Group Benefits Sales Representative, Premier - Chicago, IL

Location: Fully remote, but the successful candidate must be based in Chicago, IL, United States; up to 50% travel within the assigned territory is required.

Salary: $40,000 base pay. Anticipated total annual compensation, including sales target incentive compensation, is $222,800–$309,900.

Company

hirify.global provides group benefits and technology-enabled insurance solutions, with a focus on well-being and long-term client and broker relationships.

What you will do

• Develop and execute territory strategies to sell group benefits and technology-enabled solutions to large-market brokers, consultants, and employer clients.
• Build relationships with regional and national broker and consultant firms to generate opportunities, expand market presence, and support retention.
• Own sales outcomes and pipeline health by prioritizing opportunities, advancing complex pursuits, and meeting or exceeding production expectations.
• Lead consultative discovery and solution positioning across Dental, Vision, Life, Disability, Absence, Supplemental Health, and Worksite solutions.
• Coordinate pursuit strategies with underwriting, product, enrollment, implementation, client management, and service partners.
• Use market trends, customer needs, competitor activity, and sales data to refine strategy and improve sales effectiveness and client experience.

Requirements

• 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, including 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 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 continuing education.
• Must be based in Chicago, IL, with the work arrangement defined according to the assigned territory.
• Must be legally authorized to work in the United States without current or future employer sponsorship.

Nice to have

• Advanced knowledge of complex absence solutions, experience rating, dental network analysis, and other large-market underwriting, implementation, or service considerations.
• Experience positioning technology-enabled benefits, enrollment, administration, and connectivity solutions.
• Established credibility and relationships within regional or national broker and consultant communities.
• Experience using sales data, customer insights, competitive intelligence, and market trends to shape territory strategy.
• Thought leadership, community engagement, or industry presence that enhances market visibility.
• Experience championing process improvements and partnering across functions to improve sales effectiveness and the broker and client experience.

Culture & Benefits

• Full-time employment with base pay plus eligibility for Guardian’s sales incentive compensation plan.
• Remote work arrangement tied to the assigned territory, with up to 50% travel required within that territory.
• Skill-building, leadership development, and philanthropic opportunities.
• Supportive, flexible, inclusive benefits and resources for eligible full-time employees.
• High ethical standards, well-being focus, and commitment to diversity, equal opportunity, and reasonable accommodation.

Hiring process

• Current Guardian colleagues must apply through the internal Jobs Hub in Workday.
• Applicants may opt out of AI-assisted preliminary screening by emailing the accommodation or alternative-process request to MyHR@glic.com within ten business days of applying and providing their name and job requisition identification number.