In this episode, Brendon Dennewill speaks with Cait Grabowski, Implementation Manager at Denamico. Her experience as a Fractional CRO and GTM Strategist shapes her unique perspective on franchise operations. Cait explores the unique challenges and opportunities facing franchise brands as they work to scale through better systems and processes.
The conversation reveals how franchise organizations juggle multiple complex relationships, from franchise development and real estate teams to individual franchisees and their end customers. Cait shares insights on overcoming common strategic missteps, including the tendency for franchisors to oversell multi-unit deals to unproven franchisees and the critical importance of data transparency and proactive communication throughout the franchise lifecycle.
This episode is essential listening for franchise executives, RevOps professionals, and franchise development teams looking to transform their operations through strategic technology implementation and data-driven decision making.
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Cait Grabowski | Implementation Manager at Denamico Cait Grabowski is a Fractional Chief Revenue Officer who has partnered with 50+ companies ranging from startups to $30M ARR, helping them build sales processes, optimize CRMs, and design scalable go-to-market strategies. She specializes in aligning sales, marketing, and customer success teams to drive efficient revenue operations and sustainable growth. With a track record of success across healthcare, technology, and high-growth ventures, Cait is passionate about enabling organizations to scale smarter. |
Brendon Dennewill: Cait Grabowski, thank you so much for joining me today on Brendon Dennewill.
Cait Grabowski: Hi, Brendon. Thanks for having me. Happy to be here.
Brendon Dennewill: How are you doing?
Cait Grabowski: I'm doing great.
Brendon Dennewill: Awesome. So Cait, I'm going to dive right in. As a RevOps and CRM expert who strategically approaches business from the perspective of a CRO, what are the biggest opportunities you're currently seeing for franchises as they invest in the systems and processes that will help them scale?
Cait Grabowski: There's endless opportunity there. To start, it's really interesting because franchise models require you to support not only how the franchise brand wants to sell out its own units, but also whether you're reaching your consumer, and whether real estate and legal have processes in place too.
When you have something like HubSpot that can connect to so many different third-party solutions, depending on the vertical you're working in, it becomes a natural center source of truth for all teams to access and see their data.
Brendon Dennewill: That makes sense. Let's switch over to the flip side: what do you see as the biggest obstacles to why franchises might not be prioritizing or investing in these systems?
Cait Grabowski: Sometimes they're just not even aware of them. There are so many solutions out there, and finding one that can embrace all of the different parts of a franchise is a unique opportunity that maybe isn't as well-marketed as it should be.
You always have different pieces of a franchise company: real estate, franchise development, and then the consumer side of all the units you're trying to build out. Are you getting the right people in the door to spend money at your franchises? The opportunity to work with something like HubSpot, where everyone comes to one central place for information, is an enormous opportunity to grow from there.
Brendon Dennewill: You've touched on a few things now. Most well-run franchise organizations approach the market from different perspectives. You mentioned a real estate team that helps franchisees identify the right locations based on demographic information, a franchise development team bringing franchisees on board, and then the question of how a franchise brand supports franchisees once they've joined. Do you see specific opportunities within any of those three areas?
Cait Grabowski: Absolutely. All three can be helped with solutions like HubSpot. The unique piece is that all three teams are working within the same solution, and at the same time, they're gathering data about many different properties.
You're talking about real estate development, securing locations, getting franchise units stood up, and all of it can be associated with each other and with that franchisee. On top of that, maybe they have three locations and only need to sell one of them. That data can be held for the next person who wants to open. It doesn't go away. It doesn't get lost in the shuffle.
When you want to start supporting your consumer side, a franchise unit opens with data all over the CRM, whether it comes from franchise development, real estate, or even legal and compliance. They're gathering dates and contact information throughout the process. When a unit does open, you can use those lists and say, here are a hundred people who have shown interest in this brand at a high level. Start there, and it gives that new franchisee a leg up when they open their location.
Brendon Dennewill: Let's zoom out to fifty thousand feet. What are some of the common strategic mistakes you're seeing franchise brands make? One that seems to come up constantly is franchise development teams pushing franchisees to commit to three, four, or five units right away before they've proven they can make even one location successful.
Cait Grabowski: I would agree that is probably the biggest failure driver you see. People take on more than they're prepared for. Everything sounds great in the sales process, and that's exciting. It means you have a strong franchise development team using their systems to close the deal. But when people bite off more than they can chew, there's so much that could be tracked through a more piloted approach instead.
Let's do one. If you hit these metrics, let's talk about two and three for next year. When people commit to opening one every year for the next five years, it becomes harder to track and harder on the franchisee, who has to keep building new locations each year, navigating real estate and legal all over again, while also making sure a consumer base is showing up to the ones already open.
Brendon Dennewill: Right. Another thing that seems like common knowledge in the franchise space: whether you use the Minneapolis-Saint Paul metro or the Chicago metro as an example, it's very common for a franchise brand to find one franchisee to cover five units across the entire metro. It sounds smart, but if that franchise doesn't see the success that was promised upfront, they still hold the rights to the other four units but will never open them. And no one else can open those units either, which means that market is essentially dead to that brand until a new agreement is reached. What would you advise a franchisor who thinks that way?
Cait Grabowski: My first piece of advice would be to align all of these different verticals from a RevOps standpoint. Make sure your data is overlapping. When you sell a franchise unit for a certain investment, what are you expecting in return? Are they meeting those metrics on a monthly or quarterly basis? Have the KPI conversations.
A lot of the time, people bite off more than they can chew. The more you can direct franchisees who are opening units, give them goals and metrics to hit, the better it will be for everyone. You have your standards, you can see how they're tracking against them, and it gives the franchisee something to work toward.
Reporting is often where things go wrong. If you have reporting sitting in one solution and more in another, and you're not overlaying that data, you're missing a lot of gaps. Everyone needs the same goals, measured the same way, reviewed monthly or quarterly. It's the same idea as what the franchise brand does to get franchisees in the door: the franchise units then have to do the same to produce strongly on their end.
Brendon Dennewill: You've raised a really good point. When a franchise development team starts a year with a goal of selling twenty, twenty-five, or fifty units and comes up short, it raises a question: are one-year goals maybe too short-sighted? You have to have annual goals, obviously. That's how salespeople are incentivized. But a lot of franchise brands don't seem to be playing enough of a long game. The built-in value of a franchise brand is that it has legs. Whether you have a hundred or two hundred units, you have ten to fifty entrepreneurs who become your partners and will grow the business with you. That seems like something people want to do for fifteen, twenty, twenty-five years or more. Making decisions based solely on short-term goals feels like a disconnect.
Cait Grabowski: I agree to an extent. It's almost like EOS: what's a rock? There are different types of goals. When I talk about KPIs, I'm talking about watching the numbers we need to hit for profitability. Where are we?
A lot of people struggle with long-term goals because they're either very grand or they're not being checked in on frequently enough. I've seen this a lot in startups: we define a one-year, three-year, and five-year plan, but the three-year and five-year metrics get crowded out in monthly and quarterly meetings. You have to make a point of asking, are we still trending in that direction? Success isn't built overnight. What are the small milestones you can hit to reach that five-year goal?
Brendon Dennewill: Which leads to something that keeps coming up as a signal that a franchise brand isn't thinking strategically: you can have a conversation for an hour with a franchise brand and at the end they say, "But how many leads are you going to get me?" Everything becomes so transactional. It's another signal that they're not taking a long-term view.
The obstacle seems to be that brands keep defaulting to a short-term mentality: get leads, get franchisees, and all our problems will be solved. But if you don't support your first five or ten franchisees, your chances of success drop significantly. They are the ones who will open second and third units, and they are the ones who will tell their friends and family this is a great franchise opportunity. Your KPIs and metrics have to be aligned with that long-term thinking. The lifetime value of a franchisee, and ultimately of the end customer, has to factor in. If you can take care of the franchisee, and the franchisee can take care of their customers, the entire brand only becomes more successful.
Cait Grabowski: Absolutely.
Brendon Dennewill: On the data and reporting side: what are the most common metrics you see franchises using, and are there any they should be tracking that they're not?
Cait Grabowski: That's a great question. One metric that I find surprisingly overlooked is time. I always joke that I'm a classically trained sales rep, so my KPIs are always money, money, money, how fast can we get it. But it's really interesting to think about the time it takes to build these locations: the money, the time, the turnaround.
All of those data points have to be tracked on top of just selling franchise units. It's supposed to make a certain amount of money, and we're tracking toward that. Those are easy to measure. What's not easy to track is all the other people working toward the same goal and how much time and how many individuals it takes.
When you layer a CRM with a project management tool and give visibility to the sales rep who sold the deal, the real estate developer working on it, and the entire real estate team working through a project plan, you can start asking: once the contract comes back, how long does it take to present real estate locations? Could we start that earlier in the sales process? That timing data doesn't get talked about enough, and it has a real cost.
Brendon Dennewill: And I'm guessing timing is also closely tied to transparency.
Cait Grabowski: Exactly. For any franchise to be successful, they're relying on new, often first-time franchisees to come into the partnership. The more transparent they can be about timing and why that timing is what it is: whether it's six months, nine months, or twelve months, with data to back it up, that matters.
Brendon Dennewill: And coming back to what we discussed earlier, if the franchise development team hasn't been transparent about what success looks like for that first unit, the second, third, fourth, and fifth units are never going to happen.
Cait Grabowski: Absolutely. The two biggest things people can take away are transparency and being proactive. If you gather those data points and present them in a way that gives a clear timeline, the franchisee can proactively think through what this looks like for them. It makes a world of difference not only in the franchise development sales pipeline, but in those continued relationships and the ones that get built on top of them.
Brendon Dennewill: The more transparent and proactive you are, the more successful you'll be.
Cait Grabowski: And that goes for both sides of the coin. Both sides being transparent and proactive, imagine layering data on top of that. It becomes an unstoppable force. Friction only appears when there isn't transparency, when there aren't timelines, and when the right people can't be ready at the right times.
Using solutions that automate a lot of that based on the activity of your sales team, real estate team, or legal team removes the friction from back-and-forth emails and unnecessary meetings. You can check more boxes and move things along faster for the standard steps in the process.
Brendon Dennewill: Bringing it back to systems: for a long time, franchisees were limited to very basic tools that didn't really give them what they needed to connect with customers and grow. Now we're in a much better place. The same system can be used by both the franchisor and the franchisees, with data flowing up and down while maintaining the right permissions. A franchisee operating in one region doesn't need to market to people a thousand miles away, and the systems now give you the ability to set those parameters. What opportunities have opened up for franchise brands as that has become possible?
Cait Grabowski: I could go on forever about this one, but what I love most is the customization. That's what gives power back to the franchise brands and holding companies: they can bring in data from other solutions and map data they've been working out of spreadsheets for years into something that's a powerful resource. Everything sits in one spot, but it's unique to their business model. It's not a rinse-and-repeat setup because all franchises are wildly different.
Franchise companies have not had great systems to work out of historically. They've been very piecemeal and really hard to report on. We've seen clients be extremely happy just having one place for everyone to log in. You can set up permissions, do layered reporting, look at specific zones, track specific revenue targets against timelines.
Honestly, I won't say every single franchise client I've worked with came from spreadsheets, but pretty close. They might have had some sort of limited CRM, but they didn't even trust it to track their information. They trusted their spreadsheets more, which is quite telling. The shift is now about customizing these solutions to make sense of their specific business.
Brendon Dennewill: This is where HubSpot has done a particularly good job. They've built one of the most powerful platforms available, but it's also one of the easiest to use. That combination of power to customize and ease of use is critical, because the number one reason CRM implementations fail across any industry, including franchising, is that people stop using the system after it's been set up. Why do you think that adoption problem hasn't been solved at a bigger scale elsewhere?
Cait Grabowski: A couple of reasons. Going back to my sales background: time is everything to a sales rep. I want to spend my time with clients, not doing administrative work. If the solution was built to match what my day actually looks like and how I naturally fill things out, I would use it all the time.
It comes back to customization. What does the sales rep's day look like? What information are they capturing at each stage of the sales process? If instead you require them to fill out everything at the end of every day, they won't do it. Make certain fields required only at very specific milestones or dates that another part of the company needs, but don't require so much that it becomes death by a thousand paper cuts. Build it so that when reps log in for the day, they know their tasks and know exactly what to fill out at each stage. That's where you get real adoption.
Brendon Dennewill: That touches on something I think leaders in all industries get wrong. HubSpot's sales and marketing is second to none, and it can lead people like me, who have shiny object syndrome, to buy tools prematurely and think the software can do more out of the box than it can. Every franchise is different: different processes, different goals, different data requirements, different teams. That means the software has to be customized to match. We often get called in to fix systems where a business tried to set it up themselves because HubSpot seemed so intuitive, but they'd never done it before. For the folks listening who are thinking about doing it themselves, what are the key things they should be doing or thinking about?
Cait Grabowski: There are some fundamental basics in HubSpot, and their Academy will walk you to those if you take their lessons. They've also done a great job with short video clips. If you just want to know how to build a certain report, it might be a three-to-seven-minute video instead of an eight-hour course.
But what I see most often is clients who are ready to build a solution before they have their internal processes defined. The teams really need to connect with each other on their goals before they even start. Do you want marketing in here? Do you want service? Do you want to start with sales alone, see how that goes, and roll it into another phase?
When I work with clients, I send them worksheets: What does your sales cycle look like? How long is each stage? What do you want that to look like? Do you want to track against shortening your cycle by ninety days? Do you know where your bottlenecks are? Those are all the inputs that go into developing a real solution architecture. Where do you want a trigger that flags when a deal hasn't moved in fourteen days? That kind of intelligence is nearly impossible to pull from a minimal CRM or a spreadsheet.
Start with a strong skeleton. Make sure your core objects, properties, lifecycle stages, and lead statuses are solid before you build anything else. You can always build HubSpot further. What you can't easily do is untangle a messy foundation after the fact. Build the bones first, add naming conventions, use folders to stay organized, and document everything before you get into the system.
Brendon Dennewill: As we begin to wrap up: when you customize and build a HubSpot CRM integrated with a franchise's other systems, your team typically has three or four people with different skill sets. For franchises trying to figure this out themselves, what are those roles they should consider?
Cait Grabowski: From a build standpoint, having a HubSpot solution architect who really understands the system is important, especially someone with a background in sales or marketing, because they understand both what leadership wants to see and what makes the tool easy for the people actually using it.
I would also have an engineer on the team. HubSpot is a great tool for integrations with other software, so having a technical person ensures automations are correct, integrations are working, and data is flowing properly between solutions.
And then you need an implementation manager or project manager keeping everyone on track. This is the person who says this needs to be done by this date so we can move into the next phase. I joke with clients that I'm going to lock them out of the system until we're done building the bones, because someone who thinks they know how to build a workflow or change their view might not realize they're affecting an entire process for everyone else.
Brendon Dennewill: And I guess the other component they should think about is the training piece.
Cait Grabowski: How could I forget! Training is incredibly important for adoption. A lot of the times, especially in the way I work, we account for what the user sees on a daily basis. You don't want to change everything they're doing. You want their days to remain manageable and the solution to be adaptive.
Having a trainer come in with a change management perspective: here's what's happening over this project timeline, here's what you can expect, here's what's changing this week and what's coming next, and then working through user acceptance testing with the actual marketing, sales, and service teams makes for a much stronger rollout.
Brendon Dennewill: The training piece goes back to what we talked about earlier: adoption is the most important metric for measuring the success of a CRM. Good trainers have an uncanny ability to explain the why to people at every level, which is something leaders often skip because they're so excited to get to the benefit. If you don't explain the why, the how, and the what to everyone who has to use the system, it will never be as useful or valuable as it could be.
Cait Grabowski: Absolutely. I had a great example this week: a project that needed a push to finish a certain phase. As soon as we demoed the system and walked through why it was built the way it was, that it was designed to make their workday easier, they were immediately ready to ingest all of their 2025 data. The reaction went from "I don't need to change my day-to-day, why is this happening?" to genuine excitement once they could see the real benefit.
Brendon Dennewill: What a great example. Who doesn't want their data to look better going forward, rather than spending an hour and a half every day on manual work because you don't have a good system in place?
Cait Grabowski: Exactly.
Brendon Dennewill: As we wrap up, any final words of advice for franchises that know they need to set up a system to scale more effectively and efficiently?
Cait Grabowski: Align your teams. Every team has a purpose. Make sure your franchise development team is sending data to real estate so they can find the right locations. Make sure marketing has all the detail it needs to supply that new franchise unit with the right materials, whether that's lists of people on a waitlist or prospects interested in joining the brand.
Develop a solution that brings all your verticals into one place, collects that data, and puts it where it needs to go. That is really, really important.
Brendon Dennewill: That's great advice. Before we close, I have to ask: have you seen any particular franchise brands doing really cool things to bring their franchisees and internal teams together to continue growing?
Cait Grabowski: Absolutely. I've worked with a company that had been giving every franchisee their own HubSpot instance. We were able to bring them all into one instance instead. We're migrating data from all those separate portals, and once franchisees see how much more they can do with everything in one place, that's where the change really takes hold. There will be about one hundred and fifty new people in one portal, loaded with great data and automations to make their days easier, and a functioning CRM rather than a Frankenstein setup no one fully trusted. Seeing that transformation happen is really fascinating, and I think it's going to be incredibly beneficial for the company.
Brendon Dennewill: That's a great point, because there might be people listening who looked at HubSpot three or four years ago and it just wasn't the right fit at the time.
Cait Grabowski: It's totally different now.
Brendon Dennewill: Even so, many of those brands did set up separate HubSpot instances for the franchisor and each franchisee separately. But now, with HubSpot's multi-account management option, you can have franchisees and the franchisor all operating within one instance.
Cait Grabowski: Yes. And to round that out: something as simple as HubSpot forms for gathering data from potential franchisees or consumers becomes so much more powerful in a single instance. If someone fills out a form and selects Rhode Island but they're actually in Chicago, that can be corrected and that person can still be utilized somewhere else. They're not stuck in a siloed portal. You can always set permission structures and build your team access out, but sharing that data across one instance is just incredibly beneficial for everyone involved.
Brendon Dennewill: Right, and there are probably dozens of other examples.
Cait Grabowski: Absolutely.
Brendon Dennewill: Cait, thanks so much for joining me today. There was a lot of great content in there, and I'm sure a lot of people are going to get a lot of value from this conversation.
Cait Grabowski: Of course. Thanks so much for having me.
Brendon Dennewill: I look forward to talking with you again soon.
Cait Grabowski: Definitely. Thanks so much.