Director of Retail Sales

Director of Retail Sales - Semsee MAP  —  Wholesale Brokerage

Location: Remote - U.S.

Reports To: Head of GTM

Direct Reports: 3-7 Sales Reps

Type: Full-Time

About Semsee

Semsee is building the only independent digital platform that covers the full small commercial insurance lifecycle — quoting, binding, and policy administration — across both admitted and E&S lines. Our Managed Access Program (MAP) is a technology-powered wholesale brokerage that gives retail agents instant access to 50+ carrier markets through a single platform. Agents enter risk information once and get comparative quotes in minutes, not days.

MAP is our primary growth engine, and we’re investing aggressively in building a dedicated sales organization for the first time. Backed by Adir Ventures, we have the capital, the technology, and the carrier relationships. What we’re adding now is the go-to-market muscle.

About the Role

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.

You are the person who turns a hiring plan into a functioning sales team. You will recruit, onboard, train, and coach reps from day one. You will set territory plans, build pipeline discipline, run the weekly operating rhythm, and hold your team accountable to premium targets — while ensuring they have the product knowledge, carrier appetite intelligence, and platform fluency to win.

This role reports to the Head GTM. The right candidate has managed wholesale or MGA sales teams, knows how retail agents make placement decisions, and has a track record of building teams that hit numbers — not just inheriting teams that already do.

What You’ll Do

• Build the Team: Recruit, hire, and onboard 3–7 Regional Sales Managers in your region. Define role expectations, ramp plans, and performance benchmarks. You own the quality of every hire and the speed at which they become productive.
• Train and Develop: Stand up a repeatable onboarding and training program covering MAP’s product suite, carrier appetite, platform workflows, the competitive landscape, and consultative selling to retail agents. Continuously coach reps through deal reviews, ride-alongs, and pipeline sessions.
• Drive Regional Premium Targets: Own the regional written premium number. Translate company-level targets into territory plans, agency-level goals, and weekly activity metrics. Know where every dollar of pipeline sits and what it takes to convert it.
• Operate the Sales Rhythm: Run weekly pipeline reviews, monthly business reviews, and quarterly territory planning sessions. Build the forecasting discipline and reporting cadence that lets leadership see around corners. Ensure your team updates CRM religiously and pipeline data is trustworthy.
• Optimize Execution Day-to-Day: Diagnose rep-level performance gaps and fix them — whether the issue is activity volume, agent targeting, platform adoption conversations, or close technique. Remove obstacles. Accelerate wins. Intervene early on underperformance.
• Carry Strategic Relationships: Maintain a personal book of high-value agency relationships in the region. Model the consultative selling approach you expect from your team. Join reps on key calls and use those moments as live coaching opportunities.
• Collaborate Cross-Functionally: Partner with underwriting, operations, product, and marketing to ensure your team has the tools, carrier access, and content they need. Relay regional market intelligence that shapes product roadmap and carrier development priorities.
• Shape the Sales Playbook: As a founding sales leader, you will directly influence hiring profiles, compensation structures, sales methodology, territory design, and the tools and processes that scale beyond your region. What works in your region becomes the template for the company.

What We Look For

• 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 — you understand the wholesale value chain and how retail agents choose where to place business
• Demonstrated track record of building or significantly growing a sales team, not just managing an inherited one — you’ve recruited, onboarded, trained, and coached reps to quota
• Ability to operate as a player-coach: credible in front of agency principals on your own, and effective at making your team better through structured coaching and deal support
• Fluency in pipeline management, forecasting, and CRM discipline — you run a data-driven sales operation, not a relationship-driven one
• Comfort operating in an early-stage environment where you’re building process, not following it — your initiative and judgment matter more than your title
• Strong knowledge of small commercial lines (GL, BOP, WC, commercial property, commercial auto) and the agent workflow for placing these risks
• Experience with CRM tools (HubSpot, Salesforce) and comfort working in a technology-forward, platform-driven sales environment
• Willingness to travel within your region as needed to support team development, key agency meetings, and market presence

What Makes This Different

• You’re building the sales org, not joining one. This is a founding leadership role. The playbook, the team, the culture, the operating rhythm — you’re creating it. What you build here becomes the model for every region that follows.
• Technology is the product, not just a tool. Your team is selling a platform that gives agents access to 50+ admitted and E&S markets instantly, with AI-powered underwriting automation that processes routine bind orders without human intervention. The technology closes deals — your job is to build a team that gets agents onto it.
• Breadth across admitted and E&S. Unlike competitors focused exclusively on E&S, MAP gives agents access to both admitted and surplus lines markets — a broader solution that covers more of their book and gives your team a wider aperture for every conversation.
• Ground floor with real backing. We’re backed by committed growth capital from Adir Ventures. You’re joining early enough to shape the entire go-to-market function, but with enough runway and infrastructure that this is a plan, not a prayer.
• A stellar quote-to-bind ratio. The platform works. Agents who use it bind business at nearly three times the industry rate. Your team’s job is distribution and relationship — the technology handles conversion.

What We Offer

• Growth Opportunity: Ground floor opportunity as an early member of the Semsee team
• Our Culture: An inclusive company culture that is being built intentionally to foster 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

Compensation

Base salary of $90,000–$110,000 plus performance-based variable compensation tied to regional premium production and team development targets. Target total compensation of $200,000–$275,000 for on-target performance. 

Semsee is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, national origin, disability, veteran status, sexual orientation, gender identity, or any other legally protected status.