Senior Risk Advisor – Employee Benefits

Starkweather & Shepley Insurance Brokerage Inc.

Employee Benefits Risk Advisor responsible for developing and executing sales pipeline for employee benefits solutions. Thrives in competitive environments and collaborates with internal service teams.

Posted 7/28/2026full-timeRemote • Massachusetts • 🇺🇸 United StatesSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in developing and executing strategic sales plans for employee benefits, with a strong focus on relationship building and consultative selling. Proven ability to negotiate and close new business opportunities while maintaining a robust pipeline of qualified prospects.

Highest-signal resume keywords

Employee Benefits Sales ExperienceGroup Health KnowledgeConsultative Selling SkillsNegotiation SkillsRelationship Development

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Employee Benefits ConsultingBusiness DevelopmentProspectingCold CallingPresentation SkillsTime Management

Soft Skills

Verbal CommunicationWritten CommunicationOrganizational Skills

Industry Keywords

Employee BenefitsAncillary BenefitsInsurance AgencyClient DiscoveryPipeline Management

About the role

Key responsibilities & impact

Develop and execute a strategic sales plan to generate new employee benefits business
Build, manage, and maintain a robust pipeline of qualified prospects
Identify, qualify, and pursue new business opportunities with employers
Conduct client discovery meetings to understand organizational goals and workforce challenges
Design and present customized employee benefits solutions
Collaborate with internal account management, underwriting, and carrier partners
Negotiate and close new business opportunities
Develop trusted advisor relationships with business owners and executives

Requirements

What you’ll need

At least five years of successful sales experience within an employee benefits insurance agency
Strong understanding of group health, ancillary benefits, and employee benefits consulting
Proven ability to generate new business through prospecting, networking, cold calling, referrals, and relationship development
Extensive knowledge of employee benefits products
Strong consultative selling, negotiation, and closing skills
Excellent verbal, written, and presentation communication skills
Ability to build credibility and establish long-term relationships with clients
Highly organized with exceptional time management skills