What to Look for in an IT Partner for Your CPA Firm (A Chicago Accountant's Guide)
Most IT companies will tell you they work with everyone. Restaurants, law firms, medical offices, accountants. They do it all. That sounds flexible. In practice it means they do not really understand any of them. For a CPA firm, that matters. Your IT needs are not the same as a retail shop or a real estate office. You handle some of the most sensitive financial data that exists. You have hard deadlines that do not move. And you have a busy season that can make or break your year. The wrong IT partner does not just cost you money. It costs you client trust. Here is what to actually look for.
They need to understand tax season
This sounds obvious. Most IT companies will nod along when you mention it. But understanding tax season means more than knowing it exists.
It means your IT partner should be proactively checking your systems in November and December, before January hits. It means they have a plan for what happens if your remote access goes down at 8pm on April 10th. It means they treat January through April as a no-maintenance window where nothing changes unless absolutely necessary.
Ask any IT company you are considering: what does your tax season protocol look like? If they do not have a real answer, keep looking.
Remote access has to work. Every time.
The days of everyone sitting in the same office are over for most firms. Partners review returns from home. Staff pull files remotely. Some firms have team members in different states.
Secure remote access is not a nice-to-have for a CPA firm. It is core infrastructure.
Your IT partner should have hands-on experience setting up and maintaining secure remote access for professional services firms. Not just a general familiarity with VPNs, but actual experience making it work reliably for people who are not technical and need it to just work.
Microsoft 365 and Azure Virtual Desktop have become the standard for accounting firms in Chicago who need flexible, secure remote access without the complexity of managing their own servers. A good IT partner will know both inside and out.
Client data security is non-negotiable
Your clients share their most sensitive financial information with you. W-2s. Business financials. Tax returns. That data sits on your systems, in your email, in your file storage.
Cybercriminals know this. Accounting firms are a target precisely because of the value of that data. Ransomware attacks on professional services firms have increased significantly in recent years.
A good IT partner for a CPA firm does not just install antivirus and call it a day. They should be implementing layered security: endpoint protection, email security, multi-factor authentication, regular security assessments, and staff training so your team can spot a phishing attempt before they click it.
Ask them: what would happen if one of our staff clicked a malicious link? Walk me through your response process.
Local presence matters more than you think
When something goes wrong, remote support is fast and convenient most of the time. But there are moments when you need someone who can physically show up.
A server issue the day before a filing deadline. A workstation that will not boot. A new hire who needs their machine set up today, not next week.
For CPA firms in the Chicago area, working with a local IT partner means someone can be on-site when it counts. That is not something a national MSP with a call center can offer.
Predictable pricing matters for a firm your size
Most small and mid-size CPA firms do not have a dedicated IT budget managed by a CFO. The owner or managing partner is making those decisions.
Unpredictable IT bills are a real problem. A flat monthly rate that covers monitoring, maintenance, and helpdesk support means you know exactly what you are spending. No surprise invoices after a busy month.
Ask for a clear breakdown of what is included and what would cost extra. A trustworthy IT partner will give you a straight answer.
The right questions to ask before you hire anyone
Before signing with any IT company, ask these:
- Do you currently work with any CPA or accounting firms? If yes, what does that work look like?
- What is your response time guarantee, and does that change during tax season?
- How do you handle after-hours emergencies?
- What is your process for onboarding a new client?
- Do you require long-term contracts?
- What security measures do you recommend for a firm handling sensitive client financial data?
What we do at ITM Consulting
We are a small, woman and minority-owned IT firm based in Plainfield, IL. We work with small businesses and CPA firms in the Chicagoland area.
We are not trying to be everything to everyone. We work with a small number of clients and we take that seriously. When you call, you reach someone who knows your firm, knows your setup, and knows what matters to you.
We currently partner with a Chicago-area CPA firm and handle everything from their Microsoft 365 environment to remote access, security, workstations, and backup.
If you are a CPA firm in the Chicago area looking for an IT partner who actually understands accounting, we would be glad to have an honest conversation about whether we are a good fit.
No sales pitch. Just a straight conversation.
ITM Consulting
Questions about your IT setup?
We work with small businesses and accounting firms across the Chicago area. Schedule a free 30-minute consultation and we will tell you honestly what we see.