Chief Commercial Officer

NOTE: Must have been a commercial insurance producer

This role is for you if you have grown tired of the bureaucracy of big public company brokerages, being handed a plan to execute while working on painfully slow systems where it is all about the numbers. This role is for you if you are tired of a hands-off approach to coaching, and you want to bring the next generation of talent into the industry. This role is for you if you are tired of watching the AI revolution pass you by.

About Rosella

Rosella is an AI-native commercial insurance brokerage, built differently from the ground up. We have raised $2.6M from Peak XV (formerly Sequoia APAC) and Intact Group, the venture arm of Intact Financial, one of North America's largest P&C insurers. Our model combines commercial producers with proprietary AI workflows that drive sourcing, prospecting, and submission velocity at a scale traditional brokerages cannot match. We are scaling to 40 producers over the next 12 months, focused on SMB commercial accounts across construction, transportation and hospitality.

The Role

The Founding CCO owns Rosella's entire commercial motion. You will begin as a player-coach. You will produce, and you will show the producers how it is done. By months 3 to 6, you will shift entirely into the coach seat, helping bring on dozens of producers and training them into validation. By month 12, as the team expands and we build out a bench underneath you, you will move into high-level strategy, carrier architecture, and commercial leadership at scale.

What You Will Own

• Producers: Hiring criteria, onboarding curriculum, validation framework, coaching cadence, compensation design, and performance management for cohort one and beyond.
• Carriers: Direct appointments, wholesale partnerships, market access networks, and specialty programs. Deliver a prioritized market access expansion plan by day 45 and execute by day 90.
• Revenue: Contingencies, overrides, alternative compensation structures, and program design (retro and dividend arrangements) that pull additional margin from every deal.
• Partnerships: Trade associations, vertical channels, and structured referral arrangements positioned to activate at Series A close.
• Professional risk and compliance: Producer licensing, supervision, regulatory posture across all states, and oversight of AI-generated outputs for E&O exposure.
• Product partnership: Work directly with the CTO to translate how insurance actually works into product specifications engineers can build against.

What We Are Looking For

• CPCU designation or equivalent senior professional insurance credential
• Proven player-coach capability: the ability to personally produce at high levels while coaching and training producers (most important)
• 15 years of senior commercial insurance experience, including direct P&L ownership.
• Carrier relationship network sufficient to execute market access expansion in the first 90 days without external consulting support
• Deep institutional knowledge of market access network structures, contingency and profit sharing arrangements, and state-level carrier relationships in our primary geography
• Professional risk management training sufficient to identify E&O exposures in marketing content, AI-generated outputs, and operational decisions

Why This Seat

Building an AI-native brokerage at scale requires someone who can simultaneously coach producers, close deals, design carrier strategy, protect the business from professional liability, and compound unit economics through institutional brokerage knowledge that cannot be built from first principles by engineers. If you have spent a career inside traditional brokerage and want to build the version of the industry that should exist, this is that seat.

Total Comp $300k (this includes base, benefits and equity). Can be more aggressive with equity for the right fit.