Jobster LLC
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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.
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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
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