Senior Group Benefits Sales Executive (Chicago)

Guardian; Chicago (IL); On-site; USD 40,000 - 310,000; Full time

Job summary

Guardian is seeking a Group Benefits Sales Representative to cultivate relationships with brokers, consultants, and clients in the large-market segment, driving new business and retention across Guardian's benefits portfolio and technology-enabled solutions.

You will translate complex client needs into differentiated strategies and partner across underwriting, product, enrollment, and service to deliver a consistent broker and client experience.

Qualifications

• Bachelor's degree or equivalent combination of education and relevant industry experience.
• At least 5 years of group insurance sales experience, or an equivalent combination of Guardian experience, education, and related professional experience.
• Demonstrated success meeting or exceeding sales and retention goals in the large‑market segment.
• Experience selling ancillary employee benefits in the 1,000+ life space.
• Experience developing and managing complex opportunities and relationships with large regional or national brokers, consultants, and employer clients.
• Strong knowledge of group benefits products and sales processes, including Dental, Vision, Life, Disability, Absence, Supplemental Health, and Worksite solutions.
• Advanced consultative selling, presentation, negotiation, and relationship‑management skills, with the ability to influence external stakeholders and cross‑functional partners.
• Ability to develop territory strategies, maintain pipeline discipline, interpret sales and market data, and convert insights into action.
• Sound judgment, integrity, accountability, and the ability to deliver high-quality results in a fast-paced, matrixed environment.
• Ability to obtain required industry licensing within 90 days of hire and maintain licensure through completion of continuing education requirements.
• The successful candidate must be based in Chicago, IL, with the work arrangement defined in accordance with the requirements of the assigned territory.

Responsibilities

• Develop and execute a territory strategy that positions and sells Guardian's Group Benefits products and technology-enabled solutions to large-market brokers, consultants, and employer clients, including Dental, Vision, Life, Disability, Absence, Supplemental Health, and Worksite solutions.
• Build, deepen, and activate relationships with large regional and national broker and consultant firms to generate qualified opportunities, expand market presence, and support retention.
• Own sales outcomes and pipeline health for the assigned territory by identifying priority opportunities, advancing complex pursuits, and consistently achieving or exceeding production expectations.
• Lead consultative discovery and solution positioning, connecting client needs and market dynamics to a differentiated Guardian value proposition.
• Coordinate cross‑functional pursuit strategies with underwriting, product, enrollment, implementation, client management, service, and other partners to deliver a consistent broker and client experience.
• Monitor market trends, customer needs, competitor activity, and sales performance data to refine strategy and focus resources on the highest-value opportunities.
• Represent Guardian as a market leader by sharing thought leadership, strengthening community and industry relationships, and reinforcing Guardian's purpose to inspire well‑being.
• Identify and champion process, technology, and operating‑model improvements that increase sales effectiveness, improve collaboration, and simplify the broker and client experience.

Skills

Consultative selling

Relationship building

Pipeline management

Cross-functional collaboration

Negotiation

Education

Bachelor's degree or equivalent

Job description

Guardian is seeking a Group Benefits Sales Representative to cultivate relationships with brokers, consultants, and clients in the large-market segment, driving new business and retention across Guardian's benefits portfolio and technology-enabled solutions.

You will translate complex client needs into differentiated strategies and partner across underwriting, product, enrollment, and service to deliver a consistent broker and client experience.