Demo

Outside Sales Manager - B2B

Trelevate
Trelevate Salary
Chicago, IL Full Time
POSTED ON 5/14/2026
AVAILABLE BEFORE 7/14/2026

Location: Territory-Based | Travel Local Daily

Type: Full-Time | Base Uncapped Commission

Field Sales Leader - Territory Sales Manager - B2B Field Leader

The will be hiring a Outside Sales Manager 7 new B2B Business Advisors. This leader will work build, train and lead a team of B2B Sales Advisor with a expansion into IL

About the Role:

We’re looking for a driven B2B Outside Sales Manager who thrives on helping others win in sales. This is a hands-on, in-the-field position — not a desk job. You’ll coach, train, and close alongside our sales reps as they meet with local business owners to provide startegy plans when it comes to protecting Top 5 Operating Expense.

If you love the hunt, believe in consultative selling, and get satisfaction from seeing your work translate into real results for people and their businesses — this role was built for you.

What You’ll Do

  • Lead, train, and motivate field sales teams to exceed goals.
  • Conduct in-person meetings with business owners across your local market.
  • Demonstrate consultative selling to identify cost-reduction and risk-control opportunities.
  • Develop sales talent through shadowing, feedback, and live coaching.
  • Drive consistent daily activity and accountability to achieve results.

What You Bring

  • Field Training Experience with team of 7 in B2B - Preferred
  • Proven experience in outside B2B sales (energy, telecom, merchant services, or similar).
  • Strong communication and presentation skills — you know how to connect and earn trust fast.
  • A love for the thrill of the close and helping others do the same. Hunter/Closer Mentality
  • Solid with CRM / Technology
  • Self-discipline, coachability, and a team-first mentality.

What You’ll Get

  • Base Pay Uncapped Commission (First Year $80–$125K - depends on your drive)
  • Leadership role is a higher base, plus training & performance overrides
  • Benefits, 401K & 10 days of PTO
  • Growth Path: Leadership opportunities and national expansion potential.
  • Daily Wins: Incentives, bonuses, and recognition programs.
  • Support & Tools: Training, mentorship, and tech to help you succeed.
  • Annual Trips and More!

If you’re ready to step out from behind the desk and build something bigger — apply today and lead from the front.

Join a team where performance is rewarded, culture is strong, and growth never stops.

Check out Trelevate on : Facebook, Instagram or YouTube to learn more!

Salary.com Estimation for Outside Sales Manager - B2B in Chicago, IL
$119,879 to $163,410
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