Paragus Strategic IT

Director of Sales

Hadley or Worcester, MA - Full Time

Director of Sales
Paragus IT & WEBIT Services
Hadley, MA  |  Worcester, MA  |  Naperville, IL

The companies
Paragus IT and WEBIT Services are two managed IT 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 Worcester. WEBIT Services, founded in 1996, serves the Chicagoland 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 when something goes wrong. Put together, it is a place where people are curious, accountable, and genuinely enjoy working together.

The role
Director of Sales, reporting 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 we are looking for a leader who helps the team hit its numbers rather than one who hits them personally. You will close deals yourself, especially 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 on 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 a 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 in the Chicagoland market while Paragus continues to settle, and the two run in parallel from there.
  • Months 6 to 10: The Paragus team is producing consistently, the forecast is one you 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 matters more here than personal heroics.

What we are looking for
Required:
  • 3+ years of sales leadership in an MSP or IT managed-services business. You have sold this motion, to this buyer, in this industry.
  • 3+ years of directly managing and developing sales reps. Not dotted-line, not “led by example.” You have hired them, coached them, 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 out of the sales seat

Location and travel
You need to be within about 90 minutes' drive of one of our three offices: Hadley or Worcester, Massachusetts, or Naperville, Illinois. This seat exists to lead a team in person. Relocation into one of those areas 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 hits its target
  • On-target earnings: Approximately $210,000 in total cash compensation

Benefits
  • 100% employee ownership through our ESOP
  • 401K Plan + Matching up to 4%
  • Medical, Dental and Vision Insurance – up 100% covered premium on one 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

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 you build real ownership as an employee-owner. And our growth strategy means the function you build gets applied again rather than simply maintained.

Paragus IT and WEBIT Services are equal opportunity employers.
 
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