Jan 20, 2022

Read Time 7 min

Q&A Recap: How to Scale Your Post-Sale Teams During Periods of Fast Growth


As a Customer Success leader, you know you should invest more time and resources into planning and executing the long-term initiatives your team needs to scale. But when those short-term deliverables and constant fires always seem to take priority, how do make progress?

Rod Cherkas, CEO of HelloCCO, joined us for a webinar to share his approach to ensure your Customer Success team stays ahead of your company’s growth. Using HelloCCO’s Post-Sale SCALING™ Framework, Rod breaks down how you can anticipate future needs, evaluate opportunities, and prioritize your strategic initiatives.

During the webinar, we covered how to:

  • Assess your team’s ability to scale
  • Anticipate the challenges required to support future growth
  • Align around a small number of initiatives that will most impact your results

If you missed the webinar, you can watch it on-demand.

Q&A Recap

Speaker: Rod Cherkas, CEO, HelloCCO


Q: What best practices should a brand-new Customer Success department focus on first?

A: You want to understand what the goal is and what the outcomes and expectations are for your Customer Success department. I would have a discussion with your manager to help understand the outcomes you want. Is it thinking about getting your customers onboarded and started? Is it thinking about expansion and growing? It could also just be learning about your customers, where the most important thing you’re doing is providing a funnel of information back into the organization. I wouldn’t broaden your scope so much, but really try to understand what you can do in your early days to add as much leverage to your organization as possible.


Q: How can Customer Success manage up and sell themselves internally?

A: The dialogue that you have should be direct. Understand the role of your Customer Success organization. You want to understand what the role and the desired outcomes are. And then think about how you can be measuring those results. So, it relates to this metric around key success factors and success metrics. There may be certain success metrics in terms of customer outcomes. There may be certain success metrics in terms of financial outcomes. There’s no one answer of how to explain the value of your organization, but understanding what role it plays, trying to identify ways to capture that value and measure it, and then, most importantly, being able to communicate those results back to your organization in a regular way.


Q: What core success metrics do you recommend using regardless of industry or company?

A: There are some common trends around metrics that a Customer Success organization is focused on. One of them is around – and again, I don’t know whether it’s all post-sale or whether you’re thinking about the CSM – but one is around time to adoption. So, when you bring in new clients, how quickly can you get them using your product in some material and sticky way?

The second is around retention rates. Different companies find different focuses, but it can be net retention or gross retention, which is a focus on keeping the logo in general, and then there could be a focus on expansion. Depending on the roles and responsibilities at your company, your Customer Success or post-sale teams may be fully responsible for some of these, partially responsible, or they may work with other organizations like sales on expansion.

Then, there are some where it’s a little bit harder to measure the attribution, but some type of customer satisfaction or Net Promoter Score™. That can often be an input metric to whether you’re driving retention and growth within your organization.


Q: What size should your Customer Success team be before you hire a Customer Success Operations role?

A: This is an evolving capability in an organization. I’ll go back to the “it depends.” I don’t know that there’s a particular size that matters. I think more about the expertise in an organization. You, as a Customer Success leader, may have a broad range of responsibilities depending on the size of your team. In a smaller organization, maybe you just have a team of direct reports. In a larger organization, you may have a team of managers or a team of directors.

At some point, you might be thinking more around the responsibilities when you start to get to a place where your process improvement becomes a barrier to your growth, or the ability to successfully implement and maintain systems across your organization. Like, putting in place ChurnZero to be able to work with your post-sale organizations. Or maybe there are some data needs where reporting becomes a barrier.

A lot of what happens is that you started a company where you rely on other groups. Maybe you’re relying on your Revenue Ops, Sales Ops, or Data Analytics team and you get to a point where you’re not getting their attention enough and you need focus. That can be a good time to bring in Customer Success Operations. It’s more of a decision of do you need a team or do you need a particular person? When you start to have those needs and you’re not able to get the needs delivered from other parts of your company, then it might be a good time to hire a skillset. But I think that’s an increasingly important and valuable role.


Q: How do you determine the number of accounts that a CSM manages?

A: What you’re looking at is how do you decide when to split up a particular group into multiple people, and what is the right size? Think about the roles and responsibilities on the team. Some inputs to that might be: Are you responsible for onboarding? Are you responsible for the actual contractual retention? Are you responsible for expansion? How frequently does that happen?

For example, companies that have very high retention rates, there might not be a lot of work that the CSM needs to do on a renewal contract. Whereas, if your retention rates are very low, there might need to be a lot of interaction on a high percentage of your deals. There’s no one answer to that. But there are some generalizations about size. I’ve seen data between $2 million and $4 million in terms of portfolio value, but it depends on your product, your segment, and the characteristics.


Q: What key characteristics do you want in a Customer Success leader who is responsible for scaling a team?

A: One of the skills is being able to balance short-term priorities and long-term initiatives. So, this ability to juggle multiple things and change your perspective is important.

The second is being able to work cross-functionally because my belief is that your understanding of what’s happening in the future is going to come out of other organizations. What is your Sales team starting to see in the market? What is your Product team starting to work on? Where does your Finance organization think the company needs to be in the future? I would develop a couple of those key cross-functional relationships.

And then, the third skill is your ability to drive change in the organization that is continuous. There’s no destination; it’s just a journey. So, being able to hire people who have continuous improvement, who are always getting a better mindset, and who are driving change in your organization in a way that helps maintain your company culture and helps you get those outcomes.


Q: How do you advocate to get a Customer Success leader in the C-suite so they can help make more informed decisions about scaling?

A: As a customer-facing leader, you can be developing independent relationships with other functional organizations. It’s possible that you work at a company where peers will only talk with each other. But even if you don’t have representation at the C-level or on the executive staff, there’s no reason that you can’t be building independent relationships with your head of Sales, or with your regional leaders of Sales, or with your head of Product, or with your heads of Finance to understand what needs to happen and to get input on that. I don’t think that’s a barrier. Ideally, you would understand the role that your team needs to play so that whoever you’re reporting up to can be your advocate and you have a mutual understanding of what’s needed and what you need to deliver for that person to be successful. I would think about building out those independent relationships and making sure that your leader, who is representing you, can represent your interests. Then, identify what you need from those peers if you’re not able to drive those changes or get that input directly.


Q: How should you approach internal stakeholders who are resistant to change during a scaling phase?

A: I’m going to highlight that your peer leaders – whether it’s in your post-sale organization or more broadly or whether they could be other cross-functional peers – are key drivers of change. I’ve found a couple of techniques to do that.

One is to meet regularly with key influencers and other functional teams and make sure that both of you understand each other’s objectives. For example, if you’re meeting with a Sales leader, that Sales leader should understand what’s important to you, what your measures of success are, and the types of initiatives that you have in place to help deliver those. You also want to ask the same of those leaders so that you understand what’s important to them. Then, you can build out a mutually beneficial relationship with them. If you selectively find those leaders, even the ones that may be resistant to change, and help them understand what you’re trying to do in your organization – these small number of priorities – and are clear about how their organizations might contribute (what do you need from them?), then you’re going to start to build those relationships. I know that’s really hard in a time where we are not in the same physical spaces. Maybe we haven’t had an offsite in a long time and we’re trying to do this on Zoom. Building those relationships helps with the mutual trust and understanding. Find at least a small number of folks to invest that type of time in, so that you can work together and help overcome those potential barriers or that change resistance.

To learn more about Rod’s Post-Sale SCALING™ Framework, which is comprised of seven key inputs – Structure, Customer Value, Alignment, Leadership, Internal Processes, Network, and Growth Drivers – that need to be aligned for your post-sales team to support growth, watch the webinar now.


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