Ep. 79 – Turning Customer Success into a Revenue Engine with Jack Zimnavoda - Part 1

In this episode, co-host Mark Petruzzi welcomes Jack Zimnavoda, Head of Customer Success at Insightful. Jack shares how modern B2B SaaS organizations can turn customer success from a support function into a true driver of revenue and retention.

Together, they explore what it takes to align CS with sales, marketing, and product—without creating channel conflict. Jack reveals how predictive AI, smart segmentation, and aligned incentives can turn expansion into a scalable and proactive motion.

What You’ll Learn

• Customer Success as a Revenue Driver: Jack explains how to reframe CS from a cost center to a growth engine—through structure, ownership, and incentives.
• Avoiding Channel Conflict: Learn how clearly defined swim lanes, compensation clarity, and collaboration between CS and Sales create harmony and momentum.
• Building a Scalable CS Model: From white-glove enterprise accounts to hybrid-touch models, Jack outlines how to maintain personalized value delivery at scale.
• Metrics That Matter: Understand the importance of net retention, lifetime value, and how CS teams can build pipelines and forecast revenue just like Sales.
• AI + Customer Health: Hear how Jack uses predictive AI to monitor product usage, signal risk, and surface expansion opportunities at scale.

Key Topics

• Structuring CS to own post-sale revenue
• Aligning CS, Sales, Marketing, and Product
• Channel conflict: where it happens and how to prevent it
• Using AI in CS forecasting and health scoring
• Segmenting your customer base to drive upsell plays
• Scaling without losing the human touch
• How to hire for commercial CSMs (hint: curiosity and creativity)

Guest Spotlight: Jack Zimnavoda

Jack is Head of Customer Success at Insightful, where he leads a global team focused on retention, adoption, and expansion. With over a decade of experience in B2B SaaS, Jack has helped transform CS into a proactive, commercial function that partners across the go-to-market org to drive real business outcomes.

Resources & Mentions:

• Book: The Seven Pillars of Customer Success by Wayne McCulloch
• Podcast Mention: This is Growth by Daphne Costa Lopes
• Tool: Vitally – CS platform used by Insightful

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Mark Petruzzi (00:04.705)

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 shape

how 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 (01:20.93)

Thanks so much. Really, really excited to be a part of this podcast and ready to dive into it.

Mark Petruzzi (01:26.807)

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 important

the 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 (02:20.609)

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 or

expansion 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.

Jack Zimnavoda (04:43.532)

Yeah.

Jack Zimnavoda (05:17.42)

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 are

very very clear.

Mark Petruzzi (06:51.86)

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 (07:02.987)

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.

Jack Zimnavoda (09:19.649)

Honestl