Senior Operations Lead

The Company

We’re on the frontier of building an AI-native professional services company. We’re building the best AI commercial insurance distribution engine for scale.

36 million businesses in America need insurance—it’s not optional. 77% are underinsured. 40% have no coverage at all. Over 90% of the industry is still human-led.

We’re building the inverse: 90%+ AI-led, inching toward the higher 90s. Not by automating tasks, but by capturing the decision traces—the exceptions, precedents, and cross-system context—that let AI make the same judgment calls humans do.

The Thesis

Every industry with human-bounded distribution consolidates rapidly once someone makes it computational. Search had thousands of engines until Google made ranking computational. Ride-hailing was fragmented until Uber made dispatch computational.

When distribution becomes computational, Jevons Paradox kicks in: increased efficiency leads to increased consumption. Better search didn't mean less searching—it meant vastly more. Cheaper rides didn't mean fewer trips—it meant transportation for use cases that never existed.

Insurance will follow the same pattern. When getting the right coverage becomes fast and frictionless, the 77% of underinsured businesses will finally get properly protected. The market expands, not contracts.

We're building the engine that makes that happen.

The Role

You'll build and run the operational backbone that lets Harper scale from thousands to tens of thousands of customers monthly. Not "manage a department"—own the entire operational engine of a company transforming how insurance gets distributed.

This is hands-on leadership in the truest sense: you're building infrastructure while running it, making real-time decisions while documenting them, hiring a team while doing the work yourself. Your operational calls directly impact revenue, compliance, and customer experience—often the same day.

We're looking for a senior operator who actively wants startup intensity. Long hours, rapid change, incomplete information, high stakes. You'll work directly with the founders. There's no buffer. You build it, you run it, you own the outcome.

What You'll Own

End-to-end brokerage operations. Policy administration, renewals, endorsements, certificates, billing coordination, compliance—the full lifecycle. You're the escalation point when things break. You step in and execute when volume spikes or gaps emerge. Nothing gets dropped.

Operational infrastructure from scratch. We're not optimizing existing processes—we're building them. SOPs that balance speed with accuracy. Workflows that scale to 10,000+ customers monthly. Systems that get better as we grow, not worse.

Technology and systems integration. Agency management systems, CRMs, carrier portals—you'll lead implementation and optimization. The goal: systems that accelerate growth rather than constrain it. You'll work alongside engineering to ensure ops and tech move together.

Compliance and risk management. Full regulatory compliance across every jurisdiction we operate in, despite fast growth and changing requirements. Licensing, audits, carrier standards, E&O risk. You own it all—and you keep us clean while we move fast.

A team that performs under pressure. Hire, onboard, train, and manage operations staff in a demanding environment. Set clear expectations around output, urgency, and quality. Lead from the front during high-volume periods. Your team will reflect your standards.

You Might Be a Fit If…

You've run brokerage operations at scale. 10+ years in commercial insurance operations. You know commercial lines products, brokerage workflows, and agency management systems (Epic, Applied TAM, AMS360) inside and out. You've had full operational ownership—not just a piece of the puzzle.

You've built, not just managed. Prior experience in a startup, scale-up, or high-growth environment where you created infrastructure while running day-to-day operations. You've thrived in chaos, not just tolerated it.

You solve problems, not defer them. Ownership mentality. When something breaks at 8pm, you fix it. When information is incomplete, you make the call. Bias toward action over perfection.

You want intensity. This is explicit: long hours, high urgency, rapid change. You're not looking for predictable structure—you're looking for a career-defining challenge. You have the stamina, resilience, and accountability to match.

You have the credentials. Strong regulatory and compliance knowledge. Insurance designations (CPCU, CIC, CRM, ARM) preferred but not required if the experience is there.

Compensation

Salary: $180,000 - $220,000

Equity: Yes

Location: San Francisco, in-office. We build together.

The Process

1. Initial screen — Skills and culture fit

2. 30-min founder call — Alignment on mission and pace

3. On-site Super Day — Meet the team, see the operation, work through real scenarios

4. Paid work trial — Real work, real stakes, mutual evaluation

To Apply

We're building a vertically integrated AI platform that connects go-to-market, sales operations, customer service, and retention under one architectural roof. That integration creates compounding through feedback loops—every interaction makes the system smarter. Thousands of businesses already trust us.

The Senior Operations Lead is foundational. You'll shape how Harper scales operationally while AI reshapes what's possible. High visibility, high impact, direct founder access.

If you want to build the operational engine of a company that's never existed, work with people who show up with the same intensity every day, and own outcomes that matter—send your resume and tell us about the hardest operational challenge you've solved.

We're a championship-minded team. We push each other. We move fast. We care about craft. If that sounds like where you belong, let's talk.