VP Sales Retiree Healthcare

Amwins Group Benefits, LLC (AGBL) is conducting a candidate search looking for a Vice President of Sales, Retiree Healthcare.

AGBL is a full-service general agency complete with a full suite of third-party administrator (TPA) services, leveraging strong carrier relationships to manage retiree medical plans, voluntary benefits, and dependent eligibility audits. From underwriting on behalf of carriers to nuanced industry expertise for distribution partners, our program development simplifies day-to-day carrier responsibilities. AGBL’s retiree medical operations are located in North Kingstown, RI.

AGBL is an Amwins Group operating company in the Amwins Benefits Division. Amwins Group is one of the largest independent wholesale distributors of specialty insurance products in the United States, dedicated to serving retail insurance agents by providing property and casualty products, specialty benefit products, and administrative services. Based in Charlotte, N.C., the company operates through more than 165+ offices globally and manages premium placements in excess of $45 billion annually and employs over 8,100 people. To learn more, visit us at www.amwins.com.

Position Summary 

This role is responsible for driving net-new sales for AGBL’s retiree medical vertical. Vice President of Sales, Retiree Healthcare will operate as a hands-on producer, owning the full sales cycle and collaborating directly with brokers, consultants, and employer decision makers to originate, develop, and close new retiree medical opportunities. The position is designed to bring immediate sales energy and market feedback into the retiree business, helping validate growth opportunities, expand distribution relationships, and establish a repeatable new-business motion.

Target clients may include public sector entities, municipalities, labor unions, and ERISA-governed employer groups navigating complex retiree healthcare and Medicare-related decisions.

Responsibilities

New Business Development

• Source, develop, and close new retiree healthcare opportunities nationwide.
• Own the full sales lifecycle, from prospecting and qualification through proposal, negotiation, and close.
• Build and manage a disciplined pipeline focused on new logos and new revenue.

Broker & Consultant Engagement

• Develop and maintain strong working relationships with benefit consultants, brokers, and advisory firms.
• Educate partners on Amwins’ retiree capabilities, positioning, and ideal client profiles.
• Serve as the primary sales contact for assigned partners and referral sources.

Employer & Buyer Engagement

• Engage senior-level buyers including HR leaders, benefits directors, fund administrators, and public-sector stakeholders.
• Engage decision-makers within labor unions, municipal organizations, boards, trustees, and other multi-stakeholder governance structures where applicable.
• Understand employer objectives and align Amwins retiree solutions to meet financial, workforce, and retiree needs.

Market Expansion & Insight

• Identify new market segments, employer profiles, and distribution opportunities.
• Provide ongoing market feedback related to buyer behavior, competitive dynamics, and pricing considerations.
• Collaborate internally to refine messaging, targeting, and go-to-market approach based on field experience.

Internal Collaboration

• Partner with implementation and service teams to ensure smooth transitions post-sale.
• Remain involved through early onboarding to reinforce client confidence and continuity.

Qualifications

• 5+ years of experience selling retiree medical benefits or closely related healthcare, Medicare, or retiree-adjacent solutions.
• Experience in complex B2B, healthcare benefits, insurance, or consultative sales.
• Proven ability to sell through broker and consultant channels.
• Demonstrated success building pipeline and closing net-new business.
• Comfortable operating independently in a growth-oriented, build-mode environment.
• Experience working with ERISA-governed benefit plans, public sector or municipal employers, and/or labor or collectively bargained benefit environments is strongly valued.
• Familiarity with Medicare Advantage, Medicare Supplement, and employer group retiree medical strategies is preferred. 

Core Competencies

Build Market Relationships
Effectively builds and sustains productive relationships with brokers, consultants, advisors, and employer decision makers. Establishes credibility quickly, earns trust through follow-through, and leverages relationships to generate qualified opportunities and repeat referrals.

Demonstrates Self-Awareness & Judgment
Strong self-awareness regarding personal strengths, gaps, and selling style. Seeks feedback, adjusts approach based on results and market response, and applies sound judgment in prioritization, deal strategy, and resource use.

Drives New Business Results
Consistently delivers net-new production through disciplined pipeline management, effective prospecting, and strong closing capability. Maintains momentum even in complex, long-cycle, or ambiguous sales environments.

Creates Engagement with Partners & Decision Makers
Engages brokers, consultants, and employer stakeholders in a way that motivates action and collaboration. Communicates value clearly, aligns solutions to buyer objectives, and maintains energy and responsiveness throughout the sales process.

Operates Effectively in Ambiguous Markets
Comfortable operating without a predefined playbook. Navigates evolving market conditions, buyer dynamics, and internal processes while continuing to move opportunities forward and generate actionable insight.

Execution with Ownership & Accountability
Takes full ownership of assigned opportunities from origination through close and early onboarding. Follows through on commitments, coordinates effectively with internal teams, and holds self-accountable for outcomes and results.

Snapshot of what Amwins provides to our team members: 

• Base compensation and multi-year commission guarantee
  • Uncapped commissions
• Position eligible for annual bonus 
• Full benefits package available 
  • Most benefits available first day of employment 
• Generous Paid Time Off (PTO) 
• Collaborative, continuing education focused work environment 
• Career advancement opportunities