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.
Once a customer pays, you're the reason the deal actually closes.
The ThesisGetting a business insured is only the beginning. After that comes COIs, endorsements, billing questions, renewals, claims—the ongoing reality of being a policyholder. Most brokerages handle this with slow emails and voicemail tag. We handle it with AI and a small, sharp team that actually knows insurance.
Every issue you resolve and every interaction you document teaches our AI what to handle next. You're not just serving customers—you're building the system that makes service scale without scaling headcount. The people who learn this operation inside out become the backbone of the company as we grow 20x, 50x, 100x.
The RoleYou own sales operations—the critical last mile of every customer transaction. Once a customer pays, you guarantee that all documents, requirements, and deliverables are in place and the order is fully completed. You're Harper's face in the final stage of the process, pushing every deal through the finish line. We can't score without this team.
No two customers behave the same. Every day brings different requirements and different challenges. You capture context quickly, figure out the optimal way to solve each problem, and close it out. You'll work alongside Sales, Engineering, and our AI systems daily. Everything you do feeds back into the product.
What You'll DoOwn the customer relationship through fulfillment — From payment to certificate delivery, you're Harper's face in the final stage; guarantee every order is completed with all documents and requirements in place
Own resolution end-to-end — Don't just take the message; follow up with carriers, track status, close the loop with the customer
Know the product — Understand policy types, coverage basics, and carrier processes well enough to answer real questions confidently
Feed the AI system — Your work trains the models and algorithms that will automate the manual parts of this process; you're the human component essential for building automation while establishing trust and customer loyalty over time
Flag what's broken — Surface recurring issues, edge cases, and friction points so they get fixed upstream by Product and Engineering
Keep customers loyal — Every interaction is a chance to reinforce that Harper is different; professional, fast, and actually helpful
You've worked in sales, operations, or a similar high-volume customer-facing role
You're comfortable navigating multiple systems while on a call
You take ownership of problems—you don't pass them along and forget about them
You're detail-oriented and accurate even when you're moving fast
You're excited about AI tools and want to work at a company building the future of the industry
You have a product mindset—you want to work closely with the engineering team to shape what AI systems look like
You want to grow into operations leadership, product, or deeper roles as the company scales
Prior experience in sales, customer-facing, or operational roles
Strong communication skills—clear, professional, and patient
Ability to multitask: talk, type, and navigate systems simultaneously
Comfort with technology and willingness to learn new tools quickly
Based in San Francisco or willing to relocate
Insurance industry experience (commercial lines, P&C, brokerage, or carrier-side)
Bilingual (Spanish)
Familiarity with COIs, endorsements, claims processes, or carrier communications
Salary: $85,000 - $125,000 + performance bonuses + equity
Location: San Francisco, in-office
Schedule: Monday–Friday, 5 AM – 8 PM. The hours are long. The learning curve is steep. The people who thrive here wouldn't have it any other way.
Health, dental, and vision insurance
Commuter benefits
Team meals and snacks
Team lead screen — Skills and culture fit
Manager screen — Alignment on pace and expectations
On-site day — Meet the team, see the operation, work through real scenarios
This is a ground-floor opportunity at one of the fastest-growing companies in insurance. You'll learn the operation from the inside, work directly with the team building the product, and grow as we scale. If you love solving problems for real people, thrive in fast-moving environments, and want to be part of something that's actually changing the industry—apply.
Harper (harperinsure.com) San Francisco, California, USA Office
San Francisco, California, United States, 93134
Similar Jobs
What you need to know about the San Francisco Tech Scene
Key Facts About San Francisco Tech
- Number of Tech Workers: 365,500; 13.9% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Google, Apple, Salesforce, Meta
- Key Industries: Artificial intelligence, cloud computing, fintech, consumer technology, software
- Funding Landscape: $50.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Sequoia Capital, Andreessen Horowitz, Bessemer Venture Partners, Greylock Partners, Khosla Ventures, Kleiner Perkins
- Research Centers and Universities: Stanford University; University of California, Berkeley; University of San Francisco; Santa Clara University; Ames Research Center; Center for AI Safety; California Institute for Regenerative Medicine


.jpg)