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The Revenue Operations Blog

Energy in Sales, Evan Santa

December 15, 2021

The Interview

Kluster's Take

Theo spoke with Evan Santa, VP of Sales at Commerce Bear. He explains his fascinating approach to Leadership.

Evan began his sales career working for TouchBistro, before moving to Vidyard. He is now the VP of Sales at Commerce Bear. Evan places responsibility on leadership to create high-performing individuals and teams. The first group of hires define the culture of the company.

He tells the incredible story of hiring his barista to his sales organisation. Evan was inspired by his energy and passion. He believes you need to bring this energy into every interaction in sales. There’s nothing wrong with being competitive, if you stay compassionate.


If you can figure out the answer to this question of how do we find an A-player, it becomes so easy to scale teams. And the reason being is that when you go to hire your next cohort and your cohort, after that, they literally look at the reps who are there today and go, okay, that's who I need to be.

That's the framework.

Evan welcomes the cluster community blog. I'm super excited for this discussion on upskilling reps. But first of all, I'd like to start off with a bit about you. So Evan, what is your story in sales up until this point? Yeah. Thanks bill. I appreciate it very much. Great to be here and, and on with you. Um, Essentially, I got into software a little bit later in my career, as a lot of young professionals are now starting like right out of school into software is a little different for me.

Um, but when I identified it, I wanted to make that switch a big change in my life. And I essentially got my start at a company called touch-base Joe. Um, we were about 30 employees at the time. And in 24 months, I saw it grow from 34 employees to hiring into the 200 employee mark. Uh, from there I had great opportunity to build out a business development team, essentially from the ground up, I hired and trained, trained.

I believe it was over 20 reps. Um, if my memory serves me correctly, then that takes me to a company called  to where, uh, video enablement saw. Uh, B2B full addressable market, really, really exciting company and product. And from there, I essentially had the opportunity to build out yet, again, another team from the ground up, which was essentially taking the company downmarket.

So, um, we started selling into SMS. Organizations that typically vid yard wasn't spending time selling to previously, uh, we've created a very, very successful program in reducing the, the sales cycle greatly almost by, by 60, 70%, as well as increasing the close rates on historical business. Quite significantly from that.

After building that team. The big question that I've been answering over the last 1218 months is why did I leave that as we've grown? Because we went, I went from myself and another rep beside me to, uh, you know, uh, um, uh, a global team where I was managing a team in EMEA, as well as two teams in north America.

And why did you leave? And essentially I had the great opportunity to join. And conduct fair right now is a vertical SAS company specifically focused on, on assisting our ICP with selling their products, home goods, furniture, essentially on channels like Wayfair, overstock, Amazon, and all arrests. And as we know, in 2020 with the, um, with the global pandemic, Buyer behavior, online buyer behavior increased so wildly, significantly, and it's not going away.

So right now, as an organization, I've got a very small site sales team, and it's going to be the third one to date that I've grown from zero to a hundred. And I'm just looking to take what I've done before. Apply it to a totally different vertical and essentially grow the sales org 60. Awesome. Um, so let's, let's move on.

You mentioned that you build a, you build a team of a TouchBistro of, of, of many reps. So you've worked with many reps throughout your career. So like in your eyes, let's start off with what the fines in a player, maybe let's start with characteristics and then move into to some metrics there as well.

Sure. And I think that's the question that everybody's been trying to figure out in my, in my entire tenure. Um, so coming up on 10 years in, in, in, in software sales, Everybody's asking that question. And it gets asked before every hiring cycle it gets asked before every job description has opened up. It gets asked to every leader as to whether or not in every interview.

When you're sitting on that side of the table, you know, how do you identify an, a player? Um, It leads me to a story of when I started hiring for the first time in my career sales reps, business development reps at touch-base Joe. And I was going through interview after interview, after interview of all these individuals with resumes that were cookie cutter, some of them MBA, some of them experienced for years and they just came to the interviews and fell flat.

Now, at that point in my career, I knew that this was a make or break moment for me. If I built a rockstar team at this company, my career would take. So when I knew that the first hire was the most important because, and I, and I've proven this theory out. Time and time again, that when you build a team from the ground out, your first core group of hires literally define the culture and how the, this team is going to define itself around accountability and execution.

So if you can figure out that, the answer to this question, Theo of, of, of how do we find enable. It becomes so easy to scale teams. And the reason being is that when you go to hiring your next cohort and your cohort, after that, they literally look at the reps who are there today and go, okay, that's who I need to be.

That's the framework. So going back to touch base, Joe interviewing everybody with cookie cutter interviews, and I knew I needed to knock it out of the park. I ended up hiring an individual who worked at the coffee shop across from the street of barista. And the reason I did is one simple thing is that I would show up to the office at that.

At that time I'd be showing up at about 7:00 AM. I get off my bike, downtown Toronto, lock it up. And he would see me from across the street. And as I walked in through the door of the coffee shop, he would go. Hey, Evan, I got your coffee here. How's your morning going energy. And meanwhile, I have that beautiful conversation start my day and he impacted my mood from there.

I go across the street and a guy or gal walks in with again, fantastic, powerful resume. And I sit down in the interview room Mo moments later after that interaction. So 7 38 o'clock person's like wipe and sleep out of their eyes. They're tired. How's it going? Oh, that one's good. It's okay. It's okay. Okay.

Maybe they're five minutes late. And that to me was a huge indicating moment of going. I went blood literally after that interview went across the street and said to the, this guy who had been doing this so consistently every single day. Got your Americano. I haven't, I've got your Americana. How's your day.

How's your day. And I essentially said to him, I want you to come across the street. Talk to me about a job. The guy became an absolute monster and here's the deal. Software sales is not difficult. The entire industry wants to say that it's extremely difficult. It's not, it's having the internal personality and drive to want to wake up earlier than everyone else and provide other people that experience and bring that energy to every interaction of your day.

And I literally just trained. How did what software was, what we were selling, what the value was and how to talk to, instead of selling coffee, how to sell software and his, his career essentially took off as well. That's so interesting. I love that story by the way. And I think, I imagine you still come into contact with people who, like you said, I liked that expression, the cookie cutter, you know, CV, like it's perfect.

Um, but in reality, like you said, I mean, sales. In many ways, quite simple. It's a, it's a human thing, isn't it? Um, you don't need to have, you know, a fantastic MBA or these sorts of things. It's about, can you kind of speak to people on a level and listen, but that's the key. So on that individual who you hired that day, how important was he for the culture of the business?

Like setting a standard? Did you notice when people then joined, they followed suit and they had the similar sorts of kind of passion and. So as soon as I went to hire, and it's so funny, you say that we're going to go back to that, how important he was to the culture. And for everybody listening, this was not set up because, and I'll give you the punchline.

Now. He actually became the head of culture for that organization, not just for sales, but for the entire org. And I can't remember if the title was head of culture, but he was the only hire that was hired for culture. Anybody who got hired at that organization had to go through his training platform first.

So kudos to him. Um, but back to the early days I brought them in trained them and him and I side-by-side on the phones. He's learning from me. I'm learning from him and we're going from there, hire the next two people. And again, they came in and saw how quickly he moved. They saw how he talked. They saw so as I'm training these new reps on what we're doing and how we're doing it, I'd sit them right next to him and fun fact.

Every time I build teams, whenever I hire somebody new, I actually strategically sit them next to somebody back when we were in office. It's a little different now, but I used to strategically sit them next to people where I was like, I think that their personalities don't mesh. Furthermore, I always like to place reps very closely where somebody might have.

A really, really great ability at building business from an LVN perspective, but they struggle sometimes on closing where then I have a great closer who struggles a little bit on the outbound side of things. You sit those people together and think beautiful things happen. As long as those individuals are driven for their own success.

Fantastic. And you, you mentioned there's something so like. And what personalities tend to ramp quickly. I mean, you always want that, that ramp to be, you know, the, the golden one is, is three months. However people can do it in, in, you know, sick people take sometimes six months. Some people take two months, it all, it all varies what personality you're looking for for, for a quick and straight, straight for.

Over the last 12 months, I've really identified to myself that to be, especially now that we're digital, now that we're digital, I can't put you in a room and kind of like force you to pick up the phone. Cause everybody else's. I used to be able to do that. Now you need, it's not an, I hate the term self-starter because it's just too generic.

Like we've, we've we've overused. We've it's just, we've beat that dead horse. So. Competition like anybody with a competitive background. And I think that the thing is, is a few years back in tech sales, a competitive, like say. Somebody who is innately competitive, kinda got tied into bro culture. And it was kind of like a bad thing.

And we didn't really want to say it. But the thing is, is people who are competitive. Like we're talking about Olympians, we're talking about like, like, like team players who, although they're so competitive. I saw the Boston marathon, two people in the lead car, you know, gave up their lead position to be able to carry some guy who was, who was faint across the finish line.

There's nothing wrong with being competitive, as long as your competitor. But a competitive somebody with a background of being competitive is so important in this digital world now, because they might meet with me in the morning just to get the day started. And then I might not see them all day and they need to be a self-starter who understands that this opportunity and they're in front of their laptop is literally, could literally be game changing for the next number of years of their lives to propel their career to where they want to go.

And if they can't identify that. You're never going to be able to motivate them. And I always say that to reps that I bring on teams, there will be times when they feel motivated by me, but don't look to me to get motivated because I just simply won't be able to do that because as the team scales and all of a sudden I've got 20 reps under my umbrella.

I only have so much time and I'm only one person. So you have to look to motivate yourself. Fantastic. You mentioned this and it's something that really resonates with me. You know, how COVID has affected your leadership style. So like how, how do you find that you've had to change your leadership style?

Because of the current way of life, not seeing people's eyes, not, not, you know, going into the office and looking people in the eyes and go like you. Okay. And then now you're doing it over zoom. How have you found that you personally have had to adapt and overcome. Yeah. I've had a lot of conversations with, with my network on this, my very close network and one, one individual, a very good friend of mine.

Uh he's head of sales, operations. That actually, I should introduce them to you for another one of these. He'd be okay. Or, yeah. Um, he said to me, he's like, what he's noticing is that the impact is there. It's just slow. And I think I was, I focused so much on speed when I was in office. So, you know, prior to the, prior to this digital first, um, work workforce that we find ourselves in and evolving towards, I was really, it was all about speed time, you know, time to revenue.

So let's onboard as quick as we can. It's going to be uncomfortable for the reps, but it's okay. Cause I'm sitting next to you and you have somebody else sitting next to you and you're going to sit next to one of the best salespeople on the team. For two days and just watch what they do. Listen to the ask questions that's gone now.

Now it's Hey, watch these asynchronous videos we're going to meet. And the biggest thing that I found Theo is I used to push a lot of tools and strategies onto my team. These are tools that I've proven out, increased conversion rates, increase close rates, things like video like VR. But what I found is that.

Now that we are in a digital digital world, you can't just push those on people anymore. I used to be very successful in doing that Theo. You've never used video this morning. I need to show you how to use it. And then you start using it this afternoon. And once you start seeing, I know it's going to be uncomfortable.

What Theo, once you start seeing the, the response that you get from an outbound prospecting perspective. You're just going to fly with it. And it was like a formula that it worked every time. Now you can't do that. Now you have to let reps take a little bit more time, give them a little bit more breathing room for them to come to you and say, Evan, I want to do that.

So it's kind of changed me to, to be, um, and it's something that I keep check on. Cause I've really, I spent a lot of sleepless nights going, am I gonna put myself at risk and put my people at risk because of me looking at these things this way. But I think we just need to give people more space to, to adopt things.

And again, if they are that competitive motivated individual, they will come to you and say, I want to be part of this. I see how so-and-so is having success with that. So I'm no longer taking strategies or tools and just blanketing across the team. Now I'm giving it to those that are inspired to do it, helping them with it, and then PR you know, letting a little bit more of an organic adoption happen.

That's that's interesting. So do you find those who literally just throw themselves into this, this crazy world of sassy? And the ones that tend to rise to the top, because they're just willing to try anything. Like, you know, sales is one of those ones where it's constantly challenging. You need to do something.

Nobody likes to pick up a phone and call somebody that they've never met before, you know, halfway across the world and try to sell to them. It's not easy. Do you find that the real great, great reps? The ones like day one, I'm going to do this and I'm going to try my best to do this, and I'm going to fail 100 times, but I'm going to, I'm going to be okay once.

And that's all that. I think this is the biggest, this is the biggest egg to crack. Okay. It always said, and you just said it to you. Nobody likes to pick up the phone. If you have that mindset as a sales person, you shouldn't enter this business. And some people are going to hear that and go, wow, this guy's a.

But here's the deal. You look at professional athletes, you look at 'em, you look at EMS people working on the front lines in healthcare, especially over the past couple of years. If you don't have some type of love and desire for what you do, even though it is. You're in the wrong business. And, and again, you know, shout out to all the, all the emergency services, workers and healthcare over the past couple of years, probably the most difficult thing we could fathom that anybody in an occupation did over the last 18, 24 months.

But those individuals, you can't, they won't survive. If they wake up every day going, I don't want to do this. And we did see a lot of them quit. And, and, and again, my heart goes out to all those individuals. It's strange to compare sales to that. So let's not get it, you know, say that this is wrong or like I'm not trying to be insensitive.

I'm just saying for a sales person, it's hard to pick up the phone, but they've got to spend the time to adopt it into what they do. And then learn to love it much like those crazy people who go running and run 10 K every morning and the icy weather, but that's how they do. And that's how they do their lights.

That's a lifestyle choice. Whereas if I did it, I wouldn't be able to be on this conversation today. And. I'd be laying down on the floor, but I think that that's the biggest thing. I think that AEs need to, or account executive salespeople, especially in tech sales, digital first, if you don't enjoy, if it's hard, that's okay.

But if you can't get to a point of actually enjoying the hard work, um, you won't, you won't get to the level that you're hoping you will. Fantastic. Now you've mentioned that, you know, constantly pushing, pushing the envelope as they say, and pushing standards. Right? So in your rise, how difficult is it for reps themselves and you as leaders as well to bridge that gap between a sea level rep a B level rep and a knee level rep, is that C2 way possible?

Is that B2B possible? And even is that a. All possible. And I think that leaders should be held more accountable for reps that are a D player rep that are coming in early, making the activities. Like I've never given up on a rep who is not who's struggling, but he's putting in more work than everybody else in the team, because that to me is the leaders face.

I've had reps where they're a D player and they don't show up everybody they're showing up two hours later than everybody else. Like that is something that we cannot coach. But if you have a rep, that's shown up as D player and they just don't have it. A lot of leaders will move that individual from the organization saying they just don't have it.

They don't have it. The higher leaders should be looking at that leader saying maybe you don't have it because they showed up. They had that competitiveness. They have that grit. They're doing more phone calls and activities than anyone else, which means they want to do. So are you the best coach to be coaching that are the people who are representing our company on the front lines?

Um, it's all possible. Again, what's not possible is to take a B player rep and make them an, a player when they don't want to be. They'll say they want to be feel, but there's a difference between saying you want to be better and actually identifying steps to get there and then executing on those sets.

That's so interesting that you mentioned that, like, you know, if there's a deep player who's turning up early and putting in the work, then you should look at leadership. If you're not becoming a CP and so on, because I've actually found this myself, you know, in, in many things, talent, talent does exist, right?

Like intelligence, you know, athletic ability. But with sales, I was thinking the other day I was, I was speaking to colleagues like. It was probably one of the only kind of professions where talent that it doesn't exist. You don't, you're not born born a talented sales man or woman, you know, you're just not, um, so it's super interesting in like, W when it comes to sales, it's, it's hard work, dedication and consistency that really gets you to, to the extra extra level.

Um, but I always ask this, this question is about every sales you don't speak to. And it's always an interesting one. You know, how often does an A-player really come about in your eyes? And it's all the, all the kind of depends on how you define when, of course, but how often does one come around? You don't get a plan as you make a players.

Nice. No. And a lot of people think I get people I'm hiring. I'm giving you a lot of money. So I need you to deliver you. Don't find a players, you make them, you coach them into A-players and I'm steadfast on that. And I've seen individuals with much lesser of a resume surpassed. Those that have been a players because innate the biggest thing with the name players, that if they're told that they're a name player, you see this in pro sports.

Right. The best of the best, the best, all of a sudden young rookie comes in and replaces them on the starting lineup. So I don't believe that you, that you get people, I believe you develop people. And I think that that's also to the most important job as a sales leader. And if you can do that, you become very valuable as a sales leader, whether you miss target this quarter or not, they go, holy smokes, look at the growth, the caliber of people we're bringing in and how we're educating them.

And that's also one of the biggest things that will help you with talent retention. Because he is, don't leave a company because they don't like selling the product or they don't like, um, the organization or they're not getting paid enough. They leave because they're not getting, they're not getting leveled up by the person who is literally they report into whose job that is not to motivate them, but to level them up.

So as you say, Everyone can have an AI play a month. Can't they? Um, the hardest thing in sales is, is consistency. You know, you look at, if you liken it to basketball, there's plenty of people have kids teasing, but you know, there's only a handful who were like LeBron James, Michael Jordan, Kobe Bryant. Right.

So are you saying that like, uh, as a, as an A-player consistency is, is one of the, it kind of goes on smart and final question for you here. Like top three characteristics of an A-player is cause consistency up there as. The absolute, you know, the most important concert stick, would you say? Absolutely. I think, I think I'll, I think consistency.

I, I had a rep one time in my past, and if he watches this he'll know who he is, he was struggling to close. He was struggling to open. He was struggling to, to be as conversationally, intelligent as he is today. On these calls and you just fall fire with fire. And all he did was he put in more time, he booked more meetings.

He had a lesser close rate, but he ended up top of the board because, because he just simply had more at bats. And the thing is, is I think that this, again, we will over romanticize software sales and everybody wants to talk about closing the big deal and like, look what, like, you know, look what I did two years ago.

The thing is, is that. If you go in and work in this individual's case, well, more pipeline have more bats than everyone else. All of a sudden you're closing more revenue than everyone else in the best part is with that amount of at-bats you actually start to level up your ability to close and two and two.

And then all of a sudden this guy, this went over, everybody, um, came a leader of a team of his peers. And again, to your point, it's consistency, um, yeah. Uh, yeah, and, and it's just, it's being able to do it month over month, but you also have to break that down into week over week and day over day an hour over hour because for a sales rep, I always break it down with new ways to say you have 21 days in month, like calendar, business, calendar days give or take 21 days.

You've got. And then you break it all the way down, teach to how many, to how many hours you have to, how many meetings you need in order to hit the target. And the thing is, is the one last part I'll put on that and we can move to the next question. Theo is I've always coached leaders. When I brought in, you know, I had to bring a leader up and then I'm managing a manager.

I've always said your biggest, your biggest focus is helping reps on their recovery time and what that is. When reps are fairly new to the game, or even maybe they're not there, just haven't learned this yet. And you hear a no after a big deal, sometimes that can defeat a rep's confidence and momentum for an entire week.

Well, they just lost 25% of their. Productions window. They're beat up about it. They're still talking about it on Thursday. When it happened on Monday, the best thing you can do for a rap as a sales leader and as a coach is to help them with the recovery time. And when reps start getting really good, they'll hear no.

And, and then they'll, there'll be upset. There's a lot of passionate, of course. They'll seek to understand why they're not where the note came from. They'll do a bit of a post post-mortem in their head as to what they could have done different. They go for a coffee and they come back and then go get the next one within an hour.

And that's w that's like the true A-player mentality is like, I've only got 21 days, so I ain't letting you take, I ain't letting this situation take four of them. That's fantastic. Yeah. The way you put that is, is so true and it's, uh, I really enjoy that. That's a great one. If we move on to the last question now, uh, top three characteristics, um, we've got consistency in there.

What would be your other two that you would tell any of the aspiring high-performance rep, but they need to develop, um, characteristics to be successful or the characteristics that make you successful. And make you successful at say, so somebody comes into a org. What characters do they need to make them successful?

Yes. Yes. Again, I, again, I'm really big and this is new for me, but I'm really big on the competitive side. Um, I think what was the one that you said consistency. Consistency. Yeah, I think it's this disease there, but it needs to be developed. I think the. I think the last one is, is just coachability. Yeah. I think, I think the will like, and when I say coachability, I mean the willingness to do things, the, where I've seen reps become very successful very quickly versus not is you need to try everything and you need to lean into it full tilt.

Yeah. If you're seeing somebody on your team using video and I keep going back to video, cause it's just something I have a lot of experience with, with, with my sales teams, as well as sales teams that I sold those products to. If you have somebody on your team, who's absolutely crushing it. They're making it look easy.

Okay. And let's never confuse that with they're not working hard. Actually the most talented people in this business will make it look easy. And they're using video and you go to them and you talk to them as another AA. And you say, what is, what's your secret sauce? Well, first of all, there's a million things, but if you start to understand, it's something like he's like he, or she's going, I'm using video from my proposals and my follow-ups when they see it, I'm like, and furthermore, it's given like this personal touch for me to get garnished a response.

A lot of AEs will just go back to their desk or back to their own digital world, their environment, and go, and they won't do anything with that. The best reps out there, we'll go grab those little nuggets of information. And then that afternoon, that day it starts sending 50 videos to, and I'm using videos as an example, but, or like that talk track or whatever it is like when you pick out these nuggets of information from people.

Other people who are very successful or have a lot of experience in the space, it's what you do with it. And I think that that is one of the biggest things. So I get let's wrap that into coachability, but that's one of the biggest, biggest differentiators between somebody who's wildly successful in a 12 month time period to now.