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Entry Level Sales - Fast Track to Leadership
Evanston, ILMarch 21st, 2026
The Whittingham Agencies is expanding rapidly after consecutive years of market growth. We are seeking motivated, coachable professionals looking for a career—not just a job. We partner with local businesses to provide no-cost employee benefit programs that protect families and strengthen companies. If you’re driven, reliable, and want clear growth with strong earning potential, this opportunity is worth exploring. Compensation $60,000–$80,000 first-year earning potential Uncapped commissions and performance bonuses What You’ll Do Build relationships with local business owners Consult with business owners and HR leaders on benefit programs Conduct employee benefit enrollments Follow a proven activity model with leadership support Work toward weekly, monthly, and annual performance goals What We’re Looking For Professional, dependable, and coachable candidates Strong communication and organization skills Willingness to learn and follow proven systems Local travel required (not remote) High school diploma or GED Valid driver’s license and reliable transportation Ability to pass a background check Growth Opportunity Top performers can qualify for leadership and management roles in as little as 90 days . Advancement is based on performance, not tenure. d24ad0b8-823f-4e68-a892-2986ccdf7392
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