[Hiring] Director of Retail Sales @Semsee

Role Description

We're looking for a Director of Retail Sales to own premium growth across an assigned region by building, leading, and optimizing a team of 3–7 Regional Sales Managers. This is a player-coach role at a company that is standing up its first professional sales organization — you'll carry strategic relationships of your own while spending the majority of your time making your team better.

• Recruit, onboard, train, and coach reps from day one.
• Set territory plans, build pipeline discipline, and run the weekly operating rhythm.
• Hold your team accountable to premium targets.
• Ensure product knowledge, carrier appetite intelligence, and platform fluency.

Qualifications

• 5+ years in commercial P&C insurance sales, with at least 2 years in a people-management role leading a team of 3 or more sales professionals.
• Direct experience in wholesale, E&S, MGA, or binding authority environments.
• Demonstrated track record of building or significantly growing a sales team.
• Ability to operate as a player-coach.
• Fluency in pipeline management, forecasting, and CRM discipline.
• Strong knowledge of small commercial lines (GL, BOP, WC, commercial property, commercial auto).
• Experience with CRM tools (HubSpot, Salesforce).
• Willingness to travel within your region as needed.

Requirements

• Maintain a personal book of high-value agency relationships in the region.
• Run weekly pipeline reviews, monthly business reviews, and quarterly territory planning sessions.
• Diagnose rep-level performance gaps and fix them.
• Partner with underwriting, operations, product, and marketing.
• Shape the sales playbook as a founding sales leader.

Benefits

• Growth Opportunity: Ground floor opportunity as an early member of the Semsee team.
• Our Culture: An inclusive company culture that fosters stimulating, healthy, meaningful, and long-lasting work relationships.
• Fully Remote Team Environment.
• Time Off: 4 weeks (20 Days) + 9 company observed holidays; Total 29 Days/Year.
• Benefits: 70% Funded Medical/Vision/Dental; 100% Funded Life Insurance; 401k, Roth IRA; Generous 12 Weeks Paid Baby Bonding Leave, +more.