From SnaaS to Saas with Sean Gentry

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What up everybody?

Welcome to another episode of the live Better Sell Better podcast. This is your host Kevin Dorsey AKA kd and today we have SG Sean Gentry from SNASS to SaaS. So Sean Gentry is actually a former team member of mine, former manager that reported up to me and when he came to me he was already good and what he said to me in the interview process that he wanted to become great. And I watched Shawn Gentry go from rep to top rep to manager to top manager to taking on the entire sales training organization to then going back to management and selling to then going from Snass Snacks as a service, getting into Zillow, becoming an enterprise rep there to an enterprise manager there and now is with the dip for Darling dandy of the SaaS industry outreach as a sales manager there and what I love about Sean and why I wanted to bring him on is his journey is very interesting. There isn't a pattern in industry, there isn't a pattern in product. He's been successful across multiple industries with multiple products and has made the leap from rep to manager. And also he can give some insight on what it's like to work for a psycho like me. So I'm so excited to have Sean here. His growth has made me incredibly proud. Shawn Gentry, welcome to the show.

God, with an intro like that, why do we need the next 45 minutes or 20 minutes?

I could keep going. I got so much good stuff to say about you. Like, I could go for the whole 45 minutes.

That's really why I'm here, is just.

To boost my ego.

Super excited to be a part of this. And, yeah, just share any insight I can give. So I really appreciate it.

Well, let's go, man. We're going to go right into it because this is a question I remember asking you way back when, and we had many conversations around this, right, of like, why did you want to become a manager, say, leader over just being a rep, individual contributor? Why was that so important to you?

Yeah, and I think that's such a crucial question to ask any rep that says they want to be a manager. Right. Because I think most people want to do it for. I don't know if it's the wrong reasons, but just reasons that don't lead them to success. But I obviously remember you asking me that multiple times and the multiple times I did go from rep to manager, and it really baked into the fact that I relish seeing others succeed. And especially with the coaching that I've learned and either passed on or stuff that I've read from a book or heard from a podcast or even learned from you, and seeing just the ability for me to pass that on to them, to them to use it and come back to me and say, hey, Sean, I used this and this worked, and I got this prospect to the next level or I closed this deal. Like that, to me, makes me so much more fulfilled than somebody sending me their credit card. I feel like I'd gotten to the point where I'd done that. I'd had the repetitions of booking deals, of seeing that success. And so now when somebody comes to me and thanks me or gets to the point where they're using what I've put into practice with them and they see success with it, that's what really gets me fired up.

And I love that. But you open it up by saying, some people get in for the wrong reasons or they don't know if management is right for them. What are some of the questions they should ask themselves before going the management path? How can someone know if management is right for them?

Yeah, I Think it comes down to a simplicity of just being happy. Like, I think, you know, at the end of the day, how do they define success and happiness within their own role now? You know, and that's, I think, always a tough transition from rep to manager is that most sales reps define success or define happiness based off revenue closed. Right. And they're gonna be able to look at the end of the week or look at the end of the month and see where they are on that leaderboard and say, hey, am I doing well in management? That's a tough transition just on your emotional psyche because you don't have those checkbox wins or losses on a daily, weekly or monthly basis. And sometimes you may go a whole week without your team closing a deal. Right. And because of that, you may think, hey, I'm not doing a good job. But are you positively impacting that rep not only on a fulfillment level, but also making sure their metrics are improving? It's a different type of win. And so it even took me a little while to learn that going from rep to manager, that you're going to be fulfilled and find wins much differently than just closed revenue on a leaderboard.

And we're going to dive into that. We're going to open up the closet for everybody here. Right. So you were a top performing rep from me who I thought was going to do management for sure. And we're going to talk about how I knew that very early on you became a manager and were managing like the newer rep, but there was something missing there for a while. And you actually went back to closing for a bit. Right. Changed industries, were closing again and became a manager again. And I remember we were texting about it. I said, hold up, hold up. You did this before? Are you sure? What was the shift? How did you grow to then being able to find fulfillment differently than when you were around?

Yeah, And I think so much of that was about impact as well, and what I was able to impact because of it. So I, I obviously knew that I could close the revenue, be a top performer. I did that under you, and I wanted to have that impact. And to be honest, at that point, when I was so early into my career, I did miss a lot of those wins when I was the head of sales training there and seeing the impact there, I wanted to get back into that taste of blood, that shark mentality that I don't think ever goes away with some people. And then, yeah, you and I were texting and when I moved to Seattle and I joined Zillow, Group, they actually didn't have any management positions open. And I wanted to join Enterprise. I wanted to be a part of that team. And the leaders there said, basically, hey, if you want to be a leader here, prove it, right? So I joined as a rep, became the top enterprise rep there within a couple months, and I got promoted within the first six to become the head of west coast sales. And it's because of the impact that I could have with the reps around me. So whether. Because there's a very fine distinction between a manager and a leader, which we'll probably talk about anyways, but a manager is there that can tell you they can open up a Salesforce report and tell you which metrics to look at or what to improve by sitting behind a keyboard, right? A leader doesn't have to be a manager to lead. And that's what I always felt like made me fulfilled, was leading the people around me and having an impact on them whether I was their manager or not. But now it's my two goals. And when I sit down with all of my reps in our first one on ones is I say, hey, if I'm not making sure that your metrics are improving month over month and that you feel fulfilled every day when you walk out of the doors, I'm not doing my job. So I think all going back to the impact that I'm having, that's the reason that I find myself in this position. And I want to scale because I believe that I can impact more people as I scale up within the org.

Now, something that you did when you were working for me and I can almost guarantee you also did at Zillow Group, is you started leading long before you were a manager. I still remember this. So Sean, when he joined the team, he joined in a group of like seven or eight people and within the first week was coordinating role plays and coordinating call reviews and like helping his group come through. Like, where was that a conscious decision? Or is that just part of who you are? Because I'd be willing to bet if I was a fly on the wallet. Zillow Group too. 99.9% chance you were also helping those around you long before you were a manager. So where does that come from for you?

Yeah, I wish I could say that I went in with such an agenda at Snack Nation to make that happen, but I honestly didn't. Like, I grew up as, you know, like a huge sports fan and I've always been a huge team sport fan. Like basketball is one of my favorite sports to play and watch. And I have this whole the team wins mentality. Right. And I think going in subconsciously, I want those around me to do well. But I also feel like I had a lot of knowledge at that time to give to some of these greener reps and things that I've passed on. Now when I went to Zillow, I was a completely different beast in the sense that I soaked up your knowledge for three and a half years and I had a lot to impart there. But, yeah, it's Snack Nation. I started with a lot of reps that were pretty green, that didn't have a ton of sales experience. So I knew if I got them in a room and was able to role play with them or I remember we would make cold calls and do it on speakerphone so everyone could hear basically the objections that we were hearing going through. Because I believe that if we could level up everyone faster, we would all get to that next level so much easier and obviously help the company and make that bigger impact. So I don't know that I came in with an agenda, but it seems.

To happen where I go. So as you know, say someone's listening right now, they're a rep and they're like, yeah, I want to be a manager. I've asked myself the questions. I believe I'd be very fulfilled. What advice would you give for someone to earn that manager spot? Because management can also be tricky sometimes, right? It's hard to get a manager job without management experience. But how do you get management experience if you can't get the manager job? So what would be your advice to someone who wants to become a manager? How can they start preparing for that role? What can they do to stand out? Like, how do they get tagged as potential management? Potential. I'm going to say potential one more time just for shits and giggles, because I can't.

Yeah. It comes down to two things, I think. One is obviously what we talked about, right? There's a difference between a manager and a leader. Something that you told me, and it will always stick with me, and I'm sure probably some of your listeners have heard you say this before, is that when it comes to growth, growth is never given based off seniority. It's earned because of what you're doing outside of your role, right? So even when I'm now looking at my reps and my teams and I'm pinpointing future leaders like I'm sure you've done, and do you look at those members who are executing their role At a high level, they're doing all the small things, they're doing the big things, and then they're also impacting and making those better. Those are the true leaders. That's the difference between the leaders and the managers. They're doing what they're doing at a high level. It doesn't have to be the person that's hitting 150, 200% of quota, but they're doing everything that needs to be done while still donating some of their time to help and level up those around them. Because those are the people that truly are unselfish. Right. Like Mike Weinberg talks about this in his books and he says sales reps, the best Sales reps are 100% selfish.

Yes.

Yeah. That is their best asset is their time. Right. And the best sales managers are 100% unselfish. And I think that's a tough transition from reps to management anyways, is learning to divvy your time up. But when you look at the people on their team that say, hey, you're selling at a high level, but you're also donating your time to somebody else to get better, those are the people that can start to kind of rise to the top as future leadership. But you also want to be that person that managers can look at you and say, yes, this person's a no brainer by the time a management spot opens.

That's something that I think made you such a rare bird is you were able to be a top performing rep and still help those around. Right. Very often the one that's number one, like, yeah, that's that lone wolf, they're doing their thing. But you were often able to be number one and still impact those around you. And you mentioned something there that's important. It's a good little segue to. One of the next questions is time management. Right. So now you are a manager.

Right.

How many reps do you have right now?

Currently I have six.

Six, okay. So how do you manage your time now as a manager? So I think a lot of managers get this wrong. They don't spend their time well. So how do you manage your time now as a manager with six reps? That is fast growing startup. Yeah.

And I'll caveat that by saying this is the lowest number of reps I think I've ever had. Right. I've gone from 10, I've even had 12 at a time, which is just madness. Six is amazing because I get to spend almost an entire day with one person through my week. But yeah, you can't talk about time management and time blocking. And I think you even had a LinkedIn post about this the other day. Like sticking to your calendar. You can't talk about that enough. And I think so many people talk about it and don't often do it as well. I was just reading this awesome book so I'll plug this. It's called the Freedom Formula by David Finkel. And he was saying that every manager, every leader, every rep should go through what they do on a daily or weekly basis and categorize them into an A, a B or a C in terms of adding value. Right. He thinks that now in this type of work environment, there's a difference between what's called the action economy and the value economy. So many people think that the more actions they do, the more work they do, it'll lead them to a higher level, higher job, etc. But he's like, if you know what your A value points are versus your B or C, you're gonna spend more time doing those things. So when I look at my calendar now, and I had it up a minute ago, I like to have all my one on ones in the beginning of the week. I've always had it this way that I can get through Monday and Tuesday. So if I got action items it can execute through the week. I usually now implemented small check ins with them later in the week to make sure they've completed those action items. And also kind of like a morale check in. Aside from that, I've always have blocks to go through my call scoring, which is basically done through GONG now or any call transcription software. You have to make sure I know what they're doing on their discovery calls, their demo calls follow along on that. Additionally, I've got all the meetings that are set in there, but I like to map everything out on Friday afternoon. I know some people do it on Sundays, but it has to be done for me. And I even have it literally on my calendar, Friday afternoon set calendar so that I'll go through and block everything for the next week. And if I've got open space, I know I won't do anything practical or functional during that time. So I try to block literally every 30 minutes, even if that's to take a walk or eat lunch or meditate. I want to make sure that everything is on there so I actually stick to it.

I love that, right? The calendar management, the calendar blocking, but also the calendar adherence of like following it. Now I will do a quick tip for everyone listening. I would strongly recommend planning your week on Friday afternoon and reviewing it on Sunday. If you save planning your week for Sunday, you never really get to unplug. You never really get to shut off because you know that's coming on Sunday. And now you're spending your Sunday nights getting ready for Monday. I take 30 minutes on a Sunday evening just to review my plan. I'd highly recommend, if you're listening, end your week planning the next week. Don't save it for Sunday night, because then also too, it can get pushed off and you just don't do it. And then you walk into a Monday and you're not ready to go. Now, something you mentioned there, we have spent so much time on this together, but a lot of people still haven't call scoring. Call scoring. Everyone's listening to calls and weirdly, everyone seems to sound good, but results aren't always there. How do you score a call? What are the things that you're looking for? And is this like an app? Like, do all your reps follow the same scorecard? Or is it kind of like when you say scoring a card, it's kind of like, you know, ambiguous?

Like, oh, yeah, that was good.

This was bad. Fix this. Like, walk us through your call scoring methodology.

Yeah, well, this has been. Well, obviously you implemented this at Snack Nation. I remember we used to have like this call scoring. We'd laminate it and go through and people would fill them out as they're doing it. Like live scoring. That was before, like GONG or chorus or anything.

Yeah, it was. Oh, geez, baby, we've been doing this.

That's right. She did Sharpie on laminated paper. Oh, yeah. And so Zillow. I implemented this because I took what you built and replicated it. Now we're just doing this at outreach as well. So we've got everything loaded into gong now where we can go through and have like 1, 2, 3, 4, 5, like actual scores of what we're doing and what we want our reps to hit. So, yeah, I mean, if you ask any rep after they get off a call and how did that go? They're going to say one of two answers. They're going to say it went bad or I went good. Right.

And that's about.

That's about the most information you're going to get. I think, obviously for a lot of the leaders that are listening out there, managers, you know, you're going to go and listen to that call and then you're going to also going to say the same thing. Like, yeah, pretty poorly or, yeah, it Went pretty well. It went pretty good. But if you don't actually know what things you're trying to hit or what is going to make it good or great, it's tough to coach them to that next intricate level. And so that's when you're telling people like, hey, yeah, that was a good call, but here's how you can make it great. You missed these two questions, or I really want to see you focus on this gap, or I want to make sure that you're reiterating what problem you can solve at the end here, because you scored a three here, but you can score a five by doing it this way. And so the more, like, tactical, you can get more specific. Specific, you're going to get better results.

Now, without giving away your secret sauce there at Outreach, could you share a few things that you look for in a good call? But, like, what are some of the things that are on, like, a good demo call scorecard that people should implement?

Yeah, well, one thing that's like, one thing overall that I try to get all of my reps to know going into any call, and this can be for a cold call, you know what we call an initial meeting, a demo proposal call, is, what is your goal? What's your goal going into it? And that's a simple enough question for me to ask is, hey, you've got this demo on Thursday. What do you want that last five minutes to sound like? What is that goal that you want to walk away with? What is that actionable item number one? So when we go to the scorecard, it's, hey, I knew what your goal was. You told me what your goal was. Did you achieve that goal?

Ooh, that's good. So you're preempting the score. So it's like they're telling you the goal before. Oh, I like that a lot.

So Mondays and Tuesdays, we're going through and saying, all right, these are. And the one thing that I love, that Outreach does, and I got to steal this from Mark Kosovo, if he listens to this, is when we go through and do our forecast, our pipeline reviews, we go with the largest deal down. So what's the largest deal you have in your pipeline? And that may be forecasted for six months out. But one of the mistakes that I used to make as a manager is saying, hey, this is six months out. Let's worry about that at a later date. No, that's the first thing we talk about in every single meeting. We're going top down. So it's. If it's a 50k deal, 40k deal, 30k deal. And it may get. It may like, you know, drive these reps crazy, but that's the first deal. We talk about every forecast meeting. So as I go through, I say, all right, you've got a call on Thursday. What is your goal of this call? We write it down together. So when we listen to that call, we can say, did you execute your goal first thing? The second thing, without giving away too much secret sauce, is did you realize and discover what their problem is that we're solving for? So with it, we know at outreach that they're probably going to be looking at a couple different competitors. We're not stupid. But are we solving a problem that is significant and important to us, that we can do better than any of our competitors out there? Were you able to discover that and illustrate that to the prospect before next step? So those are usually the two biggest highlights for me. And overarching themes. If you didn't execute your goal and you don't know what problem you're solving, it's probably not the best call.

Now I love it. Those are things that we have on our scorecards as well, right? Did you get them to agree they have a problem? Did you get them to say they have a problem? Right? And the beauty of call scorecards, too, for anyone out there listening, the call scorecard is all about what your rep is doing. It's not about what the prospect is doing. You don't even have to record both sides of the call. That's something that always gets people tripped up. Well, can I record? Can I not record? Blah, blah, blah. You can always record your side of the conversation and you could still score calls. So I would recommend everybody building a call scorecard out because it's just foundational. And as a leader, you're looking for the same things every call anyway. Sit down, take notes. What are the things I look for? There's your call scorecard, right? But now here's the nesting, though, right? And you know, you read this book together with me, right? Cracking the sales management code, and one of the things it talks about is like, you know, what gets measured gets improved isn't true. Measurement allows for awareness, but coaching is what leads to improvement. So how do you coach your reps? Right? Say I'm a rep for Shawn Gentry and I'm just sucking it up at Discovery on my scorecard, right? Like, I'm just bombing. How do you coach me to actually get better? Because you can't just tell me, like, hey, KD be better. I go, oh, okay, all right, Sg I can do that. How do you actually coach your reps to improve in these areas?

Yeah. And two fundamental things that I feel like I've taken from my career so far. One is by David Brock, who I had to bring up at least once.

Deep yogurt. Let's go, baby. Deep yogurt.

I haven't read the Sales Manager Survival Guy by David Brock. Buy it now immediately after listening to this. But he does a great job of talking about the difference between direct and indirective coaching. Right. And where you always try to lead with indirective coaching by asking questions so the rep can get to the answer themselves because that's going to ingrain in their memory much easier and much, I guess, easier to implement for them moving forward. There's going to be a part within any manager's career where they have to be direct. Where I literally will have to tell you, hey, Katie, you have to ask this question at this point and just be as direct as possible. But I want to lead with the first first to try to get you to discover that yourself. So that's usually like how I'll go about it. Indirective before directive. The second thing is honestly from Freedom Formula again, where he talks about David Finkel talks about the load management on the psyche and how many things you can remember at once. He has a great analogy for this. He says the human brain can only remember seven things at once. And it's like trying to carry groceries from your car to your house. The minute you try to grab one more bag, something's going to fall out of your hands. And if you reach down to pick that up, something else is going to fall out. And so through these coaching sessions, I try to leave them with two or three tactical takeaways max. I know sometimes, and I used to do this early in my career, I would hear a call or do a role play and we would have a full list and essay of notes. Right. Like here are four things you can do in the discovery, Here are eight things you can do in the demo and here's two things you can do it in the close go do them. You're going to do one or maybe two of those things. So it's picking the most important, you know, taking those as tactical takeaways. And then that's why I like to have my check ins by the end of the week. Hey, how did this call go? Right. Did you execute your goal? Were you able to do these two or three takeaways on the call? Did that work? Yes or no? Why not? And let's move on to the next things.

If so, so what would be your advice to a manager to how to prioritize that feedback? How do you determine like, okay, this is worth the two to three, right? Because so often, right, Managers, they do, they listen to the call, they listen, whatever and it's like, alright, I want to share all the things that I know, all the things that you could have done better. How should a manager prioritize that feedback?

Yeah, it's a great question, I think. I mean, I take it as what I would do and I would look at what is the biggest needle mover, right. What is the thing that is going to move the needle in that deal or prospect's vision best? So if there's issues with the demo or closing or discovery, like I want to focus on what are the one or two things that you can take away that is going to progress this deal and help you get better faster. Now normally that centers around the discovery, right? It's for me, it's like if you don't have a strong discovery, it's pretty rare you're going to have a strong demo or strong close. Like you can't really have the second or the third without the first. So if I've got big takeaways, that's where I'm going to hit home, is like, set yourself up for success, do a strong discovery call. Because after plus if you do a strong discovery call, you'll have maybe 24, 48, maybe even a couple more days to prep for the demo. And so I want to make sure that they're going through and getting these tactical takeaways early so that we can implement for the next call.

I think that's so important. But it's also a good setup. Then it's accountability. Right. So one, I'm gonna set you up here, right? What's the difference between accountability and micromanagement? Because I think people get this twisted.

Yeah. So one thing that you've always told me that I tell my reps ad nauseam as I say, you can't micromanage somebody that over performs and over communicates. Right. Truth, you can't. Truth reps will always tell you, I don't want to be micromanaged. Great. Then just over communicate and over perform and you'll never be the same for accountability though. I know it's something that they're going to get better with. I'm not hounding them on a specific metric, but it's something that I believe that we've also agreed to, and I think that's something that's key, is that when we have these one on ones or the coaching sessions, we're agreeing on the sense that we need improvement here and we're going to work on it together and we're going to do it by X date. Like, I always view micromanagement as me sitting behind a Salesforce dash and messaging people eight times a day about a metric or report that they haven't done. Like, I don't want to be that person. I know my reps don't want to be receiving those slacks from me. So whenever we lean into these one on ones, I want them through indirective coaching to tell me what they feel like they can improve. We agree on the right tactic to improve that. Then we say, hey, by Wednesday, we're going to either go through this call, we're going to review it, or you're going to execute on this item. Is that fair to do? We get that agreement so that on Wednesday, it's me following up saying, hey, did we do X, Y or Z? Did we do this in the call? Did we execute this task? All right, we did. Yes. Awesome. What's the next one to do if we didn't know why? But that to me is the difference between accountability and just micromanagement.

And I hope you all picked up on what he was saying there too is he's getting his reps to tell him what they're going to do. It's very different if you're just telling them what to do and they agree versus them saying, here's what I'm going to do and you agree. I think that's a big shift too, in terms of accountability and micromanagement and what I teach my managers. I may have taught you this is also may have just been my own evolution through this is the can you. Will you. Okay, so you said you're going to do this. Cool. Can you do that by X? Yes. Will you do that by X? Right. That can you. Will you in that double confirmation, just like setting a meeting, just like a demo, just like next steps. That can you.

Will you.

And the little bonus tip there for me. Can you do that for me? Will you do that for me? Right. When it's attached to you as the person, it's harder to let that just go versus, like, ah, like, I'm not gonna do it. It's like, no, I told Gentry I'd do that for him. Damn it. Right. Accountability versus micromanagement. You get them to Say it's a total, total, like shift there. So now what do you do then if a rep is struggling? Right. Like, okay, like I haven't hit my number in a quarter. We're working on the call scorecards. I'm just not seeming to get it. What do you do with a struggling rep?

Yeah, well, I mean, one thing that I'll always remember, like through early of you training me as a manager and with Snack Nation, there's always a reason why, right? Of course. And it's usually something that you can pinpoint that not a lot of managers will take the time to work backwards to find out, right? So they'll say, okay, this rep is struggling, but it's pretty rare that. And I've managed managers and I'll ask them, well, why are they struggling? Well, they're just having bad calls and it's rare that they know specifically what they're missing or why they're struggling. And usually you can pinpoint it to some sort of metric or something that they're doing or not doing within the process. Right. And so that's always the first thing for me is I'm a metrics geek. Like, I will dive in and work backwards and say, okay, where is this person going wrong? Right? Are they targeting the right prospects? Are they having the right activity? Are they saying the right things on their phone? Is the process dial in and their cadence of how often they're following up? Because if you dive in that granular, you will inevitably find something that they're doing wrong. And usually sometimes it's not that difficult of a fix, right. To say, like, okay, their messaging is right, but they're only contacting them twice when it should be five or six times. Or they're reaching out to the wrong Persona, or maybe they're reaching out to the wrong industry and it's something you can tweak now that's on the process side. If it's something that they're doing on the phone, that's where the call scoring has to be there. So you can say, okay, you're missing these three questions on every single call, right? I just need you, I need you to put post its up or billboards now in your home office of these three questions and literally say them every single time ad nauseam. And can you do that for me? Will you do that for me? We're going to review it tomorrow. And did you do these three things right? But a lot of managers, even ones that I've worked with, don't know why their rep is struggling and that's where the coaching can be so far off. Or people just beating their heads against walls that can't figure it out.

I'm gonna see if you remember this. I don't want you to be a micromanager. I want you to be micro. What do you remember?

I don't know.

Micro aware. I don't want you to micromanage. I want you to be micro aware. It's knowing the small things that add up to the big results. Right. And so let's make a transition here. Right. So one of the things that I also hope people are recognizing is just your growth as an individual. But you have done it across industries. I think before you came to me, you were in the restaurant industry. I think before that it was like T Mobile. Then you do Zillow, now you're outreach. What are some things that are consistent across industries that allow you to succeed? Because there's so many people that are like, oh, nope, you haven't sold SaaS. You can't sell SaaS. In fact, there's a pretty funny backstory with you around. Oh, you can't sell SaaS, so you can't sell SaaS. Right. So what are the things that you think are consistent across being successful across industries? That's something that I think is a rarity nowadays. It's like people sell into the financial industry. That's it. And even companies are asking for that. Like, oh, we want four to five years of financial services SaaS experience.

Right?

Yeah. Jesus. Like what? So how are things that you think anyone, if they're switching industry, switching companies, things that they can hold on to are ingrained, that will lead to more success, whether it's a rep or a manager.

Yeah. I think innately one thing that I've gotten from you, and I know I keep chewing your horn, but it's your podcast, so I'll keep doing it. Is when I go into a company and no matter what the company is, I tell them point blank in the interview process that I'm going to outwork and out learn everyone around me. Right. Like, as simple as that. Like, I don't care what the industry is. I could be selling garden hoses. Like, I'm going to outwork and out learn everyone around me. I think with that being said, especially when it comes to industry sales is the same. Right. So I believe selling snack boxes at Snack Nation, selling, you know, selling lead generation in advertising, Zillow Group to brokers and real estate professionals, then now selling outreach. It's. There's no huge Differentiators between the sales process or selling well. Like, are you discovering a problem? Are you solving that problem? And does, you know, are you taking the customer on a journey just to get to the other side? Are you gap selling?

Right.

So it doesn't matter what you're selling, Right. Is the first thing. So whether you're transitioning different industries, you're just selling to a different person. Like we were selling to hr, you know, and we were selling to facilities directors with snass, and then I went to brokerages and then now I'm selling to BPs of sales and CROs. So I think with the messaging and language, that's why some people will say, okay, you've got five years of fintech. We need you to stay within fintech because you know how to talk to these people and you know the vernacular and the language, which is crucial. But on the same token, anyone can learn that through experience.

So how did you. I'm going to jump in there real quick. So how did you learn all these different customers? Quickly, right? How did you prioritize that?

Yeah, I think the biggest thing is you have to engulf yourself with the customers first and foremost. So, like when I was working, you know, let's say when I made my first big jump, right, and I moved to Zillow Group, working in real estate, I had to spend a lot of time on the phone with customers and also current customers. I wanted to learn why people were buying. So one of the first things I did is I said, hey, you've got me shadowing our account executives. Can I spend the extra time, whether it's getting in early on lunch or on my breaks, shadowing our account reps. I want to shadow the people that are actually using Zillow Group, that have purchased Zillow Group, because I want to find out what, why they like it, why they bought it, what they needed to do, maybe why they don't like it so much. And it's the same thing with outreach. Now it's like, I want to find out why people need our product and what solution it solves for them. And the more customer calls you're on, the more current customer calls you're on, you're going to learn. And it's just like picking anything. It's like picking up a new language. The more you're engulfed in that, it becomes second nature. But you have to put in the work to do that.

I love it. I absolutely love it. Now, let's talk about the reps one more time here.

What are some Things you like to.

Do to motivate your reps. Right? Motivate, inspire. Like, get them fired up. Like, what are things that you like to do there?

Yeah. I always remember when we would do the introductions with new hires and we would always do this list. I'm sure you remember this. And I'm bringing this up for the people that don't know that much about you. And you would do this list of what you're great at and things that.

You'Re not great at.

And you would always have two things on your list that you weren't great at. Number one. And I'm sure you probably remember this. Number one was email. Do you remember what the another two thing was?

Fun.

Fun, right. You weren't fun. And so whenever we onboarded people together, I knew I had to be the fun one. Right. Because you just weren't. Which I don't know is necessarily true. I think you're really funny. But I think for my team now, I'm a huge sports guy. I'm very competitive. I think a lot of salespeople are either naturally competitive, either with themselves or with other people. So I love to do competitions. I love to drive people towards things they want. Two weeks ago, we wanted people to do more sequencing and get people out there in terms of AE prospecting. Everyone wanted Friday off. So I told him, hey, great, hit this number. You get Friday off, right? Easy way to motivate people. Additionally, though, I think the core component that a lot of leaders miss is the why behind things. So we can push people to a lot of different, whether it's metrics or goals. But I always try to go over and above of telling them why we're pushing towards it. Because if you just tell me to do something, sure, you can put a carrot out there and I might be motivated towards it. But I want to know the why. Why are you being told Kevin, and you're telling me to do something? Why are you being told to do that from CEO or from anybody else? And so that I can know why? Because I believe, like, the more transparency you build, the more trust you're going to build. It gets people to lean in and that's where the activity or the motion is going to come from. So I guess that's the two things. Like the competitions, but also like the why behind it. I love it.

And just so people are clear, right. When I said I wasn't free fun, what it really meant is like, no, I said I still. By the way, I still do the same exercises ever now email isn't my number one bad thing. Spelling is my number one bad. Email is like down like 2 or 3 now. But no, it was around. Like, I believe in competitions and I believe in those things. It's just not where my brain goes, right? So I need people to bring those ideas to me. I still say that to my managers today. It's like, yo, like, give me something. What do you want to do? Oh, you want to have a left footed contest?

Cool.

Have a left footed contest. I don't know what the hell that is, but if that's gonna get people excited, it's asking people for these ideas and I love to start that with new reps. So they could from the very beginning, like, what would make this fun? Because sales is hard, right? Especially the prospecting side, the closing side, right? It's hard. And so those ideas around fun I think are so, so, so important. So now, before we wrap in a couple of our wrap up questions, I do want to throw this one out here because people ask sometimes, right? What are the pros and cons of working for kd? This is the first former employee team member rep that I've had on a podcast that I get to interview. So you get to be honest with the people and say, what are the pros? But also what are the cons? Let's open up the vault here real quick. Of working for Kevin Dorsey. Yeah.

It'S funny, I had somebody ask me this at outreach too. Somebody that I think follows you on LinkedIn and they and say, oh my God, you used to work for Katie. And I was like, yeah, I know, really well. And they're like, oh my God, what was it like working for them? So the pros is that you never stopped even today, pushing me to be better, right? So like, you only managed me for what, maybe two and a half years? And that was four years ago, maybe three, four years ago. Like, and we still talk regularly and you still push me to be better because you always saw things in me that maybe I didn't see myself. And that's what a great leader does, right? You knew I could be a better salesperson. You knew I could be a better leader, better trainer, whatever it was. So that I think is the overall arching pro. The con of that is kind of a double edged sword because I would come into a one on one thinking that I had everything dialed. I was on my shit, everything was amazing. And I came in like guns a blazing, like, yeah, check out my pipeline, everything's good. And you'd be like, yeah, I Actually saw these three things that you need to improve. And so the con is kind of like the pro. But I would always felt like I was doing a great job and you always pushed me to do more, which, like, obviously sometimes in the time, you're just like, oh, man, this is so tough. But the stuff that you can't thank people enough for in the long run, right? So I know that's kind of like overarching pro and con. The other con is that we were never able to get lunch together because you always ate a salad at your desk at 2:30 and ate three bites of it and just left the rest there.

Pretty consistent. Still, to this day, lunch has never been a thing that I could always pull off. What's fun, and I'm going to say this right now, is watching your growth and just watching how much you've still grown and improved. I'm just over here on cloud nine right now. I'm just so proud of you. I'm just so proud of what you've done and what you've accomplished. And I think even to this day, if you came and worked for me again, you would even see my growth and change. Because I do look back at some of my earlier leadership days ago. I pushed too hard or I didn't recognize enough. I didn't let people feel like they were good enough. And it came from a place of wanting people to be better. But also, if you never feel you're good enough, you start to lose that. I don't want people looking back going, actually, no, that was good. I want them in the moment also. Like, hey, I know this guy cares about me, wants the best for me, right? We grow and we learn. We go through that. That's what I valued about our relationship so much. So here we are, right? We're almost 50 minutes into this. You've been dropping bombs on people. I hope they're taking notes, because even I'm taking notes. There's some things in here I'm like, ooh, I like that. I'm gonna go run with that. So they forget everything.

They forget it all.

We've been talking about management and how to become a manager, how to manage people well, how to coach. If they forget everything we've been talking about, except for three things, what would those three takeaways be that would make them a better manager or give them a better chance to be able?

So number one is, and I can't stress this enough, is calendar adherence, right? So I think in spending time on the things that bring the most Value. Right. So if you go through and you mark up what your A value activities are, what your B value activities and activities, and you focus the majority of your time on those A's and B's, that will make you more successful, whether you're a manager, leader, rep, I don't care. I think the second thing is, especially for people that want to be a manager, it's all about doing what you're doing at a high level. Executing the small and big things while helping those around you get better. Right. Helping those around to get better but still take care of what you need to take take care of first, I think is the big caveat there. And I think the third thing that I would look for, I'm trying to think about all the stuff that we talked about now. Yeah. Is that don't be fearful or worry about going industry to industry because selling is the same if you know how to sell well and at a high level by using a similar process of gap selling. And I'll plug Keen in here. If you research how to gap sell and do it well, it doesn't matter if you're selling SAS Fintech, garden hoses, you know, anything like that, you're going to do it well and do it.

To a high level. No, I love that. Now also, to go back in the day, we were talking about gaps long before we had gaps on the wall. I still have old trainings from way back when talking about falling into the gap and all that. It's just so funny how that became now a methodology I know that people are following, which I love it like I really do, that she cracks me up. So. Alright, my man, we've made it this far. That's my second favorite question. This is my first favorite question. The name of this podcast is Live Better sell Better. Right? Like taking care of the person in salesperson. I have this weird belief that if we were living better, if we took better care of ourselves, if we were happier, if we were more fulfilled, that that translates over into our sales life. What would be your live better advice for people? Whether that's leaders, reps, in terms of how to take better care of themselves so that they're living at the level they want to.

You know, it's interesting that now during this time I think this question is so much more relevant. I mean it's always been relevant, but right now even more so because we're all transitioning to this. It's not even just working from home, it's working where you live. Right. And the big thing for Me is that when we transition to, you know, working where you live, environment, is that my life, I've got a two and a half year old, I've got one on the way, is that it would bleed, my work would bleed into the rest of the days and nights, it would bleed into the weekends. And so I had to be so diligent and get to a point where I had to stick by my calendar and say, you know what? At 5pm for this day, laptop is down, cell phone's in another room, I am done, right? And that point, I could spend as much present time with my family, be with my wife, my daughter and spend that time and be present in that moment. Because so much I was in this like work activity mode where I would be like, oh, you know what, I'm going to get a couple more emails in or I'm going to open up my calendar or I'm going to work on the weekends. And I think just being diligent about that, knowing when to shut off was just as important as when to turn it on for me. So my biggest advice even now to my reps is I say, hey, if you're knocking out Your A and Bs, your biggest value activities during the day at 4pm, if you're done, you're done. Like you're not on slack, you're not on email, you are being present with your friends, your family, you're going outside, you're meditating, working out, whatever it may be. But you need that time for yourself more than ever.

Just now, now it's funny, we were talking about calendaring earlier in this talk on my calendar at 5:30, a reminder comes up, it says shut it down. Yeah, shut it down, right? And just to remind myself, because like, you know, man, you get in the zone, you get into the whatever and you're just cranking, you don't even realize like, oh, it's 6:30, like why have I not moved in five hours? So my man, holy cow, this was good. Such good information. Super tactical. Where can people get more of you? Like where, where are you dropping more knowledge? Where can they find you? Like tell them how to find Shawn Gentry.

Yeah, yeah. So definitely follow me on LinkedIn. Check out my LinkedIn @Shawn Gentry. You can go to Outreach or find me there as well. Yeah, that's the best way. Or if you want to shoot, I'm going to give people my direct email too.

Oh snap.

I don't know if people do this or not, but I love this. If you have questions, right? If you want to know or you're hitting a wall for sales management even as a rep, anything like that. I love helping people. Hit me up at Sean gentryoutreach IO more than happy to help you guys out with the time that I have with any questions that come up.

That's the first personal contact info drop on the podcast, y'. All. I hope you wrote that down. I also hope you're ready, Sean, for all that kind of outreach because people are going to want to know more about what's in that head. So my man, thank you so much for your time. Thank you so much for your knowledge and insight. Thank you for being you. I'll say it again to end on this. I'm so proud of you and what you've achieved and can't wait to see how far you go. My man. So you know I love you like a brother. Thanks for being on.

Thank you.