Health & Benefits Sales Professional - $141K-$170K

Direct Line Workforce Solutions

Chicago, Illinois

JOB DETAILS
SALARY
$141,000–$170,000 Per Year
SKILLS
Business Growth, Conferences, Consulting, Consumer Market Share, Contract Negotiation, Develop and Maintain Customers, Employee Benefits, Enterprise Sales, Exceeded Sales Goal, Executive Relationships, Healthcare, Market Research, Mergers and Acquisitions, Negotiation Skills, Networking Events, Proposal Writing, Request for Proposals (RFP), Revenue Growth, Sales, Sales Cycle, Sales Management, Sales Presentation, Sales Prospecting, Sales Strategy, Strategic Accounts, Strategic Planning, Thought Leadership
LOCATION
Chicago, Illinois
POSTED
30 days ago

Health & Benefits Sales Professional (Central Zone) - $141K-$170K


Location:

Chicago, IL

Dallas, TX

Pittsburgh, PA

Atlanta, GA

Charlotte, NC

Fort Lauderdale/Sunrise, FL

Southfield, MI

Las Vegas, NV

Irvine, CA

Work Arrangement: Hybrid (3 Days In Office Required)

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Overview:

We're seeking a Health & Benefits Sales Professional to drive new business growth and expand relationships within the large employer market.

This role focuses on selling strategic employee benefits, healthcare, financial wellbeing, and workforce solutions to organizations with 1,000 to 5,000 employees. The ideal candidate is a proven hunter with a strong track record of winning new business, building executive-level relationships, and navigating complex sales cycles.

This is an opportunity to join a high-performing sales organization and help employers solve critical health and benefits challenges while delivering measurable business value.

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Key Responsibilities:

Execute sales strategies to acquire new clients and expand market share.

Build and manage a portfolio of complex, high-value opportunities.

Conduct sales presentations, executive meetings, and prospect engagements.

Create compelling proposals, presentations, and RFP responses.

Lead opportunities from prospecting through contract negotiation and closing.

Develop strategic account pursuit plans for target organizations.

Build relationships with C-suite executives, HR leaders, and key stakeholders.

Research markets and identify opportunities for growth and expansion.

Collaborate with internal subject matter experts to deliver customized solutions.

Participate in industry organizations, conferences, and networking events.

Consistently achieve and exceed sales and revenue goals.

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Requirements:

Bachelor's degree required.

5+ years of successful enterprise sales experience.

Experience selling employee benefits, health and benefits consulting, or related solutions.

Experience selling to organizations with 1,000-5,000 employees.

Strong hunter mentality with proven new business acquisition success.

Strong network and ability to gain access to executive decision-makers.

Experience managing complex sales cycles.

Excellent presentation, negotiation, and relationship-building skills.

Proven track record of achieving or exceeding sales goals.

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Preferred Qualifications:

Life & Health License.

Experience in employee benefits consulting.

Experience selling health and welfare consulting solutions.

Strong executive-level network.

Thought leadership and industry participation.

Proven success acquiring new logos and growing revenue.

Experience with direct competitors in the health and benefits consulting industry.

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Compensation & Benefits:

Base Salary: $141,000 - $170,000

Employment Type: Full-Time

Work Arrangement: Hybrid

Visa Sponsorship: No visa sponsorship available.

Relocation Assistance: No relocation assistance available.

Benefits and incentive compensation may be available based on employer programs.

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Apply Today:

If you're a results-driven sales professional with employee benefits expertise and a passion for building executive relationships, we encourage you to apply today.

About the Company

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Direct Line Workforce Solutions