Account Executive

Full-Cycle Account Executive (Commercial Insurance)

Quick tier list for anyone who sells for a living. If car sales is F tier and tech sales just dropped to C tier (turns out AI makes software trend toward $0, who knew), commercial insurance is quietly sitting at S tier. ;)

Here's why nobody tells you that. Every business on earth has to buy it, every single year, by law or by their lender. The deals are big. And when you win an account, it's actually yours. It renews, it compounds, and you get paid on it again next year, and the year after that.

We're Rosella, an AI-native commercial insurance brokerage. Most shops in this space bury their best closers in paperwork and hand the good accounts to whoever's been there longest. We do the opposite: a tight team, AI tools that kill the busywork, and you get renewals each year. Top brokers make $500k+ and don't have to close new deals. It might sound too good to be true, it's a grind in the first 2-3 years, but once you build a book, it's the best job in the world.

You don't need an insurance background. You need to be able to develop relationships. We'll pay for your license and teach you the industry.

The Role

This is a full-cycle seat. You hunt, you close, and you own the relationship after the signature. You work directly with founders to build the revenue engine of an early-stage company with real traction and serious VC backing behind it.

Here's the part people underrate: this is one of the easiest things in the world to sell. Every business already buys commercial insurance. It's not optional, it's not a new category you have to invent, and most owners are overpaying a broker who hasn't shopped their account in years. You're not cold-pitching a product nobody asked for. You're calling people who already have the thing, already feel the pain of rising premiums, and have never been given a real alternative. Our marketing engine and producers feed you warm, qualified pipeline on top of your own hunting. The job is to pick up the phone, win the account, and keep it.

And every deal you run feeds the product. Every call, every objection, every renewal is data that makes our AI sharper. You'll sit with engineering and tell them what's slow, what to automate, and what to build next. They ship it, you use it, you go faster.

What You'll Do

• Hunt. Run high-volume outbound and work the warm leads our marketing engine generates. Build pipeline and keep it full.
• Close. Master the playbook in week one, improve it in week two. Success is measured in revenue and accounts won.
• Own the book. Once you close it, you keep it. Renewals, and the relationship are yours, with the platform and team carrying the actual grunt work.
• Round out accounts. Spot the missing coverage and close the upsell.
• Shape the product. Tell founders and engineers what's broken and what the AI should do next. We build it, you use it, we iterate.

You Might Be a Fit If…

• You're a closer first, with a proven track record of selling at high velocity. The industry you did it in doesn't matter.
• You treat "no" as data, not discouragement. You're the first one dialing in the morning and the last one at night.
• You think sales is a system to be optimized, not an art that can't be taught.
• You want more AI tools, not fewer. "It has to be done the old way" makes you physically uncomfortable.
• You want input and ownership, not just a seat. You'd rather help redesign a process than be handed one.

Requirements

• 2+ years of high-velocity B2B sales with direct closing responsibility, in any industry.
• A track record you can point to: quota attainment, close rates, deals or revenue closed.
• Comfort with outbound, rejection, and aggressive follow-up.
• Comfort using AI tools, CRMs, and automation to move faster.
• Willingness to obtain a P&C producer license. We pay for the training and licensing.
• On-site at Rosella HQ.

Compensation

Base salary (OTE is $120k+) plus uncapped commission on new business, plus equity. We offer some of the most aggressive splits in the industry because we want owners, not seat-warmers. The exact mix of base, commission, and equity is flexible based on what you optimize for. Health, dental, vision, and PTO included.

Location

On-site, Rosella HQ.

The Process

1. 15-minute phone screen.

2. 60-minute structured behavioral interview.

3. References, which we actually call.

4. 45-minute founder and culture interview.