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
- Hiring, managing, coaching and developing the sales team, starting with the Paragus account executive team day one.
- The sales process, pipeline, discipline and forecast accuracy.
- Building the sales function at WEBIT, which today has no dedicated sales team.
- Pricing proposals.
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
- Months 1 to 3: Paragus, and you are not starting cold. An interim sales leader has kept a strong weekly cadence going sales meetings, rep one-to-ones, pipeline inspection and CRM discipline. Your first quarter is about taking it over, forming your own read on the team, and making it yours.
- Month 4: WEBIT begins. You start building the Chicagoland market while Paragius continues to settle, and the tow run in parallel from there.
- Months 6 to 10-: The Paragus team is producing consistently, and the forecast is one your trust, The WEBIT sales process is documented and in use, and WEBIT's first account executive is hired and ramping.
- Beyond that: Growth through acquisition is a core part of our strategy, and the function you build will be applied to future integrations. Building the repeatable version maters more here than the personal heroics.
Requirements
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.
Benefits
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
Skills Required
- 3+ years of sales leadership experience in an MSP or IT managed services business
- 3+ years of directly managing and developing sales representatives
- Experience hiring, coaching, holding sales representatives accountable to targets, and making performance decisions
- Experience building a sales function from zero
- Experience integrating an acquired company's sales team
- Experience taking over a founder's sales responsibilities
What We Do
You rely on technology every day, but is it really working for you? Maybe it feels like IT is just one more thing holding your business back. You’ve dealt with recurring issues, sluggish support, missed opportunities, and rising security risks. You’ve invested time and money, but it’s not translating into real progress—or a competitive advantage. You want more than a vendor. You want a technology PARTNER who listens, understands your goals, and helps your team work smarter, not harder. You want proactive strategies, not just reactive fixes. And you want technology that supports growth, aligns with your business plan, and stays ahead of threats—not one that’s constantly behind. That’s where your journey with us begins. At WEBIT Services, we work with organizations that are ready for something better. We start by understanding how your business operates, what outcomes matter most to you, and what’s standing in your way. Then, we build a long-term strategy that transforms your IT from a cost center into a value driver. You don’t need more tools. You need the right ones—backed by an employee-owner team that’s invested in your success. Let’s have a conversation about what’s not working, where you want to go, and how technology can help you get there.
