December 6, 2023

Sales Mastery: Building Winning Teams and Strategies with Ryan Wilson

In this episode of sales therapy Ryan and Alper delve into how to build winning teams and go-to-market strategies in a changing economy.

Table of contents

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.

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.

Prefer audio format? Listen on Spotify.

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.

The responsibilities and challenges as the VP of Revenue in 2023

In his current role as a VP of Revenue, Ryan is responsible for aligning functions, really focused on execution. So while the strategy and ensuring that they have the right people, and systems, and processes in place to grow the business is certainly a large part of his role, there's also a tactical element to it, ensuring that they are successful with each individual customer. 

“We understand what their success criteria are, so that we can build long-standing relationships and continue to grow those accounts over time. That represents a unique opportunity to get in a little deeper with those folks and build those relationships that stand the test of time.”

As no industry is immune to what's happening in the broader macroeconomic environment, Ryan admitted that their company has encountered budgetary restrictions with their customers, especially on the solution provider side. To overcome those challenges, they focus on their customers’ go-to-market strategy, how they're trying to grow their business in FY24, and find a way to help people to see the value they can offer and how they can help reach their top line goals. 

And just like any other type of sales, whether you're selling cars or you're selling software or you're selling B2B events, it's about “what's in it for me” as the customer. So your goal is to connect the dots for them.

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.”

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. 

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.”

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.

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.
  2. Create central repositories for each of the different teams. 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. If you don't have data you're flying the plane without instrumentation.

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.

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.

Resources

Full episode transcript

Alper Yurder: All right, so in this episode, I'm very happy to be speaking with my friend Ryan, Ryan Wilson. He is the VP of Revenue at Generis Global Partners, and they're an organizer of world-class B2B summits in both North America and Europe. Well, one thing I really like about Ryan is that he's absolutely very generous about his advice. We've had several chats about, you know, challenges that we've been through in our lives, what we like as salespeople and he aims to always create a stellar customer experience and that's what he loves training his teams on as well. We'll talk about that today because 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. Now, Ryan, welcome to Sales Therapy. How are you feeling today?

Ryan Wilson: Thank you all. Thank you all for very happy to be here. Thanks for having me on the show.

Alper Yurder: Fantastic. Before we jump into business and solving problems and challenges, because this sales therapy, we like a little bit of, you know, get to know you a little bit personally as well. A little bit of vulnerability always helps or, you know, things that you would like to share. But generally, this is a nice icebreaker to start with. Who is Ryan? Where did he grow up? What does he do outside of work?

Ryan Wilson: Yeah, well, my name is Ryan Wilson, as you mentioned. I have been in sales for, as Alper mentioned, about 12 years now. I born and raised here in Toronto in the greater Toronto area. And in terms of myself and some of my passions, I'm an avid motorcyclist, I like to travel, really enjoy kind of getting out there and participating in the arts and culture scene here in Toronto. And I think… Really what excited me about the opportunity to be a part of sales therapy was just what we're talking about here in terms of some of the challenges that people face as they grow their organizations. These are universal challenges. I think that everybody in a go-to-market function has to deal with. And I think the more that we can kind of share what we've been through and our unique experiences, the better we can help each other to rise above those challenges because a lot of these problems that we face as leaders within these organizations are not unique. Someone's always been there before. So, happy to come on and talk about some of the things that I've learned in my experience, growing companies and taking them to the next level, scaling them up. And excited for the conversation today and how I can contribute.

Alper Yurder: I love that intro from your side because obviously you know your thing and you're not shy to share them with others But also I would add to that I think sharing the human aspect and psychological aspect of it is also important because we all go through as a closer We go through the stress of not being able to hit Koda as a builder, you know, we lose sleep over certain things. So I think it's nice to make sure that you know, we're all in this together. But at the same time, we're not super humans. So let's start with that maybe, from your past experience. As I said, this is not your first video. You've grown from a closer role into a leader, and now I would say a builder, because you're actually building your team up. You're doing a lot of structuring around it, how to share your wisdom with the rest of your team, et cetera, but you didn't always know everything. Probably not either now. Still working on it. So, and...

Ryan Wilson: Still don't!

Alper Yurder: Coming to this point, I'm sure you have had lots of challenges. Any stories that you would like to share about something that where you felt really challenged or you persevered and thrived, it can be from any role in your career.

Ryan Wilson: Yeah, well, I think challenges are part of the game, right? You know, you mentioned that I've kind of had a variety of experiences having gone from an individual contributor into a department leader to now kind of aligning multiple functions across a business. And what I've 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, you know, the challenges that you have are going to be based around pipeline. It's going to be based around how do I, you know, connect with the correct decision makers? How do I build those relationships within these organizations to actually move the needle and be able to put an opportunity in Salesforce. By the time you're leading a department, your challenges are more around things like ramp time and, you know, ensuring that your reps have the right information at the right time in order to drive their opportunities forward. Your challenges start to become a little more focused on the broad nature of going and talking to customers and looking at how we might be able to improve the way that our salespeople engage or our marketing people engage with our customers or our customer success, you know, folks engage with our customers. And it really becomes about enablement more than anything else. And enablement is something that I'm very passionate about. I think it can be transformative to any organization that really invests in it. But then by the time you're in my current role as a VP of Revenue, now it starts to become structural and we start looking at how these different departments connect and collaborate. We still have enablement as being a core function of that and ensuring that each team has the right resources and the know-how in order to be successful in their individual roles. But it's also now about connecting the dots and making sure that the left hand knows what the right hand's doing and that you're breaking down silos to operate as one organization. So the challenges I would say are always unique, especially as you kind of move up within the organization and take on more responsibility. But I would say one of my favorite challenges is always kind of understanding the customer experience. And this is something that I've come to be really passionate about because everything starts and ends with customers. And so, you know, whether you're an individual contributor and you're looking at how a customer is engaging with you from that first kind of cold call or cold email that you've sent and understanding what made them convert to actually have that conversation with you, to get on a call and complete a discovery. I think that's something that, you know, is a challenge unto itself. And then as you kind of take on more responsibility, that it starts being, well, why do our most successful customers, why do they buy? What is it about our overall experience? What is it about? How we deliver our product that really excites them?

Alper Yurder: Yeah, yeah, you already started talking about your current challenges there. Can you tell us a little bit about what is the role of the VP of Revenue? And you just joined the business fewer than three months ago, if I'm not mistaken.

Ryan Wilson: Yeah, I'm still new to Generis, but I'm no stranger to this business. Actually, I got my start with the co-founders about 12 years ago in a very similar business to this one. And I left that role to get into tech and I spent the last decade working in technology and loved that experience. Obviously, the tech world is in many ways where it's at, but also tech has its share of challenges through, again, what I would call a bit of a contraction in 2023 with a lot of layoffs and, you know, funding availability became more restricted, you know, capital crunch, if you will. So I think it just represented an opportunity for me to kind of take a step back and think about what I really enjoy doing. That is working, you know, in office with a team, you know, helping to grow the business and the opportunity to get in with the co-founders here at Generis was one that former mentors of mine, amazing leaders in their own right. I learned a lot, you know, back when I was an individual contributor of my first B2B sales role from these guys. So I have nothing but respect for them. And I also really respect what we do as a business in terms of connecting, you know, these senior executives that come out as delegates to our events with solution providers, right? Who are oftentimes software companies or services providers or consultancies that are really trying to be more effective in their business development efforts. So in my current role as a VP of revenue, I'm really responsible for aligning functions, really focused on execution. So what that means is, while there's certainly a large part of my role, which is based in strategy and ensuring that we have the right people and systems and processes in place in order to be able to grow the business, because we just opened up an office in Berlin, we're gonna be expanding that presence as well. There's also definitely a tactical element to it, ensuring that we are successful with each individual customer. We understand what their success criteria are, so that we can build long-standing relationships and continue to grow those accounts over time. Because we do work with some of the biggest names in the world. Fortune 50 companies are our customers. That represents a unique opportunity to get in a little deeper with those folks and build those relationships that stand the test of time.

Alper Yurder: Yes, especially early days, you have a little bit “the luxury” of getting to know them before you're being chased by numbers, et cetera. Speaking of numbers, I'm thinking you mentioned the scrutiny. I would say that I'm a very frugal founder myself, and I see a lot more people coming into, unfortunately, my side of being very conscious about their spend. Does that somehow affect your industry, like our deals now taking longer to close, more difficult to close, more stakeholders, any of those becoming your reality in your day to day?

Ryan Wilson: Yeah, I would say that no industry is immune from what's happening in the broader macroeconomic environment. We're no different. You know, I think the way that we try and position it with our customers though, is that fundamentally, you have to spend money to make money in every industry. And what we do as a business is about connecting the dots, bringing people together so that you can accelerate your business development and sales efforts. So while we certainly encounter those same budgetary restrictions with our customers, especially on the solution provider side, where they're saying, hey, you know, I'm not sure if I can get the budget to be able to come out and invest tens of thousands of dollars to come to one of these summits or events. Fundamentally, it's about understanding their go-to-market strategy. It's about understanding how they're trying to grow their business in FY24, and about helping them to understand how making those connections on site, seeing people face to face is going to be effective in helping them to reach their top line goals, right? So certainly we're not immune, but I think that there's definitely a way that we frame it, which helps people to see the value. And just like any other type of sales, I don't care whether you're selling cars or you're selling software or you're selling B2B events, it's about what's in it for me as the customer. And if you can connect the dots for them, if you can show them how you're getting them from, you know, A which is where they're at today where they're experiencing a lot of pain, whenever that pain is to B, which is, you know, that ideal state where they're going to reach their goals, they're going to be effective and they're going to look like superstars for their boss and then showing how your product or services the vehicle to get you from A to B. I mean, it's the same sales process, no matter what you're selling.

Alper Yurder: Yeah, I think events is actually sometimes a little bit overlooked in certain industries. I used to be in, you know, training sales or HR tech or property technology. There were certain events where you definitely had to be because they were kind of no brainers. I guess now being in the business, your mindset to events might have changed, but somebody approaching events with a bit of a… like what are the key benefits they get from it? Like I already have in my mind one or two that comes to mind. Either you're upstart and you're looking for awareness or you're actually among 1,000 high intent prospects where you can actually reach them and start a connection with them because your sales cycle is long. There's so many benefits. So how do you change people's perception of if they need your product or not?

Ryan Wilson: Yeah, it's a good question. So I would say, again, it starts from understanding what are their goals, right? It doesn't, what's the saying? Nobody cares how much you know until they know how much you care, right? So I like to start every conversation with my customers around, you know, what is it that you're trying to accomplish in the next 12 months? What are the overall goals of the business, right? Because my responsibility as a salesperson, first and foremost, is to help my customers win. Right? So if I don't understand what you care about, how am I supposed to cater my offering towards you? So step one is understanding what is your strategy? What are your goals? How would you know if you were successful 12 months from now in achieving those goals? Once we understand what their goals are, then it's about ensuring that we're connecting them with the right audience. So, you know, the value that we offer as a company is that we have a very focused group of attendees at our business summits. So everybody that comes out to our summits is director level or above. So these are very senior decision makers, very senior executives from household names, companies like Kraft Heinz, Boeing, Kimberly Clark, very, very well recognized and known organizations. I was just at our American Automotive Summit this past week in Detroit. We had folks from GM, Ford, Stellantis, On-Site, Volvo. And I think when you are… Let's use software as an example, because we both come from a software background. I imagine probably a lot of people who are going to be watching this are in software and technology. The hardest part of selling in today's modern environment, if you're a software company, is that your prospects are being inundated with communication and correspondence from all the different sales tools out there like Outreach, like SalesLoft. They're just getting bombarded with emails, right? They're getting bombarded with cold calls. So how do you cut through all of that noise, right? Well, the goal I think for every salesperson is to get in front of these prospects and to have some face time with them. And look, having some time virtually to connect with people is great, but nothing beats face to face, right? Nothing beats actually going out to a customer site and being able to have that face time with them, being able to sit down and be across a table from someone and just get to know them and have that rapport and see the micro expressions and understand the broader team and see their site, see their facility. So while we can't bring you as a vendor or a solution provider to their actual site, we can put you in a room with these people and then give you an opportunity to have 10 of these one-to-one conversations with all of your target prospects in a very accelerated timetable. So after two days, you've got 10 new opportunities that you can follow up on with decision makers who you've had a very clear conversation around their challenges, their objectives, and how we're going to be able to add value as a solution provider to your business in the next 12 months. And it's just really connecting with buyers that are already in the consideration phase of their buyer's journey. These are people who are not only pain or problem aware, but they're also solution aware. And now they're in that stage of trying to find the right vendor or solution provider to work with. When you can cut your sales cycle in half, that obviously has tremendous value from a pipeline perspective. And that's what we do as a business. And that's why I was excited to get back into it because there are a lot of customers that we work with day in, day out who have really seen tremendous value, multiple thousands of percentages worth of ROI from attending our summits. And I think when we think about, especially in the technology space, the value of getting face-to-face with customers, nothing will ever beat face-to-face interactions. I don't care how good you are doing Zoom calls, face-to-face is the best.

Alper Yurder: Yeah, well, you clearly know your customer and what they're expecting. You have that customer centricity. You're able to empathize and put yourself in their shoes. But how do you bring other people to your team who will have that kind of skill or vision and how do you train them? Like, how do you approach that?

Ryan Wilson: Yeah, well, I think when we're thinking about recruitment and about bringing the right people into the team, it starts with understanding who is, what is your ideal, just like we have an ideal customer profile. I always start with what's our ideal candidate profile? What are the traits? What are the behaviors? What are the skills that we need for someone to be successful in this role? So when I'm working with our recruitment team, it's about understanding who are our most successful people that we have in the organization. What do we see as being attributes for those individuals? And how can we ensure that we're looking for those attributes in our talent pipeline? And then once we have those people in for an interview, it's like any other sales process, right? Like you 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, right? Especially during recruitment, because if we can't position the value that we bring for our customers, if we're not excited about the opportunity and the career prospects and the value that we're going to be able to bring to this individual, why should they be excited, right? So really understanding what the vision is for the organization, how you intend to grow the business, being able to articulate how this individual is going to be a key component in that transformation, I think is what really excites candidates and what makes them want to be a part of that journey.

Alper Yurder: Yeah, absolutely. And I would imagine that, you know, for you to be selling something where you need to build relations and there's an awareness phase, etc., they have to have a certain skill set around, you know, maybe being like an advisor because it's not really high velocity, like two emails and, you know, we close a low ticket deal, etc. So do you have your three or four skills that you absolutely must-have in certain candidates like, for example, for me I always tell anybody who knows me knows that I like the biggest deal breaker for me is ownership a sense of ownership for me is and I have my own ways to try and test it like do you have your own this person has this or that.

Ryan Wilson: Yeah, ownership is important, right? Like you have to be accountable and take ownership of your outcomes, right? So I would agree with you on that one, 1000% Alper. I am looking for people who take ownership of their lives, who take ownership of, you know, how they're going to pursue their career objectives. I would say, and people have asked me this question before, so I'm gonna come back to the same answer that I've given before. There's really three attributes that I look for in high performers, regardless of function but definitely for salespeople, right? The first one is being a self-starter, right? I want people who, again, going back to this concept of ownership, who are going to go and do the thing without being told to do the thing, right? And that applies if you're in marketing, that applies if you're in CS, that applies if you're in any function within the business, production, operations, doesn't matter. You gotta be willing to start doing the work without being told to do it, right? That's really important. I want a self-starter. The second thing that I look for is coachability. I think that every single person, regardless of how good you are in your role, you're going to have setbacks. You're going to have challenges, right? And you're not going to do everything at 100% out of the gate. So being willing to accept feedback, being willing to implement feedback, those are very important to me. I try and tell everybody on my team that feedback is a gift, right? Whether it's coming from our customers, whether it's coming from our loved ones, whether it's coming from our managers. When people give you feedback, so long as it's constructive, they wanna help you, right? But...

Alper Yurder: Yeah, it's just a shortcut. Take it and apply, basically.

Ryan Wilson: Exactly, but the folks who don't take that feedback, those are the ones who struggle. And then they wonder why they're struggling. Well, it's because you're not taking it. You're not implementing it. Right. I seek feedback all the time. I talk to our CEO, I talk to our COO, I talk to my team members, I talk to my managers. And I believe feedback is a two-way street. I ask them, what do you think I'm doing well? What do you think I can work on? It doesn't always mean when you're taking feedback from folks that report to you, that you're going to implement 100% of that feedback. Right. But at least understanding people's perceptions is valuable. Even if you don't necessarily agree with it or you don't think that it's founded, well-founded, you gotta know the perceptions. And so coachability, I think, is important. And then the third one is grit, tenacity. Just this, especially in sales, you're gonna encounter, like I said, setbacks. You're gonna encounter challenges. Not everybody's going to be a buyer. But the most successful people take opportunities, take setbacks as opportunities, right? It's this, I have a lot of sayings, but one of my favorite sayings is, sometimes you win and sometimes you learn, right? And so if you encounter a no, do a little bit of an after action analysis on that, try and figure out why it was a no. Where did we lose that opportunity? Where did we go wrong? And I think if you understand that, you're gonna be that much more prepared for the next opportunity that comes down the pipeline because you're gonna be preempting that no or understanding what could cause you to go in that direction. So yeah, I would say just to summarize, like I said, being a self-starter, taking initiative, coachability and grit are probably the three attributes that are most important to me.

Alper Yurder: I think I really learned from my co-founder, Adam, he's really good at, he's a product guy and he takes feedback as data. It's just that, oh well, okay, this didn't get the reaction we want, it's just data. Let's learn and move on. I don't think it's very easy when you're in sales, especially when you're a junior and you're handling rejection. So maybe before you learn, take a day of grief or have a drink or meditate, whatever it takes you out of that mind state, but then afterward, learn from it. And I remember, you know, very early in my sales career, my manager, he was the founder, and he came into the room one day and he said, you know what, I have some news for you. You won't like it. Apparently, I had pissed off a client very, very absolutely while I was thinking that I wasn't. And we'll talk about that too. And then he said, you won't like this, but take it as a learning, you know. I know you will feel like terrible today.

Ryan Wilson: Who hasn't at least once?

Alper Yurder: But tomorrow is another day. And it was just so sweet of them. You know, we learn from those. Do you have any of those like? Actually, I wanted to ask you a real-life experience of this. It's all good. We have the skills we want in the people we bring in, etc. But what happens when the people that would bring in somehow there's misalignment between the two parties? Like, how do you handle that?

Ryan Wilson: Exactly. Yeah, well, I think it's going back and resetting expectations, right? I think it's really important when you're interviewing people to set expectations of what the role is, what some of the challenges are in the role and make sure that they're going into it with open eyes. I don't think you should oversell positions. I think that you should really be careful to, you know, tell them about the opportunities and hype it up as best you can, but don't oversell it. Also let them know about some of the challenges and make sure that they're going into it. Expecting that it's not going to be, you know, a bed of roses, there are going to be some thorns and they got to be willing to work through that, right? But if we have an individual that's joined the team and there are, you know, performance issues or perhaps, you know, they're not really grasping the fundamentals, I'm going to sit down with that person. I'm going to ensure that I understand from their perspective why they feel like they're not performing. And then I'm gonna go back and we're gonna reset expectations around what the role is and what we need from that person. I'm not a big fan of traditional performance management methods, but they do have a place in every organization. Nobody likes to put people on performance improvement plans, but fundamentally, if they're being done with the right intentions, which is to get the person back on track first and foremost. I'm not a big fan of using performance improvement plans to get people out. I think performance improvement plans should be based around achievable objectives, achievable metrics that are going to help people to get back on track in their role. I think as leaders too often we look at our people as being interchangeable and saying, oh well you know this person didn't work out let's just get rid of them and we'll hire someone new. Well, people are still people at the end of the day. And if you hired that person, you hired them for a reason. There was obviously something redeeming that you saw in that person. So you got to at least make an effort to try and help them to get back on track. And then look, if the performance is not there, it is what it is. You have to make a business decision. But the two things that I don't negotiate on, um, are attitude and effort, right? 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, I'm going to make every effort that I can to help you to get back on track because obviously you're a good culture fit. And so there's obviously something that's happening behind the scenes. Yeah, there's something happening behind the scenes. It could be a personal issue. It could be that their dog died. It could be that they got a family member that's sick. It could be that they broke up with their partner. Could be a million different things. We still have to be human beings at the end of the day and be sensitive to that and try and help our people wherever we can.

Alper Yurder: No. Rolls are lying. I'm sorry. Do you think those attitudes towards, let's say, being a little bit more understanding versus cutthroat, hard culture, you either perform or not, do you think culture or geography has a share in that, like shaping that culture? To be very specific, like for example, we're in the UK, we're based in the UK but our team is a global team and everybody comes with different attitudes. At the end of the day, we try to share the same values as you aptly call, like around performance, motivation, et cetera. But different people pursue different things in different ways. And Canadians are notoriously known for being nice and kind and et cetera, versus in the US sometimes the culture is a bit more cutthroat. You either make it or you're out. Do you feel like there's a role of culture and geography in those decisions?

Ryan Wilson: Believe me, we have those types of companies here in Canada too. Not everything is sunshine and rainbows north of the border. And I actually think that's a bit of a misconception about Canadians. We have this reputation as being very kind and polite. Canadians are not really kind, but they are polite, right? Like we're very, we know how to say things in a way that is not super direct, but it's cold up here, man, and that tends to freeze people's hearts to a certain extent, right? So there's certainly no shortage of organizations here that have a cutthroat attitude. But look, I would say that cultural differences are certainly a factor. I would say it's up to us as leaders if we want to build a culture and engage in cultural direction setting, we have to practice what we preach, right? We really have to embody it. It starts at the top. If the CEO of the company embodying those values, then how is anybody else supposed to? The VPs can't change the culture if the CEO is not on board. You know what I'm saying? Really, I think it's incumbent upon the C-suite, it's incumbent upon the executive leadership to set the tone for what is and is not acceptable in the organization. When it comes to things like performance management, look, we're in business to make money. We're in sales to make money. Obviously, salespeople especially are coin-operated, which is great. You should be, you should be money-motivated. But at the same time, like real life happens, you know? And there's a saying that my parents imbued in me, which is, you know, life is what happens when you're busy making other plans, right? So if we can't be cognizant of that, if we're going to have the type of culture within our organization where, you know, you miss one quarter and then you're out you're gonna lose really quality talent that way, right? So I've always thought about thinking about relationships on the aggregate, thinking about the contributions of individuals. Obviously, you have to have performance management, as I've said, as part of the structure, but you gotta work with people, especially if they've contributed in a big way in the past. Like you gotta give people a little bit of leeway when there are significant challenges in their own life. Because when you show a little bit of compassion to your people, and I've had this happen. Like I've had team members that have, you know, had a family member that passed away unexpectedly. I've had team members that went through a really rough breakup with someone that they've been with for, you know, five-plus years. I've had team members that had a sick parent and that needed to take some time off work. When those scenarios come up, they're watching to see how you respond to that. And not only is that individual watching to see how you respond to it, the rest of the team is too. And if you lead with compassion, if you lead with empathy, people will love you for it. They'll give you back that love and support and their energy and their commitment in spades, right? And so I would rather, you know, make an error one out of 10 times in giving someone, you know, a little bit of a longer leash or a little bit more compassion that maybe didn't deserve it and have the other nine people be really grateful for me and sing my praises and work, wanna work for me for the longterm then just cut everyone loose and then lose out on a lot of quality people that otherwise could have done big things for my team. You know what I'm saying?

Alper Yurder: Yeah, we're going to be going out there and looking for those people again anyway. Yeah. Unfortunately, when the economy

Ryan Wilson: Exactly.

Alper Yurder: Outside factors kind of push you into that box of being very cutthroat and like either you're in or out. I think we lose sight of that. So I think it's a good reminder. Um, to, to wrap up the section, you mentioned that very much top of mind for you is building that playbook and creating that enablement structure. I think we've, we've talked about a lot of psychological and motivational enablement. How about the tools and strategies that you implement to create that concept of enablement in-house. And I know that you're very, uh, keen on, you know, diagnosing different power enablement tools, et cetera, which, which are quite effective for your line of business too. What would be your recommendations?

Ryan Wilson: Yeah, and Flowla has obviously got some pretty cool tools for buyer enablement and sales enablement more broadly. So a little plug there for you guys. But no, I would say, look, if you are a first, if you're a first-time sales leader or you're even an experienced sales leader and you're trying to figure out how to move the needle for your team or your marketing leader or CS leader, ultimately you have to get a couple of things right. The first one is that you have to have every single process documented, right? If there is a correct way of doing something in the business, and there always is, there needs to be a flow chart for it. There needs to be a process document that sits alongside the flow chart, 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. If you don't have a flow chart for every process in the business, you gotta start right away and get that documented. There's great tools like Lucidchart and Miro that make this a breeze, but somebody's got to take ownership of that in your team, because if you don't have that, how do you know when things are done correctly? And how do you diagnose problems in your workflows if you don't understand what the process is, what the workflow is. So step one, process documentation. Step two, creating central repositories for each of the different teams. So in my previous role, we built out a knowledge base using a tool called stonely.com for the sales team. This was like a centralized hub where the entire sales organization was able to go and find scripts. They were able to find talk tracks around different elements of our platform. They were able to find, you know, comparison sheets, battle cards as other organizations would call them that were customer-facing that they could then send out to customers to clearly articulate how our solution differed from some of the other players out there in the market. We had all sorts of testimonials and reference examples where we could bring customers to a website that was using our software to show them how that software was integrated. We had all kinds of information in there about as well how our team would interact with other departments and what the steps were you know, when a customer signed up, how are they gonna move through the onboarding phase? What are the service levels for each of the teams in onboarding and support? You know, the more information that you give to your salespeople and the better you organize it, especially when it comes to things like handling common objections and what the pre-approved rebuttals are for those, if you don't have a central repository for all of these things, your team is flying blind, right? They're essentially trying to fly the plane without an owner's manual, right? Without any instrumentation. So you have to get the organization piece right and create that centralized repository for this information. It doesn't have to be with Stoneley. You can do it on G Drive, right? I'm, you know, or any other type of internal drive, but there's gotta be a place where people can go and find what it is that they're looking for in order to do their job more effectively. And then I would say the third piece is having very strong reporting, right? So I think most VPs, CROs are aware of the importance of having good reporting. It goes without saying our process and our roles are very data-driven. But I don't think that frontline managers appreciate it enough about the importance of data, about the importance of availability of data, about having those reports and dashboards set up, whether you're using Salesforce or HubSpot or any other CRM. If you don't have data, again, 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. So I would say those are kind of the three elements that are really important from an enablement perspective, both buyer and sales.

Alper Yurder: Excellent. I think data is very important. Everybody's talking about it. But when I think about almost forcing reps to enter data, which kind of, you know, doesn't flow very naturally with people, like how do you make it something that is easy to do, but also at the same time shows value, like you have to show the value, what's in it for them. It's good for the leader. They're going to do what you're, what you know, you are doing as a rep, but what's in it for me, that's, do you have any tactics to make sure that you know the whole team is up to those objectives.

Ryan Wilson: Yeah. That's the biggest challenge, right? I mean, what's the saying? Salesforce is not really built for reps. It's built for managers. It's built for VPs and CROs to know what's going on in the pipeline. Look, that's always gonna be a challenge, right? I don't know any town executive or frontline salesperson who's like, oh man, I love going into Salesforce and updating my deals and updating my close dates and adding contact roles and all that kind of stuff. So I think… If you want to get people to use these CRMs effectively, like you said, you got to explain what's in it for them. You got to show them how it's accelerating their deals. You got to show them how it's giving you valuable insights as a manager to help them, right? You also have to show them, you also have to show them a way to do it without too much friction, right? You got to be there to really coach them to understand the process, right? Like, especially using Salesforce, like, okay, you set up a lead, and then after you set up a lead, when you convert it, well, don't worry, it's gonna create an account, it's gonna create a contact, it's gonna create an opportunity, it's gonna save you three steps, right? Because if I'm a sales rep who's never used Salesforce before, maybe I think that I have to create an account, create a contact, create an opportunity manually, whereas if I just started with a lead, I can create all three immediately when I convert it. Oh, okay, now it doesn't seem so arduous. It doesn't seem so onerous for me to get in and start using Salesforce as long as I understand the order of operations and how to do it correctly, right? And then the other piece I think is as leaders, especially if you've got a Salesforce admin, you have to be looking at how do I make this process simple? Right, like what steps can I remove? How can I boil this down to the minimum requirements of inputs? So that it's not so difficult for my salespeople to give me the data that I want because I'm not asking them for 1800 different things. The opportunity record, the contact record, the account record, they should be as simple to fill out as possible and only give you the data that you actually require. And then once you've done that, you're reducing the workload for your reps, which means they're more likely to give you what you want. But I always think of my role as being, I am responsible for helping my team to get value out of this, which means I need to help them to do their jobs effectively and not give them a bunch of busy work. You know what I'm saying?

Alper Yurder: Yeah. So you do your job as a leader first and then expect people to do their job, like make their jobs easier in the first place. Excellent. Well, this was a great chat. So moving on to the final section of the conversation, this is where we go into three rapid fire questions. So I'm going to ask you three recommendations, very specific, and I'm going to ask you to be under a minute or two max on those. So these will be as a leader, as a closer, and as a Canadian, okay? Ready?

Ryan Wilson: Shoot. Sure. Go.

Alper Yurder: Excellent. So first one as a leader, what pieces of recommendation would you have for someone who is just starting a VP of revenue role? Maybe their first time being in that leadership position. Like, how should they plan their next six months? What should they be conscious of?

Ryan Wilson: Yeah, so if it's your first time in a VP role, you gotta remember that the first team that you are responsible and accountable to is your executive leadership, right? The C-suite, the board of directors. Those are the first team. You have to get really dialed in on their objectives in order to understand how you're going to execute on their strategy. Because at the end of the day, in my role, I'm not the one who sets the entire strategy, right? I have some ideas about things that we can do to execute on the strategy of the business, but I'm not the one that's kind of charting the course. That's the responsibility of the CEO and the COO. So remember that you are accountable to your first team and everything that you do has to be in lockstep with your C-suite. Beyond that, 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, right? 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.

Alper Yurder: Excellent and if you're watching only this short clip then you should go back into the podcast where Ryan shares some really valuable insights on Skills you should be looking for in your talent Next question as a closer. So what challenges did you face and overcome as a closer? What advice would you give to your team who closes complex deals?

Ryan Wilson: Yeah, so always start with what's in it for them. I would say that's the most important thing to understand. When you're working complex deals, you need to understand the goals, objectives, responsibilities of every stakeholder. If you're working on an enterprise deal, there's a lot of people who have a stake in the outcome of this project. So understanding what operations cares about, understanding what the compliance team cares about, understanding what the sales team cares about, the marketing team, anybody who has a dog in that fight, anybody who cares about the outcome of that project. You have to understand what their priorities are and how this project is going to affect them, what their success criteria are going to be on the project. Never rely on one individual champion to get the deal done for you. I would say one of the biggest challenges that I had when I was first making the transition at Enterprise Sales was I would rely too much on one person to help me navigate the organization and help me to get, you know, the understanding of what their peers cared about. What I changed in my process that helped me to be far more effective was I started asking who gets involved in the decision? Who are the players, right? And then I would get their contact information and I'd reach out to them directly, introduce myself, say I'm working with John and your operations team. You mentioned that you'd be involved in this project. I wanted to reach out to you personally and understand what's going on in your world and how if we are gonna work together, how can I make sure that you're hugely successful? And that was absolutely transformative in working on the large enterprise opportunities.

Alper Yurder: So the A in BANT Authority and MEDDPICC criteria still hold to this day and something to add from my side is one of the five reasons why winnable deals don't close is a lack of multi-threading. And three months down the line somebody pops out of nowhere and your deal slips. So don't let that happen. Don't be that person. And the final question is, as a Canadian, we alluded to this briefly, but I will say… How do you think the sales process should be adapted in different regions for success, especially now you're looking for a global expansion, entering into different geographics, etc.? Is the working culture different in all those regions that you face? And how are you planning to preempt some cultural issues, or how will you adapt to those cultural differences?

Ryan Wilson: Yeah, so I think sales processes fundamentally should follow a similar structure regardless of where you are in the world. They're called best practices for a reason, right? So understanding who the stakeholders are, understanding the buying criteria or decision criteria, understanding the success criteria with deployment, understanding the cost structure and how it affects your customer. All of these things are going to be consistent regardless of where you are in the world. But I think there is absolutely a difference in how buyers behave, depending on what region of the world that you're selling into. If anybody tells you that Canadians and Americans buy the same, they're wrong, right? That's just not true. Same thing with how folks in the UK buy or folks in the APAC region buy or folks in the Middle East. Buyers and buyer behavior is always going to be different. Thinking about the Canadian and American example, when I think about selling into the US, there usually does tend to be one decision maker who can actually get the deal done for you as the final, let's say, signing authority in the US. And if you get to that decision maker, you can absolutely accelerate your deals, 100%. In Canada, it tends to be more of decision by committee. So understanding that nuance is very important when you're selling into different markets because you wanna understand how deals are typically done. Now, is that to say that 100% of Canadian companies don't have a command and control structure where the CEO makes all the calls? No, absolutely not. But if you understand what the overarching tendency is in terms of decision-making process in that region, you will be far ahead of your peers who are treating every opportunity, especially if they're calling into multiple countries, the exact same way, right? So understand the buying culture, understand the decision-making process in your region, and you'll be light years ahead of your competition.

Alper Yurder: I think the key is empathy and being biocentric again. Like we go back to it. It's about them, it's not about you. Wonderful. So thank you very much for that, Ryan. Now, as any good therapist, I have to cut us on the clock because we are just on time. If people wanna find you, where's the best place for them to reach out, LinkedIn or somewhere else, what should they do?

Ryan Wilson: Yeah, you can find me on LinkedIn, linkedin.com/in/ryanwil. And yeah, happy to connect, happy to talk shop about anything sales, revenue, marketing growth, really passionate about that stuff and always looking to expand my network.

Alper Yurder: Now that's a wrap on this episode of Sales Therapy. If you enjoy the show, subscribe to us on YouTube and on your favorite podcast platform. I'm your host, Alper Jurder, and thank you for listening. Bye bye.

Ryan Wilson: Thanks, Alper.

Alper Yurder: Thanks, Ryan.

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