What’s Cheese Got to Do With Customer Success and Sales?

The trick to seeing through a challenge? Charge ahead with change by using cheese — metaphorically speaking.
Written by Kim Conway
November 19, 2021Updated: November 19, 2021

What’s your cheese?

Provolone, Swiss, Gouda. Perhaps a cheddar — or better yet, a sharp cheddar.

Jessica Sharp, director of customer success at Neighborhoods.com, refers to writer Spencer Johnson’s self-help parable Who Moved My Cheese when she thinks about the challenges that can often arise between customer success and sales teams — especially when leaders consider how to help the differing teams adapt in tandem as a company scales.

However, in this context, Sharp suggests that, instead of being the person whose cheese was moved, customer success and sales leaders should be the ones moving the cheese with intention. “By incorporating people and input at every stage, the team can be part of molding the change instead of reacting and adapting to a decision that may not fit the bill across the board,” Sharp explained.

Change can be difficult, and leaders need to find strategies to keep the experience palatable. Sharp, in particular, values communication as an additional key in the process of managing scaled growth. Keeping those lines open throughout the transition not only benefits the team’s collaborative efforts, but it also adds a level of transparency to a leader’s expectations during a period of growth. 

Built In Chicago sat down with this local tech leader to learn more about the challenges she has faced in her efforts to better align customer success and sales and the strategies she put into practice to navigate them.


Jessica Sharp
Director of Customer Success


What are some strategies you’ve developed to create alignment between your customer success and sales teams?

Be transparent. Sometimes there is a lack of understanding about what is happening behind the curtain, both in process and expectations for each team. We have found that sharing videos, shadowing and opening access to processes helps everyone understand what each group is working on and allows us to collectively achieve goals with the tools and resources available. 

Have open communication. Providing the forum to receive and give feedback, ideas and opportunities keeps everyone better informed and allows us to iterate as individual and collective teams to improve where there’s room. By giving kudos and coaching, we’re able to collaborate better too. 

Use roadmaps. If it isn’t on the list, it isn’t going to get fixed. We are all growing and learning, but if we don’t take opportunities and add them to a roadmap then our words are only as good as air.


Describe the challenges that can arise in this relationship as a company scales, and how your customer success and sales teams have been able to manage them.

In operations, as you scale a business — particularly in customer success or sales — you have to move peoples’ “cheese” so to speak, which can be uncomfortable at times. The best advice I can give is to be very hands on and bring in team members along the way to test ideas. By incorporating people and input at every stage, the team can be part of molding the change instead of reacting and adapting to a decision that may not fit the bill across the board. 

During this process, be mindful and remember to communicate, communicate and communicate again. It’s all about setting the stage for success, and that means making sure everyone knows what to expect and when. This lends itself to alignment, communicative practices and transparency, but it’s not always perfect. Be quick to admit when something isn’t working and pivot if need be.

Be quick to admit when something isn’t working and pivot if need be.”


When customer success and sales teams are aligned at scale, how does it affect the business overall? 

It’s all about conversion. When a machine is working well, the outcome shows positive results, which ultimately drives more revenue for the sales team and business at large. Our goal is to continue work on the machine to improve and expand it so achieving goals is manageable as the organization grows. 

Here at Neighborhoods.com, we recently revamped our quality assurance program within the customer success department. The goal was to uncover additional information to help the sales team without impacting the customer experience — in fact, we wanted to make that better too. This required us to examine pain points and identify areas where we could improve how we interact and handle user inquiries. Since implementing new processes, updating scripts and making sure all appropriate stakeholders were part of every decision, we had a successful rollout and have seen an increased lead conversion rate within our program.


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