Sales Executive – Employee Benefits | Chicago, IL (Hybrid)
Excellent Opportunity Placements
Chicago, IL
Permanent
Full-time
28 days ago
Apply easily
Position: Sales Executive – Employee BenefitsLocation: Chicago, IL (Hybrid – 2 to 3 days/week in office)Department: Employee BenefitsJob Type: Full-Time | PermanentReports to: Sales Team LeaderTravel: Quarterly travel to South Bend, IN requiredVisa Sponsorship: Not availableAbout the RoleAs a Sales Executive, you will play a key role in expanding the organization’s Employee Benefits business in the Chicago market. This is more than a sales role—it’s a leadership opportunity to help build the office from the ground up, develop market strategy, and influence recruiting and M&A initiatives.Key ResponsibilitiesBuild and grow a book of business through strategic prospecting and relationship buildingLead sales efforts across Employee Benefits accounts, supported by internal service teamsAct as an advisor to clients on risk management, insurance program structure, and solutionsIdentify cross-sell and upsell opportunities across other insurance linesUse internal CRM systems to manage pipeline and track sales activityDevelop new relationships through industry networks, referrals, and eventsStay current on market trends, carrier updates, and product innovationsParticipate in mentorship, leadership, and team-building activitiesIdeal Candidate ProfileMinimum 6 years of agency-side sales experience in Employee BenefitsProven track record with mid-to-large group clients (100+ lives)3+ years tenure in one role (stable job history required)Currently licensed and actively working in the insurance industryStrong closer with a consultative and relationship-based sales approachExperience with independently owned insurance agencies preferredInterest or experience in leadership, mentorship, or market developmentBased in or willing to relocate to Chicago (relocation assistance may be considered)RequirementsBachelor's degree preferredActive Life & Health license (or willingness to obtain within 60 days)Proficient in MS Office (Outlook, Word, Excel)Excellent verbal and written communication skillsMust be authorized to work in the U.S. without sponsorshipWhy Join?Be part of a growing national agency with a collaborative and entrepreneurial cultureDirect equity potential tied to performanceHigh visibility and long-term leadership opportunityCompetitive compensation package with strong backend incentives100% Employee-Owned CompanyDesignated as one of the Best Places to WorkPlease answer below screening questions1.) What are you doing in your role today and what are you looking for in your next move?2.) Are you currently licensed?3.) Are you actively working in the insurance industry today?4.) Have you worked for an independently owned insurance agency? If so, which one(s)?5.) What size groups (in terms of number of lives) have you typically worked with?6.) What is your availability to start if selected?7.) Are you willing and able to travel to South Bend, IN for quarterly meetings?8.) Are you comfortable working in a hybrid model with regular in-office presence in downtown Chicago (2–3 days per week)?9.) Please provide the link to candidate’s LinkedIn profile:10.) What is the candidate’s highest level of education?11.) Has the candidate applied or been interviewed for any role with this company in the past? If so, please provide details.12.) Where is the candidate located? If candidate is not near the job location, please explain relocation plan in detail (e.g. timeline, relocating with family, selling/buying property)13.) Is the candidate legally authorized to work in the US for any employer?14.) Will the candidate now or in the future, require immigration sponsorship for work authorization (for example, H-1B status)?15.) What is the candidate’s desired total compensation? (Please specify base salary vs. commission/bonus expectation)