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Driving Strategic Vision in Customer Success, with Rod Cherkas, HelloCCO

Strategic thought leader and customer success pioneer Rod Cherkas shares his secret sauce 

In this episode of CCO Secrets, we had the pleasure of speaking with Rod Cherkas, CEO and Principal of HelloCCO

HelloCCO is a consulting firm that works alongside CEOs and their post-sale leaders at fast-growing enterprise SaaS companies. 

And when it comes to the world of customer success, Cherkas is a true pioneer. We spoke with him about how aspiring CS leaders can and should be more strategic across an organization. He also provided eye-opening advice that is invaluable to all professionals, not only those in CS. 

Meet Rod Cherkas 

You may know Cherkas from his time at Gainsight as VP of Global Professional Services. His impressive career spans multiple VP, SVP, and C-suite roles at Intuit, RingCentral, Marketo, and Narvar

His journey to customer success was serendipitous, starting with his role at Intuit. 

Intuit was one of the early leaders in developing software for consumers and small businesses and was initially known for CD-based software sold in a retail store. 

Cherkas led the operational execution of Intuit’s online payroll business, one of its first recurring revenue businesses. 

“I recognized that you could apply the same type of innovation and sort of experienced design improvements that Intuit was so great at doing on the user interface and software,” Cherkas said. 

He then went on to work at several fast-growing startups — RingCentral, Marketo, and Gainsight — where he helped each design and successfully execute post-scale experiences. 

At different stages, he led what we now think of as the customer success management function, an account management function, and some of the operational teams supporting each. 

“I've had leadership roles in each of those functions that I think helped give me perspective about how those metrics and experiences all work together to deliver great outcomes, not just for our customers, but also for companies and employees,” he said.

Diving deeper into the role of Chief Customer Officer

With vast experience at the forefront of building and implementing innovative post-sales experiences, Cherkas has a unique perspective on the role and layers of CCO. 

While the title implies obvious customer-facing responsibilities, the less obvious part is that a CCO manages different elements of various functions within an organization. 

“The expectations are that that individual is able to connect the dots across functional teams and identify the trends of how results in one function affect another,” Cherkas said. “They want to be able to make sure that their leaders are collaborating on the long-term improvements and the experience design that is so important to driving successful first impressions, perhaps during implementation, expanding adoption and usage, driving retention, and ultimately expansion.”

All leaders across an organization’s various functions need to play specific roles on the team, collaborating and aligning on cross-functional dependencies. 

This approach should especially include how the CS team works with the sales and product team. It’s crucial to stay informed on new features, releases, issues, as well as provide feedback. 

Monitoring various expected metrics and outcomes from post-sale organizations is critical, too. 

“It’s not just single metrics like retention or expansion. That [CCO] leader needs to understand operating margin and costs and how to hire,” Cherkas said. “They need to think about employee satisfaction. [Sometimes] the CSM is tied to CAC or acquisition cost. And so, they really need to have an understanding of how all of these pieces fit together to deliver against the expectations of a CEO or a CFO while balancing the needs of our customers. So it's a particularly challenging role.”

The lack of executive representation

While customer support and professional services have been around for many years, customer success is still a relatively new function. Moreover, some of the leaders in this space are still relatively young in their careers and evolving best practices and methodologies, Cherkas says.  

Additionally, there are a lot of leaders who are playing this type of role without the title. 

“Now, my hypothesis is to operate at the C-suite level, you not only need to be good at just the functional expertise that maybe you grew up in, but really be able to connect the dots across all of your functional teams … which is a very different set of skills that I think people are growing into” Cherkas said. “So I would expect over the next couple of years, we're going to see more people operating at that C-suite level, and then earning the right to the titles, while there are people in little bit lower levels of the organization that are responsible for those functions.”

And while some individuals may be handling some of the same responsibilities that a CCO would, there is still a difference in earning that title. It's about being part of the strategic vision of the company as well. 

“A CEO, from what I've seen in my career, has a different set of expectations that the [CCO] is not just thinking about executing well in the day-to-day, and in their particular function, but they're also preparing the organization for the longer-term initiatives and where the company is growing. So they're successfully able to balance delivering in the short term, and also in the long term,” Cherkas said.

Additionally, a CCO or aspiring CCO should be adept at thinking, operating, executing and delivering results at that type of executive level, according to Cherkas. 

Because a customer success leader's department is the closest to the customer experience, contributing to the company's overall strategic vision is crucial. Cherkas broke down the skills to accomplish this:  

  • The ability to understand all customer trends and insights, and interpret that into useful data for the rest of the organization. 
  • Understanding owned metrics beyond retention or expansion—employee cost management and support as a cost of revenue—and how all metrics affect the financial performance of a company. 
  • The ability to think strategically and anticipate what’s happening in the future and ensure that you’re getting the time to think about that. 

“One of the opportunities that encouraged me to start HelloCCO was that these leaders aren't able to dedicate enough either time to do the strategic thinking, or to have time that they can pull out of their existing leadership team to actually execute against those small number of strategic priorities,” Cherkas said. “How they balance the short and long is a really great development opportunity for folks that want to become leaders of either the functional teams or this chief customer officer role.”

Advice for aspiring CCOs

When it comes to advice on Cherkas' side of a very successful career, he's humble enough to recognize that he's never had all of the answers. And, in fact, being a good leader is being able to recognize that you don't always have all of the answers.

He offered up three specific pieces of advice for us. The first is to look for the individuals who are doing best practices. 

“There's lots of communities evolving, there's conferences, Gainsight has its pulse conference coming up that enables people to connect and learn what's happening in the industry. So one thing is to role model your own behaviors and operating mechanisms on what's working with other companies, you don't necessarily need to create it. There's lots of innovation that's happening.”

The second is to think about and seize opportunities to take on roles and leadership. 

“Whether it's specific roles or interactions with other functional organizations, I believe that leaders of the future will not just have had a career moving up the ladder in one particular function, but may become leaders of different post-sale organizations,” Cherkas said. “So take opportunities through your career to become responsible for those and earlier in your career, maybe work on cross-functional initiatives, so that you at least understand what some of the challenges and day-to-day activities are.” 

And the third is to think about how to connect the dots across various parts of your organization and tie them together into simple themes or trends. This enables you to focus on delivering against these themes or come up with ways to improve areas that are most going to move the needle. 

“There's so many choices that an executive or leader has of what they can do and where they can spend their time and their organization’s time. And really, you have to figure out, what are the two or three things that are going to most impact your customer experience, your financial results, your ability to attract and retain employees, and leaders in your organization? And so being able to anticipate what those things are is going to be an incredibly helpful skill set.”

About the Author

Chelsea Castle is the Director of Content Marketing at Chili Piper. A journalist turned empathy-driven marketer, she's also a concert junkie who can often be found #doingthings outside and crafting creative ways to be sustainable.

Profile Photo of Chelsea Castle