Head of Sales

Head of Sales - Harper

The Story

In August 2023, we had 5 customers and were writing $2,000 in monthly premium.

Today, we represent over 3,000 insurers and write $3M in monthly premium with just 4 producers.

Now we're scaling to $10M in monthly premium sold by Q1 2026, and we need someone to build the sales machine that gets us there. Ultimately, we look to have the size and scale of the giants – think Marsh, Gallagher, and Brown.

What You're Actually Building

You're not just managing a sales team. You're architecting the entire sales function at a company that's about to explode.

The Mission: Build a lean team of elite producers supported by embedded engineering that can write hundreds of millions in premium. Think 50 people doing what traditional brokerages need 500 people to do.

Right now: 4 producers writing $3M/month

Your mission: Build a team of 8-10 elite producers writing $10M/month

The future: A scalable sales machine where engineering is embedded in your function, enabling your team to operate at 10x the efficiency of traditional brokerages

You'll own:

• Recruiting & hiring top talent from insurance, tech sales, and finance
• Building scalable playbooks that work across different producer backgrounds
• Performance management \- reviewing calls, coaching, driving consistent execution
• Compensation design that attracts and retains A-players
• Deal intervention \- stepping in to save deals and close when needed
• Carrier relationships \- managing E&S wholesale brokers and direct appointments
• Technology partnership \- working directly with embedded engineering to build AI tools that make us unstoppable

Key relationships: You'll work directly with our Head of Operations and Founder on strategy, growth initiatives, and building the systems that enable this vision.

This isn't about managing what exists. This is about building what comes next.

Who You Are

Non-Negotiables

• 5+ years crushing it in commercial insurance sales yourself
• 3+ years building and managing P&C producer teams
• Deep expertise in both admitted and E&S markets
• Proven track record scaling sales operations from early stage
• Can close deals \- you're the person we call when a big deal is going sideways
• You need to have the ability to travel for work to see clients and oversee teams at various office locations

The Perfect Background

You've done one of these:

• Scaled a producer team at a brokerage, MGA, or carrier
• Built an independent agency from the ground up
• Led sales at a high-growth insurance company
• Managed both wholesale and retail distribution channels

What Makes You Different

• You can recruit anyone - a used car salesman, a former insurance producer, a Goldman Sachs investment banker, a software sales rep from Salesforce - and turn them into a top performer
• You build systems that scale, not just processes that work today
• You're obsessed with performance and comfortable giving direct feedback
• You get excited about using AI to eliminate busywork (not relationships)
• You thrive in chaos and build order without killing speed
• You want to get rich alongside the people you develop

The Economics

Total Cash: $200K - $350K+ depending on performance

• Base: $125K - $175K

Equity: Real upside - 0.5-1% equity in the company

Benefits: Premium healthcare (90% covered), meals covered while at work, development budget, flexible PTO

The Real Upside: When we hit $100M+ annual premium, you'll have built something legendary alongside meaningful ownership.

The Reality Check

This Isn't For You If:

• You need perfect processes before you can operate
• You want to manage from a distance
• You think insurance is boring and can't sell the vision
• You're looking for work-life balance
• You've only worked at established companies with unlimited resources

This Is For You If:

• You see the $100M+ annual premium opportunity ahead
• You get energy from developing top performers
• You want to build your own legacy, not just manage someone else's
• You can balance empathy with ruthless accountability
• You want meaningful equity in something that's already proven it works

What We Need You to Know

The Market: Commercial insurance is being disrupted. Digital-first brokers are winning while traditional agencies struggle. We're perfectly positioned - tech-enabled enough to dominate operationally, insurance-focused enough to actually serve clients.

Our Advantage: We've built something that scales. Proven unit economics. Clear path from $36M to $120M annual premium. AI that eliminates the manual work traditional brokerages drown in. Your producers will focus on what matters: relationships and deals.

Apply

Send your resume and answers to these three questions to [founders@harperinsure.com](mailto:founders@harperinsure.com):

1. Describe your biggest personal production win and how you'd teach others to replicate it

2. How would you recruit a top software sales rep or investment banker into insurance?

3. How have you used technology to improve sales operations?

We're moving fast. The right person could start before year-end and own our entire 2025 growth story.

Build something legendary with us.