Sales Executive

Jobster LLC; Illinois; Hybrid; USD 100,000 - 150,000; Full time

Benefits offered by this job

Competitive base + uncapped commission structure

Equity opportunity based on performance

Full suite of benefits including health, dental, vision, 401(k)

Job summary

A leading employee benefits firm in Chicago is searching for an experienced Employee Benefits Sales Executive. This pivotal role requires a strong background in insurance sales, especially within the middle-to-large group market, and offers opportunities for leadership development. The position is hybrid, demanding local presence, and provides a competitive base salary with uncapped commissions, along with a flexible work environment and strong growth prospects.

Qualifications

• 6+ years of agency-side insurance sales experience in Employee Benefits.
• Proven success in the middle-to-large group market (100+ lives).
• Strong consultative selling and closing skills.

Responsibilities

• Cultivate new relationships with C-suite and HR.
• Grow into a Sales Team Leader with leadership potential.
• Conduct risk analysis and propose innovative solutions.

Skills

Agency-side insurance sales experience

Consultative selling

Professional network in Illinois

Leadership qualities

Education

Licensed in Life & Health

Job description

6 hours ago Be among the first 25 applicants

Get AI-powered advice on this job and more exclusive features.

Direct message the job poster from Jobster LLC

Location: Chicago, IL | Hybrid (Local Presence Required)

About Us

As an employee-owned organization, we believe in empowering our people to take charge of their careers. Our mission is simple: provide exceptional service while living our Core Values:

• Create a Great Experience
• Do the Right Thing
• Play for Each Other
• Pursue Growth
• Own Your Future

With a national footprint and deep-rooted expertise, we’re expanding westward—and Chicago is our next major growth hub. We're building from the ground up and seeking an experienced, entrepreneurial Employee Benefits Sales Executive to help lead the charge.

Why This Role Matters

This is more than a traditional producer role. As the anchor hire in a new market, you will play a pivotal role in shaping our presence in Chicago:

• Lead market strategy and territory development
• Influence office growth, recruiting, and onboarding
• Participate in strategic M&A conversations
• Grow into a Sales Team Leader with leadership and equity potential

Backed by a Top 40 national insurance agency, a collaborative leadership team, and direct access to cross-selling in P&C, you’ll have the tools and freedom to build your legacy.

What You'll Do

• Cultivate new relationships with C-suite, HR, and benefits decision-makers
• Leverage referrals, networks, industry events, and outbound outreach to generate leads
• Actively maintain a robust pipeline (3x annual sales goal minimum)
• Present tailored, consultative insurance and risk management strategies
• Utilize sales enablement tools and CRM to track activity and progress
• Serve as the account lead, supported by a dedicated client service team
• Conduct risk analysis, program reviews, and propose innovative solutions
• Educate clients on marketplace options, compliance changes, and cost-containment strategies
• Partner with internal teams to deliver seamless renewals, carrier negotiations, and implementation
• Maintain high retention and satisfaction through consistent engagement
• Contribute to the development of go-to-market plans for Chicago
• Mentor junior producers and participate in talent recruitment
• Collaborate with executive leadership and HQ on quarterly initiatives
• Help evaluate local acquisition or tuck-in opportunities

What Makes You a Great Fit

• 6+ years of agency-side insurance sales experience in Employee Benefits
• Proven success in the middle-to-large group market (100+ lives)
• Licensed in Life & Health (or willing to obtain within 60 days)
• 3+ years of tenure in a previous role (no frequent job changes)
• Based in or willing to relocate to Chicago, IL
• Willing to travel to Corporate HQ in South Bend, IN quarterly
• Strong consultative selling and closing skills
• Strong professional network in the Illinois market
• Leadership qualities or interest in mentoring a growing team
• Background in both sales and client strategy or servicing

What We Offer

• Competitive base + uncapped commission structure
• Equity opportunity based on performance
• Direct support from marketing, sales enablement, and executive leadership
• Full suite of benefits including health, dental, vision, 401(k) with match
• Flexibility and autonomy to build your market your way
• The chance to own your future as we grow this region together

Are you ready to create something impactful in Chicago?

We’re looking for a passionate, connected, and entrepreneurial Employee Benefits leader who’s ready to go beyond “business as usual.”

Apply now or reach out to learn more about how you can Own Your Future with us.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales, Management, and Strategy/Planning

• Industries

  Insurance

Referrals increase your chances of interviewing at Jobster LLC by 2x

Sign in to set job alerts for “Sales Executive” roles.

Mid-Market Account Executive - Sales Solutions

Chicago, IL $131,000.00-$188,000.00 2 weeks ago

Chicago, IL $97,000.00-$140,000.00 1 week ago

Chicago, IL $45,000.00-$55,000.00 3 days ago

Mid-Market Relationship Manager, Sales Solutions

Chicago, IL $131,000.00-$188,000.00 1 week ago

Chicago, IL $81,450.00-$103,950.00 1 week ago

Chicago, IL $100,000.00-$120,000.00 1 month ago

Mid-Market Account Executive ‚ Talent Solutions, Academic

Chicago, IL $131,000.00-$188,000.00 5 days ago

Chicago, IL $106,000.00-$152,000.00 5 days ago

Account Executive, Strategic Inside Sales

Account Executive 2, Online Sales, Marketing Solutions

Chicago, IL $133,000.00-$190,000.00 1 week ago

Chicago, IL $145,500.00-$185,500.00 2 weeks ago

Chicago, IL $70,000.00-$80,000.00 2 weeks ago

Chicago, IL $123,000.00-$224,400.00 2 weeks ago

Chicago, IL $56,000.00-$85,000.00 5 days ago

Chicago, IL $50,000.00-$120,000.00 1 day ago

Account Executive (Remote) | No-Code SaaS | 100% Remote

Oak Park, IL $70,000.00-$75,000.00 6 days ago

Chicago, IL $85,000.00-$115,000.00 5 days ago

Global and Regional Account Executive, GCAS

Chicago, IL $134,000.00-$196,000.00 6 days ago

Chicago, IL $100,000.00-$125,000.00 2 weeks ago

Mid-Market Talent & Learning Account Executive (Learning & Engagement )

Chicago, IL $125,000.00-$180,000.00 3 weeks ago

SaaS Sales Executive - (OTE $175,000/year USD), CXT Software

Chicago, IL $200,000.00-$225,000.00 2 weeks ago

SaaS Sales Executive - (OTE $175,000/year USD), CXT Software

Chicago, IL $127,800.00-$183,655.00 1 week ago

Chicago, IL $70,000.00-$118,000.00 1 week ago

Chicago, IL $127,800.00-$183,655.00 5 days ago

Chicago, IL $65,000.00-$150,000.00 2 weeks ago

West Lincoln, IL $129,000.00-$206,000.00 2 days ago

Chicago, IL $220,000.00-$235,000.00 1 week ago

Chicago, IL $151,000.00-$230,000.00 6 days ago

We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.