to people all day energizes you — call 50 gets the same energy as call 1.

• You don't need hand-holding. You need a shot.

• You get that high standards and high growth come together, and you wouldn't have it any other way.

This is high-volume, high-rejection phone work, on-site in San Francisco, Monday–Friday, 8am–8pm ET, 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.

• Salary: $75,000–$125,000 OTE based on experience; higher for top performers.

• Location: On-site, San Francisco. Full-time, in-office.

• Schedule: Monday–Friday, 8am–8pm ET. The hours are demanding; the people who last here know that and choose it anyway.

• Uber commuter benefits

• Meals provided — breakfast, lunch, and dinner

• Snacks, drinks, and coffee stocked daily

• Free gym membership

• Health, dental, and vision insurance

• Fluency in fast-paced, demanding environments (new grads OK)

• Strong multitasking ability: talk, listen, and log simultaneously

• Professional, confident, and clear on the phone

• Based in San Francisco, in-office, full-time

• Insurance, fintech, or financial-services background

• Bilingual+

• SDR or BDR roles at high-volume SaaS or AI companies

• Outbound or customer-success-focused experience

We run a tight, no-fluff process and move fast, because that's how we operate.

1. Fit and alignment call — who you are, what drives you, and whether Harper is the right environment for you to do the best work of your life.

2. Super day — 3–4 hours on-site: case exercises, hands-on work with the team, and a real look at what it means to be part of something built at this level. As much for you as for us.

Send your resume and tell us about the highest-rejection stretch of work you've ever pushed through — and why you kept dialing.