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TTSG · Chicago, Illinois
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
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
Details
| Company | TTSG |
| Location | Chicago, Illinois |
| Type | FULL TIME |
| Niche | Full-time |