The Simple Guide to Choosing a CRM in 2026

[00:00:00] So let's talk about how to choose the right CRM. There's a great way to waste six months, a bunch of time and a bunch of money and frustration, and that is choosing the wrong CRM. I've managed over $50 million in closed deals, hundreds of millions of dollars in pipeline in over 10 different CRMs in my career. And I'm going to give you some of those insights today of how I would choose a new CRM if I were picking one from scratch to get started.

[00:00:28] Because let's face it, most of them are pretty good. They can all do a lot of the same things, but there are a couple of things that might differentiate what makes the right decision for you and your organization, and most importantly, your sales process. Welcome to Payrollin'. And now, here's your host, Matt Vady. Let's go.

[00:00:55] Your sales process and work backwards from there. So what is your actual sales process? What stages do people move through in the pipeline before you close one deal? And if you don't have that written down today, you almost certainly do have a sales process. You just need to document it. So what happens from the time a lead comes through? Do we have, you know, we call it, it goes from a lead to a first date, to an analysis and a demo, and then to proposal, and then to close one or close loss.

[00:01:23] And that pipeline varies slightly for our PEO versus our ASO versus our payroll services. But understanding what the pipeline looks like and what your sales process is first will help you to roll into the second thing I would look at is optimizing for adoption. The worst thing you could do is have a CRM that can split an atom that can do anything under the sun, and nobody on your team is using it, including you. So if you're the executive, either the business owner or sitting over sales,

[00:01:52] you need to make sure that it's a tool you're comfortable with, that you're going to adopt, and that is going to be easy to use. That's the most important thing is ease of use. So how many clicks does it take to get into where you need to update your pipeline? Can emails automatically sync from your Gmail or from your Outlook? Does it have a native extension that sits over top of your Outlook or your Gmail so that you can make sure you're in there consistently? Can you log calls in there? Even if you don't have salespeople today, if you're thinking about hiring a salesperson,

[00:02:21] can they call directly from inside of the CRM? Is there an integration there? Do the meetings automatically show up in the contact profiles? All these things matter because the adoption is going to make or break your success with the CRM. And let's face it, we have an old acronym or an old analogy in sales. If it wasn't in the CRM, it didn't happen. And so if we aren't keeping up with the CRM, then it's pointless to even have because our salespeople only have one job. And even if you're the founder and you're the lead salesperson,

[00:02:50] your job is to go out and find new customers and continue to grow the top line, whether or not you want to add salespeople down the road, critically important. But you want to make sure you have a system that you can use. So if you lose somebody on your team, whether that is a key salesperson, sales leader, you're not starting from scratch and having to learn and possibly even overhaul your CRM, which is what I've done in the past at times is change out a CRM that a sales leader really wanted and convinced me was the right fit.

[00:03:17] And then we ended up making a move back to our old CRM because that's where my comfort level was. So the third thing I think about is automation. We're in an environment today where all these things kind of interplay the same way a lot of people, you know, we're talking about our payroll systems. What do they integrate with? Do they integrate with retirement benefits, all the different platforms around the ecosystem of serving an employee? Your CRM has to integrate the same way, whether or not you've got a form builder on your website where the leads need to flow into your CRM.

[00:03:47] Do you need to be able to notify vendors when a new client starts? Do you need to be able to notify different people on your team? Do you need rotations for leads getting assigned correctly to people as they come in? All these automation pieces should be pretty native for most CRMs now. And you want the ability to set up if this, then that integrations, ideally inside of the CRM, especially all those things I just mentioned. Most CRMs have an ecosystem that can handle that itself. But, you know, big thing for us is once a deal closes,

[00:04:15] we have a bunch of automations that occur as far as notifying one of our vendors that we need to send a box of cookies to the new customer, all the way down to who needs to set up what and what system and trigger the implementation process. So automation is critical. And speaking to your other systems is the next thing that I would really be looking at. I talk to founders in the payroll, HR, and accounting industry every single day.

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[00:05:40] For me, the biggest, most obvious thing I want my CRM to be as native as humanly possible for is my operating system, whether that's Google or Microsoft. Choosing a CRM that integrates tightly, that HubSpot's a great example of somebody who has a really nice Gmail overlay. If you get the Chrome extension, you can send all your email templates directly from your Gmail.

[00:06:07] You can see who viewed your emails directly from your email. You can update prospects and contacts directly from your email. That, to me, is a critical driver in terms of which solution you're going to choose, because if it's native to the other things that you do all day every day, then you're highly more likely to use and adopt that solution. So everything from proposals to website forms to marketing automation, is it triggering drip campaigns after somebody does a certain action? Maybe a new lead downloads an asset from our website.

[00:06:37] Do we have the ability to easily trigger a drip campaign from there? I'll tell you, we use Zoho CRM, and it's not as easy to do those things as I would like. And we have to have a secondary CRM for those automations. And so thinking this through on the front end, before you get buried in technical debt like we are, is a great idea to make sure that it is your native ecosystem and integrates with the other things that you use and do as it relates to your sales process. The next thing I would say is don't overbuy.

[00:07:05] It's very tempting to say, hey, once I add this salesperson or we have two or three or four salespeople a day, we're going, you know, we need something enterprise. We need Salesforce.com because of where we're going as a sales team. The more likely thing you want to do and consider is where are we going to be in six months, 12 months? And we can predict that. And we make sure that we're buying for what we have today in terms of a sales team, in terms of a sales process, and a couple of legs out in front of us, not a marathon out in front of us.

[00:07:33] We want to make sure we're buying what we need, not too much because it is hard to change CRMs. And if you're getting something that's more enterprise level and your sales process doesn't require enterprise level technology, then all you're going to have is more configuration, more administration, more consultants you're hiring, more training of your team, a whole bunch of things that you don't need to do in the short term if you have a small sales team or even a founder-led sales team. And then finally, we always want to think about

[00:08:02] what's the cost to change? And I go beyond all of the SIT pricing. I mean, look, you have to invest in a CRM. It is critical for your sales operations. It's critical for your customer success operations and should be both. I should be managing my customers and my prospects in my CRM. So what I don't want to do is get too caught up in trying to save $10 a seat a month. That is not a good thought process in terms of how I want to view this investment. However, there are costs of change that can be much more cumbersome.

[00:08:31] What I mentioned earlier is that one time we went from Zoho to HubSpot and we had to bring on a third-party agency. We paid them for the implementation. It was very disruptive to our sales team. They were all trying to learn the new system. They were all trying to migrate all the data. They were looking in two different systems for an extended period of time, only for us to then realize that HubSpot was far too complicated, surprisingly, because it used to be such an easy CRM to use. It had become so much more complicated over the years and didn't check a couple of key boxes

[00:08:59] that we didn't learn until after we had it set up for months. And so we ended up going back to Zoho. And that's a costly decision for us. It slowed us down a great amount of time and it took our salespeople away from doing what they're supposed to be doing, which is selling. So you definitely want to make sure that you're considering what the cost of change is and be very pragmatic in making the decision. So a couple of things I put on my scorecard if I were looking at it. First and foremost is ease of use. Does it embed in my day-to-day? Can it automate the things that we're doing manually today

[00:09:29] from prospecting all the way through to when they are an existing customer? Does it integrate with my email and calendar? Does it email or integrate with any other critical marketing tools that we have set up or that we're thinking about rolling out in the near future, whether that be, you know, cold email platform or some sort of landing page builder or anything you may add there? And, you know, what does it have in terms of customization on top of it? And I think that you'll find once you're able to look at those things on your checklist and score those against each other

[00:09:58] and your total costs and can it scale with you, you'll be able to make a much more educated decision on the right CRM for you. Now, if you're just watching this video after the fact, you're missing the real conversation because I have got about a dozen people here sitting with me that are all going to share what the best parts of their CRM is, what they like about Zoho, what they like about HubSpot, what they like about Salesforce, why they would change, why they did change. And if you look at the link in the comments, you can see how to join the show every week and be a part of the real conversation that happens when we turn this off. Thanks so much for joining us today.

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