The CRO Approach to Getting Your CRM Right

The CRO Approach to Getting Your CRM Right

Brendon Dennewill: Welcome! Can you introduce yourselves and share your background?

Cait Grabowski: My name is Cait Grabowski. I'm a Senior Implementation Manager at Denamico, but also a Fractional Chief Revenue Officer. I've partnered with over 50 companies now, ranging from startups to anywhere around 30 million ARR, helping to build those sales processes, optimize design for scalable go-to-market strategies, specifically within CRM and specifically within HubSpot as my favorite tool.

Kristen McGarr: I work as a Fractional Chief Revenue Officer, typically coming in and kicking the business owner out of that sales seat when they're still involved in that, and really taking over running those sales teams. So seeing what that day to day looks like and then impacting the strategy of the organization with that. And then of course, do the CRM implementations that go alongside of that. Work with a lot of a variety of tools, HubSpot being one, Zoho is another. So we work with a lot of different CRM systems depending on what the client's needs are.

Brendon Dennewill: Can you share an example of a client who came to you convinced their CRM was the problem, but when you dug in, you discovered the real issue was actually more of a strategy or process issue? What was the symptom versus the actual diagnosis?

Kristen McGarr: One client that I worked with recently came in looking to streamline their process because they had one person in Salesforce, they had somebody else in Zoho, and then they had a whole bunch of spreadsheets that they were using. The real reason why they came to us was that the leaders couldn't get the information that they needed in order to make any decisions with, because it was coming from so many different sources. So they just assumed, put everything in one place and we'll get the data we need, right? And as we started to dive in and do some more discovery with them, we realized that the reason why they were in so many different systems was because there was no defined process that everyone was using. So because there was no process to follow and there was no real clear direction on where they should be going aligned with a strategy, everyone just formed their own path.

Cait Grabowski: I run into that same issue all the time. The root cause is inconsistent sales definitions and missing those process steps. A lot of the times people will say maybe like, my reporting is the problem. And it's not that your reports are the problem, it's that your data is the problem because everybody has these very different levels of definitions when you talk about lead statuses or sales cycles and things like that. So I think it's really, really important to come in and define that before you even dig into building out a CRM. That stuff's got to come first.

The CRO Mindset

Brendon Dennewill: When you join a company as a fractional CRO, you're not there to fix the CRM—you're there to drive revenue growth. In those first few weeks, what are you assessing first? What are the big picture or strategic elements you're looking at that have nothing to do with technology?

Kristen McGarr: I look at process, people, and then tech—in that order. Sometimes you have to flip-flop process and people or do them in tandem, but technology coming last. Some of the key things that we're looking at is strategic alignment. Is strategy truly a strategy or is it just kind of thrown out there as a "we're doing something"? Or was it a strategy that the whole team has gotten aligned around? A lot of times we see top-down strategy that has not been informed by the bottom up. My first thing I love to do is sit there and have an interview with every single person, each salesperson, no matter what stage they are in their career there, how long they've been with the organization. Those individual conversations really shed a lot of light on what's going on within the organization and challenges that a lot of the leaders who have just been in there so deep for so long are missing.

Cait Grabowski: I start with other revenue leaders as well, because I like to find out: are we acquiring? How are we converting? How are we retaining these folks? What do they believe to be true at this status before we even go into technology? What do you believe your definitions are? Where do you believe your money is coming from? All of that sort of stuff is really, really important to start with. And to Kristin's point, talking to your people—they know. Whether they're working in spreadsheets or multiple CRMs, maybe during an acquisition of a company and you're trying to align them all, talk to your people first that you're working with and kind of understand what really works for one group and maybe not another and get that alignment down before you ever start building a system out or even mapping for it.

Brendon Dennewill: You're meeting with a leadership team and the CEO says, "We need to grow revenue by 35% next year." As a CRO, you know that's not a strategy, that's just a goal. Walk us through what you're thinking in that moment and what does that statement NOT tell you that you need to know?

Cait Grabowski: That's great that we have a number around something, but what does that 35% represent? What does it mean in real terms? Are we talking about growth and pipeline volume? Are we talking about conversion rates? Are we talking about deal size? Are we talking about ARR? What is that 35% growth to you? And then on top of that, we can't operate operationally just giving a percentage around that, but we can use different levers to kind of get us there. So you have to find out where we're going to get it from. Is it that new business? Is it expansion? Is it retention? And do we have a funnel that can support that type of growth? Giving an arbitrary number does nothing, but taking a look at real numbers and saying, where are we at and where do we want to be? Is it realistic and how can we get there?

Kristen McGarr: It really is asking: why didn't you hit that 35% last year? It's asking those questions: What are those elements that we know lead up to that kind of growth? One of the things I always tell people when we're thinking about this: did your growth strategy also consider operations and fulfillment? Because most businesses have some sort of recurring revenue that's gonna build into that too. Is this 35% all brand new or is any of that based upon retention or growing with the client base that we have? If you end up not fulfilling as well because you grew faster than your operations can handle, then you've got—yeah, I grew 35% brand new, but I just lost 20% in retention that I used to get. So it's really weighing out each one of those individual elements. A goal is never just one number and a strategy definitely is not.

Brendon Dennewill: Can you give us a specific example of a time when a client told you what they wanted and when you dug into the why, you realized they needed something completely different? How do you help people realize the gap between these two things?

Kristen McGarr: This really does come down to the data a lot of times. When we talk to the people and I've already had that conversation and we understand what everyone's vision is, where they want to go, it's getting to that next step of: Okay, your vision is that you want to see growth, you want to be able to deliver this more to people. There is this big disconnect from how we're currently doing things. And a lot of what's missing is a process. When we look at what are those steps in the process that get us there, that's when some of the gaps start to be filled in. If you've got A, B, C, D, E for your steps and you're just leapfrogging C every single time, there's probably something that we need to evaluate there. Maybe C is absolutely unnecessary, but we have to understand that it was there at one point. Why were we considering this a very important stage? If we can look at what has been measured—how long did you stay at each stage in your process, what stages did we typically lose a deal at—so many people just go, "yep, marked as lost. Put a reason why, oh, they stopped responding." What part did they stop responding at? How many times did we attempt to follow up with them? All of this goes back to what Cait was talking about. The keys are in the data of these activities that are taking place.

Cait Grabowski: Kristen's example is phenomenal and I've seen it so many times. A specific example would be around that contractual stage. I had a specific client and their sales cycle was great—it was like 30 days—but once it got to the contracting stage, deals fell. They were gone or they disappeared for like 60, 90 days. And it was all because of something that was in the contractual language. But they would have never known that had we not started defining these, saying, what are we finding out in each one of these stages? How long should they be taking? And why is it here that we're falling off? If it's the same reason over and over again, that's something that we can change and then make that really productive for ourselves. And all of a sudden we saw that gap close and the contracts come through when we were able to remove and edit what was actually just in the language that was stopping people from moving forward from a compliance perspective. So it's not always necessarily your reps. It's not always necessarily your system. It could be something outside of that control, but if you build a CRM the right way and you have those defined stages, assign ownership within there and map those metrics to your actions, you can really surface a lot of things that you wouldn't think you're able to.

Translating Strategy to Revenue Operations

Brendon Dennewill: How do you take those strategic priorities and then turn them into operational processes for those teams?

Cait Grabowski: I think a lot of the disconnect comes from siloed KPIs. When they're not matching, there's no single owner of the revenue process. It becomes: this is what marketing does, this is what sales does, this is what customer success does. They have to all align to that major goal. And if they don't, how would you ever be able to spin that data up and understand where any of the discrepancies are? There are three completely different verticals. What I like to do is come in and I can diagnose that by mapping those goals, setting metrics to them, watching behaviors that are happening and using whatever system that we either have in place or don't have in place to support and see where that chain breaks. That's where you can kind of find that issue and start saying, are we all on the same page of what the bigger goal is? We always say we're aligning sales, marketing, and customer success, but I think we're also aligning really finance, sales, and leadership at the end of the day. So that's kind of like the other fold to it. And it's really, really important that you define all those metrics for the same goal and not keep people siloed.

Kristen McGarr: When you have silos, there's a lot of finger pointing. Oh, it was marketing's fault. Those leads were terrible. Oh, it was sales' fault. They're not following up. When you have unified metrics, you really do just get a much clearer picture of what's going on. I really also like to look at this from the people perspective. What are the handoffs? What's a true handoff look like? What kind of data needs to get passed from person to person? What's the cadence for that? How quickly—what are our service level agreements and expectations that we have internally for our own teams? Like you've got to get this turned back around to me within 24 hours so I can take on the next step of it. I need some quoting information. I need rate information. If I wait four days before getting back to the client, they've lost interest. I need this within 24 hours. So having those expectations really clear among all the teams is just absolutely critical to making this happen. And tracking it in the CRM allows you to see when have we fallen off of those expectations versus just gut feel and finger pointing.

Questions to Ask Before CRM Selection

Brendon Dennewill: What are the top three to five questions they should be asking their marketing, sales, ops, service teams to understand what you actually need before evaluating technology?

Cait Grabowski:

1. What decisions are you making as a business without data? What are you already making choices off of based on that? That's what we want to make sure we're solving for when you are picking the right CRM—what business questions do we have that we need the CRM to surface for us and give us answers to?
2. How do you lose deals? Where do we lose them in the sales cycle? Is it when they're already a customer? Do we know why? Is it price? Is it timing? Do we need to pay attention to their fiscal years? All of these data points can be tracked within a CRM to make your sales reps' lives easier, to make your marketing teams' lives easier and know when to reach out to the right demographics and groups.
3. How are we doing this now? And how do we want to be able to surface that in an instant for ourselves? That'll help you drive that decision of what kind of software would probably work the best for your team.

Kristen McGarr: The data is so critical—how are you using it? What do you need from it? I also look at this from the process side of things. Your CRM can support process, it can't create process. So if you don't have a process that the team has bought into already and can follow, then that's a hurdle you have to overcome or be at least evaluating first. And the vision—what is the overall vision? What's the strategy that we have as leadership and why is that our strategy? And has everyone else bought into that and understand it? Are the doers who are going to get you the data understanding why we're doing this in the first place? Because if there's a misalignment in that, you're going to constantly be fighting this battle with the team: "Put your data in the system. I need this data in the system." "Why? It feels like an administrative burden for me as a salesperson to have to do this." When they feel part of the strategy that's been created as the organization, they're more likely to get involved behind that other than just data for the sake of data.

Diagnosing the Strategy to Execution Disconnect

Brendon Dennewill: Where does the disconnect between strategy and execution usually come from and how do you diagnose that before layering in technology?

Cait Grabowski: The disconnect comes from those silos—silos of individuals, silos of processes, silos of definitions, silos of KPIs. It will absolutely kill your RevOps strategy if all of those things are not aligned across the three distinct verticals that we've talked about: sales, customer success, and marketing. Marketing wants to bring in X amount of leads, so we expect sales to convert X amount of leads—and maybe sales isn't meeting those metrics because it's not the qualifications that they would consider to move somebody forward in a deal. I cannot stress it enough: define your process, define what your lead status is, lifecycle stages—all of that good stuff across all three. And you'll have a lot clearer insight into what's happening in your organization.

Kristen McGarr: That clarity of process is so key because it really does help you then identify when something's not working so much faster. If there is some vagueness and ambiguity in how your process is going, it takes you so much longer to identify the source of an issue. If the process is very clear, like the earlier example, I could know that there was language in my contract that was causing the problem because I have a very solid process and I saw exactly what was happening. So super critical there.

How to Choose the Right CRM

Brendon Dennewill: When you sit down to evaluate CRMs, what should you know about your technology requirements that you didn't know when you started? And how is that different from how most companies approach CRM selection when they skip those first two steps?

Cait Grabowski: One of the things that we're definitely seeing today a lot of is people will take the time to set that process with me, and then they become feature led. "This product does this, this has AI, this has this." Great—let's evaluate all those things, but let's not let that lead or dictate our decision because of a feature. What we want to do is make sure that we have a simple matrix of must haves, nice to haves, non-negotiables—almost like when you're looking at real estate. You're going to bend and break on a few things, but we can't just be excited because it's the penthouse. Maybe it's missing all of our non-negotiables. And then you also want to get a little bit into the evaluation of how do our working styles, our workflows, how do they fit into each one of these solutions? I think a huge one is reporting capabilities. It's something that I hear from clients on a daily basis when they are switching systems: is this going to be able to spin up the reports that I'm either used to or I'm looking for and can't surface right now with the data that we're collecting? And then that third one is probably going to have to be adoption potential because you can spend all this time and money building processes and software. If you don't have a team that's aware of that or understanding what the gift they're going to get out of this big change, you're not going to have that adoption and it will fail. So it's really important to have a change management strategy into the software that you're picking in order to make sure that it will get adopted.

Kristen McGarr: I would line up those three exactly like you laid them out. I would also just add scalability. You are looking at a CRM likely because you want to grow your organization. You're in a growth-ready mindset. As you grow, your process is going to change. Things are going to change for you. If you get a CRM that fits exactly where you are right now, that might feel really good. And you might get the user adoption, you get the reports you need today, but now you've grown 35%. Now things have changed in how you are delivering. You've got more people. Can the system accommodate that? Are you going to be able to add extra features, functions, integrations, things like that that you need? Can you just ebb and flow in the system to be able to achieve that growth goal that you're hitting? Because you're not investing in technology and CROs and all of this stuff in order to stay in the same place you are today.

Brendon Dennewill: What are the three things that need to be true about the strategy and the operations before you're truly ready to evaluate the technology?

Kristen McGarr: It really is alignment on the strategy. It's understanding what technology do you use elsewhere in the organization that has some level of rigidity to it? Are you using some sort of proprietary tool that's necessary for operations, but you need to integrate with? What does that look like? And then really for successful adoption: what does the overall user sentiment regarding buy-in look like right now? And what do you need to do and change within the organization in order to get the rest of the way there, to get that buy-in before you even put the tool in place? Get people excited about a technology switch instead of terrified, which is a very common sentiment.

Cait Grabowski: Just agree again—super, super important to be aligned. I think it's also really important when you're picking the tool to try and mirror your flow, your sales reps' flow, your marketing flow, because it will help that adoption. Creating a net new, all new procedure, product, everything—that's when you do get the scared look. So it's really, really important to understand current processes. And then there's always iterations to make them better down the line. It's just: how do we get all the data into a working solution? And like Kristin said, maybe also with integrations involved—now we can have multiple solutions feeding into one central source of truth where we can get that reporting surfaced. And it's really exciting. You just have to make sure you're taking the right steps in the right order in order for all of that to come to fruition.

Signs You’re Over-Engineering Your CRM

Brendon Dennewill: What are the warning signs that a company is about to over-engineer their system? What should leaders be watching for?

Kristen McGarr: I think the key thing is over-automating. Cool, we're going to have this technology and it can make everything simpler for everyone because we can automate and automate and automate. And if you automate so much that if I push one button, I'm not sure what's going to happen, I'm going to run away from that tool. And the other component is so much time and arguments and things like this trying to solve for the 10%. When we look at simplicity of a CRM, how do we focus on the 90%? What are the majority of the scenarios, not just that 10%? So many over-engineered systems are because of that 10%. And in reality, that 10% usually only ends up being a 1%. They just think it's bigger than it is until you really start to break it down.

Cait Grabowski: I totally agree. Those automation triggers—if you have too many, no one knows what's happening. Not only do your reps or your marketing or your customer success—maybe they're afraid to touch that button because it feels like a big red button and they don't know what's going to happen after that. So that's a scary thought. We don't want them to feel that way. And on the other side of the coin is your engineers or your system admins. If they didn't build the solution, they have no idea how this stuff is getting automated, especially if it's layered incorrectly. So it's super important to take the time and make sure that you're not over-engineering because like I said before, you can always add. It is so much harder to untangle and to unweave all of the automations, especially if they're dominoed or waterfalled into one another. It's a lot easier if you start small and keep adding.

Diagnosing CRM Problems

Brendon Dennewill: For anyone listening who's three months into their new CRM and it's not going well, can you walk them through your diagnostic process? How do you figure out if this is a tool problem, a training problem, a change management problem, or a "we skipped the strategy step" problem?

Kristen McGarr: Hopefully when you set this up, you put a lot of those KPIs in place. You put those measurements in place right off the bat. If you didn't, put those in place now because that's going to be the key to your diagnostics. You're going to be looking for activity, trends, usage. Is the team actually going into the system and taking the steps in a timely manner or is all of the updates taking place 24 minutes before a sales meeting? Or are they using it daily? Looking at that activity that's happening and how people are engaging with the system is just a critical component to understanding where some of the resistance is. Is it a people issue—and it could be training, could be just adoption? Or is it something else where maybe the process is flawed? If we've got these indicators, we can start to identify that the process does have a gap in it that needs to be filled.

Cait Grabowski: On top of that, it's something that I find quite often when I come in fractionally: is leadership using the CRM data in their decision-making or are they ignoring it? A lot of the times, I'm a classically trained sales rep. So when I'm putting in that data, I want to know: what am I getting out of this? Are we making choices based off everything I'm putting in here? If you're asking me to do it and I'm doing it, what is my gift? What is my benefit for that? As the user that's gifting you all of this great data to make these business choices. I see a lot when there is poor adoption is that the leadership isn't even using the tool for surfacing that data. And I think that that's a huge issue—they're expecting everybody to use it, but they're not calling it back in front of those users and saying, "Hey, thanks for filling all this out. We now understand our contracts were the issue. It was never you guys. We're going to fix that. And now you're going to be able to close your deals in 30 days instead of 60." And then you're getting that velocity and you're getting exponentially faster in your sales pipeline, making money quicker, maybe even more at that point. So I think it's really important for leadership buy-in to continue and to stay and to lead the charge on that.

CRM Selection Done Right

Brendon Dennewill: Can you share an example of a company that did this right from start to finish, where they built the rev ops foundation strategically before choosing their CRM? How did their outcomes differ from those where the approach was the opposite order?

Cait Grabowski: I'll use an interesting example where a client had already had a CRM in place—very low level. I call it jokingly "the little black book in the sky." We're just keeping some data points in there, some contacts, maybe things like that. What we ended up doing was reconstructing their entire go-to-market strategy and process and metrics first. Then we selected a CRM that reflected those choices—not led by features, but led by how will this work with what we know to be true for us and what works for us. Once we were able to do that and implement that CRM, we were then able to highlight something that was really interesting: they were actually selling to the wrong vertical. We realized they were selling to a completely different group of people that don't have the funds to pay for that. And then we were able to actually find their ICP from building from go-to-market, the process, the metrics, selecting the CRM. Once we spun that all up and we had all that old data that we put in and was clean data, we were able to figure out that they weren't even selling to the right group of people in the first place. So we were able to change that strategy afterwards, keep everything clean and keep their process the same. We just realized they weren't getting the checks from the right people. So I thought it was really, really interesting, but these people took the time, took a step back, did all the hard work and it paid off in dividends for them.

Kristen McGarr: I have one where it was really the cross-departmental impact that came about it. We did marketing and sales and customer service, and we also included operations and finance in the discussion. The entire team had been somewhat disjointed. Their growth was really stifled. People were sitting in multiple seats and working overlapping multiple seats, not necessarily because it was too small of a team and they had to, but because there was no trust going on from team to team. We sat back and really spent a lot of time on these discussions about what the process should look like, how we should be working together as a team before putting the system in place. And then once we implemented it, it really had all of those checks and balances, those SLAs cross-departmentally that they agreed to. And in this, they were able to easily add new people into the organization because that strife was gone. There was greater just satisfaction among all the team members. Just happiness in the job just went up significantly because the battles were gone, because this was all alleviated. And it was really just because everyone had a clear picture of what was supposed to be done and who was supposed to do it and why they were doing it, why they were working together on this. And so just to be able to take frustration that existed within a small organization and eliminate that by putting a process in place and the tool that supported that process to make sure that once the CRO left the room, it was still going. That was fantastic to see that happen.

The Most Expensive CRM Mistakes

Brendon Dennewill: Based on everything we've talked about, what's the most expensive mistake you see companies make during CRM implementation and what's the early warning sign that could have caught it?

Cait Grabowski: The biggest mistake is buying tech before you know your process. The excitement around the AI and all of these wonderful, honestly fabulous tools that exist—we don't need all of them. We cannot be feature led. We have to have process clarity first. And I think a lot of the times people get stuck in contracts where they realize: I'm not using that tool. My reps aren't using that tool. We paid way too much for this tool, and it's not necessary. So I say I'm fiscally conservative when it comes to buying tech, but that's because a lot of the times it's not needed at the quantity or the scale that people are starting at. Not to say it's not needed, but it's an expensive mistake to have to pay those contracts and not be utilizing it or maybe not be ready to utilize it. Trying to do everything at once is going to be a huge, expensive mistake. You have to roll things out in phases, not only to protect your budget, but to protect the adoption.

Kristen McGarr: Over-buying and over-engineering. You bought technology simply because it was like, "Oh, well, it's the flashiest one out there and everybody says I should use it" and it doesn't align with your process at all. And that over-engineering where you're customizing and configuring everything and tweaking every little aspect of the system until it's almost an unrecognizable software from where it started. And if you're doing that before you've kind of tested out the core basics of it and know that it works for you, that ends up being a really costly mistake that you're going to have to unwind as you grow, as you scale, and as that process really gets solidified for your organization.

One Piece of Advice for CRM Selection

Brendon Dennewill: If each of you could give our audience one piece of advice about making their CRM selection, what would it be?

Cait Grabowski: If it's not going to help you make better business decisions, it's just another expense. So you can buy every tool under the sun, but if it's not helping you make better decisions and scale your business out, if that's your goal, it's just going to be a waste. So you definitely, definitely want to make sure that it's helping give you insight into what your team has already collected.

Kristen McGarr: I agree on that and just adding that kind of the catchphrase of the strategic alignment. When you're looking at that technology, when you're looking at what to do, have that strategy in place—and strategies are not goals. It's got to be a true strategy and we've got to align with it in order to not make costly mistakes in purchasing or be premature in jumping into a CRM system.

Audience CRM Selection Q&A

Brendon Dennewill: When is switching CRMs the right answer versus when is it just going to repeat the same mistakes with a different logo?

Kristen McGarr: Same mistake, different logo is if you don't have a strategic strategy and a process. If your process is not clear to your organization, you are just going to repeat the process over again.

Cait Grabowski: And on top of that, when you talk about integrating systems, I constantly have to tell clients: we're not recreating that system. We're integrating it with a new one. So I think that's really important to understand.

Brendon Dennewill: How do you balance current needs with future scalability so we don't end up with a big system we cannot use at all, but also don't want to have to do this twice?

Kristen McGarr: One of the things I love about tools like HubSpot and Zoho and some of these other ones out there is that they have switches—basically on/off switches. So you can turn on all features. Go for the simplicity, go for the basics like we've described throughout this time together today. And then when it is time to scale, have something that has the ability to just flip the switch. Now I can turn that on. The feature wasn't there before, now the feature's there. So you're not putting this massive intense overwhelming system in front of people. You're putting the basics and the simplicity there and then you're just flipping switches as time needs.

Brendon Dennewill: What's one thing clients are convinced they need during the selection process that they end up not using? Or what's a feature that seems boring during demos but becomes mission critical once they're actually in the system?

Cait Grabowski: I think I probably have a twofold there. One is their reporting. A lot of the times you'll meet clients that say, "I'm using a different system for my reporting. So I'm not worried about how we can use it in there." And a lot of the times CRMs actually can use multiple objects and cross in their reporting, which is really nice. Instead of having a bunch of different systems, you can kind of have it all in that central source of truth. So I think that's really important. And then another thing is those workflows. It's super, super important to know your sales process and to have workflows that kind of help your sales reps go through that. But you can always scale it out. So it's just important that it reflects what you're looking to start with.

Kristen McGarr: Analytics, reporting, integrations, and workflows were the two things I was going to say. So Cait nailed it