Outside Sales Manager - B2B

Trelevate • Chicago, IL

2d • $80,000 - $125,000 • Onsite

About The Position

We are hiring an Outside Sales Manager to build, train, and lead a team of 7 new B2B Business Advisors with an expansion into IL. This is a hands-on, in-the-field position where you will coach, train, and close alongside sales reps as they meet with local business owners to provide strategy plans for protecting their top 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.

Requirements

• 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.

Nice To Haves

• Field Training Experience with team of 7+ in B2B

Responsibilities

• 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.

Benefits

• Base Pay + Uncapped Commission
• First Year $80-$125K+ (depends on your drive)
• Higher base for leadership role, 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!

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed