Building customer success: How to grow, scale and retain a best-in-class CS org

in collaboration with Natalie Wolf

Building a strong Customer Success (CS) program can be the key to setting oneself apart from the competition in an increasingly competitive landscape for technology vendors. But it is all too often left as an afterthought. The best CS programs should drive early-stage decision making for growing companies. Understanding every stage of the customer journey is how truly dynamic GTM and sales strategies develop, whereas leaving CS at the bottom of the task list leads to teams that apologize for shortcomings rather than informing sales and marketing in a meaningful way. Creating a solid framework for your CS platform as a new startup will not only improve operating success but will lead to fewer growing pains as you scale. 

I myself got a first-hand look at how critical good CS foundations can be when I held the dual role of CIO and VP of Customer Success at Moveworks, where I built the CS function out from three people to a team of 16 that included success managers, implementation engineers and support. Even so, I am by no means an expert. For more insight, I reached out to Natalie Wolf, a seasoned leader who has built Customer Success programs for multiple high-growth companies. 

We first met when I was CIO for Pure Storage and Natalie worked for Anaplan, where she built Customer Success from the ground up. At Anaplan, Natalie successfully oversaw Customer Success as the company grew from 200 employees to over 2,500 while annual revenue increased from $20 million to more than $500M. More recently, she led successful CS teams for Celonis and is now leading Customer Strategy and Operations at Fourkites. In addition, she serves as an advisory board member for the Leeds Business School’s CX Program at CU Boulder. Recently, we sat down to discuss the importance of early-stage customer success frameworks and how best to implement best-in-class CS strategies for B2B tech startups. 

YK: Let’s start at a high level. Why is customer success important, and what does it look like when done right? What are the downsides to getting it wrong?

NW: Customer Success is rooted in genuinely caring about customer goals, their wins, and their outcomes and then matching products to support that success. You want to do this in a way that is both inquisitive and thoughtful, and that supports your role as a trusted advisor.

This is done well when you onboard a customer seamlessly – tell them what is to be expected, understand where they are on their journey and where they want to go, and put timelines and expectations in place. Good CS leaders act as strategic advisors, constantly thinking about value, from pre to post-sale, measuring it to show support, and thinking beyond to help customers achieve their goals. 

The best CS teams have built mutually trusted relationships for the long run, have mastered the skills required of them, push the customer to be their best, and listen well. In addition, the best CS teams are important torch carriers that help keep the customer's goals, vision and ideas at the heart of the organization. This is what customer first is truly all about. 

When it is done poorly, customers don’t know what to expect or when. They don’t know who to talk to for which issues and needs. In addition, it becomes clear through net revenue retention (NRR) that customers really aren’t on the necessary path to realize any value outcomes, which shows up about a year after the effects of this problem begin manifesting throughout the organization.

YK: How should founders be thinking about customer success in the earliest days of their company? 

NW: The relationship and collaborative connection between sales and CS is most critical. Understanding the customer's journey, what the buyer and people using the product experience, and what we should do to best support that effort is paramount. Mapping out the customer journey end to end and then applying the sales and CS motion on top of that is a fundamental first step. This is a company-wide activity. Sales and CS must be in the front seat driving the car together. Doing this early creates shared commitment and fosters an environment of collaboration and innovation. 

Talking to many SaaS companies out there, they have a few common pitfalls. They are losing deals because of the complexity and confusion associated with the products and services they sell. Customers need to know who they should talk to and when. They need to understand what is important and why. Think of your CS team as the solution that makes it easy for your customer to say “yes,” and empower them to do so. Building out that framework, positioning CS and sales as a two-hander, is important to do at the outset. 

YK: What are the most important aspects to consider as you grow and scale your CS organization? 

NW: Initially, the CS team needs to prioritize onboarding, advocacy, and fast turnaround times. As you grow, the main priority should be an investment in the talent you already have, arming them with the right tools to feel like they are achieving success. Many people start at hyper-growth companies and come up through the organization, so we have to find a way to invest in the first-line managers who have never done this before. They need to start to see what “good” looks like through programs like leadership development and coaching. They need clarity around their role and the associated responsibilities and a clear line of sight to success. 

It’s also important to find ways to equip leaders with the skills and insights required to shape the company's future. It allows them to learn how to be a great coach, learn from other people in cohorts and cultivate collaboration and team building. Tech companies are constantly changing, so you must intentionally walk people through the change curve and enlist them in the “why” repeatedly. 

Your focus as a CS leader should be on behavior and values instead of job specifics– you can call out actual job responsibilities prescriptively through the customer journey. 

YK: What does a high-functioning CS org look like? What are the signals that you’re on the right path? 

NW: Measuring, knowing, and acting on customer value outcomes is the clearest sign that you’re doing things right. If you speak about demonstrable value from the top down, this becomes embedded in everything the company does. Sales should be using their CS teams to uniquely show customers the value proposition and how that team is positioned to support them throughout their journey. The customer value must be framed up in sales, committed to in the implementation and realized as they adopt. And this must translate to dollar savings, efficiency or whatever is the highest impact outcome for each individual customer. 

The first step is to ensure thorough discovery and documentation of value outcomes occurs in the pre-sales cycle. This is the first step to really communicating the translatable value that can be used to carry the torch down the road. If the proper expectations, discovery and documentation is not done in the pre-sale, then we are setting up CS for failure.

Measuring the success of the customer's outcomes should really be a collaborative approach with that customer. This alignment is critical to creating the trusted advisor relationship and helps set the tone on what every quarterly business review will be about: keeping the vendor and customer anchored to what they set up to achieve, and driving to it with maniacal focus. You know when CS is done well when your customer calls you for advice, and thinks of you as a coach. 

YK: Let’s talk about employee retention. From the outside, it might seem that having a best-in-class CS org would take care of retention naturally. Is it that simple? If not, how come? 

NW: Much like growing the team, retention has a lot to do with whether or not people feel like they are being set up for success, and that largely comes down to clarity in roles, and responsibilities and making sure key touchpoints are well-defined and understood.  

This is role progression and understanding of growth. Understanding the skills you require by level, and measuring performance, gives people who want to be in CS a realistic picture of what is required and helps those in it know how to grow, learn more, and do more. 

YK: What are some of the most common or avoidable mistakes you see leaders make when it comes to CS? 

NW: There are a couple of areas that companies commonly miss. The most obvious is when CS is trying to make up for a product that cannot meet expectations of what was sold. You don’t want your CS team answering and chasing support tickets or doing the job of other functions as a catch-all for everything else. You really want to empower this team early on so that they can help guide the GTM and sales process.

But the single biggest threat to a successful CS team is a lack of consistent prioritization and goal setting within the larger organization. I have seen so many organizations change their focus month after month, not giving the CS team an understanding of what torch to carry, what is the most important thing they should focus on, and why. You want to get very specific and clarify top priorities for the year. Tenaciously manage the rest of the organization to understand why these are the most critical, rallying everyone around the common goal. 

YK: What final advice would you give to startups or founders building a CS org from scratch?  

NW: I think the strategies and roadmap that we discussed can best be summed up in nine key takeaways. Following each of these points, being careful to ensure you are not missing anything or rushing the process, is fundamental in building a strong CS org:  

• Invest in employee and customer onboarding early to create a unified vision of success.
• Set up your customer relationship management (CRM) team and associated support processes early to manage scale down the road. 
• Think about customer value throughout the entire sales process, keeping the same message consistent and clear throughout the customer journey. 
• Enlist one person or group to focus on the customer experience to build a customer-first mindset, and to work cross-functionally and intentionally to design these experiences as you scale. 
• Build intentional connective tissue between CS and sales to keep focus on the customer experience.
• In hiring and managing CS teams, emphasize behavior and values over job specifics. 
• Continuously over-communicate, and manage people through change repeatedly. 
• Focus on value outcomes first, being a trusted advisor second, and everything else thereafter. 
• Prioritize maniacally, obsess over accountability, and during this economic climate, don’t try to do more with less. Be more intentional, with less.