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 ThesisEvery 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 RoleHigh-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 DoOwn 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’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
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
Experience in insurance, fintech, or regulated industries
Bilingual (Spanish)
CRM or sales engagement platform experience
Track record of exceeding quotas or metrics
Salary: $60,000–$80,000 base + Commission & performance bonuses
Location: San Francisco, in-office
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
Founder screen — Initial fit and alignment
Lead screen — Skills and culture fit
Super day — See how you operate in real time
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.
Top Skills
What We Do
Harper is a commercial E&S insurance brokerage. From prospecting and quoting to binding and service, our proprietary AI-native tech stack powers our organization.
