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Podcast Recap: Sales Leader Explains The Relationship Between Sales & Customer Success

Updated: Jan 31

The relationship between Sales and Customer Success isn’t ideal––and this may be an understatement.

So when I saw that Justin Welsh, one of the top Sales professionals on LinkedIn, joined Jeff Breunsbach and Jay Nathan on their podcast, I knew it had to recap it!

The details

In this post, we are recapping an episode from the Gain Grow & Retain podcast with Justin Welsh, a Sales advisor and executive mentor in the SMB SaaS space.

What’s great about Justin is that he doesn’t have this perfect story of succeeding at Sales from the start. At the beginning of the podcast, he admits that early on, he failed in Sales. He got fired 3x and never hit his quotas. After moving to Zocdoc, things changed for him and he learned the meaning of hustle. He then took that over to Patient Pop where he became VP of Sales and helped grow the company from $0 to $50M in just 4 years. 

The Gain Grow Retain Podcast focuses on sharing conversations about growing and scaling subscription businesses with a customer-first approach. Jay and Jeff are also the founders of Customer Imperative, a consulting firm that helps companies scale their revenue growth in a customer-centric way.

So let’s get into these three takeaways:

  1. Having one continuous conversation

  2. Defining objective customer fit

  3. Effortless transitions between customer-facing teams 

Having one continuous conversation

In some companies, it’s common to see Sales, Implementation, and a Customer Success team. And to Justin, all of these are way more alike than we think.

The best way these teams can work together is when they have one continuous conversation. He uses Patient Pop as an example, for a physician customer, when they’re having a conversation with someone in Sales then moves to Implementation and then goes to Customer Success, they want to feel as though they’re talking to one person. These conversations should flow and to do that, all three teams should be talking about the same value points. When this doesn’t happen that’s when things fall apart.

How can we achieve one continuous conversation?

This isn’t something that can be led tactfully, it’s something that needs to start with a strategy. But this strategy shouldn’t be defined by a specific team like Sales or Marketing, it comes from the CEO.

The power of the CEO setting this strategy is that they can provide the why behind the software, the product & the services we’re providing to the customer. When the responsibility falls on a specific team, it’s common to see a discrepancy between the “right way” to talk to customers between the teams. The CEO should say what’s the mission/vision of the company, how do we talk to our customers, and what’s our value proposition. Once we have this, it needs to be adopted across all teams.

To have this one continuous conversation, it’s really critical that everyone understands each other’s job. Marketing has to understand what Sales is doing, Sales needs to understand why Marketing is choosing to target the lead they’re marketing to. When it comes to an Implementation Manager, they need to understand the anxiety and struggle the Salesperson went through. And the list goes on… It’s like a family. Everyone needs to understand the roles they’re all playing.

One of the most under appreciated things in the Customer Success world, says Jay, is that we don’t fully understand how hard it is to get a dollar through the door.

Justin says it’s really important to have that appreciation and respect for each other. There are misconceptions and miscommunication within all teams. You may hear the Head of Product say, “once we do X, it’s going to be easy, customers will line up at the door.” But in many cases, the product doesn’t sell itself. These sorts of comments all fall on the CEO.

It’s giving the right vision/mission values and then compensating people accordingly. He’s seen places that give Sales all the money, meanwhile, Marketing and Customer Success don’t get much. In today’s world––which is no longer growing at any cost–– it’s about strong growth margins, expansion revenue, and increasing your install base…Customer Success is crucial. Justin, a Sales professional, goes on to make the argument that right now, Customer Success is the most important part of pre-sales and post-sales and he’s always believed that.

To add, in 2-5 years Justin sees a big shift in compensation for these teams. CSM and post-sales folks will see an increase in compensation and closing salespeople will see a decrease. He sees things stabilizing as people start recognizing that not one of those pre-sales roles drives the valuation of the business. “You could go out and make a bunch of sales and they all churn, if they’re not taken care of, it doesn’t matter, your business is not highly valued. If you open the door well, close the door well, take care of your customers, sell back into your install base, and increase your expansion revenue, increase LTV… that’s a valuable business.”

Defining Objective Customer-Fit 

Was the customer an actual fit? Fit can’t be subjective!

When Justin takes on a new client today, he asks them “who do you sell to and why?” and if there are 7 different answers, it’s a recipe for disaster. It’s best to have objective customer-fit that’s been determined by the stakeholders across the organization.

Here are the stakeholders and the input they provide:

Product – this is how the product is designed to work and this is who gets to take advantage of the product. This is who uses the product effectively and here’s who doesn’t (based on data).

Sales – Who does this message resonate with/who listens to us when we speak?

Marketing – who is raising their head and opting in?

CS – who are the lowest value/highest pain customers and who should we not be servicing based on interactions we’re having?

These stakeholders need to discuss these points to define objective customer-fit and accountability. He gives an example of what that may look like: “The right customer has ABCD so if we sell and the customer only has AB and not CD then it’s on Sales. But if the customer has ABCD but Implementation doesn’t show up to implement and they churn, then that’s on the Implementation team.” Everyone has to be crystal clear, land in the sand, accountable for meeting those criteria.

Testing new market segments

Instead of approaching new market segments with ad hoc strategies, Justin recommends creating assumptions/hypotheses and going through the exercise of defining customer-fit with stakeholders. What’s wrong is saying “I have a hunch” and then onboarding 100 customers to then realize you can’t meet their needs.

Once the criteria are defined, it’s best to bring on 5 customers to test out the new market. You can do this by bringing them on at freemium/low cost and agreeing with them on expectations (they’re beta customers and will be providing feedback on an ongoing basis).  

Effortless transitions between customer-facing teams 

If you take an Account Executive, they know what information they need to close the deal. They need to know the challenges, the competitors, what the customer has spent money on, etc.

At the end of closing the deal, they have a collection of info they then add to Salesforce and they push that over to the Implementation Manager. It’s messy and also the Implementation Manager needs to decipher what happened during the Sale.

Instead, Justin says that there needs to be a process in place. The Implementation Manager outlines the six things they need to know to have an excellent conversation with customers and to guide them through the implementation process effectively. By defining very rigidly what those things are, this can then be built into the Sales process so that Sales is asking the questions that Implementation needs answers to.

Implementation then needs to do the same for Customer Success and the list goes on. To Justin, it’s about being educated and learning what the next person needs from you for them to do their job and teach/train them. 

Who implements the process? 

When just receiving a pile of notes for Customer Success is an improvement, that’s disappointing. Tactically, department leaders need to come together to build a process around what’s needed from each department.  If you try to bully another department into doing something you want, it doesn’t work. Part of being on the leadership team is knowing that you have to work closely with other department leaders. People that are new to leadership often get confused about what team they’re on. Just because they run the Customer Success team doesn’t mean they are on the Customer Success team. They are on the leadership team. It’s all about the top-down culture. 


  1. Having one continuous conversation for customer-facing teams falls on the CEO

  2. Defining customer-fit needs to be defined by stakeholders across the organization––it’s not a team specific job

  3. If you lead CS, you’re not on the CS team, you’re on the leadership team. It’s your job to work with other department leaders to create/implement processes.

Shout outs

Thanks to Gain Grow Retain for hosting Justin on their podcast! You can go follow them on LinkedIn. And if you want to hear more from Justin, follow him on LinkedIn.


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