As you climb the career ladder in Customer Success, it can feel natural to operate in the same way you did at lower levels. But according to Rachel Orston, without a significant shift in mindset and habits, new leaders 1) won’t be able to get out of the tactical day-to-day work, and 2) will never become the strategic customer champions companies need from their head of CS. 


Rachel would know. She’s been a CEO and has held executive roles in Marketing, Operations, and Customer Success at companies like IBM, UserIQ, BetterCloud, and now SmartRecruiters. Her varied experience has helped her to deeply understand the makeup of a successful leader and strategic CCO. 


This issue is an excerpt from an interview I had with Rachel where she explained how CCOs can pull themselves out from being too tactical. 



Probably the most common pattern I see with Customer Success leaders who can’t scale themselves is a tendency to manage for today. They're stuck in a whirlwind of dealing with people and the day-to-day tactical issues CSMs throw at them.


Don’t get me wrong, leaders who are stuck in this trap aren’t bad people leaders. In fact, their teams usually love them because they're the go-to person who can solve all the problems that pop up. They’re the hero. The problem is that at the end of the day, CS leaders in this habit become exhausted, and they don’t get any strategic or proactive work done. They've spent all day reacting to the problems du jour. And this happens at all levels; VPs managing global teams at $100 million+ in revenue companies have come to me completely drained. 


There’s a 3-step system I’ve used to help get out of the weeds. In short, it’s a “people, process, and systems” analysis. 


One note before we dive in: even after doing this analysis, CS leaders must reframe how they think about their priorities on an ongoing basis. No more “I’m going to get 30 things done on my task list.” Focus on the highly important, longer-term initiatives. The A+ problems. 

#1: Do you have the right people? 

Sometimes leaders get so close to their work that they can’t see beyond it. A year passes and the CS leader will realize they haven't kept up with the current hiring profile, how the market has evolved, if the product has gotten more technical, whether CSMs are well aligned to drive value, and where they have skill gaps.

That’s why the head of CS needs to consistently assess if the right CSMs are being hired to drive the right outcomes to deliver the right value. In a company growing in size and complexity,  at regular points you’ll find the CSM profile you need moving forward will not match the profile of the past.  

Before you proceed with hiring a new profile of CSMs, ask these questions: Do you need more enablement and skills training? Do you need more relationship building with your Product team so CSMs can level up technically? Or do you actually need to start looking outside your existing team? 


I'm a firm believer in team development and building folks from within your team. But there are times, for example, when you start to close multi-million dollar accounts and the profile of someone who can manage those relationships is very different from the CSMs that are managing 40-50k deals. 

#2: Are you building a proactive muscle? 

One way to know whether a CS leader is moving strategically is if they pause every quarter to do churn insights and analysis. Do they spend time going back through detractor NPS and lost accounts? Do they surface patterns in lost deals or in wins? 


Are they stopping to identify repetitive activities that their team does that either leads to success or loss? Do they work on building a “proactive muscle” so that they don't keep falling in the same hole over and over again? Where are they creating their own problems?


Patterns are self-evident—they're not one-offs. Typically the fires that come up are not new for the team or for the leader. So if a CS leader is not able to see trends and act on them, or doesn’t set aside the time to look into patterns and how their team can become more proactive, it’s almost a given that the leader is or will be stuck in a reactive mode (as will their team). These leaders are missing out on the opportunity to be the strategic leader their team and company needs.

#3: Do you have the right systems to drive desired behaviors in your team? 

The mistake too many CS leaders make initially is when they start with a system (e.g. purchasing AI or fancy reporting) before they think about the people and processes to make that system effective.

Once you have the correct people in the right roles, proper processes in place, and when you understand where you are creating your own problems, then it’s time to think about the best way to automate it. Do you need a playbook? Do you need a new system? Do you need a tool?

When you’re adopting new systems to support your business, it’s crucial to think about behaviors you want your people to be showing. How are you going to drive consistency in the business? What predictable behaviors do you want to see as a result of implementing a certain system? How would a new system change how you lead day-to-day? 


Let's take call recording tech as an example. I love listening to call recordings and I spend time doing it because it drives a behavior that I expect of leaders—to coach their team, to listen, and to detect patterns. By using a recording tool, leaders can not only coach the individual on the call, but also the broader team. 


But part of purchasing new technology is considering why you are buying a certain tool and what culture you want to drive with the tool. If you don’t present a call recording technology in the right way, team members will likely think you’re auditing them and using it as a performance management tool. Whereas if you present it as being part of your coaching culture, where the team is constantly learning and sharing from collective experiences, people will happily adopt it.


To be influential, leaders need to set the bigger “why” behind systems to get people into a shared narrative. When we make a big platform or tool decisions, I believe in storytelling and developing clear visions of success.



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