Sysdig increases marketing-sourced contract sizes 36%

To power the company’s next phase of growth, Sysdig needed to know their ideal buyer—and to be certain they were targeting them correctly. “When I joined Sysdig, we were just around that $10 million mark,” says Rich Copenhagen, Senior Director of Business Operations. “We had established product market fit and understood that we needed to sell to enterprises. But of course, success is in the details.”

Sysdig had already developed its own ideal customer profile by analyzing past close rates and contract values. But to operationalize that ICP across their entire revenue function, and to create campaigns around it, Rich hired Inverta. And Inverta asked a difficult question:

Wasn’t Sysdig leaving a lot of revenue on the table by only considering new deals, and not also net-retained revenue (NRR)?

That changed everything. Inverta brought in AlignICP to refactor Sysdig’s ideal customer profile to consider NRR. Together, the three teams conducted a thorough investigation to identify which customer segments would be most profitable. They then worked through the hard task of operationalizing it and getting marketing and sales to start thinking of their ICP in a new way. Only then could they move on to address buying groups.

But all that change required serious internal commitment—executives are tough critics by design, and they had to believe that the change would help and not hurt. And then, sales would need to change its deeply ingrained habits. And that’s where Rich started to encounter resistance. 

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Sysdig hadn’t been viewing the whole opportunity

Many companies hack their way to tens of millions in revenue but to go beyond, they must build a go-to-market apparatus around a clear and specific understanding of who buys and why. Rich knew this instinctually and had done all he could with the data he had. But he was looking for better technographic data.

“We’d landed a few enterprises and realized we could deliver the scale they needed. That was an ‘aha moment.’ But when you say you want ‘more enterprises,’ the next question is, ‘But what does that mean?’” explains Rich. “Does that mean it's the Fortune 500 list? Is it based on employee count? What makes us successful with some enterprises and others not? We needed to be more data-driven, so I called Inverta.” 

Inverta applied the Demand Continuum approach to step back and ask, “Yes, but where is the greatest long-term opportunity?” And after an initial analysis, it seemed that actually focusing on net-retained revenue would be better. Some enterprises would deliver a quick hit of revenue, but ultimately churn. Which type of buyers would grow and expand? Which companies were those?

Inverta brought in AlignICP, who ran a quick sprint to evaluate Sysdig’s customer data. They used their software to identify which segments could provide the highest return on investment based on Sysdig's ability to acquire, retain, and expand within those segments. AlignICP cross-referenced this with data from Intentsify and HG Insights and worked with Sysdig’s finance team to validate the view. It’s essential that marketing and finance calculate NRR, GRR, and all bottom-line metrics the same, so there are no discrepancies later.

Once AlignICP prepared the data, Inverta dissected it to produce actionable takeaways Sysdig could implement, and assessed how many actual accounts existed in the world that could fit into each category to ensure the company could hit its revenue goals. Those categories were:

1. Acquire and retain—A good dual fit
2. Strong acquisition, weaker retention—Aka message–market fit
3. Weak acquisition, weaker win rates—Aka product–market fit
4. Segments to avoid—Low return, not worth pursuing

The conclusion about the “acquire and retain” list was clear: What mattered about good-fit enterprise accounts is not how much money they make, but how big their security team is. Focusing on NRR had completely changed the target list and approach.

“What I love about working with Inverta is they stepped back and asked, ‘Are we optimizing for the right thing?’” says Rich. “That was really eye-opening for me. We were looking at these companies with no consideration for whether they retain and grow.”

“What I love about working with Inverta is they stepped back and asked, ‘Are we optimizing for the right thing? That was really eye-opening for me. We were looking at these companies with no consideration for whether they retain and grow.” - Rich Copenhagen, Senior Director of Business Operations

It was a great idea—but Rich had to sell it internally

To test the theory, Rich and team would need buy-in. “If Invera and AlignICP’s simplified ideal buyer model gave us a predictable benchmark for hitting world-class revenue retention of 125%, we should be going all-in on that approach,” says Rich. But Sysdig was in the midst of a leadership transition, and Rich had to both explain how things were done currently and argue for change.

“The hardest part initially was getting executives to believe in the model,” says Rich. When a company has been successful, it tends to want to continue with the same tactics. It’s difficult to convince a team currently growing revenue that they could grow it even more by focusing on fewer accounts. But Rich knew it was the key to their next phase of growth. He was persistent. 

“The hardest part initially was getting executives to believe in the model.” - Rich Copenhagen

The sales team was receptive, but when it came down to it, they weren’t ready to switch. “No rep wants to hear ‘corporate knows better,’” says Rich, “But sales reps were picking their own accounts and requesting marketing support, and the model shows we could be doing much better.” He pressed them and was told that “Now wasn’t a good time”—and in strategizing with Inverta, he found a time that was good.

Sales and Marketing agreed to roll out the new ideal buyer progressively—so they could test, and so as not to throw off salespeople’s entire years. As they back-filled and hired for new sales roles, those reps would begin on the new schema. And at the start of the next fiscal year, everything would switch over. This also had the benefit of giving Rich more time to communicate the value of the change—and show how early deals fit their profile, and proved the point. Starting that next year, 90% of target accounts in the Americas would match the persona, and 75% in EMEA and APAC, where the data was less clear. 

“We took a more measured approach to institute this change, and Inverta was a huge help in that strategy, plan, and rollout,” says Rich. “Ultimately, phasing it was the right decision.”

The results speak for themselves: 

• Marketing average contract sizes rose 36%
• The list was far more predictive
• They drove an uplift in pipeline and sales
• All despite fewer accounts and fewer sales activities

What’s it like to get your ICP right? “You can hear the difference in quarterly business review meetings,” says Rich. “People can feel the impact of having better customer growth and larger deals. It’s like, ‘Ah, I see why we’re doing this. Yes, I do have a bigger pipeline despite fewer deals. Yes, I do feel more successful with these customers.’ When you start landing those bigger deals, it proves the point.”

“You can hear the difference in quarterly business review meetings.” - Rich Copenhagen, Senior Director of Business Operations

Now Sysdig is accelerating its revenue into the next phase of the business, and it’s a sustainable, data-driven source. They don’t have to rely on reps picking good accounts—marketing has a technographic view of the market, a list to go after, and an easy way to find new accounts.

“Bringing in Inverta was crucial for me and our company, not only in helping us properly identify the problem, but to execute on a solution,” says Rich. “The way I think about it, Inverta is this unique bridge between strategy and execution. It’s not just a big, theoretical plan, and not just doing the work—it’s a complete, methodical process from a business problem to ‘printing’ revenue. Wherever you need to get, they’ll get you there.” 

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