Sales Executive
$175kJobster
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. #J-18808-Ljbffr
- ...use their expertise to identify and qualify leads, leading to sales opportunities with both new and existing customers. Responsibilities... ...accounts Manage complex negotiations with senior-level executives Build rapport and establish long term relationships with customers...SuggestedFull timeRemote work
Bigtincan
Springfield, IL3 days ago $115k
...can count on, and a team that succeeds together. Because at UKG, your work matters—and so do you. UKG is seeking a highly motivated sales professional as a Strategic Development Manager who will be responsible for net-new logo sales in the mid-market space. If you are a...SuggestedLive inLocal areaRemote workUKG
Springfield, IL1 day ago$85k - $90k
...Publishing Sales Representative - Higher Education Base pay range : $85,000.00/yr - $90,000.00/yr Responsibilities ~ Field-based consultative sales role, calling on professors at colleges/universities during the Spring and Fall semesters ~ Work from your own...SuggestedFull timeSummer holidayWork from homeHome officeNight shiftECA Recruiters
Springfield, IL2 days ago$50k - $80k
...About the Job We are seeking a highly motivated and results-driven Sales Executive to join our team. This individual will be responsible for generating new business opportunities, building strong client relationships, visiting clients in person and promoting our staffing...SuggestedBase plus commissionWork at officeLHH
Springfield, IL3 days ago- ...Head of HR @ Mitra Innovation | MBA, HR Expertise We are seeking a high-energy, results-driven Sales Executive / Hunter to accelerate MitrAI’s growth across Global 2000 enterprises in the U.S. This role is centered on new client acquisition - identifying, engaging...SuggestedFull timeRemote workFlexible hours
Mitra AI
Springfield, IL2 days ago $100k
...potential, you NEED to apply for this position! Must have insurance sales experience and a valid Property & Casualty License . Come work... ...interviewing at Allstate by 2x Get notified about new Sales Executive jobs in Illinois, United States . Illinois, United States...Base plus commissionLocal areaRemote workAllstate
Springfield, IL2 days ago- ...actively prospects for new clients and business for the profitable sale of core and supplemental products for a business segment in an... ...the changing political environment. Develop, implement and execute business plans and metrics for retaining and growing membership...For contractorsWork at officeLocal areaRemote work
Highmark Health
Springfield, IL3 days ago $115k
...can count on, and a team that succeeds together. Because at UKG, your work matters—and so do you.UKG is seeking a highly motivated sales professional as a Strategic Development Manager who will be responsible for net-new logo sales in the mid-market space.If you are a...Live inLocal areaUkg-6
Springfield, IL1 day ago$112.4k - $194.4k
...Job Description Are you a sales pro looking to excel in an exciting, large-scale arena? Oracle is a market leader in Cloud ERP because... ...splash in your career. We’re looking for an Industry Sales Executive to provide expertise in finance and budgeting solutions tied to...Temporary workRemote workFlexible hoursOracle
Springfield, IL3 days ago$59.5k - $126.6k
...from the bank, we're involved. If you want to make an impact on a global scale, come make a difference at Fiserv. Job Title Sales Executive About your role: At Fiserv, a successful Sales Executive II is a dynamic leader who excels in driving revenue generation...Full timeContract workTemporary workH1bFiserv
Springfield, IL2 days ago- ...As a Warehousing Sales Executive for TQL, you will play a key role in expanding our warehousing services business. This role is focused on developing new customer relationships and growing existing accounts by delivering customized warehousing solutions. You will work...Contract workH1bWork at office
Total Quality Logistics
Springfield, IL3 days ago $69k
...Genuine desire to help others by providing guidance and solutions Strong verbal communication and relationship-building skills Sales or customer service experience is helpful but not required Qualifications Laptop or desktop computer with a working camera...Remote jobWork from homeFlexible hoursLone Star Careers
Springfield, IL5 days ago$72k
...prospects, clients and intermediaries for solicitation of new business opportunities. The incumbent is responsible for the profitable sale of core and supplemental products, directly or through intermediaries, in an assigned geographic region, territory or distribution...For contractorsWork at officeLocal areaRemote workFlexible hoursHighmark Health
Springfield, IL1 day ago$125k
...1 Web Fraud Detection Fast Company rated them most innovative financial tech company in 2013 Job Description Position to fill: Sales Executive, Fraud Solutions Industry: Specialized IT Services Location: Candidate may be located anywhere in the US (NE preferred). 75% travel...Temporary workTecTammina
Springfield, IL3 days ago- ...Chicago area. In this role, you will be responsible for identifying and pursuing new business opportunities, developing and implementing sales strategies, and building relationships with clients and prospects. Responsibilities Identify and pursue new business opportunities...
hXpath
Springfield, IL3 days ago $73.5k - $110.3k
...purpose-driven company that will invest in your professional development. Job Summary This position is accountable for delivering sales results across a defined portfolio of health, life and ancillary insurance products within the Southern Illinois and St. Louis...Remote workWork from homeNight shiftHCSC
Springfield, IL1 day ago$78.5k - $167.1k
...from the bank, we’re involved. If you want to make an impact on a global scale, come make a difference at Fiserv. Job Title Sales Executive - Plastics What does a successful Sales Executive, Card Plastics Production do at Fiserv? As a successful Sales Executive,...Temporary workH1bRemote workFiserv
Springfield, IL4 days ago$92.2k - $115.3k
...Job Title: Sales Development Executive Department: Sales, Marketing & Product Management Country: United States of America State/Province: Georgia City: Atlanta Full/Part Time: Full time Job Summary: Under general supervision, this...Full timeContract workTemporary workPart timeWork experience placementRelocationVisa sponsorshipJ.B. Hunt Transport
Springfield, IL1 day ago- ...Discover more by following us on LinkedIn! General Function The Sales Representative's responsibility is to achieve sales targets and... ...Loyalty Rewards program. The incumbent is responsible in executing brand strategies while also maintaining the established standards...Minimum wageFull timeLocal areaNight shift
EssilorLuxottica
Springfield, IL22 hours ago $100k
...Why Work with Bath Planet?An incredible opportunity as a Sales Representative for Bath Planet is now available! Bath Planet is the largest national provider of residential bath remodeling, and we are hiring for sales! We specialize in amazing bathroom remodeling in residential...Weekly payFull timeLeafHome
Springfield, IL3 days ago- ...Sales Coordinator Driftwood Hospitality Management's company culture empowers our associates to take initiative, be proactive, and... ...and hands-off to the Convention Services department for the execution of details. Is available to solve problems and/or suggest alternatives...Contract workTemporary workWork at officeLocal areaImmediate startShift work
Driftwood Hospitality Management
Springfield, IL3 days ago - An established industry player is seeking an Office Representative to join their dynamic team in Lincolnwood, IL. This full-time role involves building customer relationships and promoting a variety of insurance products, including auto, home, and life insurance. The ideal...Full timeWork at office
Sfdino
Springfield, IL1 day ago - Medium is seeking a dependable Client Support Specialist to assist with travel-related inquiries and provide client support. This remote position involves timely assistance, request management, and ensuring a smooth travel planning experience. Ideal candidates will ...Remote workFlexible hours
Medium
Springfield, IL2 days ago $95.56k - $133.75k
...5,560.00/yr - $133,750.00/yr Responsibilities Drive profitable sales growth within an assigned, established account base of CPA firms... ...in target accounts and engaging client accounts at management/executive levels to identify business issues. Plan and schedule all required...Full timeWork at officeFlexible hoursWolters Kluwer
Springfield, IL3 days ago- A global travel management company is seeking an Ovation Specialize Travel Consultant in Springfield, Illinois. This role involves providing exceptional travel service to corporate clients, managing travel bookings, and ensuring adherence to customer policies. Candidates...Remote work
American Express Global Business Travel
Springfield, IL4 days ago $46k - $52k
Amex GBT is a place where colleagues find inspiration in travel as a force for good and - through their work - can make an impact on our industry. We're here to help our colleagues achieve success and offer an inclusive and collaborative culture where your voice is valued...Contract workPart timeLocal areaImmediate startFlexible hoursAmerican Express Global Business Travel
Springfield, IL1 day ago$46k - $52k
Amex GBT is a place where colleagues find inspiration in travel as a force for good and - through their work - can make an impact on our industry. We're here to help our colleagues achieve success and offer an inclusive and collaborative culture where your voice is valued...Contract workImmediate startFlexible hoursAfternoon shiftAmerican Express Global Business Travel
Springfield, IL2 days ago$39.2k - $72.8k
Amex GBT is a place where colleagues find inspiration in travel as a force for good and - through their work - can make an impact on our industry. We're here to help our colleagues achieve success and offer an inclusive and collaborative culture where your voice is valued...Immediate startRemote workFlexible hoursNight shiftDay shiftAfternoon shiftAmerican Express Global Business Travel
Springfield, IL4 days ago- ...safety and loss control. Professionally represent Verisk and our customers via phone, in person and in written correspondence. Execute on our data quality commitment using your eye for detail and communication skills in completing accurate and customer-centric...Full time
Verisk
Springfield, IL15 days ago $39.2k - $72.8k
Amex GBT is a place where colleagues find inspiration in travel as a force for good and – through their work – can make an impact on our industry. We’re here to help our colleagues achieve success and offer an inclusive and collaborative culture where your voice is valued...Immediate startRemote workFlexible hoursShift workNight shiftWeekend workAfternoon shiftAmerican Express Global Business Travel
Springfield, IL1 day ago
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Sales Executive. Be the first to apply!
- technology sales representative Springfield, IL
- sales representative insurance Springfield, IL
- field sales representative Springfield, IL
- sales agent Springfield, IL
- sales representative flooring Springfield, IL
- commercial banking specialist Springfield, IL
- sales specialist flooring Springfield, IL
- inside sales representative Springfield, IL
- local sales representative Springfield, IL
- telecommunications sales representative Springfield, IL