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 OPPORTUNITYOur 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 DOLead, manage, and motivate a team of 10–15 sales reps in the Chicago officeHold weekly 1:1s with every rep to review activity, pipeline, goals, and developmentGo on client meetings with reps to coach in the field, help advance deals, and model a consultative sales approachTrain reps on Managed Print Services: assessments, device fleet and cost analysis, contract structure, and positioning MPS against competitorsRecruit, onboard, and ramp new reps to productivitySet and track activity, meeting, and revenue targets; hold the team accountable to themRun team meetings, pipeline reviews, and forecasts for leadershipEnsure accurate CRM use across the team and report on performancePartner with the internal quoting, proposal, and solution design team to move deals forwardHelp reps cross-sell the full TTSG portfolio, including Managed IT, Cybersecurity, and CloudWHAT YOU BRING3–5 years of experience in the print / office technology industryProven experience managing and developing salespeopleDeep knowledge of Managed Print Services and the ability to teach itA track record of hitting or exceeding quota, personally and as a team leaderStrong coaching skills — you run productive 1:1s and give direct, useful feedbackComfortable in front of C-suite and operational decision-makersExperience with CRM and sales reporting tools