Autonomous IT

Evan Kiely (00:02)
Hey there, buckle up for a new episode of Executive IT—Autonomous IT’s podcast designed to equip you with the insights you need to make smart, informed decisions about efficient IT investments.

Today, we’re diving into a timely topic: spring cleaning—not in your closets, but in your company’s tech stack. Tool sprawl has gotten real, and many teams are trying to consolidate. But the question is: at what cost, and for what gain?

We’re thrilled to have our guest host today, Paul Shoning, General Counsel here at Automox. In addition to keeping us on track legally, Paul brings a diverse leadership background and a unique perspective on the issues businesses face day to day.

Appreciate you being here, Paul. Anything you want to share with the audience before we dive in?

Paul Shoning (01:04)
Thanks for having me, Evan. Some folks might wonder what the General Counsel has to say about IT tool consolidation.

First, I’m the main buyer of legal tools, so I’ve gone through this process myself. But more broadly, I see every contract that comes through Automox. When teams are looking at tool consolidation, I spend a lot of time with them to ensure their goals align with their agreements and the outcomes they want. I’ve seen this play out well—and I’ve seen it backfire when people come back asking how to undo a bad move.

Evan Kiely (01:53)
Yeah, you’ve got a unique view—both as a legal contact and a tech stack manager. Let's kick it off with motivation. Why consolidate? Is it usually for cost savings, improved functionality, or both?

Paul Shoning (02:27)
Those are the right buckets. Tool consolidation often means moving from a smaller provider to one that offers multiple tools. As spend increases with a vendor, you often get better discounts.

Larger vendors also pitch improved functionality through integrated ecosystems rather than standalone solutions. Sales reps will promise cost savings and better functionality—sometimes it’s a mix of both.

Evan Kiely (03:14)
When functionality is the goal, how do you vet the promise of a tool before purchase? We’ve all seen dazzling demos that flop post-implementation. Any rules of thumb?

Paul Shoning (03:33)
The biggest one: give yourself enough time to really vet the product.

Don’t just watch a demo—do a proof of value or, at a minimum, talk to other customers. Ask them what didn’t meet expectations. If they can’t give you a real answer, that’s a red flag.

And even then, demos don’t always show how well a tool integrates with your ecosystem. A lot of the value comes from how well it plays with Salesforce, Marketo, billing software, etc.

So I ask teams: if you only got 80% of what you expect, would you still be happy with the investment?

Evan Kiely (04:52)
You mentioned something we’ve heard before: plan ahead. Communicate with stakeholders and cross-functional teams early. If you don’t give yourself time to switch tools properly, you might create more problems than you solve.

Paul Shoning (05:30)
Exactly—and that shows up in a couple of ways.

Plan ahead on the front end to vet the tool properly. But also build in overlap between the old and new tools. Don’t shut one off the same day the other goes live. Give yourself a few weeks of buffer so your business isn’t impacted if something goes wrong.

Evan Kiely (06:04)
That’s such a good point. Finance folks get this more than people realize. We expect and hope you plan for some overlap. We know migrations take time and come with risk—so don’t wait until the old contract expires to act.

Paul Shoning (06:52)
Exactly. And planning ahead also gets you a better deal.

If you’ve only got two weeks to negotiate, you lose leverage—especially if the vendor knows you're desperate. Start early and you reduce risk and costs. Sometimes, your current vendor might even offer a better deal to keep your business.

Evan Kiely (07:38)
Well said. Let’s shift to another core piece of your role—risk management. Besides planning ahead, how do you reduce risk during a cutover?

Paul Shoning (08:01)
Time and communication.

No tool operates in a vacuum. You’ll likely need help from other teams—like your Salesforce admin or sales ops. But if it’s quarter-end, good luck getting their attention.

Think about who else needs to support your cutover and coordinate timing well in advance.

Evan Kiely (08:37)
Right—bring stakeholders in early. There are often downstream impacts you might not know about, so the earlier you communicate, the better.

On that note, how do you prepare for “what if it doesn’t work”?

Paul Shoning (09:32)
Start by debunking a myth: legal can’t magically get you out of a bad contract.

Especially with smaller contracts, it often costs more to fight than to just walk away. So don't rely on legal remedies—protect yourself through due diligence before signing.

Also, consider your vendor’s level of support. When consolidating tools with a big provider, you might go from being a top customer with a small vendor to just another number in an enterprise portfolio. That means slower support and less customization. It’s a common trade-off.

Evan Kiely (11:06)
Good callout. A move to a large enterprise vendor often comes with trade-offs like slower support. Any other common trade-offs to watch?

Paul Shoning (11:46)
One big one: how did that enterprise vendor build their platform?

If they built it thoughtfully, great—you’ll benefit from true integration. But sometimes they grow through M&A and just wrap a bunch of point solutions in a shared UI. On the surface, it looks integrated—but under the hood, it’s the same old mess.

Evan Kiely (12:42)
Have you seen tool consolidations that backfired? Any warning signs?

Paul Shoning (12:55)
Definitely. The biggest red flags: teams that don’t start early or vet the transition well.

The risk is higher if you’re moving multiple tools into a new vendor with no track record. That’s where I see the most problems.

And the worst move? Signing a multi-year agreement with a new provider before testing the relationship. I've lost count of how many times folks come back asking how to get out of a 3-year deal.

Evan Kiely (14:08)
Exactly—start early, loop in stakeholders, and give the process the time it deserves. Don’t wait until the last minute and make a reactive move.

All right, with that, thanks Paul—and thanks to all of you for listening to this week’s episode of Executive IT. Join us next month when we dive into data-driven decision making.

Paul Shoning (14:47)
Thanks, Evan.