Marketing 911

From Leads To Loyalty: Turning Marketing Into A Retention Engine

• Brian Bakstran and Richard Bliss

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Growth doesn’t stall because you ran out of leads; it stalls because customers don’t stay long enough to realize compounding value. We sit down with veteran revenue leader Jim Tedesco to unpack how SaaS companies can move from a logo-first mindset to a retention-first engine that consistently pushes gross retention above 90 percent and net retention toward 115 percent. The conversation reframes the CMO as a chief retention officer and shows how marketing, sales, renewals, and success can rally around one shared scoreboard.

We break down the practical levers that keep customers, expand accounts, and create advocates. First comes time to value: engineer 7, 15, and 30-day activation milestones and measure them. Then build a true lifecycle—evaluation, purchase, adoption, value, advocacy—powered by proactive health scores that blend usage telemetry, feature depth, license utilization, NPS, and support signals. When risk spikes, automated triggers cue human outreach with relevant plays, not generic check-ins. Dynamic segmentation makes every touch land: tailor education and messaging by role, vertical, size, and maturity so admins, end users, and executives each see the features that matter to them.

Because SaaS reveals real usage, we dive into using that data to guide enablement, shape product decisions, and focus sellers where expansion is likely. Jim shares why marketing operations is the most important seat on the field right now, translating data into dashboards, alerts, and campaigns that prevent churn and surface cross-sell moments. We also explore compensation models that weight expansion and cross-sell more than routine renewals, incentivizing teams to lift net revenue retention quarter after quarter. If you’re ready to stop hoping at renewal time and start building a predictable retention motion, this one gives you the blueprint.

If this conversation helped sharpen your retention strategy, follow the show, share it with your team, and leave a quick review so others can find it. What’s the one metric you’ll improve this quarter?

SPEAKER_00:

Welcome to Marketing 911. I'm your co-host, Richard Bliss. And today I'm joined by my other co-host, Brian Baxtrand. Brian, and today, as we talk about marketing in the field and sales and everything that we've going on, you went ahead and found us a guest that uh I know and that you've known for quite some time and who has some really great insights. So tell me, who have we brought on today?

SPEAKER_02:

Yeah, really, really lucky to have Jim Tedesco. Uh I've worked at him at several companies. Um outstanding leader. Uh, and for anyone who follows him on LinkedIn, you know, each and every day he puts out a very positive uh little quote. And he's got great experience across the entire sales lifecycle, including being a CRO, uh, head of sales, and most recently, uh head of renewals and customer success at a$2 billion company. And so, Jim, want to welcome you to the show.

SPEAKER_01:

Yeah, thanks, Brian. I appreciate it. Richard, nice seeing you again. Hey, um, I didn't purposely quote anything on LinkedIn this morning because I figured you'd have something really provocative to say during this little broadcast. And I would use that as a quote and uh post that at some point. So that is huge. I'm waiting on you to come back with something really juicy for me.

SPEAKER_02:

Yeah, that is huge pressure. Absolutely huge pressure. Uh so let's jump into the topic. So uh just as a point of reference, for years and years, marketing has been really focused on opening doors for sales. New logos, yeah, we did some work in terms of helping existing accounts, uh, but really focused on get us in the door where sales isn't today. And that pendulum is shifting to more of we need to retain our existing customers, we can't lose them to the competition, and it's easier to upsell cross-sell than to go into new logos. So I certainly have my opinions on them, on that, and Richard does as well. But as someone who's on the other side of the fence for marketing and focused exclusively on renewals and existing customers, I'd love to hear your thoughts on what you're seeing.

SPEAKER_01:

Yeah, I mean, it comes down to a couple of statistics and a couple of metrics that the street, the finance community analysts roll track, it comes down to gross retention and net retention rate. And so gross retention, so the the customers that have a contract with you are licensed, and if they continue to do business with you and and how you measure on that, most analysts are saying you need to be over 90%. Uh you kind of look at it as a renewal rate. And and if you're below 90%, you're losing more customers than you're gaining. It's a it's a bad strategy. And and net retention rate really is the combination of those customers that you have today, plus any expansion, upsell, cross-sell, and any net new customers that you add to it. And that should be around 115%. So 90% gross retention, 115% net retention rate. Um, I would say that the chief marketing officer today is being called on to do something a little different. They should be really called the chief retention officer. That's how important it is.

SPEAKER_02:

Excellent. Yeah, 100%. Although their attention to new logos never wanes, uh, but absolutely losing customers has now become part of the responsibility of CMOs, or more importantly, retaining them. Uh so on your side of the house, uh, were you calling on marketing? And if so, what specifically were you asking them to do?

SPEAKER_01:

Yeah, I mean, I had a marketing team reporting directly to me over the last several years. And it's that important. When you're running renewals, customer success, and overall customer support for a$2 billion company, you have to be really focused on the things that'll drive a customer's mindset around being an advocate. And there's a couple of priorities that we concentrated on. And whether they're an established customer and they're adding net new product to that portfolio, or they're a brand new customer off the street, the on-time value, the onboarding process, trying to get them to really figure out how to use your product and get some sort of an activation capability and start return on an investment, that has to be 7, 15, 30 days. And you should be tracking that. That is key. So uh getting that onboarding going and getting that established is key. The other thing is realize that with customers, when they implement your product and they're using your product, you have to make sure there's continuous product adoption. In other words, there's a there's sort of a life cycle where they they buy your product and there's been a sales cycle involved in that. And they might have been working with your field sales teams, your inside sales teams, your channel teams, or your renewables teams, but there's some sort of a negotiation process. And then they go through an actual purchase, and that's where that adoption and that onboarding comes into place. But then there's the value proposition where they're actually using your product, they're gaining some sort of a capability, some sort of a feature. And then they become an advocate. And you have to look at that kind of life cycle and say to yourself, how do I touch them in that life cycle to ensure that they're not only adopting my product, but I'm getting it to the point where I think I need this, so I gotta have it. And then I'm gonna tell everybody I know about how good it is. And that's really where you want to get to. And so your different touch points, your email nurturing, your your physical phone calls, and those types of things have to lead that customer down that journey. And you should have that in some sort of a, I mean, Brian, you you were the king at putting together optimization and systems and uh different types of uh avenues to drive emails and um field marking events and and different types of uh remote conversations with customers. You have to take that as a prescription and drive this constant touch where you're driving a customer to understand the benefits of your product and not only to drive adoption, but to also see that roadmap in a future where they can start taking advantage of other capabilities. And that's the key that gets you that total gross retention mindset.

SPEAKER_00:

I've got a question, Brian. I've got a question on that because um, as I'm hearing, Jim, as you're talking, it sounds like, and I'm thinking about my own experience, this is a relay race, right? Marketing has the first touch point, usually, with some kind of ad, with some kind of brand, with some kind of presence. Then sales gets involved, they build that relationship with the customer, they talk to them, they make that sale. And then it sounds like it's now handed back to marketing to maintain that retention and make sure that touch point, but you said two things. One is that you you keep reminding them, but that phone call, marketing's not picking up the phone and calling them, are they? That's a isn't is that a salesperson? Is that an account rep? And how do you how do you keep that relay going back and forth so that the baton isn't dropped in between? Because oftentimes we hear that's the worst problem, is that sometimes that baton gets dropped, and who's being blamed? And I hate to say the blame, but right, that's one of the biggest challenges is keeping that consistent communication with those two different teams. Isn't that is that fairly accurate?

SPEAKER_01:

You're absolutely right. And and I would say it is there's a reactionary mindset and a proactive mindset, and you have to have both, right? What I mean by that is proactive, meaning you're measuring your customers' health score. You're surveying them, you're determining what features they've adopted and what they're using. There's all different sorts of um uh demographic information and detailed um licensing information you can gather from your product that tells you what the customer has implemented, what they're using, what features they're capable of, and how much of that that they're using based on what they purchased. And proactively, you have to put together this kind of the whole company. I'm not just talking about your renewals team or your sales team, but marketing and operations and your back office finance people all have to be of this mindset that that customer's health and that health score that you determine is so important that everybody rallies around it. So you have to proactively be looking at their ability to implement your product and use your product. And whether it be by NPS scores or surveys or looking at licensing information in terms of usage, you have to make decisions quickly. And as customers may maybe change their health score, there has to be some automated triggers. And then there's that that sort of reactive. And and really what marketing was in the past was branding, was getting messaging out, getting customers to hit your website, maybe download some assets and provide their information and you call out to them. That's not happening as much. Like that reaction to a customer raising their hand and saying, hey, I'm a potential buyer, contact me. That doesn't really happen. When when they appear, when they present themselves, they've already done the research, they've gone to the market, they've understand what the competitors are doing, what features they offer. They actually even know the licensing offerings and they know the pricing. So when they when they do appear, they're not only just a buyer, they're down that pipeline into making a decision. And it's up to you to really drive and and map their real requirements to how you can provide value. So it's that reactive and proactive that you have to balance. And I think really to address your question, it it's not any one particular team's responsibility. It's everybody's responsibility to be focused on that customer's usage, adoption, and success. And whether it's a salesperson reacting to a hand raiser or it's a renewals team in that renewals window. And when we say renewals window, we mean there's an expiration of a contract at some point in the future. And four months prior to that, 120 days, five months prior to that, you need to be contacting that customer to ensure that they understand what additional features and functionalities coming and mapped. If you wait and you say to yourself, hey, I'm gonna contact my customers just around that renewals window, right around that period where they're about to sign a check, it's too late. They've already churned, they've already gone to the competition, they've already mapped you out, and they're gonna just basically give you the cold shoulder and not respond to you. You have to provide value up front, and there has to be a time frame where you're proactively driving value, features, new adoption, new capabilities. I would say you have to even go down to the point of doing dynamic segmentation. And what that means is really figuring out if there's a group that are power users that are very successful, and you're utilizing them as case studies, and then geographically and by size of customer and specific verticals, and you're marketing to them, each of them totally different in a different persona, different voice.

SPEAKER_02:

You know, it's interesting to think of uh the board meetings or executive meetings that we've all been in, and it used to be from a marketing standpoint, the questions began with what are you doing to pull in prospects, pipeline creation, and through how many deals closed that you brought in, and then it was kind of back to the quote top of the funnel. And what I what we're seeing now is marketing responsibility goes yes all the way through to close deal, but then closed deal kind of never-ending retention, right? Never-ending upsell cross-sell. And you've said several times it's not just one group, it's all groups. I would put forward marketing is the one organization that can pull sales and renewals together from the standpoint of how marketing can help both, how we all need to stay connected, how we all need to be looking at the same target. You you agree with that, Jim?

SPEAKER_01:

Yeah, I actually do. As a matter of fact, that in the last several months, I've been working with lots of uh technology, software technology companies. Um, and and and I've been listening to really what their challenges are. And everything that we're talking about here today is really coming to head in the industry. And and and what I've told them is hey, you know, you you've had this marketing blueprint that you've used for many, many years, and you're spending lots of money in driving and adopting a branding message and adopting a specific field marketing presence, and and all of that is good, but maybe scale back on that a little bit and use your time and energy and build a churn prediction model and do something that's going to give you a kind of like a radar into your customers with usage and adoption. And if you can be more proactive into your customer base, how they're using your products, how they're expanding their portfolio, and even giving your sales teams a challenge and say, hey, look, it we're gonna pay you differently. We're gonna pay you more on the expansion within a customer than we are with getting a uh renewal. And we're gonna pay you more on getting a customer to cross-sell into a different product within the portfolio, something that they don't even have within their environment. And we do that at a higher um spiff rate or a higher compensation rate, because it's that important. I think that if if we kind of turn our mindset into this proactive churn prevention model, put our time and energy into analyzing our customers, looking at their usage, looking at their support tickets, looking at the rate of of how they're actually responding, and trigger some sort of an automated human interaction. I think that'll help us with health scores and the NPS overall, but really driving that that net retention rate, which is the biggest driver of success in a SaaS-based customer.

SPEAKER_02:

Did you view that as you were you were expecting all of that from your organization? In other words, you can only do so much, you were doing the best you could, you were looking at those renewals with the highest possible uh dollar amount or ARR. And then, as uh are you realizing, well, wait a minute, marketing needs to be deeply involved in even potentially leading this idea of a uh you know measurement stick on retention.

SPEAKER_01:

Yeah, I mean, I look at it as any kind of sports team, right? There are certain positions, certain people on the field that are key and strategic. And I think that if I look at where the business is for a SaaS-based vendor, I think marketing operations is the most important position on the field today. I mean, you might have someone who's writing really good messaging, and you might have someone who's really good at branding and logos and colors and can really knock out your website. Those are great things. And so my my message is hey, that's table stakes. You need to do that. Don't stop. You need to do that. But the marketing operations person who can take a look at the firmographic information, look and optimize the details and the analytics of the business and help you build these dashboards and drive these triggers, that is key. And I would say that that's probably the most important position on the team.

SPEAKER_00:

I was gonna say for for a SaaS company, the advantage a StAS company has over traditional software is you get to see the features and functionality that your customers are using in real time, right? You sell a piece of software to somebody and it's got all these bells and whistles, you have no idea what bells and whistles they're using. But SaaS, you get to go in with that data and say, look, nobody's using this functionality. The engineers thought this was great. We put it out there. Nobody's using it. And so when you talk about that upselling and that continued retention and that adoption, it's also then actively finding ways to educate your customers about how they can use, particularly SaaS, to get deeper into their organization because you can see who's using it and who's not.

SPEAKER_01:

That's right. You're absolutely right. And and so we look at that as the journey. And I talked about that kind of customer lifestyle, but you do that to measure the aha moment, like the onboarding, where they're actually getting some sort of uh feature adoption. So you can measure that and how that time to value, and you can measure that in statistic, and that can help you generate, you know, an onboarding team, a customer success team that's welcoming customers when they're buying new product or they're they just renewed or they're expanding their portfolio. And they've got a measurement and metric that focuses on that on-time value. So that's that's one piece of it. And then it's really, you know, you can measure deeply into what features they're adopting and what features they're using within their licensing. And then you can measure that as well. And if you're doing both, you're doing that onboarding and an activation rate, you're doing that feature adoption scoring, and you're measuring both of those, you could get a very quick health score. And and and by the way, if they're not using those features and they're not adopting, that health score is in red. That health score is down, and someone has to be focused on that customer. And then that's what I'm talking about, these triggers, activating some sort of a human interaction to make sure that, hey, did we miss it? We we had this sort of sales cycle, we had this kind of feature parity with what your requirements were. We dressed your business needs and you haven't adopted it. Where do we go wrong? And and that really, and there's a couple of reasons for that. And then there might have been an acquisition, a merger, or something like that. That might have been the person you were dealing with. They left the company, maybe that team was disbanded, maybe the budgets were reassigned, but you need to know because these are these are the keys. And and by the way, that's a selling opportunity. That's when, you know, and and you know, it's funny, when people ask me about sales, and I've run sales teams for close to 30 years now. Um, you know, the know and and when the customer is not happy, and when there's a um, you know, kind of a downsell in the marketplace, this is when it's time to step up and do your job. This is when it's time to bring value. This is when it's time to go to work, boys. And and that's what I keep on saying. You gotta really figure this out. And and having this health score type of mindset, this this churn prediction model, can only give you more um advantages in touching the customer at the right time.

SPEAKER_00:

You know, it's Brian, it reminds me of Tom Mendoza's quote. Your number one job here is sales, your number two job is whatever we hired you for.

SPEAKER_02:

Everybody, everybody sells. You know, it's can I use that one on LinkedIn today?

SPEAKER_01:

It's awesome.

SPEAKER_02:

Absolutely.

SPEAKER_00:

That's Tom and quote Tom Mendoza. Tag him. Uh, he'll uh he'll respond to that. Brian, we're just about out of time. You want to you want to wrap us up?

SPEAKER_02:

Yeah, I just uh the the visual I have is you know kind of the typical funnel that marketing's always focused on, right? But it now becomes one funnel down to the close and then the next funnel below it, right? That's right, a hundred percent. So uh Jim, outstanding uh discussion. Uh excellent speaking to you and seeing you. Um, and thank you so much for joining. Greatly appreciate it.

SPEAKER_01:

Hey, my pleasure, guys. I'd love to uh come back on a deep deep dive, if you will. Um awesome, awesome time. And I think this is most relevant in any marketing environment, any any area where you're driving, where is it that we want to put our time and energy? This is really where it is. It's all about this focus on retention. So good luck, guys, and uh happy to help in the future. Excellent.

SPEAKER_00:

You've been listening to Marketing 911. I'm your co host, Richard Bliss, been joined by Brian Baxtrand. And our guest today has been Jin Todesco. Uh, it's been a fascinating conversation about the marketing and sales and the concept of retention. And hopefully you found something fascinating. I know I always do. Thanks for listening. We'll catch you next time. Take care.

Contributor

Brian Bakstran

Co-host
Contributor

Brian Bakstran

Co-host
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Richard Bliss

Co-host