Health & Benefits Sales Professional

Top T Recruiting | Confidential Client Opportunity Location: Chicago, IL 60606 Work Arrangement: Hybrid — 3 days in-office, 2 days remote Employment Type: Full-time Minimum Experience: 5+ years About the Opportunity Top T Recruiting is partnering with a leading organization in the Employee Benefits and Health & Benefits consulting industry to identify an accomplished sales professional with a proven history of developing new business and growing employer relationships. This opportunity is ideal for an experienced sales professional who understands the mid-market employee benefits landscape, can navigate complex employer sales cycles, and has demonstrated success securing new business. The ideal candidate will have experience selling to organizations with approximately 1,000–5,000 employees and the ability to engage senior-level decision-makers, including HR executives, CFOs, and other C-suite stakeholders. Key Responsibilities - Develop and execute strategies to identify and acquire new employer clients. - Generate new business through prospecting, cold outreach, networking, and relationship development. - Sell Employee Benefits and Health & Benefits consulting solutions to mid-market organizations. - Manage complex sales cycles, proposals, presentations, negotiations, and client acquisition. - Build and maintain a strong pipeline of prospective employer groups. - Develop relationships with C-suite executives and key organizational decision-makers. - Expand existing business relationships and identify additional revenue opportunities. - Maintain consistent sales production and achieve established sales targets. - Research market opportunities and develop strategies for territory growth. Required Qualifications - Minimum of 5 years of relevant Employee Benefits or Health & Benefits sales experience. - Demonstrated experience selling to organizations with approximately 1,000–5,000 employees. - Strong understanding of Employee Benefits products, consulting services, and the employer benefits marketplace. - Proven record of achieving sales goals and generating new business. - Ability to independently identify, develop, and close new business opportunities. - Experience presenting complex solutions to senior-level decision-makers. - Ability to work a hybrid schedule requiring three days in the Chicago office each week. Important: Experience supporting an existing book of business alone is not sufficient. Candidates must demonstrate personal involvement in generating and closing new business. Preferred Qualifications - Active Life & Health insurance license. - Experience with a major or regional employee benefits brokerage. - Established relationships with mid-market employer decision-makers. - Experience managing complex employer benefits sales opportunities. - A bachelor's degree is preferred but not required for candidates with demonstrated sales success and relevant industry experience. Work Arrangement This position is based in Chicago, Illinois, and requires three days per week in the office and two days working remotely. Candidates must be able to meet this hybrid schedule. Compensation Compensation will be discussed during the recruitment process and will depend on experience, qualifications, and overall fit. Applicants will be asked to disclose their expected annual base salary and total compensation expectations during the application process. Application Requirements Applicants will be asked to provide information regarding: - Annual sales performance and quota attainment. - Production numbers and new business acquired. - Size and value of their book of business. - Typical employer group size and total employee lives. - Geographic territory and market size. - Personally generated new-business opportunities. - Relevant employment history and industry experience. - Annual base salary and total compensation expectations. Candidates must provide meaningful examples of their sales achievements to be considered.