Director of Sales

Rather than make you dig for it: the base is $135,000, on-target earnings are roughly $195,000, commission is uncapped, and because we are 100% employee-owned through an ESOP, you participate in ownership automatically, on the same terms as everyone else here. Combined with the 401(k), that is worth an estimated 12–18% of base salary each year.

The job

We are two managed IT services providers under common ownership, about $18.6 million combined. Paragus IT serves small and mid-sized businesses across Massachusetts from Hadley and Worcester. WEBIT Services, founded in 1996, serves Chicagoland from Naperville.

We are hiring a Director of Sales to own the combined new-revenue number across both, reporting to the CEO.

This is a leadership seat. You own the number, and you hit it primarily through the reps you manage, hire and develop. You will close deals yourself (large ones, and relationships you bring), but we are not looking for a senior individual contributor with a title. The CEO carries this work today and is handing over all of it, including the large deals. Nothing is held back.

What you would actually do

First three months. You are not walking into a mess. An interim sales leader has been running the Paragus team since September (weekly sales meeting, one-to-ones, pipeline inspection, CRM discipline), so you inherit a working cadence rather than build one. Take it over, decide what to keep, absorb the CEO's pipeline, and get each rep on a path to $5,000 in new MRR per month, at a floor of $3,500 by month six.

From month four, both at once. You start on WEBIT while Paragus is still settling. WEBIT has no dedicated sales team today, so you are building one from nothing: the process installed by month nine, its first account executive hired by month ten, $25,000 of booked MRR by month fifteen.

Year two. Scale it. We expect to acquire another MSP inside eighteen months and to open a new regional hub within twenty-four. The playbook you build gets used again.

What we need

Two things, and we are strict about both:

• You have led sales in an MSP or IT managed-services business. This motion, this buyer, this industry.
• You have directly managed and developed reps. Hired them, coached them, held them to a number, and exited the ones who did not get there.

Helpful but not required: you have built a sales function from nothing, integrated an acquired sales team, or taken a founder out of the sales seat.

How the money works

Commission is 0.25× new-logo MRR sold. In any quarter that hits the target, that rate doubles to 0.50× on everything sold in the quarter, including production above target. The quarterly target is $15,000 of new MRR for each account executive who has been in seat twelve months or more, and each rep you hire adds to it only after their first twelve months, so building the team cannot raise your bar before the team can produce. Uncapped. No margin gate.

Total cash earnings by new MRR delivered in the year:

Location

You need to live within about 90 minutes of Hadley or Worcester, Massachusetts, or Naperville, Illinois. Relocation into one of those areas works. This seat leads a team in person.

Travel to the other market is part of the role: regular time in Massachusetts early, regular time in Chicago later.

Interested, or know someone?

Either answer is useful. If this is for you, apply here or book directly: https://calendly.com/delciebean/30

If it isn't, and someone comes to mind, I would welcome the name.

Delcie Bean, CEO