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How technology can help recruit and retain a happy Sales Team

Barry: Tell us about your background and experience at Qualia and Scott Leese Consulting

JM: So over the years, I’ve done all types of sales roles from management to SDR management, always in the background doing the process and come to the realization years later that that is what I love doing. I love doing process, and I like to be as efficient as possible so we can drive the right insights. So I got the pleasure of working at such a great company, like Qualia, where we were doing a lot of cool things and just getting started and disrupting an industry.

We got to test a lot of different things and to help make sure that we could drive those types of insights to get to a point where the employees were happy, they liked their process, they liked their tool stack, and it made sense it wasn’t going into 20 different places to do one thing. It was how do we keep the flow as good as possible because when they didn’t, I will tell you, you know that they’re not happy. And so keeping them as happy as possible so they can focus on what they do best.

Barry: Okay. Awesome. I love that your job is the unofficial chief of happy officer for sales.

JM: As cheesy as that is but yes. That’s what I feel. I know that it’s important to keep AEs happy. Everyone wants to be happy in what they do. No one goes into a job saying, or maybe some people do, but I don’t think that’s very fun. So how do we make sure that people can focus on what they do best and to drive whatever role that they’re in? But especially here when we’re talking about sales, how they make sure that they can drive as much as possible and focus on managing their pipeline to drive and close as much revenue.

Barry: That’s great. And I’m assuming, or I’m positive, that a good sales ops person or a good rev ops person is effective and brings happiness to their sales team. Sometimes unnoticed, sometimes it’s not some sales reps, at least from what I’ve seen, don’t recognize it, but they are happier even if they don’t publicly recognize it or if they don’t even understand how different it is and how much better. But has that ever happened to you personally?

JM: Yeah. That’s a hundred percent. It’s a little bit of a thankless job. But what I would say to my team was we know we’re doing a really good job when we don’t have a ton of cases, and we don’t have a bunch of people doing this, and we’re proactively getting feedback as opposed to people just offering up tons of different things. Because salespeople are commission-based, it’s important that you can be as efficient as possible for them to focus. And they’re not doing all these activities that don’t contribute to the bottom line. And so it’s fun to do. And once you realize that piece of the process was not good, we then got to rewind here, keep an eye and a pulse on that, and keep that connection to the team too, so that they feel comfortable giving you the feedback and making sure that they’re doing their best.

Working with Different Sales Styles

Barry: Absolutely. To piggyback on that and this is just me thinking out loud with you, some salespeople act differently than other salespeople, so how do you manage, how do you evaluate how happy they are? Let’s say one person is what we call ‘old school’ versus like some of the ‘new school’ sales reps that work a certain way. And then some sales reps work a certain way that may be less efficient, but more their style. What’s your experience been working with the different types of sales reps? 

JM: There are a couple of main things. The first thing is specificity and clarity. You can’t have a good process if you don’t have those two things. Make sure that it’s as clear as possible to all those different people. If I have this new school way of doing something versus an old school. What are the commonalities still? Because sales are still sales at the end of the day. So how do we make that as easy as possible and clear to both sides? And then from there it’s getting the feedback and watching them do it. I’m so big on talking about the why behind it, why we’re doing certain processes in certain ways, and making sure that it resonates. And if someone doesn’t believe in it and understand the why then that’s on me.

So constantly asking people, especially as I’m doing training, I will ask: what’s that metric and why is it important? Okay and then what does that do? And what’s the outcome of that. I’m calling on people where maybe it’s not comfortable for them, but I have no problem with it. And so making sure that I’m constantly asking people in these group settings, individual settings, and to make everything becomes one and the same. Then getting that feedback, and they feel comfortable in the safe space to do it.

Sales Processes Benefit the Rep and the Team

Barry: I actually love that “calling out” methodology. Have you started doing that now at the consulting company or even before when you were still at Qualia?

JM: Both. I feel like I’ve always done it. “Calling out” can have a bad connotation. I’ll put it in quotes too, but it’s basically making sure, especially in this remote world, that people aren’t falling asleep. Ops are not exciting. Let’s be honest. It’s not the most exciting thing to learn. People don’t wake up in the morning and say, “Yay, I get to have an ops training!” So how do I make that as beneficial as possible and keep people awake, keep them engaged, and make sure that they understand the why? Because otherwise, if people don’t understand the why and how it relates to their bottom line, then it doesn’t matter. It’s not going to be done and it’s not going to be done accurately.

And if your data’s not accurate, then it doesn’t matter. You might as well throw it out and they can’t get the insights either. So then it’s also showing them that you are using it and that the process does work and that this is how much time they’re saving. And where there’s a lot of sales involved, it’s important to constantly point out that this is the process, this is why, this is how it’s benefiting you, and this is how much time you save this month. Or this is an insider. This is something that marketing did differently because of it. Make sure that you’re constantly showing those. And then if there aren’t any, then that’s probably not good. And that tells you that you probably should make an adjustment.

Barry: I love that. I’m thinking what would be super cool is if there was like an ROI playbook calculator for sales operations that shows this is how to prioritize, and when you get to this, this is exactly what you’ll show your team and this is the amount of time you have this many sales reps and then this is how much time they’re saving with this thing on average.

JM: Definitely. I remember one time we did something and we were showing our work because we were trying to get a different tool and we found that we’re spending hundreds of hours on running commissions at the end of every month or something like that. So you look at it and when you actually put pen to paper, it’s usually shocking to people how much time people spend on one task. You time them, go on zoom and you tell them, I want to see how you work, share your screen with me. And you’re timing them and it’s shocking. And it’s really not good. How do we trim that? Because if you’re doing 300 accounts and you’re spending an extra three minutes on each of them, that’s hours and hours, hundreds of hours a year that you’re spending on one thing.

Barry: And probably a boring thing if it’s 3 minutes

JM: I like ops. I think it’s exciting when you have a good process, but I don’t think that a lot of people would say the same thing.

How the Sales Tech Stack Influences Sales Employee Retention

Barry: Important, specifically, a three-minute thing that you have to do to those 300 different accounts. So this is a great segue into the topic of the importance of the sales tech stack to sales employee retention. It seems that you have a lot on this, so I’ll let you get started where you think it makes sense to get started.

JM: I like to do the same thing of going to the why. So first, how do I clearly define what is a happy employee? I guess I’d ask you, what do you think makes a happy employee?

Barry: Okay I like this. The “calling out” is here. Everyone listening can see.

JM: Now everyone can see.

Barry: Happy employee. These are off the top of my head. I think it starts with salary as the foundation. Am I getting paid fairly? Am I able to maintain the life I want at home at this job? I think that’s one part where usually ops have less connection to.

The next thing is and these again are mine from our product marketing, but I’m sure there’s some overlap with sales. Next, is the work that I’m doing being retained by other people? Are people using the assets I’m creating? Is the work I’m doing helpful for others? I’m sure as a person, you can relate to that. A lot that you do, all these processes, you create case studies, for example, you create all these things that enable your sales team. Is it actually being adopted? That’s something that even though it really doesn’t matter. I created the output. It shouldn’t matter, but it does matter and does show my happiness.

And then another thing for me is, and again, it’s not things offensive to ops, I don’t think, but I don’t like boring, repetitive tasks. So getting rid of boring, repetitive tasks that could be automated. That is something that I like when things are automated when they can be.

And have the coworkers, a good boss who I’m able to collaborate with and able to be with a team that wants to grow together versus like push each other down.

JM: No, I think those are spot on. And you said a couple of things that stood out to me. So you mentioned that the salary isn’t necessarily something that ops can control, but we can show how are people hitting commission and how we help people hit their commissions faster and more often. And so that does tie into it. With a bad process, it’s going to be way more difficult to sell because you don’t know that if I do this action, where do I go to do the next action? Or if I’m doing this action, and I’m trying to put an example would be, there might be a status on a contact and an account, and there’s an opportunity and then a task status.

And if people have to write these things down every single time, that’s probably a pain in the butt. And so similar to what you said which is nobody likes to do busy work. You want to again, focus on the thing that you’d love doing and be able to clearly problem-solve with your teammates. And you can’t do that if you don’t have a clear process that’s easy to follow. And so how do you make sure that you’re automating that? How do you automate where you can? How do you make sure that if it could be a one-click world that would be the ideal? Obviously, that’s not possible. However, how do you get to that? How do you go every single month look at your list of fields and say, all right, which one’s automated, which one’s manual?

And every month you could probably delete fields. You could probably go through it and say, all right, so I’m going to delete these fields. And then I’m looking at this and thinking why is that not automated? So constantly challenging yourself and thinking of new ways. And if you don’t think of it, it’s looking at your team, that’s where that great team comes into play. I don’t know. I know some, but there’s a lot I don’t know. And people think of really great solutions. So being super open and sometimes being open means, you might get feedback that the whole thing is terrible and that you need to start from scratch. So not being emotionally tied to the process either.

I used to do this work and put together this process, and then someone would say that it is awful. Or I’d look at a rep and say, this is awful. And of course, they will think, I just spent 40 hours on that. But it doesn’t matter because it’s not good and it’s better that it’s good. And that the person enjoys it and because everyone’s going to be happier down the line. Again, what makes people happy is that they can hit their goals and focus on things in the best way possible. And that’s where again, that process and tooling, but the process with the tooling becomes so important.

And that then ties into, how do you make somebody efficient? How do I define efficiency? What does it mean to me? How often should you look at it? So having a process to evaluate your process is also a really important part so that you’re constantly changing too. And it’s not just like, well I built this great process a year ago. It’s how do I just make sure that I’m constantly looking at it and making tweaks here and there. Obviously not tweaking every single month, but how do I make sure that I’m removing any roadblocks and duplicative efforts?

Barry: Absolutely. I love that. I have a few questions that I’m going to ask, but let’s save this for later. Because it’ll be too much of a tangent, but I’m curious how you balance being shown as a leader like that confidence versus learning from people. Because you mentioned that you want to ask the sales reps for their opinions, but then if you ask them in a certain way, then they might think, oh this person doesn’t know what they’re talking about, etc. I want to put that on the side. I just want to say it so I don’t forget. I guess we could start thinking about it.

JM: We can tackle that one.

Barry: All right, let’s tackle that one.

RevOps Leadership Skills

JM: That’s a good question. I mean that’s definitely a key one. You need your salespeople or if you’re rev ops, you need the teams to feel confident that you know what you’re doing and you understand, but also that you’re going to take feedback in, and you’re doing research on your own too, to make sure that you have this best in class operational excellence in your org. And so there are a few things that I’ve found have been super helpful in doing that.

One is just integrating yourself and being a part of the team. What that might look like is running some of the sales meetings. As in, I would run a sales meeting just like some of the other managers. The first thing is that they know that you understand sales or they know that you understand marketing better than anybody because you can kind of walk in their shoes, so that’s part of it.

The second piece is thinking of these new processes, explaining, and setting the expectation that the feedback is going to be so that we can make sure we have the best version. Here’s the V1 and we’re going to make some tweaks. It’s not, “Hey, help me build this process from, soup to nuts.” It’s “Hey, l have something. This is what I think is best. Here’s why I think it’s best. This is how it’s going to benefit you. And tying it back to, their pain or their revenues just like sales. This is going to help you sell more and sell faster. If you made this one tweak. Imagine if you could set one more demo a week from that you think you could set, close one more deal a month from that.”

And making sure that you have that loop in there, and then you just get that feedback as opposed to, just saying, “Hey, let’s do this together.” Unless you know that there are some people that are good at that. And you say, “What do you think about this?” But it wouldn’t be like, “All right, tell me how you build this process” because then you’re going to have 20 different opinions on how to build a process. And that actually makes your job way harder.

So I like to say that this is what I think is best and own the confidence. I think before, I was not super confident in what I did. It was, it makes a big difference in that leader piece. And so be really confident because you have the knowledge. I’m constantly seeking out communities and listening to podcasts all the time. Maybe reading books on things, talking to different people on different roles, and then also integrating myself and the team. That’ll help establish you and build that confidence too in your leadership ability.

Giving Your Sales Reps a Reason to Stay

Barry: I absolutely agree with that. Your own confidence shows when you speak. I’m glad we took a pause to answer that. So companies are investing in their stack and they’re investing in their processes. How do they make it clear as they speak to their sales rep that they are important? “You guys are important to us. We’re investing in you. This is a reason to stay.” Is it more of just a natural way for the sales reps, they think that “things are easy for me, I can focus on sales.” Or, is it something that has to be communicated subliminally or outright?

JM: Which part of the communication are you thinking of?

Barry: Specifically I’m discussing, and it could be multiple parts of it, but one of the thesis of this podcast is that your processes and your tech stack will help retain employees. Does it retain employees because everything’s easier for them, or because they actually view it as a characteristic of the company that they are enabled?

Some people have values on their website’s ‘About Us’. A tech-enabled company moves quickly and they talk about it, they repeat it. The CEO talks about the all-hands. Or, is it more of a “wow, I’ve never had an experience like this. Everything’s so smooth. I want to stay here because I’m continuing to hit my numbers because of the smoothness.”

JM: I think it’s both of those things combined. It’s talking about it as a value, and the value is that we are going to help enable you to be successful. And part of that is having a really good process, being able to drive those insights from it, and being able to hit your number. If you’re putting in the effort, you are able to hit your number better and more consistently because you understand why and why you’re not, and what’s leading to that.

So it’s a little bit like I said, it’s a little bit of both of those. But I think it’s also on the ops person to be constantly selling the process and making sure that people understand. And I do think part of it is if you’ve had a bad process and come into an organization that has a really good process, that’s usually when you see it a little bit more. And when there’s a lot of value in that sales op person, I think sometimes, organizations might just have a Salesforce admin and that’s not really a true generalist. That’s going to be that leader on the team to really make sure that they’re doing all those different things. And so that’s part of it too, making sure you put your sales ops person just like a sales manager.

I was so lucky at Qualia. They were so great to me and how you can succeed and make sure that people knew that I was a part of the team and it wasn’t just like, ‘oh, don’t kind of listen to her’ type thing. It was great. And that’s the exact kind of thing that you want is that you have a seat at the table. You’re going to all the sales leadership meetings and things like that. And people see that and you might think it’s something little, but it does make a big difference.

RevOps Involvement in Sales Team Meetings

Barry: That makes sense. And the sales leadership meetings, can you elaborate more on that? Which specific meetings? They have a lot of meetings.

JM: I would try to do a variety. I’m not going to go to every single pipeline meeting. I’m not going to go to every single team meeting, but when all of the sales leaders meet on a weekly basis to talk about what’s going on in the business and where the focus is to make sure that we’re aligned. Because what if I’m way over here, dealing with some other process that I think is important and they’re like, “Whoa, no, we’re all way over here”. And that trickles down to the AEs.

So I need to know how to fix this right now. There’s obviously a combination of working on some of that stuff in the background, but we have to be aligned just as an organization and that would lead to the happiness. Because when you are in an organization where you have one person telling you one thing and another person telling you to focus on something else that is super frustrating. And so that’s where it helps with that alignment. And then again, trickles down to that happiness of the AEs.

Barry: Absolutely. I’ve had that experience and it is super frustrating. Can companies use this as a recruiting thing? Retaining maybe is easier to communicate or even without even needing to communicate, but what about recruiting? Is there a way to grab AEs to your company through a streamlined effort?

JM: I don’t really think that you can sell somebody on the process and have that being the reason for people to come on. What usually the sexier shiny object is going to be, “Hey, we have the best in class tech stack. And with that, we have the best process to go along with it so that our AE can be more successful and really focus on the selling activities that they’re doing.”

But I don’t think that you can say, “Hey, we’ve spent a lot of time and effort on having a really good process in someone’s life”. Because I have my own process and everyone has their own way of doing it. So I think it’s a matter of them seeing it once they get there and then talking to each individual. It’s how I make sure that I have that personal relationship with them when they do come on so that even if someone has this process that they came on board with it’s again from the get-go becoming a leader to them and building that relationship.

Recruiting Sales Talent

Barry: That makes sense. I had a feeling that was answered, but I wanted to see if you could bring up how do we talk about processes? How do we communicate the sales stack? How do we communicate that when recruiting? Is it just a comment or is someone posting on LinkedIn, here are all my here’s our whole sales stack and you can join this”? What are some methodologies you’ve seen or some tactics?

JM: I think it’s a combination, but I don’t think posting your sales stack is going to be what’s driving people. People aren’t going to be a hundred percent tied to a certain tool. They know that it’s going to change when you go to a new company and you’re going to get new tools that you never knew even existed because there’s a different problem that business is solving. So I think it’s a matter of it comes in conversation as you’re talking to the person and you realize that you want this person to work there, it’s talking about, “Hey, we have these best in class tools to help you do X, Y, Z task.”

It’s not like sales acceleration, or “We have the best enrichment you can have, or we have X, Y, Z”. You have the best CPQ around, through you all. So things like that are really going to help make sure that, they understand, but also they’re not married to their past.

Barry: Absolutely. So it’s not often I get to speak to someone on our podcast that went from 50 to 500 at their company in the sales op world. I wanted to hear about how your job changed through that growth because the company changed. Could you tell us about that trajectory and what changed? And it’d be cool I think to talk about it in the context of, if someone is looking to join a sales ops at 50 versus 500, what are the differences, I think that added information could be valuable.

The Differences Between a Team of 50 and 500 Sales Reps

JM: The biggest differences between the 50 to 500 are process, the process for doing things. Not just your sales rep process, but if I need to go do a certain thing, there’s a person now that I can go to, it’s not me having to figure it out. I think that journey is extremely exciting. Being able to come in and you’re being okay with failing a lot at the beginning, having to figure things out, and you’re going to get frustrated, but try to remove the frustration and try to say, “All right, I’m going to focus on this, on this thing, and I’m going to solve it”. And then the other thing that I think really changes is you because you have more people that are there to help. You’re able to automate so much more. Because it’s at the beginning, it can be frustrating. And you’re like, “Ah, I don’t know. That one thing it’s like, we’re not there yet. We need X, Y, Z to get there.”

And it also might not make sense to automate everything at the beginning because your process is going to change. And so it’s making sure that you’re okay with that and being ready for that journey and knowing that you’re going to build things and then they’re going to get scrapped the next day because the direction’s going to change and being able to, duck and weave and go this way and that is exciting.

And it’s fun to see the growth and fun to continue to problem solve in new ways. But then also part of that is going back to the efficiency conversation we had earlier. It’s having a process of how you evaluate these things and making sure that every month you’re looking at things because as you grow, it’s really easy. And I made this mistake a few times. Which is all right, cool. So we’ve added on these other teams. Have I even sat down with one of these teams because it’s slightly different? And so making sure that I’m reviewing if these metrics still make sense for that team or does this one process make sense for that team?

Barry: Absolutely. That’s awesome. Well, JM, you’re an All-star. It was awesome. Having you on the podcast. Thanks so much for joining.

JM: Thanks for having me.

Barry: Of course in touch and learning more from you. I think the community can learn a lot from you. If one of our listeners wants to reach out, what’s the best way that they can contact you.

JM: LinkedIn is the best way I’m super active on LinkedIn and it’s just under JM, Wilke, JM two letters. Wilke W I L K E. I think I’m the only one. I’m pretty sure I’m the only one. So I hope to connect with you there and I love talking to new people. So if I can never be helpful to anyone, don’t be a stranger that’s what I do.