Job Description
Join our award-winning sales team as a Senior Outside Sales Representative in Chicago! We're seeking a driven professional to expand our B2B client base across Illinois. This is your opportunity to build a career with unlimited earning potential while representing industry-leading SaaS solutions. Enjoy comprehensive benefits, uncapped commissions, and a dynamic work environment that rewards top performers.
Why You'll Love Working With Us:
- Industry-leading uncapped commission structure (average earners exceed $120K annually)
- Company-provided vehicle and expense account
- Clear career advancement path to Sales Director
- Flexible hybrid work model with 3 remote days/week
- Annual sales retreats and recognition events
Responsibilities
- Prospect and develop new business relationships across Illinois territory
- Present complex solutions to C-level executives in target industries
- Exceed quarterly sales targets through strategic account planning
- Manage full sales cycle from lead generation to contract negotiation
- Collaborate with marketing team on lead generation campaigns
- Maintain CRM pipeline with accurate forecasting and activity tracking
- Participate in quarterly sales strategy planning sessions
Qualifications
- 5+ years of B2B outside sales experience
- Proven track record of exceeding $500K in annual sales
- Strong familiarity with SaaS or technology solutions
- Exceptional presentation and negotiation skills
- Ability to travel 60% of time throughout Illinois
- Bachelor's degree in Business, Marketing, or related field
- CRM proficiency (Salesforce preferred)
- Valid driver's license and clean driving record