Sales Manager

TTSG is a fast-growing Managed Print Services company founded in 2010 by entrepreneur Tim Ward on one belief: technology should make work easier. Starting with print, we’ve expanded into Managed IT, Cybersecurity, Cloud, and Marketing Solutions — giving our clients a single trusted partner for the technology that runs their business.

Our sales team sells complete business solutions across the full portfolio: Managed Print Services, Managed IT, Cybersecurity, Cloud, Office Technology, Document Management, and Marketing & Creative Services.

THE OPPORTUNITY

Our Chicago Loop office at 230 West Monroe opened in July 2026, and we need a hands-on leader to build it into a high-performing sales team. You’ll own the office’s results and develop 10–15 reps through daily coaching, weekly 1:1s, joint client meetings, and Managed Print Services (MPS) training.

This is a player-coach leadership role, not a desk job. Your success is measured by your team’s activity, pipeline, and closed revenue.

WHAT YOU’LL DO

• Lead, manage, and motivate a team of 10–15 sales reps in the Chicago office
• Hold weekly 1:1s with every rep to review activity, pipeline, goals, and development
• Go on client meetings with reps to coach in the field, help advance deals, and model a consultative sales approach
• Train reps on Managed Print Services: assessments, device fleet and cost analysis, contract structure, and positioning MPS against competitors
• Recruit, onboard, and ramp new reps to productivity
• Set and track activity, meeting, and revenue targets; hold the team accountable to them
• Run team meetings, pipeline reviews, and forecasts for leadership
• Ensure accurate CRM use across the team and report on performance
• Partner with the internal quoting, proposal, and solution design team to move deals forward
• Help reps cross-sell the full TTSG portfolio, including Managed IT, Cybersecurity, and Cloud

WHAT YOU BRING

• 3–5 years of experience in the print / office technology industry
• Proven experience managing and developing salespeople
• Deep knowledge of Managed Print Services and the ability to teach it
• A track record of hitting or exceeding quota, personally and as a team leader
• Strong coaching skills — you run productive 1:1s and give direct, useful feedback
• Comfortable in front of C-suite and operational decision-makers
• Experience with CRM and sales reporting tools

Tagged as: Pipeline Management