Health and Benefits Sales Professional

Title: Health and Benefits Sales Professional
Status: Full-Time, Hybrid (3 Days Onsite / 2 Days Remote)
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 accomplished Health and Benefits Sales Professional to expand its mid-market employee benefits consulting business in Chicago, Illinois.

This opportunity is designed for a proven new-business developer with a strong track record of generating revenue, acquiring employer clients, and managing complex sales opportunities within the 1,000-5,000 employee segment.

The ideal candidate brings direct experience in Employee Benefits or Health and Benefits consulting, demonstrated success winning new accounts, and the ability to build relationships with senior executives and key decision-makers.

Work Schedule: Hybrid, requiring three days per week in the office and two days working remotely.

Key Responsibilities

·       Drive new business growth by identifying, prospecting, and securing mid-market employer accounts with approximately 1,000–5,000 employees.

·       Develop and execute strategic sales plans to achieve revenue, production, and client acquisition targets.

·       Demonstrate strong independent prospecting and hunting capabilities, including cold outreach, networking, referrals, and direct engagement with prospective employers.

·       Manage the complete sales process, from lead generation and qualification through presentations, proposals, negotiations, and closing.

·       Build relationships with C-suite executives, HR leaders, benefits decision-makers, and other senior stakeholders.

·       Assess employer needs and recommend appropriate employee benefits, health benefits, and consulting solutions.

·       Prepare and deliver customized proposals, competitive presentations, and responses to requests for proposals (RFPs).

·       Maintain an active sales pipeline and track opportunities, production performance, and revenue forecasts.

·       Identify market trends, competitive opportunities, and potential areas for account growth.

·       Collaborate with internal consulting and service teams to support successful client transitions and long-term relationships.

·       Expand professional networks through industry associations, business events, and strategic partnerships.

·       Consistently achieve or exceed established new-business sales objectives.

Required Qualifications

·       Bachelor's degree or equivalent demonstrated professional sales success.

·       Minimum 5 years of relevant experience in Employee Benefits, Health and Benefits consulting, or closely related sales.

·       Direct experience selling to employer groups with 1,000–5,000 employees. Employee lives refers specifically to employees, excluding dependents.

·       Demonstrated success in mid-market employee benefits sales, including measurable new-business revenue and production results.

·       Strong working knowledge of Employee Benefits or Health and Benefits consulting products, solutions, and market dynamics.

·       Proven ability to independently prospect, develop opportunities, and close new business rather than relying primarily on existing broker relationships or referral channels.

·       Experience managing complex, consultative sales cycles involving multiple stakeholders.

·       Ability to engage and influence C-suite executives and senior organizational decision-makers.

·       Consistent professional employment history, preferably including meaningful tenure with an established brokerage or benefits consulting organization.

·       Ability to work onsite three days per week in Chicago.

Preferred Qualifications

·       Active Life and Health insurance license.

·       Experience with an established national or regional employee benefits brokerage or consulting firm.

·       Five or more years of continuous tenure with a recognized brokerage or consulting organization.

·       Established relationships with senior HR executives, benefits leaders, and business decision-makers.

·       Demonstrated success managing a substantial book of business and generating new employer accounts.

·       Experience navigating competitive RFP processes, complex pricing discussions, and consultative sales negotiations.

·       Familiarity with medical, ancillary, and employer-sponsored benefit offerings.

Key Skills Required

·       Mid-Market Employee Benefits Sales (1,000–5,000 Employees)

·       New Business Hunting and Prospecting

·       Health and Benefits Consulting

·       Revenue Generation and Sales Production

·       Consultative and Solution-Based Selling

·       C-Suite and Executive Relationship Development

·       Pipeline Development and Management

·       Complex Negotiations and Deal Closing

·       RFP Development and Sales Presentations

·       Strategic Territory and Market Development

Why This Location?

Chicago provides access to a substantial employer market and a thriving professional services community. Professionals can enjoy diverse dining, live entertainment, professional sports, renowned museums, and cultural attractions. Lake Michigan offers waterfront recreation, beaches, and scenic trails, while the city's neighborhoods provide a variety of urban lifestyle options.