Ep. 197 - The SaaS Retention Problem Starts Before the Customer Signs

Guest: Jason Roberts, Fractional Client Operations Executive at Scale CxO  

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In this episode, we explore why SaaS retention problems often begin long before renewal—inside the sales, onboarding, and customer handoff process.

Jason Roberts, Fractional Client Operations Executive at Scale CxO, joins us to discuss how growth-stage SaaS companies can unintentionally create retention risk while they’re focused on filling the top of the funnel and closing new deals.

We talk about why customer outcomes need to be carried from sales into onboarding, implementation, customer success, and ongoing account management. When that context gets lost, teams can create misaligned expectations, slow time to value, and revenue leakage that may not show up until a renewal cycle or two later.

Jason also shares why time to value, change management, and client operations should be treated as core parts of the go-to-market motion—not back-office issues to fix later.

Key takeaways:

• SaaS retention starts before the customer signs.
• Growth-stage companies often underinvest in client operations.
• The “why” behind a customer’s purchase must survive the handoff from sales to implementation.
• Time to value is a critical retention metric.
• Revenue leakage can appear long after the original operational mistake.

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Transcript

Welcome and Guest Intro

Intro/Outro 0:06

Welcome to the SaaS Backwards Podcast, where we reverse engineer the success of fast-growing SaaS firms and explore strategies CMOs and CEOs are using to drive their businesses forward.

Jason Myers 0:24

Welcome to SaaS Backwards, a podcast that helps SaaS and AI CEOs and go-to-market leaders accelerate growth and enhance profitability. Today our guest is Jason Roberts. Jason has spent the last 15 years as an executive with B2B SaaS organizations in a variety of industries that were in growth stages and into PE investments and transactions. He's led the transformation of organizations go-to-market operations functions to align the client life cycle to driven and solidify retention and become the foundation for growth. Jason, thanks for joining the podcast. Can you tell me about what you're involved with a little bit more today?

Jason Roberts 1:06

Yes. Thank you, Jason. I appreciate the invitation to be on the podcast. As you mentioned in the introduction there, I've spent a number of years in the B2B SaaS space, but over my 30-year career, it's always been focused around the client experience, more specifically, the client outcomes, solving problems that the client has with technology, but supporting the process around that. And the last year, I decided I wanted to focus on helping small to mid-sized B2B SaaS customers or service providers get ahead of the curve in their growth cycle by providing my experience and strategy to these companies before it becomes a clear investment that they're making. So many companies grow and bring on these clients, but this problem is already starting to show, but it just hasn't reached the surface yet of there being a significant problem. And so I've been looking at how do I offer my services as a fractional executive and partner with these companies at a lower investment amount so they can avoid some of those issues that come up with growth and without having their operations mature. And so hopefully I can help them avoid some of those mistakes and missteps that erode retention and slow down growth as they continue to go forward. And as you probably already recognize, but retention starts with a go-to-market process. Sales and marketing motion is a key part of what drives through to retention. And so what we're here to talk about today is, I think, all connected together from the sales and marketing process on through the client operations.

Retention Starts in GTM

Growth Pains and Symptoms

Jason Myers 2:36

Absolutely. You know, we here at Austin Lawrence Group certainly are aware of the challenges that growth stage SaaS companies face when it comes to building the top of the sales funnel, especially, and building a demand gen engine. But one of the reasons I asked you to join us on the podcast today is that, you know, we based our discussions around your operational work ties and the go-to-market activities to the retention operations that can unfortunately be deprioritized in the growth stage, especially when they're uh still kind of under this growth at all costs mentality. So tell us more about your perspective and approach.

Jason Roberts 3:15

Yeah, definitely. The early stage growth is obviously very focused on the activities that lead to more prospects in the top of the sales funnel and these prospects have to be qualified and more deals get signed and so on. However, when all the attention is on attracting the new customers, the existing customers, and those are still in that new customer process, it can be in a challenging situation, especially as you really get traction in that growth stage. Some are just part of the normal growing pains, but they're always made worse because the internal operations are trying to play catch up. They're not invested in, they're not thought of, the process isn't really laid out. And so it turns into this brute force activity where you're hiring more people, but they're not really putting together a more refined process. And so it shows in a number of different ways. A few of the symptoms, and this is a wide-ranging amount of symptoms that you could see. You know, it could be that you're you're selling a new product or capability and and the minimum viable product is really all that exists in the product, but is being sold as the full robust features. It could be positioning those new features in a way that conflicts with the way existing clients are set up or with the way that they're using what already exists, and that creates some some tension and some challenges. A new client could be dealing with new team members, right? You're throwing people at the problems, and and every step of the way they're having to reintroduce themselves or repeat why they're buying and doing all these different things that leads to a very disjointed and clumsy feeling. Or maybe the situation where there's really one person that knows everything about it, and they're the only one that the clients trust because they're the and that creates obviously bottlenecks and challenges for the ongoing relationship. And then, of course, there's always the typical delays and missed expectations and changes in plans and timelines, critical defects that come up, or blockers that prevent somebody from going live with the system. Those are all symptoms of similar issues, but the root cause of it is associated to that go-to-market operations, the client operations processing and connections that need to happen there. And it touches all parts of that go-to-market process: sales and marketing with the expectation setting, product with the MVP definition and user experience, implementation, support, customer success, whatever label you want to put on these different groups, if they exist already or they will at some point, it is all connected and around that customer. And you have to make sure that they're aligned and heading in the same direction through that. And obviously, selling is a critical part of the growth stage. So without being successful at the selling part of it, the company is not going to survive. But maturing that go-to-market and client operations piece is critical for really stacking that growth and building retention while you're minimizing those revenue leaks down the road. And as we already mentioned once, renewals are part of the go-to-market motion. So it needs to be a closed loop environment. All these pieces feed off of each other and need to continue to get better.

Why Customers Buy

Jason Myers 6:14

So conceptually, that all makes sense. But tell me a little more specifically what this means for a specific opportunity for a client.

Jason Roberts 6:22

Yeah, there's there's a lot of different examples like I was discussing, but I'm going to focus on one very straightforward element that if it's not carried through the sales funnel and into the client lifecycle, it creates a real unstable foundation for retention and for growth. And that's a simple question of why did this customer buy from us? What is their expected outcome and why are they working with us and this product itself? Too often this understanding is lost somewhere between us positioning our product and service and explaining why we're the best at X, Y, and Z and building up our proposal and putting them into contract details that accurately track how much of whatever they are buying and what's included. But it's not always a simple understanding of why they're buying, what are those expectations? Strong, successful team members, whether it's on the sales side, a customer success, or any step along the way, they know the information and they prioritize knowing it and tracking it and sharing it. But when you're growing and you're adding people on the organization scaling, this can get lost in the shuffle, whether it's using new tools, a new process, new people, all of these things create more of that friction and more opportunity for that risk to become a bigger problem. Ensuring that this is a priority and that it's a living piece of information that should be part of the relationship going forward and not just a field in the transition document or in the CRM is an important viewpoint to have.

Jason Myers 7:50

Yeah, let's tap in a little bit more on this knowing why the customer has bought and what their desired outcome is. We talk about that a lot. I don't think a lot of marketing and sales teams do enough of that work to really understand it. But I mean, we commonly talk about it as part of the qualification and part of most sales methodologies, if they're doing it correctly, or consultative sales methodologies. So what are you talking about that's different?

Time to Value and Change

Jason Roberts 8:15

Yeah, it's a great point. The concept isn't new. It's the operational focus and alignment, is where these things tend to fall off the path and become a bigger issue. So let's talk about a few of these examples. Like we're describing a little bit before, you know, somebody goes through the marketing qualification process to become a qualified lead and the reasons they're interested fall into those measurable fields that we want to track and understand. You know, sales qualification obviously confirms that that they have the problem and that they're willing and able to pay to fix it. And our goal is to align and translate the client needs into these leads and opportunities, into these categories and the contract details. But the voice of the customer, the decision maker's definition of why and and what success means is not the focus of that. The focus of reporting on and tracking through the sales process is definitely needed and should be understood, especially from the overall success of the sales program and what product is looking for. But that voice of the customer and that understanding of it can easily get lost in the shuffle and translated into different things. So in the contract details, you're never going to have the true voice of the customer in something that can be a living reflection of what that is, right? If you're referring to the contract, a lot of times that's that's not a good thing, even when a client is just coming through the pipeline and starting the onboarding piece. But understanding why and what their definition of success is needs to be a key part of those discussions and how those transitions happen within your process. And it becomes the foundation of starting the implementation or onboarding and the ongoing customer success functions. In addition to that, what can be lost is not only the impact in the internal transition. So not having that can really cause some transition problems and success becomes harder to track. But many times the client decision maker, the one that's been involved from the beginning, hands off their implementation to one of their team members, and they are not really on the same page potentially as the decision maker. So what's expected of them to move forward and what the definition of success is, these are key alignment pieces that you would want to have at the start of any real project. But in terms of this process for B2B SaaS, it can be easily ignored or glossed over because, you know, with SaaS, it can be a much more streamlined onboarding process, but you're still not understanding and factoring that in. And the other part to that is, you know, these teams that you're working with on the client side, they don't do this for a living. They're not moving on to another implementation after this. They're the ones that are going to be living and breathing with this new platform or a new service that's being provided. And so it's really important that we're clear with them on what their ownership is of these things, that their understanding and the expectations for how they're going to continue to build upon that knowledge and work towards that outcome that everybody is aligned on as part of that. So understanding why they bought and how success is being measured, it drives for a stronger implementation and onboarding process, and it sets you up for stronger success going forward, especially on the retention and the growth side.

Jason Myers 11:31

I'm wondering also what are some of the other challenges and laying the foundation for retention that you've experienced or that you've seen in the companies that you're advising?

ADKAR Change Framework

Jason Roberts 11:42

There's always a handful of items that are common and they can show up in different ways and in different levels of severity, but a lot of it comes down to alignment on the expectations, you know, the outcomes like we're just talking about. But it's aligning on those expectations and making sure that everybody is on the same page throughout the course of that relationship, right? Yes, it's critical to start on the implementation or onboarding, but even as you go forward, how they're using the software, what they're getting from it, things change in your client's world. And so you have to keep on top of what's happening, what are their expectations and how are those changing? But when we look at starting off on the right foot, not only is it the transition from the sales motion to the implementation, it can also be a reality check that now there's work to be done, right? So it's there's kind of these high and low points, and the high is, hey, we've made a decision, we bought the software, yay, we're we're fixing something that's been a problem for us for the client. But now there's really work to be done. And that change can really be a drag because they're they're doing their day job and they're doing this as well in most cases. And so it becomes a very hard balance and and critical that things are clear and upfront and we're not allowing surprises to to show up if they can be identified earlier. So aligning with those expectations on timing and all those things are important. How long it's going to take before they see the benefit is one of the pieces that's critical in the investment, right? We would refer to it in as a SaaS business, we should be thinking about it as our time-to-value metric because that that metric allows us to have a definition that says once we start that implementation or onboarding, how long does it take before they start to see value? It doesn't mean everything is done, but when are they going to start seeing value in some cases, right? In very complex, very robust systems, you know, CRMs, ERPs, those types of things. We're talking months, if not into years, to get fully deployed. But that time to value is about not only just getting them access to something, but it's when they can actually use it to do part of their job, to start to fill that gap that they had before or to deliver some value to them and their customers that is critical for why they made the decision. So as a company, we should be looking at measuring and trending that time to value. And with a client expectation, we need to align on what their expectations are and help set that as well. We should rely on them to define what their implementation timeframe should look like. We need to work with them proactively on that. So when we talk about all these different metrics, especially on the time to value and client satisfaction obviously is directly tied to that. And we don't want to underestimate that function and how long that transition is going to really take to make for them. And change management is that underlying theme that is often, I don't want to say overlooked, but it's it's assumed that it's going to happen. Just like assuming that the client knows why the decision maker bought this or that they're on board with the timeline and they don't really understand the work that needs to happen. Change management is another one of those areas that is critical for that ongoing success, and especially in a more timely manner, because if you don't plan for it, if they're not planning for it, that change to the new system, to that new process can take two to three times to what it really should if you don't take those steps up front. I've gone through training through a company called ProSi and they have an acronym called ADCAR, and it really resonated with me, not as a, hey, every little detail of that process, while it's very good, it's understanding those key parts of that change management process that can help even in these smaller projects can make a lot of sense. So ADCAR stands for awareness, right? How much does the team understand that this is a problem that needs to be solved? Why is this something that we are prioritizing, right? Getting the team and especially the the leaders on the client team aware is a key part of that. The desire to make the change. Why does this change make sense? Is it is it about doing things more efficiently? Is it filling a gap? Is it solving a problem that they have, right? Build that desire for why they want to see the change. Knowledge of, hey, what's happening? What's it going to take to do this? And and how is this going to all come together? That's keeping them up to date on what's happening, how is this going to come together, even before it's them logging into a new tool or whatever it is. It's it's around that building that train the trainer type mentality when you have a larger group of users ability that that gets to the training side to it. So how are they going to use the tools and build their skills within that new system? And the reinforcement piece, the the R of ADCAR is also something that often can be underprioritized. It's that reinforcement of, hey, we're doing something new. We got this the solution. Now we're bringing in more leads or we're doing these new things that we weren't able to do before. But it's important that you continue to reinforce what those expectations were for using this. It's not just that it's up and running. It's how are we continuing to get better at this? How do we stay engaged with the performance that they're seeing? And that's really the foundation for customer success, right? It's the ongoing pushing them forward, the reinforcement of what they need to be doing and not getting sidetracked with falling back into their old ways.

Scrappy Growth vs Retention

Jason Myers 17:14

Let's take a quick pause here to hear from our sponsor about the go-to-market analysis. If you're building a SaaS company, here's some data that's certainly worth paying attention to. According to Kyle Poyar's research across 6,500 software companies, only about one in five ever reach 5 million in ARR. And just one in 10 make it to 10 million. Now, those are some pretty sobering numbers. If you've got funding in a solid product, but you're still missing revenue targets, the culprit is almost always somewhere in your go-to-market. Now, maybe you're losing too many deals to no decision, and many times pricing hasn't changed and it's opened the door to competitors. And often sales and marketing are hitting their activity KPIs, but that's where the good news ends. Now, these are all solvable problems, but you have to know where to look. And that's exactly why we built the SAS Doctor's Go-to-Market Checkup. It's a free diagnostic where we assess 12 critical components of your growth engine, from positioning and pricing to your sales tech and metrics. We'll come back to you with a clear picture of what's holding you back and what to prioritize next. No 80-page decks that you'll never implement, just a sharp, actionable read on why you're stuck and what needs to change. So if your product should be growing faster than it is, check out the link in the show notes and let's talk. And now, back to the podcast. We all know that growth stages, decisions, and activities have to be kind of scrappy to drive success, right? There's nothing that can be done perfectly. So what's your recommendation to those companies that are really sprinting ahead with their growth execution, but have not put the same time and effort into retention strategies?

When to Engage Jason

Jason Roberts 19:07

Yeah, that pressure to sell, sell, sell is critical. And the success of that is obviously really important, especially with new funding and growth expectations that are there. It's that challenge of, you know, how do you prioritize these other areas? How do you get the time and energy around these other areas when you're already a lean organization or you don't have uh that type of experience on staff that's really focused on these types of pieces? And that's where leveraging other services, other ways to approach this is critical. And you might have team members that have that inherent understanding, that passion for customer success that are, you know, just at the starting point, they just need to build their knowledge and grow from there. The important thing is that you can you recognize the need to do these things and you recognize that even when you start to see the growth showing up like you expect and you're just and the retention is solid, that you may not see some of the revenue leakage until you get to a next renewal cycle or two that are going through that full new process with at scale. And so that's an important piece of how you need to lay out your strategies. You need to be thinking ahead, you need to be planning before it starts to show up on your dashboards or the red flag is being raised by the CFO or finance saying, hey, our growth we thought it would look good, but all of a sudden we're getting clients that are dropping unexpectedly this quarter or this month. It's always a different story, but it's it's similar things that are happening and you're not sure exactly why it is. That's why it's critical to start investing in that. And there's opportunity to start looking at those things early on, just so that you're not you're not building perfection, you're building towards an end state, though, that you understand and that you have a roadmap for. So understanding where your risk is starting to build up, understanding what your priorities are now and what you're planning to do next is all part of that kind of maturation that you need to go through before it becomes a fiber and fire.

Jason Myers 21:15

One last question. Where are clients typically struggling to make progress in their own worlds that they would engage you? And what does an engagement with you look like? Like what are the symptoms that show up that they should be, you know, talking to you?

Assessment and Key Metrics

Jason Roberts 21:30

There's a variety of different stages. You know, I'm coming from working with PE companies that had recently been acquired or had a few years under their belt, and and they were having the retention type issues were already showing up, and it was getting to the point where it was red flags were already appeared, and they were realizing that, hey, what we're doing isn't working. As I discussed earlier, with moving to earlier stage companies that are really still in that pure. Growth stage side of things, I think it's really about understanding the challenges that they see once they sell a client to their pipelines are building, but the process that it takes to get them live and the feedback from customers. If you aren't listening and closing the loop after a customer's gone through that onboarding or implementation process, or if you aren't getting that feedback from them and really understanding where you are outside of just a renewal timeframe, that's where you have risk that's that's growing. And it's not always evident, right? Doing an NPS or a CSAT survey is is good. It's a good piece of information, but it's not always the answer to knowing where there's risk because the person that did the NPS may just be the day-to-day admin. They may not be the decision maker. There's CSAT that maybe one person gets to and the other person, they didn't spend the time really getting into these things. So there's a variety of different issues that may appear within your environment that could be an indication of it. I think overall, though, the key thing from my perspective is that if if you haven't brought on experienced client operations, go-to-market operations resources, or people that have lived and breathed in an environment that this has already kind of gone through several times or you've grown and matured, you're just missing the opportunity to really get that advice and see where things are going, especially with AI. AI is a great addition to these pieces. It doesn't solve it by itself. You don't just go plug into an AI chat and say, run my operations and everything magically happens. It can make things better, but you have to have that foundational process and understanding of how to connect these dots and how to make this a scalable operation.

Jason Myers 23:49

And as part of your process too, you do uh quick assessment, right, across uh different dimensions. You want to talk a little bit about what that looks for. So if somebody's wondering, you know, if potentially we have some problems, can you potentially diagnose that or tell them that they don't have any problems? Or what does that look like typically?

Contact Info and Wrap Up

Jason Roberts 24:10

Yeah, that that's a great point. You know, most companies don't know what they don't know at this point of where they stand and where they need to go. And so the assessment is a great starting point to this. And and that's where some of the opportunity comes to connect that early stage go-to-market, the sales pipeline development, and and those pieces and the key metrics that are there into the metrics of, hey, once they've they've bought, how are we delivering to the client, right? I mentioned the time to value, the CSAT, NPS, growth, and those pieces. But looking at some of the core metrics that we look at and understanding the process that's there or not there is what the assessment's there to do. There's, you know, 10 to 12 different key areas that I typically include. They're not always the in-depth focus areas, but of those 10, there's a handful that really are where we would focus based off of the client's needs.

Jason Myers 25:07

Great. Well, this was a great conversation. If people want to get in touch with you, what's the best way to do that?

Jason Roberts 25:12

Yeah, the easiest way to do that is through LinkedIn. If you just search for Jason Roberts KC, all one word, on LinkedIn, you will go directly to my profile and you'll find me there. My company is Scale CXO. That's also out on LinkedIn. The website is still in its building stages, but for now, LinkedIn is the best place.

Jason Myers 25:32

Great. And if you want to reach out to me, my name is Jason Myers, and my email is jm at austinlawrence.com. Our demand generation agency is for software and AI companies, and it's called Austin Lawrence. And that's found at AustinLawrence.com. And if this episode didn't convince you to subscribe to the podcast Sass Backwards, I'm not sure what will. Jason, thanks for joining us today. There's a lot of good information.

Intro/Outro 26:00

Thank you, Jason. Thanks for listening to the SAS Backwards Podcast, brought to you by Austin Lawrence Group. We're a growth marketing agency that helps SaaS firms reduce churn, accelerate sales, and generate demand. Learn more about us at www.austinlawrence.com. You can email Ken Lempett at kl at austinlawrence.com about any SaaS marketing or customer retention subject. We hope you'll subscribe and thanks again for listening.