[Sales Therapy] Ryan Wilson on Building Winning Sales Teams and Strategies

Elen Udovichenko
November 22, 2023
0 min read
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Sales Therapy podcast episode 1

Table of contents

Sales is not everyone's forte, some people actually dread it. But for successful growth, you need to make sure that you master certain skills, and selling is one of them.

In this episode, we talk about how to build winning teams and go-to-market strategies in a changing economic environment.

Meet our guest

Ryan Wilson, the VP of Revenue at Generis, a full-service organizer of world class business summits.

Ryan has over 12 years of experience under his belt in B2B sales, mostly in startups and technology companies. And he has been advising startups on go-to-market strategies at his practice, the GTM Playbook as well.


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If you’re too busy to listen to the whole episode, here is a summary of the conversation with some key highlights for you to skim through 👇

From a closer to the leader in a go-to-market role

Over his 12 years in sales, Ryan has grown from an individual contributor into a department leader to now kind of aligning multiple functions across a business. And what he has learned over that time is that tenacity is probably the number one trait that you need to possess in order to succeed in any go-to-market function.

As an individual contributor, the challenges that you have are going to be based around the pipeline — how do you connect with the correct decision makers and build those relationships within these organizations to actually put an opportunity in Salesforce? 

By the time you're leading a department, your challenges start to become a little more focused on the broad nature of going and talking to customers and looking at how to improve the way that your salespeople engage with your customers. And it really becomes about enablement more than anything else. 

But then by the time you're a VP of Revenue, it starts to become structural and you start looking at how these different departments connect and collaborate. You should still have enablement as a core function. But it's also now about connecting the dots and breaking down silos to operate as one organization. 

As a result, the challenges are always unique, especially as you move up within the organization and take on more responsibility.

Ryan Wilson quote number 1

How to build a winning revenue team?

Getting that customer centricity is one thing, but bringing other people to the team who will have that kind of skill or vision and training them is a whole different story. 

Ryan claims that recruitment and bringing the right people into the team starts with understanding what is your ideal candidate profile, just like we have an ideal customer profile. What are the desired traits and behaviors? What kind of skills do you need to be successful in this role? This starts with understanding who are your most successful people that you have in the organization.

“Once we have those people in for an interview, it's like any other sales process. You’ve got to sell the dream, sell the vision, help them understand what it is that we're working towards. Because fundamentally we're always selling.”

For Ryan, understanding the vision of the organization and being able to articulate how this individual is going to be a key component in it, is what really excites the candidates and what makes them want to be a part of that journey.

There are three attributes that Ryan typically is looking for in high-performers (regardless of function, but specifically for salespeople): 

  1. Being a self-starter. He is looking for people who have a sense of ownership, who are going to go and do the thing without being told to do the thing. 
  2. Coachability. Because every single person, regardless of how good they are in their role, will have setbacks. So being willing to accept and implement feedback is very important. 
  3. Grit, tenacity. Again, there will be setbacks and challenges. Not everybody's going to be a buyer. But the most successful people take setbacks as opportunities. 

Yet, regardless of how good your interviewing process or the people you bring in are, there always might be some sort of misalignment. Ryan finds a solution to that in resetting expectations. 

Ryan Wilson quote number 2

At the same time, if you have an individual that's joined the team and there are performance issues or they're not really grasping the fundamentals, you should sit down with that person and try to understand from their perspective why they're not performing. And then it’s best to go back and reset expectations around what the role is and what you need from that person.

Performance management in revenue teams

Ryan claims that a common pitfall for leaders is to look at people as being interchangeable — if one person didn't work out just get rid of them and hire someone new. But if you hired that person, you hired them for a reason. So you got to at least make an effort to try and help them to get back on track. And if the performance is not there, you have to make a business decision.

“The two things that I don't negotiate on are attitude and effort. If you have a bad attitude or you're not putting in the effort, there's no room for that. But if you have the right attitude, you have the right effort, I'm going to take every effort that I can to help you to get back on track because obviously you're a good culture fit.”

At the same time, cultural differences are certainly a factor. So as a leader, if you want to build a culture and engage in a cultural direction-setting, you have to practice what you preach. You really have to embody it. 

When it comes to things like performance management, according to Ryan, salespeople especially are money motivated. But at the same time, real life happens — there might be different scenarios or significant challenges people have to face. So you have to show a little bit of compassion to your people.

Ryan Wilson quote number 3

Obviously, you have to have performance management as part of the structure. But if you have the type of culture within our organization where you miss one quarter and then you're out, you're gonna lose really quality talent. 

How to enable your team with the right processes and tools?

Whether you’re a first-time sales leader building a team or you're an experienced sales leader trying to figure out how to move the needle for your team, there are three elements that Ryan considers really important from an enablement perspective, both buyer and sales:

  1. Have every single process documented. If there is a correct way of doing something in the business, and there always is, there needs to be a flowchart and a process document which goes into more details about each of the process steps. It needs to be very clear who's doing what, especially when processes intersect across departments. You can do that using tools like Lucidchart or Miro, but somebody has to take ownership of that in your team.
  2. Create central repositories for each of the different teams. So in his previous role, Ryan built out a knowledge base using a tool called Stonly for the sales team. This was a centralized hub where the entire sales organization was able to go and find scripts, talk tracks, comparison sheets, testimonials and reference examples. This also contained the internal playbooks on how to interact with other departments as well as the steps for customer-facing processes. The more information that you give to your salespeople and the better you organize it, the better. 
  3. Build strong reporting. Most VPs and CROs are aware of the importance of having good reporting. It goes without saying that those processes and roles are very data-driven. If you don't have data you're flying the plane without instrumentation. You don't really understand where your team is doing the right things, where they're putting in the right inputs and where they're missing steps in the process that can be transformative to outcomes. 

Yet, what’s good for the leader doesn’t always come easy to people. For example, your reps might be resistant to entering data simply because they don’t see why it’s important. Ryan offers his tactics to make sure that the whole team is up to those objectives:

“If you want to get people to use these CRMs effectively you have to explain what's in it for them. You have to show them how it's accelerating their deals. You have to show them how it's giving you valuable insights as a manager to help them. You also have to show them a way to do it without too much friction. You got to be there to really coach them to understand the process.”

Once you do that, you're reducing the workload for your reps, which means they're more likely to give you what you want.

Ryan Wilson quote number 4

Getting started as a VP of Revenue

As an experienced leader, Ryan shares his recommendations for someone who is just starting a VP of Revenue. 

  1. Remember that the first team that you are responsible and accountable to is your executive leadership — the C-suite, the board of directors. You have to get really dialed in on their objectives to understand how you're going to execute on their strategy. Because in your role, you’re not the one who’s charting the course. That's the responsibility of the CEO and the COO. 
  2. Remember that your people are your greatest asset. It is your responsibility to ensure that you have the right people on the bus to help you to get to the destination. Focus on bringing the right people on board, have faith in your people, empower your people, encourage your people, give them the resources to be successful and they will help you get to where you need to be.

Key takeaways

  • Tenacity is the number one trait that you need to possess in order to succeed in any go-to-market function.
  • Your responsibility as a salesperson, first and foremost, is to help your customers win.
  • Top three attributes of a top-performer are being a self-starter, coachability, and grit.
  • If you want to build a culture as a leader, you have to practice what you preach.
  • To enable your team, you need documented processes, a central knowledge base for each team, and strong reporting.
  • When getting started in the role, remember that you’re accountable to your leadership but also treat people as your greatest asset.


Enjoyed this episode? Subscribe to the Sales Therapy podcast to get notified about the new episodes. 

And make sure to follow Alper and Ryan on LinkedIn for more sales wisdom or simply say hi!

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