DMS Conversion Checklist: An IT Plan for Switching Dealer Management Systems

A DMS conversion checklist is the IT plan for moving a dealership from one dealer management system to another. It runs in three phases: the device, network, access, and data work before the install, the cutover itself, and the training and cleanup after go-live.

Last updated: October 9, 2026

Early in my career I worked in a three-person IT department supporting 100 actuaries at Aon. I wanted to make file storage easier, so I loaded a module onto the servers. The server went down. My boss got it back up, and then he told me something I still think about: “That worked out for us. If it hadn’t, you’d have lost your job.”

I hadn’t planned it. I hadn’t tested it. I hadn’t mapped out what it touched.

A DMS conversion is that same mistake at dealership scale, if you let it be. The DMS touches every department in the building, every printer on the service drive, and every integration your F&I and BDC people depend on. And the go-live date usually gets set on the software side, long before anybody at the store has counted the signature pads.

So here’s what I tell every dealer principal planning a switch, whether it’s to Tekion, CDK, Reynolds and Reynolds, or anything else. You need to spend time before, during, and after the install. Most stores spend nearly all of it during. That’s a real problem.

If you’re moving to Tekion, our Tekion enablement services cover the platform side, from launch prep through ongoing optimization. This post is the IT checklist that sits underneath it.

What Belongs on a DMS Conversion Checklist

A DMS conversion checklist is a phase-by-phase list of the IT, security, data, and training tasks a dealership owns when it changes dealer management systems. The DMS vendor handles data mapping and software training. The dealership owns its network, devices, user access, integrations, old data, and its people’s time.

That split matters more than most people expect. Tekion’s got trainers and project managers who help dealers through the conversion, and they know the platform cold. But they rely on the dealership to watch the training, to learn the software, and to keep learning it. Dealers don’t have the bandwidth to engage. So the store’s half of the work slides, and nobody notices until a service advisor can’t close a repair order on day one.

Not sure you should switch at all? Settle that first. It’s its own decision, and our post on when to optimize a legacy DMS and when to migrate walks through it. Everything below assumes the ink is dry.

Before the Install: The Checklist That Sets the Date

Longest list in the post. On purpose. Most of it is cheap now and expensive later, and a few items, like a second internet circuit or a box of signature pads on backorder, carry lead times long enough to move your go-live date all by themselves, which is exactly why they go first. If Tekion is the destination, our Tekion readiness guide goes deeper on circuits, cabling, and security.

Count Every Device the New DMS Will Touch

• PCs, rooftop by rooftop. Write down the operating system on each. A Windows 10 box with no extended security updates is a bad first home for a brand-new DMS, and we covered the Windows 10 deadline for dealerships on its own.
• Printers. Every one. Deal-jacket lasers, the label printer in parts, that ancient impact printer accounting refuses to give up. Get the vendor’s supported list. Then print from each one before go-live.
• Signature pads and check scanners.
• The tablets and phones your advisors and techs will use on the drive and in the shop. Who buys them, who manages them, and what happens when one walks off?

Check the Network at Every Rooftop

A cloud DMS moves the dependency instead of removing it. When the server sat in your building, a bad internet circuit slowed down email. When the DMS lives in the cloud, a bad internet circuit stops the sales desk on the last Saturday of the month. Who owns that? Someone should. Not a vendor. A person, by name, and they should be looking at a second circuit with automatic failover, wireless coverage that actually reaches the service lane and the back of the shop, and the firewall rules the new vendor needs before anyone shows up for training.

Map Every Integration Before Anybody Turns One Off

CRM, F&I menus, credit bureaus, OEM systems, parts ordering, payroll, the phone system, digital retailing, the accounting exports your CPA pulls every month. Write all of it down. Every one. For each one you want four things: a vendor contact, whether it has a certified connector to the new DMS, what credentials it uses today, and who pays for the new connection. That last one causes more arguments than the other three combined. Trust me.

Rebuild Access Instead of Copying It

Your old DMS has accounts for people who left years ago. I’d bet on it. That’s a mess. Don’t migrate it. Build the new system’s roles from today’s org chart, give each person only what their job needs, and turn on multi-factor authentication from day one. If your store arranges financing, the FTC Safeguards Rule at 16 CFR 314.4 already requires MFA for anyone accessing an information system, unless your Qualified Individual approves an equivalent control in writing. A conversion is the cheapest moment you’ll ever get to do it right.

Get the Data Questions Answered in Writing

• Back up every category before anything moves: customer records, contracts, deal and sales history, accounting, inventory, service history, and warranty documentation. In more than one place.
• Who owns the data, what format does it come out of the old system in, and how many days of read-only access do you keep after cutover? Ask the vendor you’re leaving, not just the one you’re joining.
• Ask the new vendor for its security documentation. Under section 314.4(f) of the same rule, you have to pick service providers that can protect customer information, require it in the contract, and check on them periodically. A new DMS is a new service provider. The paperwork changes the day you sign.

Block the Training Time on the Calendar Now

This is the bandwidth problem again, and it’s the item I see skipped most. Name a champion in each department. Put training on calendars like customer appointments, and protect it from month-end. If your sales manager can’t spare four hours in a training room before go-live, they’ll spend a lot more than four hours fixing deals after it.

During the Install: Cutover Week

Cutover week is when a dealership is most exposed. Everybody’s logging into something new, resetting passwords, and taking calls from people who say they’re from the vendor. Attackers know the timing. An email that says “your new DMS login expires today, click here” has never looked more believable than it does that week. We wrote about the cyber risk of changing DMS in more detail, because it gets ignored.

• Freeze every other change. No new phone system, no firewall swap, no PC refresh in the same window. The Safeguards Rule’s section 314.4(c)(7) requires covered dealers to adopt procedures for change management. Cutover week is when you find out whether yours exist on paper only.
• Verify every “vendor support” call. Hang up and call back on a number you already had.
• Put help desk people on site, or at least on the phone, for the first morning at every store, starting when the service drive opens and the first advisor tries to log in, not at 9 a.m. when the vendor’s team gets settled. That gap is where day one goes sideways.
• A 15-minute check-in each day with the vendor’s project manager, IT, and every department head, working from one shared issue list.

And keep a paper fallback ready. When CDK Global was hit by back-to-back cyberattacks on June 19, 2024, it shut its systems down, and roughly 15,000 dealership locations lost the platform they ran on. Many went back to writing deals by hand, as news coverage at the time described. That had nothing to do with a conversion. The lesson carries over anyway. It always does. A store that has practiced writing a repair order and a deal on paper gets through a rough cutover morning a lot faster than one that’s never tried.

After the Install: Where the Conversion Is Won or Lost

Asbury Automotive Group is close to finishing one of the biggest Tekion moves in the industry. Its second-quarter 2026 earnings release said 70% of its stores had converted as of July 28, with the rest on schedule for this fall, and that the company was “encouraged by the operating improvements in our converted stores.” It also broke out $4 million of Tekion implementation expenses for the quarter as their own line. A public dealer group treats the conversion as a project with a budget and a long tail. Most single-point stores budget for the subscription and stop there.

That’s the long tail. Here’s what’s on it.

• Keep training going after the trainers leave. Thirty, sixty, and ninety days out, check who’s using which features and retrain the people who drifted back to workarounds. New hires get trained on the new system, by someone who knows it, not by the person at the next desk.
• Test every integration with real transactions. A green status light isn’t the same thing as a credit app that actually landed in the lender’s portal.
• Turn the old system off on purpose. Disable every account, end the old vendor’s remote access, and decide what data you keep. Section 314.4(c)(6)(i) calls for secure disposal of customer information no later than two years after it was last used, unless you have a legitimate business or legal reason to keep it.
• Re-check your security baseline. The posture you had before the migration should still be there on the other side of it, not weaker.
• Update the incident response plan’s phone list with the new vendor’s support numbers. Small thing. Nobody does it. Do it.

For Tekion stores, this is where enablement takes over: adoption, workflow tuning, and performance scorecards by department. That work continues after Tekion’s own launch program, extending the momentum their team built, and it’s where we spend most of our time with Tekion clients, because the stores that keep training, keep measuring, and keep tuning workflows a year after go-live are the ones whose numbers look like the ones Asbury is talking about.

Who Should Run the IT Side of a DMS Switch

To be fair, your current IT person might handle it fine. Some do. Really. The risk isn’t general IT skill. It’s the specific, temporary gaps a conversion opens that don’t exist on a normal Tuesday, and the fact that the person running your day-to-day IT still has a day job while all of this is happening.

We helped Rosner Auto Group through a group split and a DMS transition at the same time, untangling phone, network, and dealer management systems that had been built for eight stores so they could run as a standalone three-store operation. That’s the kind of work our DMS transition services are built around. Heavy truck stores have their own version of this list in our IT checklist for Karmak and DSI dealers.

We’ve spent nearly 30 years supporting 2,000-plus dealerships, with a 98% client retention rate, and all of our clients are on the same roadmap. The firewall, wireless, and PC configuration your new DMS lands on is one we’ve deployed tens of thousands of times. If you’ve got a conversion on the calendar, start with a complimentary IT and cybersecurity assessment and we’ll tell you what the checklist looks like for your stores.

Things Dealers Ask Before a DMS Switch

The go-live date is one day. The conversion is a year. Plan for the year.