Regional Sales Director, Medical Stop Loss

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Regional Sales Director, Medical Stop Loss based in United States.

This remote sales leadership role is responsible for driving growth and strengthening relationships within the Medical Stop Loss insurance marketplace. The position focuses on developing new business opportunities, expanding existing partnerships, and delivering consultative solutions to brokers, consultants, and customers. The successful candidate will leverage deep industry expertise to execute sales strategies and support long-term business objectives. This role works closely with underwriting, distribution, account management, and internal partners to deliver exceptional customer outcomes. The position offers the opportunity to influence market growth while serving as a trusted advisor and subject matter expert. With a focus on collaboration, innovation, and relationship building, this leader will help expand product reach and improve customer experiences.

Accountabilities:: The Regional Sales Director, Medical Stop Loss will lead business development efforts, strengthen producer relationships, and execute strategies that drive profitable growth across assigned markets.

Grow and retain Medical Stop Loss revenue through new business development, renewal management, and expansion of existing coverage opportunities.

Build and maintain strong relationships with brokers, general agencies, consultants, customers, third-party administrators, and strategic partners.

Deliver consultative sales solutions by understanding customer needs, market trends, and evolving industry challenges.

Provide strategic guidance on Medical Stop Loss products, services, competitive positioning, and market opportunities.

Partner with regional distribution leaders and underwriting teams to develop business plans supporting sales targets and retention goals.

Serve as a subject matter expert by providing product education, market insights, and professional development support to internal teams.

Develop and manage a strong pipeline of producer opportunities, including RFP activity, account implementation, and renewal workflows.

Collaborate with internal teams including underwriting, claims, contracts, commissions, and operations to ensure successful customer outcomes.

Analyze market conditions, competitor activity, and industry trends to identify growth opportunities and business risks.

Address customer and broker questions, resolve issues proactively, and maintain high levels of service satisfaction.

Champion continuous improvement initiatives that enhance product delivery, customer experience, and operational effectiveness.

Requirements:

The ideal candidate brings extensive experience in Medical Stop Loss and self-funded insurance sales, along with strong relationship-building and strategic execution skills.

Minimum of 8 years of proven sales experience within the self-funded insurance and/or Medical Stop Loss marketplace.

Demonstrated success building and managing a profitable book of Medical Stop Loss business, including new and renewal accounts.

Strong network and established relationships with brokers, general agencies, and producers in the group insurance marketplace.

Deep understanding of self-funded insurance products, Medical Stop Loss solutions, underwriting considerations, and market dynamics.

Ability to analyze financial and performance metrics to support informed business decisions.

Exceptional communication, influencing, negotiation, and presentation skills.

Proven ability to collaborate effectively across cross-functional and matrixed organizations.

Strong strategic thinking, problem-solving abilities, and ability to navigate ambiguity.

Ability to identify business trends, competitive changes, and external market opportunities.

Active Life and Health Insurance license, or ability to obtain within 30 days of hire.

Willingness to travel up to 50% as required.

Ability to work effectively in a remote environment with strong accountability and self-direction.

Benefits:

Competitive base salary with annual bonus potential.

Comprehensive medical, dental, vision, life insurance, and disability coverage.

Paid time off and leave programs, including parental and military leave.

401(k) plan with company match.

Company-funded pension plan.

Wellness programs offering reimbursement opportunities for eligible wellbeing expenses.

Work/life resources supporting family needs, financial wellness, mental health, education, and career development.

Education benefits supporting approved degree programs and professional certifications.

Employee stock purchase opportunities.

Remote work flexibility with opportunities for professional growth and leadership development.

How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best!  Why Apply Through Jobgether?    Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.     #LI-CL1