Sales Executive - Employee Benefits

Job Title: Sales Executive Employee Benefits
Location: Chicago, IL (Hybrid)
Employment Type: Full-Time | Permanent

About the Role

We are seeking an experienced Sales Executive (Employee Benefits) to join a rapidly growing national insurance agency expanding into the Chicago market. This is a high-impact opportunity for a motivated and well-connected insurance professional who thrives on building strong client relationships and driving new business growth.

The Sales Executive will serve as the anchor hire in Chicago, leading growth in this new market, shaping strategy, and collaborating closely with leadership to expand the client base and service offerings.

Key Responsibilities

Developing New Relationships:

• Build a network of outside influencers using referrals, industry associations, and other professional channels.
• Actively prospect for new business opportunities using sales tools, personal/professional networks, events, and referrals.
• Identify cross-selling and account-rounding opportunities across practice areas.
• Follow up on leads promptly and maintain all sales activity within the CRM system.
• Engage in professional networking to maintain and expand the current book of business.
• Maintain an active pipeline of 3x the annual sales goal and achieve or exceed annual sales targets.

Leading Risk Management Strategies for Existing Relationships:

• Provide efficient, professional, and courteous service to clients in collaboration with service teams.
• Analyze risks, coverage, and program structures; recommend and execute changes as needed.
• Offer innovative solutions, educate clients on available insurance options, and resolve complex risk issues.
• Collaborate with service teams to review carrier proposals, analyze market summaries, and prepare renewal documents on schedule.
• Stay current with carriers, strategic partners, products/services, and relevant legislation.
• Perform additional duties, special projects, and act as a backup for team members when required.

Candidate Profile Must Haves

• 6+ years of insurance agency sales experience in Employee Benefits.
• 3+ years of tenure in one role (no frequent job changes).
• Current license and actively working in the insurance industry.
• Proven track record as a strong producer/closer, ideally in the middle to large group market (100+ lives).
• Demonstrated consultative sales approach and strong relationship-building skills.
• Agency-side experience preferred (carrier-side considered).
• Interest or experience in mentorship, leadership, or market expansion.
• Comfortable working independently in an expansion market.
• Based in or willing to relocate to Chicago, IL.
• Willing to travel to corporate HQ in South Bend, IN quarterly.
• Stable work history.

Skills & Competencies

• 5+ years of sales/consulting experience in a professional services industry.
• Bachelors degree preferred.
• Life & Health license preferred (or ability to attain within the first 60 days).
• CEBS designation preferred.
• Strong presentation, communication, and client relationship skills.
• Proficiency with Microsoft Outlook, Word, Excel, and CRM systems.
• Self-starter with strong problem-solving and analytical abilities.
• Ability to work independently as well as collaboratively in an advisory team environment.

Why Join

This is an exciting opportunity for a seasoned Employee Benefits Producer to take ownership of their career, help shape market strategy, and grow with a nationally recognized, expanding insurance agency.