Director of Sales
WEBIT Services
Director of Sales
WEBIT Services
Proactive IT services partner for growth
WEBIT Services · Naperville, United States (Hybrid) · Full-time · Posted 2026-11-12
Salary: Up to USD 150,000
Workplace: hybrid
Department: Sales & Marketing
Paragus IT and WEBIT Services are two managed services providers under common ownership, with combined revenue of approximately $18.6 million.
Paragus, IT serves small and mid-sized businesses across Massachusetts from offices in Hadley and Worchester. WEBIT Services, founded in 1996, serves the Chicago market from Naperville, Illinois.
Both are 100% employee-owned through an ESOP. Every employee is an owner, and that is not a benefits-page line. It shapes how we think about the business and how we work together: owners care about results, speak up, and look out for each other.
Our two companies grew up in different places, but they share a lot. Both have been recognized as Forbes Small Giants for their culture. Paragus is built on giving back, staying humble, asking questions and having fun along the way. WEBIT has twice earned the BBB Torch Award for Ethics and is built on doing the right thing and owning the outcome if something went wrong. Put together, it is a place where people are curious, accountable, and genuinely enjoy working together.
The Role
The Director of Sales reports to the Chief Executive Officer.
You own the combined new revenue number across Paragus IT and WEBIT. This is a leadership seat, not a senior individual contributor seat: the number is achieved primarily through the reps you manage and develop, and the long-term intent is a leader who helps the team hit is numbers rather than the one who hits them personally. You will close deals yourself, large deals and relationships you bring, but that is the exception rather than the design.
The CEO currently carries this work and is handing over all of it, including the large deals.
What You Own
- The total new-revenue number across both companies
Marketing is peer function reporting to the CEO. You will work closely alongside our marketing leader rather than manage the function.
The First Eighteen Months
What We Are Looking For
Required:
3+ years of sales leadership experience in an MSP or IT managed services business. You have sold in motion, to this buyer, in this industry.
3+ years of directly managing and developing sales reps. Not dotted line or "lead by example." You have hired them, coached and held them to a number and made the hard calls when needed.
Preferred, and genuinely valued:
- Built a sales function from zero.
- Integrated an acquired company's sales team.
- Experience taking a founder seat of the sales seat.
Location and Travel
You need to live within about 90 minutes' drive of one of our three offices: Hadley or Worchester, Massachusetts, or Naperville, Illinois. The seat exits to a team in person. Relocation into one of those area works, and we are open to discussing relocation assistance for the right candidate.
Expect to travel about 15 to 20% of the time, including regular time in both markets.
Compensation
Base salary: $150,000
Commission: Uncapped, paid on new client monthly recurring revenue, with a quarterly accelerator that doubles your rate in any quarter the team meets the target.
On-target earnings: Approximately $210,000 in total cash compensation.
Why This Seat Is Worth Taking
You will own revenue for two companies and report to the CEO., with no sales leadership layer above you. The CEO is handing over the function rather than keeping the interesting parts. The business is 100% employee-owned, so yiou build real ownership as an employee-owner. And our growth strategy means the function you build gets applied again rather than simply maintained.
100% Employee-ownership through our ESOP
401k Plan + Matching up to 4%
Medical, Dental and Vision insurance - up 100% covered on premium on Medical Plan
Monthly stipend for your cell phone
Flexible time off - provides an uncapped bank of paid time off to use for vacation
Up to five days of sick time and six paid holidays
Hybrid Work Policy - up to two days per week remote after onboarding
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Proactive IT services partner for growth
WEBIT Services acts as a technology partner for organizations, providing managed IT services and strategic guidance to turn IT from a cost center into a value driver. It begins by understanding how the business operates and which outcomes matter, then creates a long-term IT strategy and implements the right tools backed by an employee-owner team. The approach is proactive, focusing on prevention, security, and alignment with growth plans, rather than just reactive fixes. What sets WEBIT Services apart is its emphasis on true partnership with clients—listening to goals, tailoring strategies to the business, and committing to the client’s success rather than selling standalone tools. The goal is to help clients work smarter, reduce risks, and achieve growth by using technology that supports their business strategy.
Explore more opportunities at WEBIT Services