AI Sales Development Operator
AI Sales Development Operator
The Mission
Harper is building the first AI-native commercial insurance brokerage. We're not just trying to make humans 10x better—we are shifting the atomic unit of work from human judgement to systems. We believe this will remove inefficiencies, helping businesses around the country that need coverage and carriers who provide it.
Venture-backed by Y Combinator, our founding team brings experience from Coatue, Carlyle, Goldman Sachs, Tesla, Alloy, and Boston Consulting Group. We've achieved $5M in ARR in under a year, with over 3,000 active clients and 200+ new accounts every single day. We're building the team that will service over 10,000+ new customers per month by the end of next year.
To do this, we need to engage ~50,000 businesses monthly, and every one of those conversations is training data for the AI systems that will transform a $100B+ industry.
This role is the revenue engine of that transformation—and you're building the playbook.
Why This Role Exists
Most commercial insurance is sold like it's 1999 - over the phone, through emails, and with manual processes that don't scale. Sales at a commercial insurance brokerage is complex: prospecting, quoting, carrier submissions, underwriting negotiations, relationship building, and closing deals. There's no way to scale to 10,000+ customers monthly without doing this work manually first, then standardizing it, then automating it, then scaling it massively—all while maintaining quality and conversion rates.
You are the operator who documents, templates, and designs the systems that will automate sales operations. You're not just closing deals—you're building playbooks, designing workflows, and creating the automation infrastructure that will replace manual sales work.
You're the human in the loop who ultimately automates your way out of this job. That's not a threat, it's the point.
What You'll Do
Work the pipeline and close deals: High-volume calls working deals from quote to bind while documenting decision points, objection patterns, and carrier nuances
Build carrier relationships: Develop underwriter relationships, document appetites and submission preferences, and match accounts to carriers
Design automation systems: Map sales workflows, identify what can be standardized, and create templates that scale to 10,000+ customers monthly
Advise product and engineering: Test internal tools, provide CRM feedback, and suggest automation opportunities that make sales more efficient
Build operational infrastructure: Document underwriter preferences, create relationship playbooks, track win/loss patterns, identify pipeline bottlenecks, and design training protocols for future hires
What We're Looking For
Recent graduates or early-career professionals who want to build something from zero
Fascination with how businesses work
High tolerance for repetitive work when it's in service of something bigger
Autonomy—you figure shit out without needing hand-holding
Pattern recognition—you spot trends others miss
Grit—delayed gratification is your superpower
Required:
Obsessive attention to detail
Incredible organization
Proficiency with technology and AI tools
Clear communication under pressure
Willingness to grind when the work is unglamorous
Preferred:
1+ years of sales experience
Experience at a technology company in a highly regulated industry (does not have to be insurance)
The Culture
We're building a team that works hard and wins together.
In-office in SF: Trading floor energy, NOT SF WeWork vibes
Group lunches and dinners: We eat together at 6:30pm most nights
Intense but fun: The hours are long, but you're doing it with people you actually like and building something that matters
Meritocracy: Excel here → fast track to leadership roles.
The Progression: This is a 6-18 month intense marathon sprint that launches you into AI Operations Leadership, Product Management, Strategic Operations, or Business Intelligence roles.
Think less "insurance company" and more "elite team on a mission to transform a massive unsexy industry using AI."