VP Sales Retiree Healthcare

Amwins•North Kingstown, RI

13d•Remote

About The Position

Amwins Group Benefits, LLC (AGBL) is seeking a Vice President of Sales, Retiree Healthcare to drive net-new sales for its retiree medical vertical. This is a hands-on producer role responsible for the full sales cycle, collaborating with brokers, consultants, and employer decision-makers to originate, develop, and close new retiree medical opportunities. The role aims to inject sales energy and market feedback into the retiree business, validate growth opportunities, expand distribution, and establish a repeatable new-business motion. Target clients include public sector entities, municipalities, labor unions, and ERISA-governed employer groups facing complex retiree healthcare and Medicare-related decisions. AGBL is a full-service general agency with TPA services, managing retiree medical plans, voluntary benefits, and dependent eligibility audits, leveraging strong carrier relationships. AGBL is part of Amwins Group, a major independent wholesale distributor of specialty insurance products.

Requirements

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.
Effectively builds and sustains productive relationships with brokers, consultants, advisors, and employer decision makers.
Strong self-awareness regarding personal strengths, gaps, and selling style.
Consistently delivers net-new production through disciplined pipeline management, effective prospecting, and strong closing capability.
Engages brokers, consultants, and employer stakeholders in a way that motivates action and collaboration.
Comfortable operating without a predefined playbook.
Takes full ownership of assigned opportunities from origination through close and early onboarding.

Nice To Haves

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.

Responsibilities

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