Health and Benefits Sales Professional

Title: Health and Benefits Sales Professional
Status: Full-Time, Hybrid (3 times a week Onsite)
Location: Chicago, IL 60606
Salary: $141,000 - $170,000
Visa Support: No Visa Sponsorship Available


Position Overview

A leading professional services organization is seeking an experienced Health and Benefits Sales Professional to join its Chicago-based team. This hybrid position requires a minimum of three days per week working from the office.


The successful candidate will drive growth by developing relationships with employers and senior decision-makers, identifying complex employee benefits needs, and presenting solutions involving healthcare, benefits, financial security, and employee-related programs.


Key Responsibilities

• Develop and execute sales strategies for complex, high-value accounts.
• Conduct prospecting activities, including cold outreach, presentations, meetings, and client calls.
• Build compelling proposals, presentations, and RFP responses tailored to prospect requirements.
• Manage the full sales cycle from initial opportunity identification through negotiations and closing.
• Lead pricing discussions and establish appropriate expectations with prospective clients.
• Research industries, markets, and organizations to uncover new business opportunities and expansion opportunities within existing relationships.
• Build and maintain strong relationships with client stakeholders while supporting service satisfaction and business objectives.
• Identify opportunities to introduce additional solutions and create cross-selling opportunities.
• Develop a strong professional network through industry organizations, conferences, and regional events.
• Engage effectively with C-suite and other senior-level decision-makers.

Required Qualifications

• Bachelor's degree or equivalent demonstrated sales success.
• At least 5 years of relevant professional experience.
• Demonstrated success consistently meeting or exceeding sales objectives.
• Experience selling into organizations with approximately 1,000-5,000 employees.
• Practical knowledge of Employee Benefits and/or Health & Benefits consulting, products, or services.
• Proven ability to establish relationships and gain access to C-suite executives.
• Strong enterprise sales and new-business development capabilities.

Preferred Qualifications

• Life and Health insurance license.
• Experience selling into organizations with 1,000+ employees.
• Established network of senior-level contacts within the Employee Benefits or healthcare space.
• Experience managing complex sales cycles, negotiations, proposals, and RFP processes.

Key Skills Required

• Enterprise Sales and Business Development
• Employee Benefits / Health Benefits
• Consultative and Solution-Based Selling
• C-Suite Relationship Development
• Prospecting and Client Acquisition
• Sales Negotiation and Closing

Why This Location?

Chicago offers a major business environment with extensive dining, entertainment, arts, sports, and cultural attractions. The city also provides access to Lake Michigan, waterfront recreation, diverse neighborhoods, and a broad range of professional and lifestyle amenities.