16 Questions to Ask Before You Hire an IT Company in Greater Boston

A plain-English guide for Massachusetts business owners comparing IT providers, or wondering whether their current one is still the right fit.

Most business owners don't change IT providers on a whim. Usually it's a slow buildup of unanswered tickets, a security scare, or a growing sense that no one is really looking ahead. This free guide gives you 16 practical questions to ask any IT company before you hand over the keys to your network, email and data. They work just as well for checking in on the provider you already have.

Download the Free Guide

 

In this free guide, you'll learn:

  • What response time you should expect, and how to tell whether a provider can actually deliver it.
  • How to tell whether your backups are being tested, not just running.
  • Which contract terms and "all-inclusive" promises deserve a closer look before you sign.
  • Who should hold your passwords, licenses and network documentation, and why it shouldn't be just one person.

What Makes Systems Support Different

Systems Support has been family-owned since 1989, working out of Marshfield with businesses throughout metro Boston. Our President, Will MacFee, brought one idea with him from the Nuclear Regulatory Commission: no business can seal every door, but every business can understand its risks and take sensible, verifiable steps to manage them. That's still how we work.

Here's what that means for your business today:

  • Support that answers. We respond in an average of 15 minutes, with coverage 24/7/365. The people who pick up are our own team, not an outsourced call center.
  • Security you can verify. We cover multifactor authentication, phishing protection, patching, backups and monitoring. We also show you the evidence that each one is working, instead of asking you to take it on faith.
  • Microsoft 365 and the cloud, set up properly. That means secure configuration, Teams and SharePoint set up the way your people actually work, and remote access that holds up for hybrid teams.
  • Practical guidance on AI. Through our AI Office Hours and AI guide, we help business owners work out where tools like Copilot and ChatGPT fit, what policies they need, and which risks deserve attention.
  • Flexibility for teams with in-house IT. If you already have IT staff, our co-managed support adds capacity, after-hours coverage and specialized expertise without taking over.
  • No long-term contracts. We earn your business every month, starting with a face-to-face onboarding where we meet your team and learn how the business actually runs.

Are You Ready For Better IT Support?

Then call us at 781-837-0069 or fill out the form on this page to schedule a 10-minute Discovery Call.

Schedule A Discovery Call Today

What Our Clients Say About Our Services

“The Best Firm at the Best Value”

Systems Support has kept my business safe from malware and scams by continuously updating our protections and keeping a look out for threats on the horizon. They respond to incidents right away, and most of the time take care of them before I know they're a problem. They put in the defenses to...

Systems Support has kept my business safe from malware and scams by continuously updating our protections and keeping a look out for threats on the horizon. They respond to incidents right away, and most of the time take care of them before I know they're a problem. They put in the defenses to cover you top to bottom and keep your business running smoothly. 10 out of 10!


a man smiling for the camera

Kevin Hennessey

President
Brabo Payroll
Plymouth, MA

"Seamless Communications"

"Seamless Communications" Since signing up with Systems Support, the single biggest benefit has been the seamless communication with their technicians. They do an incredible job of helping us understand our technology and what our options are. Between the incredible support and understanding...

"Seamless Communications" Since signing up with Systems Support, the single biggest benefit has been the seamless communication with their technicians. They do an incredible job of helping us understand our technology and what our options are. Between the incredible support and understanding of the challenges of small business, this family-owned business is the best choice.


a man wearing glasses

Peter Brown

President
Tiny & Sons
Pembroke, MA

Solving Technology Problems for our Fast Growing Company

We were getting notifications that our website was compromised and from there our email was compromised. I was looking for somebody to own both ends of what I consider my technology needs: email reliability and security and the website. I went with their ReliaNet Complete solution and they cover...

We were getting notifications that our website was compromised and from there our email was compromised. I was looking for somebody to own both ends of what I consider my technology needs: email reliability and security and the website. I went with their ReliaNet Complete solution and they cover both internal and external security. Setting up new employees is a breeze, I just send Systems Support the contact information and the systems my new employees need configured. They're the go-to people for our technology needs. And taking a step back, I take the security for granted.


a man smiling for the camera

Scott Hokanson

President
Brabo Benefits and Insurance
Plymouth, MA