Founding 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.

You’ll be the first voice customers hear—and the engine that feeds our entire sales machine.

The Thesis

Every conversation you have becomes data that makes our AI smarter. Every business you qualify correctly means faster closes and better coverage. This role is the front line of a company transforming how millions of businesses get insured—and the fastest path to becoming a closer yourself.

Top performers promote to AE within 6-12 months. We’re not hiring for a seat-warmer position. We’re hiring future sales leaders who want to learn the business from the ground up.

The Role

High-volume, high-intensity phone work with a purpose. You’ll talk with business owners all day—contractors, restaurant owners, consultants, trucking companies—qualifying opportunities and setting up our closers to win.

You’re not just booking meetings. You’re learning every business type we serve, understanding their risks, and building the intuition that makes great salespeople. You work directly with our AE team, and everything you capture feeds directly into our AI training pipeline.

What You’ll Do

• Own the top of funnel — Generate and qualify leads through outbound and inbound; your pipeline feeds the entire sales org

• Run high-volume calls with precision — Back-to-back conversations, capturing information accurately while building rapport

• Be the first voice 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

• Learn the business — Understand how different industries operate, what risks they face, and what coverage they need

• Build toward closing — This is a launchpad, not a landing pad; top performers move to AE

You Might Be a Fit If…

• You’ve done high-volume sales or customer work before (SDR, BDR, call center, inside sales)

• You’re hungry to close deals and see this as a path to get there

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

• You’re comfortable with technology and excited about AI tools

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

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

• You stay organized under pressure with shifting priorities

• You want to be at a company that’s building something massive

Requirements

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

• Strong communication skills and professional presence

• Ability to multitask (typing while talking, navigating systems while listening)

• Reliable internet and quiet home environment

• Hunger to grow into a closing role

Nice to Have

• Experience in insurance, fintech, or regulated industries

• Bilingual (Spanish)

• CRM or sales engagement platform experience

• Track record of exceeding quotas or metrics

Compensation

• Salary: $60,000–$80,000 base + Commission & performance bonuses

• Location: San Francisco, in-office

Benefits

• Health, dental, and vision insurance

• Commuter benefits

• Team meals and snacks

• Clear promotion path to AE (6-12 months for top performers)

• Direct exposure to founders and sales leadership

The Process

1. Founder screen — Initial fit and alignment

2. Lead screen — Skills and culture fit

3. Super day — See how you operate in real time

To Apply

This is the best entry point into tech sales. We’re rapidly growing, and for the right person, this is a foot in the door to a closing role at one of the fastest-moving companies in the industry. If you’re hungry, coachable, and want to learn the business from the ground up—apply.