Business Development Executive

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 isn't limited to a single product line. You sell complete business solutions, which means more entry points, deeper client relationships, and significantly higher earning potential than a traditional print or IT sales role.

We're hiring Business Development Executives for two locations:

• Chicago Loop, IL — brand-new downtown office opening July 2026

This is a hunter role built for B2B sales professionals who thrive on prospecting, consultative selling, and closing. Your job is one thing: book the meeting. Once you get a prospect to the table, our dedicated internal team takes it from there — handling quoting, proposals, and solution design so you can stay focused on what you do best.

Most sales jobs hand you a phone and wish you luck. At TTSG, we invest in your success from day one:

• Qualified prospect lists and lead generation support delivered daily — you always have someone to call
• Dedicated internal team handles all quoting, proposals, and solution design — your job is to book the meeting, we do the rest
• Strong operational and technical support so you stay focused on selling, not admin
• Access to multiple revenue streams across print, IT, cloud, cyber, and marketing — more ways to open doors and close deals
• Established customer base ready for expansion and cross-selling opportunities
• Modern technology stack and sales tools designed to keep you efficient and productive
• Direct access to company leadership and decision-makers — no bureaucracy, no red tape
• Entrepreneurial environment where your ideas and contributions directly impact company growth

• Year 1 On-Target Earnings: $120,000
• Uncapped commission structure — no ceiling on what you can earn
• Competitive base salary commensurate with experience
• 401(k) with company match
• Paid Time Off
• President's Club and performance incentive programs
• Professional development and real career advancement in a growing company

• Prospect, outreach, and book meetings with key decision-makers — our team handles the rest
• Build and maintain relationships with C-suite and operational decision-makers
• Generate pipeline through cold outreach, networking, referrals, and strategic prospecting
• Develop and execute territory plans aligned to company growth goals
• Represent TTSG at industry events, trade shows, and professional networking
• Maintain accurate CRM records and collaborate with internal support teams

• 1 year of B2B sales experience with a proven track record of hitting or exceeding quota
• Background in managed print, office technology, managed services, SaaS, or telecom preferred
• Hunter mentality — comfortable with cold outreach and building pipeline
• Consultative approach — you ask great questions and connect solutions to business outcomes
• Exceptional communication and executive-level presentation skills
• Experience with CRM and sales enablement tools
• Self-motivated, competitive, and coachable

Most sales roles lock you into one product. At TTSG, you represent a full portfolio — giving you more reasons to start conversations, more problems to solve, and more ways to grow an account: