Group Benefits Sales Representative, Premier - Chicago, IL

Chicago - Regional Office · Remote
Full-time
$222,800 to $309,900
Posted Nov 9, 2026

Skills

Sales
Leadership
Teamwork

Job description

Position Summary :

Guardian is seeking a Group Benefits Sales Representative to build and deepen relationships with leading brokers, consultants, and clients while driving profitable new business and retention in the large-market segment. You will bring Guardian's full portfolio of benefits and technology-enabled solutions to market, translate complex client needs into differentiated strategies, and serve as a trusted resource throughout the sales lifecycle. Success requires disciplined territory and pipeline management, strong cross-functional partnership, and a consistent focus on the broker and client experience. This role reports to the Market Leader for the assigned territory.

You are :

•A consultative, externally focused sales leader who earns credibility with sophisticated brokers, consulting houses, and large employers.

•A strategic relationship builder who combines market insight, executive presence, and disciplined follow-through to create durable growth.

•Comfortable navigating complex, multi-product opportunities and aligning underwriting, product, enrollment, implementation, service, and client-management partners around a clear client strategy.

•A collaborative and accountable teammate who uses data, technology, and competitive intelligence to prioritize opportunities and improve sales effectiveness.

•Committed to acting with integrity, inspiring well-being, and representing Guardian as a visible market and community leader.

You have :

Required 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.

Preferred qualifications :

•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 and translating capabilities into a compelling client value proposition.

•Established credibility and relationships within the regional or national broker and consultant community.

•Ability to use sales data, customer insights, competitive intelligence, and market trends to shape territory strategy and strengthen pipeline quality.

•Demonstrated thought leadership, community engagement, or industry presence that enhances market visibility.

•Track record of championing process improvements and partnering across functions to improve sales effectiveness and the broker and client experience.

You will :

•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.

Reporting Relationships :

As a Group Benefits Sales Representative, you will report to the Market Leader for the assigned territory (Central Region).

Location:

The successful candidate will be based in Chicago, with the work arrangement defined in accordance with the requirements of the assigned territory.

Travel :

Up to 50% travel within the assigned territory is required for this position.

Salary:

$40,000

The salary reflected above is a good faith estimate of base pay for the position. The salary for this position ultimately will be determined based on the education, experience, knowledge, and abilities of the successful candidate, as well as market factors and business need.

This position is also covered by a Guardian sales incentive compensation plan, making the successful candidate eligible to receive sales incentives subject to the terms and conditions of the applicable plan, in addition to base pay. The anticipated total annual compensation range inclusive of base pay and sales target incentive compensation is $222,800 to $309,900.

Our Promise

At Guardian, you’ll have the support and flexibility to achieve your professional and personal goals. Through skill-building, leadership development and philanthropic opportunities, we provide opportunities to build communities and grow your career, surrounded by diverse colleagues with high ethical standards.

Inspire Well-Being

As part of Guardian’s Purpose – to inspire well-being – we are committed to offering contemporary, supportive, flexible, and inclusive benefits and resources to our colleagues. Explore our company benefits at www.guardianlife.com/careers/corporate/benefits . Benefits apply to full-time eligible employees. Interns are not eligible for most Company benefits.

Equal Employment Opportunity

Guardian is an equal opportunity employer. All qualified applicants will be considered for employment without regard to age, race, color, creed, religion, sex, affectional or sexual orientation, national origin, ancestry, marital status, disability, military or veteran status, or any other classification protected by applicable law.

Accommodations

Guardian is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. Guardian also provides reasonable accommodations to qualified job applicants (and employees) to accommodate the individual's known limitations related to pregnancy, childbirth, or related medical conditions, unless doing so would create an undue hardship. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact MyHR glic.com . Please note: this resource is for accommodation requests only. For all other inquires related to your application and careers at Guardian, refer to the Guardian Careers site.

Visa Sponsorship

Guardian Life is not currently or in the foreseeable future sponsoring employment-based visas (e.g., such as an H-1B). In order to be a successful applicant, you must be legally authorized to work in the United States, without the need for employer sponsorship/support now or at any time in the future.

Notice Regarding Guardian’s Use of Artificial Intelligence in Recruitment

As part of Guardian’s job application process, Guardian may use artificial intelligence tools (“AI Tools ) to automate the sorting and filtering of information provided by applicants as part of its preliminary screening. This preliminary screening may be used to help identify applicant materials and resumes relative to their indication that the applicant meets the requirements for the specific job for which they are applying, as specified in the listing posted on Guardian’s jobs website (Careers at Guardian at https://www.guardianlife.com/careers ). At Guardian, we do not use AI Tools to substantially assist or replace human judgment or discretionary decision making in our hiring process. All hiring decisions will be made by Guardian colleagues.

Please be aware that if you apply for a specific position with Guardian, you will have the choice of opting out of Guardian’s use of AI Tools during the job application process. If you would like to request an alternative process that does not utilize AI Tools or would like to request a reasonable accommodation, within ten business days of your position application, you must email your request to MyHR glic.com , making sure to provide your name and job requisition identification number. Guardian will retain your applicant materials and resume and all information therefrom in accordance with Guardian’s document retention policy, a copy of which you may request via MyHR glic.com .

Additionally, at applicable times, Guardian will make public the most recent bias audit results for such AI tools, which may be found here .

Current Guardian Colleagues: Please apply through the internal Jobs Hub in Workday.