My client is a $14M scale-up looking for the next milestone of $50M. They are an Agentic AI Underwriting platform for the Commercial space.

This is a condensed version of the Questions I ask the Hiring Manager to get a better understanding of the Opportunity, the Culture and the Solution.

My Client would look at a VP or SVP of Sales that is ready for a CRO role or a current CRO.

Unlocking the P&C AI Market with Proven, Tier-1 Traction

The Company has successfully cracked the change-resistant commercial P&C insurance market by delivering validated business outcomes rather than artificial intelligence hype. While competitors struggle with technology fatigue, this platform is already in production with 7 of the top 15 commercial carriers, driving over 50 successful implementations. The solution fundamentally solves operational bottlenecks by reducing data entry by 65%, slashing quote turnaround times from 20 days to 4 days, and doubling quote-to-bind ratios. This established credibility gives top-tier enterprise sales professionals immediate market authority to displace legacy systems.

A Rare Transition from Point-Solution to Value-Based Scale

The organization is at a pivotal inflection point, evolving from selling technology to IT departments to delivering strategic business outcomes for underwriting and operational leaders. Backed by a newly formalized marketing department and automated business development technology, the foundation is set to scale. The immediate mandate is to inject strict sales methodology—specifically leveraging MEDDPICC—into the current team to accelerate deal progression, refine pipeline quality, and establish a repeatable new-logo acquisition engine.

The Elite Blueprint for Success

The ideal sales leader is a hands-on player-coach who respects "the grind" and thrives in early-stage, startup environments lacking massive back-office GTM support. To achieve executive alignment, the candidate must possess a verifiable track record of consistent quota achievement and experience successfully launching a new product or vertical. Essential skills include navigating complex, multi-stakeholder enterprise buying groups within admitted carriers, E&S carriers, or large wholesale MGAs, alongside a strong preference for commercial P&C underwriting workflows.

Fostering a Resilient, High-Performance Culture

Culturally, the company rejects "ivory tower" management in favor of collaborative, cross-functional execution and extreme ownership. The existing team operates with a high-belief mindset born from a proven track record of solving complex data-science problems, resulting in an exceptionally low voluntary turnover rate. Sales professionals are fully supported by an engineering and product organization that never overpromises and always delivers, ensuring that client health remains a core company value.

The Pathway to Full GTM and CRO Leadership

This role is specifically engineered for an ambitious builder who wants to define a business rather than just manage a pipeline. Success in the first 12 months by installing sales discipline and accelerating new lands directly unlocks the opportunity to absorb marketing and account management. This evolution grants full ownership of the entire revenue engine (new + expansion), positioning the leader to architect the ultimate scaling strategy ahead of a major growth-funding initiative.