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In this Part 2 episode, co-host Mark Petruzzi continues the conversation with Jack Zimnavoda, Head of Customer Success at Insightful. This time, they explore how Jack’s team is scaling Customer Success by embedding AI, aligning post-sale marketing, and applying smart segmentation strategies.Jack shares how predictive tools, data-informed health scores, and hybrid touch models enable CS teams to identify churn risks, streamline workflows, and drive expansion; all while maintaining a personal touch.What You’ll LearnPredictive CS in Action: Jack explains how his team uses AI within their CS platform to surface risk, recommend proactive next steps, and highlight expansion-ready accounts.Marketing + CS = Growth: How Insightful brings CS and marketing together to educate customers, promote feature adoption, and scale communication—without losing personalization.Segmentation for Scale: Why Insightful uses a hybrid touch model to support over 5,000 customers across different industries and sizes—without compromising value delivery.Retention Forecasting: Discover how qualitative inputs, usage data, and AI models combine to anticipate churn and improve long-term customer outcomes.Key TopicsBuilding a predictive, AI-supported CS platformAligning CS, product, and marketing post-saleHybrid-touch models for scaleCustomer health scoring and churn predictionOperationalizing expansion strategyCreating scalable CS motions with a human touchGuest Spotlight: Jack ZimnavodaJack is Head of Customer Success at Insightful, where he leads global efforts in retention, adoption, and expansion. With over 10 years of experience in B2B SaaS, Jack has developed practical, scalable strategies that connect Customer Success with revenue growth.Resources & MentionsBook: The Seven Pillars of Customer Success by Wayne McCullochPodcast Mention: This is Growth by Daphne Costa LopesTool: Vitally – CS platform used by Insightful🎧 Listen now and follow Selling the Cloud for more expert insights on scaling GTM teams. Subscribe wherever you get your podcasts.Mark Petruzzi (00:04)Welcome to today's episode of Selling the Cloud podcast. We're thrilled to welcome Jack Zimnavoda, Head of Customer Success at Insightful. Jack is a seasoned CS leader with a deep passion for helping companies retain and grow their customer base through intentional customer success strategies. He has built teams that drive renewal, expansion, and adoption at scale, and he's helped shapehow modern B2B SaaS companies think about customer-led growth. Today, Jack will explain how customer success can become a core growth engine through better cross-selling, upselling, and alignment with the rest of the go-to-market organization. Today, we'll explore four areas. One, we're thinking customer success as a revenue driver. Two, building a customer-centric expansion motion.three, partnering with sales, product, and marketing for go-to-market impact, and four, metrics and models that power scalable CS growth. All right, well, again, Jack, welcome. We're very excited about having you here, and we can kind of kick off into topic one. But again, first, welcome.Jack Zimnavoda (01:20)Thanks so much. Really, really excited to be a part of this podcast and ready to dive into it.Mark Petruzzi (01:26)Perfect, all right. Topic one, rethinking customer success as a revenue driver. That is something that I have been in the middle of for many years. And it's funny, you get all different views on this straight up to the CEO and the board. You have a typical customer success mindset of, I don't wanna be selling, I'm not sales. But at the same time, that's evolved as we all know how importantthe upselling and cross-selling process is and how that can't be done successfully without the support of the CS team. So Jack, know, CS has been viewed as a post-sales support function in the past. What needs to change in mindset and structure for it truly to become a revenue driver?Jack Zimnavoda (02:20)Yeah, so it's a totally fair ⁓ mindset that go-to-market leaders have there of customer success being an offshoot of support, particularly for leaders that have been around in go-to-market ⁓ leadership for 20 plus years, because truth be told, customer success was an offshoot of support. ⁓ I started in this career back when it was account management, and then it's gone into its own... ⁓know, evolution since then. But also, I think it's fair to say that that gap in the understanding of customer success being a support function versus what it's really intended to be these days is narrowing, right? I think these days, customer success, especially at SaaS firms, is kind of a core piece of the go-to-market team. And I think most people don't view it the way that they might have 15, 20 years ago.⁓ In those instances where it is still viewed as a higher level of support, think really what needs to happen is a change in mindset first. And that doesn't happen by somebody saying, this works well at other companies, we should do it. ⁓ I think it kind of happens by experimentation, right? Letting the customer success team ⁓ go to their customers and offering ⁓ new things to them, whether it's new use cases orexpansion to different teams or through different product offerings. And the proof is in the pudding in those cases. So I think with that experimentation, when you show small wins like that, it automatically changes the mindset. ⁓ And once that happens, you could think about changing the structure of teams.Yeah.Yeah. These are really, you know, very real problems that customers have, or sorry, companies have when they start introducing customer success as a revenue generator, right? The truth is there's no one way that this works well. I've seen it done in so many different ways. I've seen pods created where CSMs are coupled with salespeople. I've seen, you know, customer success managers own all revenue operations post the initial point of sales and own a quota.And I've even seen, you know, and I don't recommend this, I've seen CSMs essentially treated as SDRs to go out and find opportunities and feed them back to the sales team to manage. You know, I'll just speak to the way that my team is set up because I think it works quite well in the way that we're working it today, which is that my team, ⁓ the way that that insightful works is that the sales team has a certain period of time whereby they're able to expand the accounts that they bring in.⁓ But if that period passes, then the success team has the obligation really to nurture those accounts, find opportunities to take them from identification of the opportunity all the way through through close. And really we incentivize the team to do exactly that. So ultimately, I think any of those types of structures can work. It's just a matter of ensuring that incentives are aligned and that expectations between the teams arevery very clear.Mark Petruzzi (06:51)Great. So Jack, where do you see most companies going wrong when they're trying to turn customer success into a profit center instead of a cost center?Jack Zimnavoda (07:02)Yeah, great question. Two things every time. The first thing is that there's a lack of understanding sometimes when you want the customer success team to take on ⁓ the ownership of the revenue. ⁓ Lack of understanding of what the CSM team has on their plate already from a responsibility standpoint. And then blindly thinking that they could add opportunity, identification, and realization.without negatively impacting those other areas that are already on their plates. So I think when you look at bringing this into a customer success team for the first time, it's really crucial that there's a plan in place to offload some of that non-value added work prior to making the shift so that hopefully the customer success team has a bandwidth to focus on this area plus the core competencies that they've always had.I would say the other thing, and I mentioned this in the previous answer, which is not aligning incentives to the intended outcomes. So, you know, if you're starting this out and you've got your customer success managers judged on things like client sentiment or the number of quarterly business reviews they're doing or gross retention, there's really no incentive for the CSMs to grab onto this opportunity for them with everything they've got.And just bringing this once again back to my team. I handle this by giving them incentives in two ways. The first is by giving them quarterly bonuses that's based on that retention, which of course factors in expansion dollars, but is really rooted in retention. But then on top of that, there is a small commission opportunity, but they're focused on non-organic expansions, meaning these opportunities have to be identified.by the CSM, they really have to be the ones responsible for drumming up this business and owning it from identification through close to get that commission.Honestly, I have not dealt with that struggle too much. And the reason is we set expectations extremely clearly upfront. We explain why the business is going in this direction, which is ultimately to grow revenue business-wide. And also, for me, it's a matter of showing them the previous data. Most of the time, salespeople can get territorial over their accounts, and that's understandable. But when you take a look at their commission payouts,I'd say nine times out of ten, the vast majority of their commission is coming from new business anyway. It's just kind of a mindset that needs to shift of, I should just be focused on new business and that's the key area that the company needs me to focus on and that I'm getting paid for.So I think it should work together pretty seamlessly, right? think sales and customer success need to be working hand in hand. And that is regardless of if customer success is owning the expansions or not. There needs to be a very solid understanding, foundational understanding of what the accounts need, what their use case is, what are their goals that they need to achieve to be able to say, yes, this expenditure was worth it.⁓ As long as you have those kind of key points in play, then the rest I think falls into play pretty naturally. Again, making sure that you're not overloading any particular team with so much that they can't handle their responsibilities.Mark Petruzzi (11:22)Cool. I've got one more on this to double down a little bit. What are the early signs, Jack, that you see that gives you the indication that a CS team is being too reactive instead of being able to make that jump over to the strategic side?Jack Zimnavoda (11:42)Yeah, that's a great question. ⁓ For me, it's really simple. If we're finding examples of churn, customers leaving us, and they come as a surprise to the CSM, it is a clear cut sign to me that they're just too in the weeds of resolving issues that are brought to them and not taking the time to have proactive conversations with their customers about what their goals are, what kind of value they expect to see. ⁓ Any time that thatchurn is brought up and we don't know what's going on there. I need to take a step back and I want my team to take a step back to really understand what happened there in terms of their involvement with that account because it shouldn't be a surprise.Yeah, think there are a couple of things that are constant, whether it's a new logo or an expansion, right? Those things are, you know, solid understanding of what levers there are to pull for increases or expansions, right? Is this a play to sell professional services or is it add-ons that are available to them? Just understanding, you know, what's in their tool belt that they can rely on. And the other thing that I think is a constant betweenwhether it's an existing customer or a new customer, is a really solid understanding at the very minimum of the industries that you're serving and what challenges they're facing. Even better, obviously, if you have a solid understanding of the customers specifically and what their challenges are. But then there are things, I guess you call them ingredients, right, that are a bit more unique to existing customers.The first is incredibly simple but incredibly powerful, think, and that is, are they a happy customer? You can have great products, ⁓ you can have a really solid process for onboarding those customers, but at the end of the day, if a customer is giving you feedback that, for whatever reason, they're unhappy, maybe they're not able to achieve their goals or they felt that the onboarding process didn't work for them,The focus can't be on selling that customer more at that point. It needs to be on fixing that problem. So I think there are a ton of signs that you could get for existing customers that you can't necessarily tell with a new, a net new account in terms of whether or not they're set up for a good expansion conversation. And then the other thing, the other ingredient I would say that's really great to have. I don't think it's a must have, but it's...certainly nice to have, is there's no shortage of tools that a customer success team can rely on to know whether their accounts are primed for expansion. I'm a big proponent of using predictive AI tools that help you analyze the conversations that are happening between the CSM and the account that are able to take a look at the data in your customer success platform or in your CRM.and predict whether or not this account based on a lot of their traits or whatever are a good candidate for expansion. When you're a company like Insightful where you've got 5,000 customers plus, don't have time, or the CSMs don't have time to sort through all the data on their own. So having that kind of predictive insight is really valuable in using their time wisely and focusing on the accounts that areyou know, really ready for that expansion conversation.I'm sure there's more, I'm ⁓ I'm blanking out the others.Mark Petruzzi (16:19)So Jack, tell us about how you work on training CSMs to have these types of commercial conversations without turning them into full-fledged sales reps.Jack Zimnavoda (16:32)Yeah, ⁓ I think part of it doesn't really go into training. It comes into hiring the right people. ⁓ And what I mean by that is, you know, when I'm hiring for CSM roles and I just actually had a couple of interviews this week for a new CSM role in New York, the two kind of mindsets that I'm looking for that I think are great for this position are curiosity and also creativity.⁓ I think when customer success managers can go into conversations with the mindset of genuine curiosity about, you know, customers' businesses, you know, how they're making money, ⁓ what their challenges are, and also creative approach towards problem solving for those challenges, conversations that lead to upsells or cross-sells really just happen naturally. So I think that's the first piece of it, is hiring for the right...sets of soft skills, if you will. ⁓ Having said that, there's also tactics that we could train on. ⁓ One of those tactics for my team is when we're running quarterly business reviews, before that takes place, I'm having my team do a lot of research on the accounts that we're working with outside of just the departments we're working with. We're trying to identify stakeholders that may not even know about Encypheal, could find value in it.And then we're going back to our champions and we're saying, Hey, let's bring them into the quarterly business revie…
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