Head of Sales, Consumer Driven Health & Wellness

Position: Head of Sales, Consumer Driven Health & Wellness Benefits
Summary Capital Community Bank is launching a full-spectrum Health Savings Account (HSA), Flexible Spending Account (FSA), Health Reimbursement Arrangement (HRA), and wellness benefits program. To drive this expansion the Bank is seeking a dynamic, highly experienced Head of CDH Sales to build and lead the sales organization from the ground up.

The bank is entering the CDH market as a disruptor, not a follower. As a high-performing community bank, we earn more margin on deposits than the "big box" HSA players, and we're passing that advantage directly to consumers. Our HSA accounts will pay significantly more interest (targeted to be ~3-5x higher) than that offered by ‘big box’ HSA peers, with a radically simplified fee structure: ranging from $0.75 per account per month max for smaller groups to zero fees for larger groups.

The bank has validated that this combination will generate immediate and significant interest. We are looking for a Head of Sales who understands how to weaponize superior economics, someone who can walk into an employer or broker's office, lay our rate card next to the incumbents', and move entire deposit books. This is not a caretaker role. This is a ground-floor opportunity to build a national sales engine around a product that wins on the math.

This leader will serve as the face of the bank’s HSA program nationally, responsible for training, and managing a geographically dispersed team of independent (1099) sales agents while personally driving channel growth through broker relationships, employer group sales, TPAs and consumer direct sales. This is a player-coach role with full P&L accountability for CDH sales performance, including revenue growth and expense management.

Key Responsibilities Sales Leadership & Team Management (70%)Recruit, onboard, train, and manage a national network of 1099 independent sales agents (target: 4–8 agents within the first 12 months).Set sales strategy, performance expectations, KPIs, and activity metrics; conduct ongoing pipeline reviews and performance coaching.

Develop and implement the HSA Sales Playbook, including value propositions, competitive positioning, objection handling, and broker/employer presentation materials.

Personally develop and close employer group; broker channel and TPA relationships, particularly in the Mountain region.

Represent the Bank at industry conferences, benefits trade shows, and broker association events.

Negotiate and execute client and channel partner agreements in coordination with Bank leadership and counsel.

Partner with external recruiters as necessary and other recruiting resources to identify and vet 1099 sales candidates.

Operations, Marketing & Data Path (software, onboarding and call center service provider) Coordination (30%)Serve as the primary Bank liaison to Data Path (DP) for sales-related operations, including employer implementations, onboarding workflows, and broker portal configuration.

Collaborate with Marketing and DP to develop and refine program branding, collateral, broker kits, and digital marketing campaigns.

Coordinate with Bank compliance, risk management and DP to ensure all sales activities, marketing materials, and agent conduct comply with UDAAP, BSA/AML, KYC/CIP, and applicable state regulations.

Deliver regular reporting to the Bank senior leadership and Board of Directors on pipeline status, deposit growth, revenue projections, and competitive intelligence.

Manage the CDH/HSA program’s sales budget, including 1099 agent compensation structure, marketing spend, CRM tools, and travel.

Specifications

Required:

8-10+ years of progressive sales experience in consumer-directed healthcare (HSA, FSA, HRA), employee benefits, health plan administration, or TPA/custodian services.

Demonstrated track record of building and managing independent or distributed sales forces in the benefits or financial services space.

Deep working knowledge of HSA and other CDH regulatory requirements (IRC Section 223, HDHP qualification rules, contribution limits, ERISA considerations).Experience selling through broker/consultant distribution channels; established relationships with benefits brokers, TPAs,…