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Your CRM Buying Guide: Avoiding Pitfalls, Planning for Growth, and Driving Adoption

Few decisions shape your business quite like choosing a CRM. That’s why you need a solid CRM buying guide to steer you clear of the pitfalls.

Meet Jason Kramer, Founder and CEO of Cultivize, a CRM consultancy. In this episode of Closing Time, Jason shares the must-ask questions to ensure your CRM fits your needs today—and scales with you tomorrow.

Plus, he reveals why a top-down commitment is the secret to avoiding common implementation traps and driving lasting success.

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When it comes to buying your first CRM, few decisions carry as much weight for your business. With over 1,700 CRMs on the market today, selecting the right one can feel overwhelming. Jason Kramer, CEO of Cultivize, a CRM consultancy, shares his expert advice on navigating this crucial choice in an episode of Closing Time. Here’s what you need to know.

Start with an Internal Conversation

Before diving into CRM options, take a step back. Jason recommends starting with an internal discussion to identify the needs of your team. Ask questions like:

Who will use the CRM? Sales, marketing, operations, or customer service teams might all have different requirements. Understanding their workflows is key.

Where will they use it? Are they desk-based or mobile? For example, a sales team constantly on the go will need a CRM with a robust mobile app.

How will the CRM fit into their day-to-day tasks? The tool should simplify processes, not add complexity.

Jason emphasizes the importance of aligning the CRM with your current workflows to ensure a smooth adoption process.

Look Beyond the Shiny Features

It’s tempting to pick a flashy CRM with a freemium model or cool features, but Jason cautions against this. Instead, focus on two critical factors: Scalability and Support.

Scalability: If your team grows from two to ten salespeople in the next year, will the CRM still fit your needs? Choosing a platform built to scale effortlessly ensures you’re investing for the long term, not just today.

Support: Many CRMs offer technical support, but Jason points out that this isn’t always enough. You might need strategic guidance, like leveraging your CRM for a webinar or an ad campaign. Working with a consultant or selecting a CRM with robust customer success and support can make all the difference.

Understand the Total Cost of Ownership (TCO)

When choosing a CRM, it’s crucial to look beyond the sticker price and consider the total cost of ownership (TCO). TCO encompasses all expenses associated with the CRM over its lifecycle, not just the licensing fee. This includes costs for implementation, training, ongoing maintenance, and any additional resources needed to maximize its value.

Total cost of ownership for a CRM

Jason explained that many businesses overlook hidden costs, such as integration fees for connecting the CRM to other systems, charges for exceeding contact or user limits, and expenses related to scaling as the business grows.

Additionally, TCO includes the time and effort required to customize the CRM to fit your unique workflows. Customization often demands resources like a dedicated team, external consultants, or marketing professionals to create content, design workflows, or set up automation. For instance, if your CRM is meant to nurture leads, who will write the emails, design templates, or manage campaigns? These often-overlooked factors contribute significantly to the true cost of owning a CRM.

Understanding TCO ensures that your investment aligns with both your current needs and future goals. A solution like Insightly, which offers robust customization options without the need for extensive third-party tools, can help businesses keep TCO manageable while delivering long-term value.

Look for Unified Functionality

Jason highlights the growing trend of CRMs and marketing automation platforms merging into unified all-in-one solutions. Today’s businesses need more than just contact management—they need a CRM platform that integrates seamlessly with marketing automation, customer service, and other go-to-market tools. A unified platform ensures that tools speak to one another, oftentimes sharing the same data set across teams.

This seamless connectivity is where Insightly shines. By consolidating marketing and sales tools into a single platform, Insightly eliminates the inefficiencies of siloed tools. Marketing can see what sales is doing, sales can track marketing efforts, and everyone operates from a shared source of truth. This alignment fosters better collaboration, reduces data inconsistencies, and accelerates decision-making. With all your critical information in one place, a unified platform like Insightly doesn’t just make work easier—it helps teams work smarter.

Adoption is Everything

A CRM is only as effective as the people using it. Jason emphasizes that adoption is the cornerstone of a successful CRM implementation. Even the most advanced platform will fall short if it doesn’t integrate seamlessly into your team’s daily workflows or if the users don’t see its value.

The key to adoption lies in clear leadership and a thoughtful rollout strategy. Jason notes that 72% of CRM implementations fail because decisions are made at the top without input from the people who will actually use the system. This disconnect can lead to resistance, especially if the CRM is seen as extra work rather than a tool for productivity. A champion within the organization—a leader who can advocate for the tool and hold the team accountable—is essential for driving engagement.

One effective tactic Jason recommends is piloting the CRM with a small, enthusiastic group of users before rolling it out to the entire team. These early adopters can serve as internal experts, demonstrating the CRM’s value and helping others navigate the platform. This approach not only builds excitement but also addresses potential roadblocks early in the process.

Finally, Jason stresses the importance of addressing behavioral hurdles. For instance, team members who are accustomed to spreadsheets or manual processes may view a CRM as unnecessary or cumbersome. Overcoming this mindset requires clear communication about the CRM’s value—how it saves time, boosts productivity, and ultimately makes their work more effective. Gamifying the process, offering incentives, or showcasing success stories from within the team can also help ease the transition.

The Bottom Line

Choosing the right CRM isn’t just about finding a tool—it’s about finding the right tool for your business. Start with your needs, plan for scalability, and consider total cost and customization. Modern platforms like Insightly offer scalable, all-in-one solutions that grow with your business and keep marketing and sales aligned.

 

To dive deeper into Jason’s advice or explore his free CRM Fit Assessment, visit his website. Or, check out Insightly to see how an integrated CRM can transform your workflows.

Transcript

Buying the first CRM for your business.
There are few decisions that are more important than this one.
Let’s learn how a CRM consultant approaches this crucial purchase.
On this episode of Closing Time.
Thanks for tuning in to Closing Time, the show for Go to Market Leaders.
I’m Val Riley, VP of marketing for Unbounce and Insightly.
Today I am joined by Jason Kramer.
He is the CEO of Cultivize, a CRM consultancy firm.
Jason, welcome to the show.
Thanks, Val. Happy to be here.
at last count there were more than 1700. CRMs on the market today.
Now most of those are niche players for specific industries.
But even with that, that is a very large number.
Val, there are so many options.
And the reality is, is that a lot of people are looking at
sometimes the features and benefits or the shiny object syndrome,
you know, and another kind of issue, in my opinion, is like the freemium model
where you’re going to sign up for something that’s free,
but then you don’t realize the costs involved and what it really can do,
and sometimes it then becomes a little bit difficult
to get out of that free tool because it’s actually expensive.
And we all know moving from one. CRM to another, it’s not impossible,
but it’s just a real headache. Sometimes.
Yeah.
It’s not something you want to do frequently if you can avoid it.
So let’s get into it.
So what are some key questions a business should ask
when they’re seeking out their first CRM?
Well, I think before they even get into looking at any software,
it’s really an internal conversation.
So it’s understanding who in the organization is going to be using it.
Is it sales marketing? Is it operations?
Is it your customer service team finding out what their needs are
and how the use cases might kind of flow, if you will?
I think is a really important step.
I think the other thing to think about is
in terms of who is using it, where are they using it?
Are they using it at a computer or are they using it on the phone?
You know, how often are people driving in software?
And then it’s like, oh wait a second.
Our whole sales team is mobile and there’s no mobile app.
And that way.
And so you really want to understand like how they’re going to use it in terms
of, you know, sitting at the desk or being on the road.
Another thing too they should be considering is support,
I think is something
that’s often overlooked in the beginning of the research process.
Most companies, if you’re going direct, are going to provide technical support.
And while that might be okay if you have a technical question,
maybe your question is not technical.
Maybe it’s, hey, we’re going to be doing a webinar
or doing this trade show or running this new AdWords campaign.
You know,
what should we be doing in terms of the CRM to leverage it for this effort?
No technical support team is gonna be able to answer that question.
And so whether or not you just work with a consultant like Cultivize
just for your research or it’s going to be an ongoing relationship.
I think having a consultant that can help understand and be an asset
to those types of questions that will certainly come up is really vital.
Another thing also, I think lastly, and there’s a lot of them, in fact,
on the Cultivize website, Val, we have something called the CRM Fit
assessment where we go through the free one hour consultation.
Sometimes it’s a little bit longer if needed, which is okay.
But we go through or at least like 30, 40 questions
to really drill in more to you than what we even have time to discuss today.
But I think the last one that I think
that’s most important out of all of these is scalability.
So in other words, you know, are you looking at a CRM
that’s going to fit your problems and needs today,
or you’re looking at something
that is going to fit your needs a year or two years down the road?
And what I mean by that, Val, is let’s say you have a sales team of two people
and you’re like, oh, Pipedrive.
All these different tools are kind of small.
They’re they’re cost effective.
I have a small team. It’s perfect.
But if you’re trying to invest in your company and grow
and you expect by the end of next year you’re gonna have ten salespeople,
that product may no longer be a fit.
So rather than trying to be budget conscious,
you really want to be looking at the future
and kind of what you want to grow into versus growing out of.
great advice.
Yeah, I, I mean, you have to approach tech as, the text
not going to solve the problems, right?
That people are going to solve the problem.
So let’s make sure we’re solving for the right thing.
Yeah. That’s right.
So when it comes to pricing, you’ve touched on this a little bit.
What are some common pitfalls that people fall into when they’re buying a CRM?
Well, I think one is for sure, you know, when you look at demos, you’re
looking at typically, you know, example platforms
that have been built out and it’s, you know, unclear and kind of maybe
sometimes what those capabilities are and what’s included.
So I think one of the biggest pitfalls, especially like I mentioned for
on the freemium, is,. The free version is extremely limited.
So I think that’s one aspect is like what features are included in the pricing?
And then I think the other thing is scaling, right?
So a lot of these platforms might be kind of relatively low in terms of cost,
but the only allowing for let’s say a thousand contacts,
which is a really low number in the world of business.
So what happens to the pricing when you have 10,000, 20,000 contacts
and it might get cost prohibitive?
So it’s really important to kind of look at what all the different pricing is,
is a price on user, is a price on the number of contacts of emails you send.
Every platform operates a little bit differently.
And I think the other piece of pricing that is usually most
unlocked is integration.
If you have all the software, is this software
and you’re going to buy the CRM, going to charge you
to integrate to other systems, does it offer integration?
And so that’s something also that isn’t
typically not asked in the early stages of when you’re doing your research.
Yep. Great advice.
Total cost of ownership is something that is often overlooked.
And when you think about total cost of ownership,
you’re trying to position it as, hey, like, not just the license fee,
which is very prominently displayed on the website, but
what else goes into the total cost of ownership?
So you mentioned integrations.
You mentioned, contact limits, you mentioned, support.
Are there any other things
that you wrap up into that total cost of ownership piece?
Well, yeah. Of course.
I mean, so a big one is the time and energy
to create the actual CRM, to customize it and also the content.
Right.
So if you’re buying a CRM, let’s say to nurture your leads,
that’s one of the common things that most businesses are trying to do
now is educate people through that long sales process.
Who’s going to write the content?
Who’s going to design the emails?
Is that an internal person you have?. Then you have?
Or do you have to hire
an external marketing agency or a copywriter or a graphic designer?
So those are all things that you typically don’t think about
when you’re buying a new CRM. You know?
I think that’s really common on like the social side,
even though not talking about CRM, but you buy a new piece of social media
sort of posting software to make life easier,
but it’s like, well, who’s going to create all the content?
You know, if you want to post, you know, twice a day
to make really good content, you need a team to do that.
And so I think those certainly things are definitely for sure overlooked.
Do you find, as a CRM consultant
that some of the requests you get really bleed over into
what is more considered to be part of a marketing automation platform.
And do you see those two platforms kind of merging more in the future.
I think they’re merged already personally.
I mean, so, I mean, a lot of platforms.
You mentioned HubSpot, constant contact as we were talking before we started
the call.
Bought a company three years ago called. Sharp Spring, which is a really powerful,
CRM and marketing automation and even sales enablement tool.
There’s a lot of them out there. Already.
But so I would actually make the argument, if you want to call that to say
that your CRM should be able to do
marketing automation, it should be able to do sales enablement.
Otherwise you’re going to have siloed tools.
You know, and I’m not talking bad at about anything.
There’s a lot of great tools out there.
So I want to come across the wrong way.
Like a tool like Klaviyo is really good, but it’s not a CRM.
It’s not a sales enablement tool.
It’s a good marketing automation tool.
And so how are you going to connect all that data into your CRM?
And so that’s something. I think that’s really important
because it just makes life easier when all the data lives in one place.
Quite honestly, it’s less headache.
Absolutely.
I’d like to throw Inslightly into the conversation.
I’ll put my…
Yes, Insightly. Yes, of course Insightly.
Well, that goes without saying.
Well, it is a joy to be on a platform
where the marketers can see what the salespeople are doing,
and the salespeople can see what the marketers are doing.
And it’s not a separate login. Right?
Like we’re all on the same platform where we all share the same data.
We’re not throwing data from one platform to another.
After some, you know, random, milestone has been hit
with that lead. It’s when everything is together,
it really does align teams in a different way.
Yeah.
I think the most powerful thing,. I mean, yes,
aligned teams because we all know, like,
you know, usually it’s kind of like, you know, head butting
when it comes to marketing and sales in organizations.
And it’s quite frankly, they don’t always communicate that No.
You’re crazy. Just kidding.
It’s the all it’s all like I think it’s like the brother
sister rivalry or the sibling rivalry, you know, like blaming each other.
I got two teenagers.. I know what that’s all about.
But anyway, point being is that you could also make effective decision, right?
You can make decisions, say, okay, this is working.
This isn’t working when it comes to marketing and sales.
And so having that data is really going to allow a company
to make very important decisions, which right now, quite honestly,
most companies are running blind and they can’t make those decisions.
Yeah.
Access to data in an organized way, would just solve so many problems.
So I was going to say when, when searching for a CRM,
what’s one question or one tactic
or one feature that people often overlook.
to add to what we’ve already talked about.
I think customization is another thing that people often overlook.
We see that a lot.
We’ve been working even this summer we’ve acquired
a handful of home service based businesses.
So a roofing company, a pool construction company.
And while there’s tons of you mentioned before, there’s, you know,
thousands of different options.
There’s a lot of CRM software customized to the dental industry
to like home service, to like all these different industries.
A lot of them, some of them are okay, but most of them
that I’ve seen, you can’t customize them.
It’s very difficult or it’s complicated
and the user interface is not, is, ideal, if you will.
And so what we find is even though the cost might be low for those,
the customization is difficult.
And when there’s no customization, Val, you know what happens.
You we’re both in the CRM world, right?
Now you’re forced to change the way you do business to fit your software versus
the software adapting to the way you do business, which nobody wants to do that.
I mean, it doesn’t make any sense.
Yeah.
It’s one of the aspects of Insightly that’s super interesting
It’s one of the aspects of Insightly that’s super interesting
is how much the guardrails are down and people can customize
and some businesses honestly want those guardrails up
because they don’t trust their systems.
They don’t trust their people.
And so really that’s comes
into the choice of what type of software you’re looking for.
Are you looking for something
that’s super customizable, or do you not have the capacity for that?
And maybe they need something right
out of the box that they can just plug and play.
So let’s commiserate over a statistic together.
It’s from HBR, and it is saying
72% of CRM implementations fail.
So we’ve both been in the trenches with CRM.
Why do you see this is happening?
And what do you think can be done to improve it?
Well, I think that, you know,
sometimes the decision to buy a CRM is coming from, you know,
senior leadership or, you know, the CEO who’s really not going to be using CRM.
So they’re,
you know, buying a piece of software because they’re
their pal over at another company has it and they’re like, hey, this is great.
And they’re buying it for emotional reasons
and not practical reasons.
I think another reason they fail is they don’t really fully comprehend
what it’s going to take to onboard that
piece of software and to adopt it into their organization.
And so if there’s not somebody in the company
that is going to be what I call the, you know, the champion to be behind it
and to keep everybody accountable, it’s never going to work.
And so, you know, a lot of times. CRMs are brought in, oh,
we need this tool for the sales team.
But then the sales manager is never going into the CRM themselves.
Or if the sales manager is never going
in, why would the sales team go in if no one’s going to check on that?
So it really has to be from the top down that you have buy in,
and that they recognize that there’s going to be a need for this,
and there’s an accountability system in place to make sure that everybody
that is expected to use it is using it and is being productive with it.
had a tactic that you mentioned that. I thought was quite brilliant, actually.
It’s, when you’re trying to get CRM adoption.
You mentioned maybe piloting with a couple of reps, really getting them
involved and excited and showing success, and then subsequently doing a rollout.
So a lot of times it’s interesting.
So there are organizations we work with that will have all different types
of people on the sales team.
Most of the companies you work with have a sales team, I’d say, of on average
five to maybe 30 people.
And so when you have teams are a midsize or a little bit bigger.
And of course, there’s companies out there with teams of hundreds
of salespeople, right?. We both know that and work with them, Val.
But the point being is that you’re going to have people
that are sort of set in their ways. Right?
So it’s I always like to use the example of, you know, you go to the gym
and you’ve been working out for years, but are you doing it the right way?
Right.
And are you getting results?
And you may not be right. Some people are.
And so the people that are set in their sort of bad
habits, it’s gonna probably take them longer to adopt.
Because they’re used to writing things down on paper.
They’re used to using their Google. Excel sheet, you know, and it’s hard.
And in their mind it’s like, oh, this is extra work.
It’s double data entry.
It’s it’s not going to make life easier.. It’s gonna make life harder.
And so what we find in those scenarios is we get,
you know, just a handful of people on the team
that are really excited about the new CRM, get them going.
And then typically what we see is after, like,
you know, anywhere from like 60 to 90 days, the other team members
that are not using it, they’re like, hey, why is David getting more leads than us?
Or why is this happening?
And you’re like, well,
because they’re using the CRM and they’re creating,
you know,
they’re putting people into these nurture campaigns
and they’re closing more and they’re
getting more appointments booked, and they’re getting more callbacks.
You know, if you want all that, we can do that for you.
We just have to get you going in the platform.
And so it also creates motivation, but it also allows the people
now that have been in that pocket for the last few months
to sort of become subject matter experts internally.
So if Mary or David or whoever needs help, you have other salespeople
that are really comfortable now in the platform that can help them,
in addition to the Cultivize team helping as well.
Nice.
Little peer pressure never hurt anyone, right?
No, a little competitiveness.
You know, why not? Yeah.
So I think you mentioned that you have a CRM
fit assessment on your website available, and it’s free.
So where could people go to find that?
So you could go to the cultivize website.
You can also go the easiest place, because cultivize, you know,
it’s a made up word and I like to make things,
you know, when I made that name,. I was like, it sounds like a great name.
You know, the idea was cultivate relationships, seize opportunities.
And but then years later, you’re like, you’re leaving voicemail message
and you’re like, it’s cultivize, c-u-l…
and you’re spelling it out.
You’re like, I probably could have made an easier company name.
We’ve all been there, right?
But the easiest place, Val is to go to learn, sorry, afterthelead.com.
So afterthelead.com has information
about what we’ve been talking about today, you can sign up for our newsletter.
You can download our playbook and how to nurture leads.
So regardless of the CRM you have, I’m sure Insightly has something similar.
It just gives you all the step by step instructions of what you need to do
and how to do it.
And then also, you know, as the listeners probably heard today,
I love to just sort of talk, educate, answer questions.
So, they could book a call with me.
It’s not a sales call.
It’s just getting on the phone with me for an hour or, you know, whatever.
They need to answer any questions.
So that’s available at After the Lead as well.
Awesome is great.
Talking CRM with you today, Jason.
Thanks for your time.
Thanks, Val. Yeah, this is really great.
and thanks to all of you for tuning in to Closing Time.
Remember, you can sign up for the Closing Time
newsletter to get this show delivered to your inbox.
Just click the link in the show notes below.
We’ll see you next week.

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