Thomas is currently VP of Sales at Luxury Presence, and all-in-one online marketing platform for realtors.
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Derek: [00:00:00] All right, Thomas. Thanks so much for joining me, man. I’m really excited to have you on the show.
Thomas: [00:00:07] Yeah, absolutely. I’m excited to be here.
Derek: [00:00:10] Could you kick us off by telling us a bit about your history? How did you end up. You know, VP of sales.
Thomas: [00:00:20] Good question. you know, as a finance degree, in college and went into a finance role at a rather small investment bank and, really that role was a sales role.
It’s where I had my first exposure to, to cold calling. I was calling high net worth individuals. I at a pretty small investment bank. and really quickly learned that I didn’t really like the investment banking industry. So I actually joined a company called Yodel, as an inside sales rep there.
And, you know, Yoda was a really interesting environment to be a part of. this was a SAS online marketing company signed a small to medium sized businesses. but they just had a crazy sales culture. It was very, very polished in terms of how they drove performance and really. Helped you establish the entire framework of, of how an inside sales team or how sales teams in general should be running, like how to down to a science, you know, I had sales labs, script and testing, extensive reporting, managerial training, it’s all geared towards running a highly effective sales team.
So, That really allowed me to, to develop the general framework that I really operate off of of today, which has been extremely helpful. And it’s really the main reason why I’m in the position that I’m in as a VP of sales.
Derek: [00:01:35] Did you say labs had like a self, like what is, what is that?
Thomas: [00:01:40] When I say that we had things down to a science, we would have 15 people testing one line of an intro versus another line of an intro to see what would actually produce better results and get those reps on average, further, along in the call, it was, it was a lot of stuff. So
Derek: [00:02:01] how big was that sales team
Thomas: [00:02:04] that Salesforce was spread across five to six markets. It was about 600 salespeople.
Yeah. Somewhere between 60 to 70 new managers running, you know, you know, 10 person teams, 10, 10 to 12 person teams.
Derek: [00:02:17] Okay. So just like, just like startups, right?
Thomas: [00:02:20] Exactly.
Derek: [00:02:23] Was your, how did you end up becoming a sales manager?
Thomas: [00:02:29] Yeah. So I started at Yodel, as, as a salesrep, I had a really healthy $20,000 base salary, living in New York city, but it was a heavily, heavily based on commission and performance, obviously. and you know, initially I wasn’t a good performer. I started out, I sucked, I was on a, on a performance improvement plan, which I don’t tell many people, but I guess I’m telling everyone now, but I actually needed that because without that, I don’t think I would the sales rep or manager or leader that I actually happened today.
but I got my stuff together. After the first 30 days I really started, treating. The sales process like a science. I did a extensive amount of it work. I would work all day, come home, listen to calls of top performers. and I took really my success in my own hands, as much as I could. and that turned me into.
My first 60 days of mediocre performance and very stressful, by the way, in New York city, I’m on the 20 K base salary to actually become in one of the top performers at the company out of, out of 600 people by, by end of year. so really strong turnaround and, yeah, as a top performer, what I ended up doing is.
I started, you know, taking ownership and sort of a team lead position. So when we had new hires coming in, I would take one or two of them under my wing. I would give them call coaching on my own. I would hop on their calls and help them close deals. because the reality is, you know, one manager doesn’t have the bandwidth to do that for 12 people all day, every day.
so I, I started providing con you know, constant, consistent support to some of my younger peers, my less tenured peers. it turns out I really liked it. And, and that was really the, the spark that made me realize that moving into a managerial position was actually for me.
Derek: [00:04:17] Thanks for sharing that you were on a PIP, by the way.
I don’t think we talk about this in our industry. Very much. I also was on a PIP early one of my companies, zocdoc had me on a a pit my second week. Like that, that was, that was a ruthless org at the time, man. And, other guests that we’ve had on here were on pips and their first jobs before becoming leaders.
I feel like, I don’t know, not quite a trend, but, but anyone out there listening to this that, you know, just turn it around. It’s not the end of the end of the world.
Thomas: [00:04:51] Yeah. You know, it’s funny. I look back at it. and also the manager who had put me on that trip is a very good friend of mine. and, and it’s the reason for a lot of my success.
He said he did it on purpose. Cause I thought I was too cocky coming out of the gate. And, he was probably right. We joke about it probably every time we have a beer together. but you know, the reason I was actually on a PIP is I had never been exposed to an inside sales environment. Okay. And I knew I was going to sell, you know, the SAS online marketing software at a cool, you know, they a mid stage company that had a great culture.
And then when I walked in and I saw a hundred salespeople and you know, pretty much a call center and it was kind of chaos. I reading off a script, I was like, I thought it was crazy. I thought I was above script reading. when it came to trying to sell a product, I honestly was a nonbeliever. you know, I thought it was better than that.
I thought it was better than their process. That seemed kind of cheesy. I just didn’t believe that that would work. and, and that very quickly found me, you know, in the position of, of being on a plan. And when I said I turned it around, I turned it around because I started, I started buying into the process and I forced myself to, until the point where I actually started to get some wins.
but yeah, belief, belief is, is the killer. if you don’t believe that you’re able to do something, you don’t believe in something that you’re doing, You know, you’ll certainly find yourself down a dark path pretty quickly.
Derek: [00:06:19] Can you, can you tell us about that first, your first six months, say as a manager, what are some mistakes that you made?
Thomas: [00:06:28] Yeah. you know, everyone is different, meaning all of your reps are different. They have different personalities. they respond differently. I most importantly, they’re not you, you know, one of the main mistakes that I made or one of the ones that stands out is, you know, like I coached everyone on the team and treated everyone on the team, the way that I used to like, to be treated or coached, which was very direct.
And that certainly didn’t work. and you know, as a result, you know, some people take to it, but you’re not bringing the team up as a whole. And you really got to get to know your people. You know, one of the most crucial meetings that you have in any given week as a one-on-one and they need to be consistently need to happen, and they need to go below the surface because if they’re surface level conversations with the people that you’re trying to manage, you’re not going to really know how to speak to them.
You’re not going to know what makes them tick. And you’re having a really tough time, driving performance consistently over a long period of time when you’re likely going to lose a lot of people.
Derek: [00:07:31] When you say, get below the surface, like, what does that mean? How does somebody do that?
Thomas: [00:07:36] It’s a good question. It starts with questions and not just, you know, generic, close ended questions. Right. you know, a lot of it has to do with, would making a portion of, of these conversations. Just not necessarily about work. work is one portion of their lives, but a lot of what happens, you know, someone’s going through outside of work, can certainly.
impact performance as well. So yeah, you got to have those conversations. You need to have them over time. It’s not going to happen in your first one on one. you know, it takes time to build trust. You need to need to be able to show people that you’re going to consistently be there for them. And you gotta actually genuinely care about them as a human being.
you know, if you do want to have the ability to effectively get below other surface
Derek: [00:08:20] So, how would you have done that? How would you have done that differently? Like if you could go back in time and say, here’s a, like, give yourself a couple tips, go, go do this. As if you were coaching yourself, like what, what might that look like? Or something like,
Thomas: [00:08:37] yeah. You know, When it, when it comes to that sort of thing, my expectation or my expectation was that it would just happen overnight.
and just like anything, it doesn’t happen overnight. It takes time. So, you know, it’s not that you can just go and have one conversation and get to know a little about, about another person and all of a sudden, you know, they should be responding. It’s, it’s something that. As conditioned, in a relationship as you’re, as you’re getting to know them over an extended period of time.
So, the thing that, that is most important, and I mentioned this earlier is consistency. and early on, I was inconsistent with the frequency of conversations I was having. It also probably hindered my ability. to really build a strong bond with someone, and also drive performance in the right direction as well.
especially with some of those individuals where, where that bond or that connection, wasn’t natural. Right? so on the topic of, of one on ones, I would suggest to any manager, like don’t push them off, don’t reschedule them, take them seriously, come prepared and, that’ll help you effectively not just drive performance, but really get to know your people.
Derek: [00:09:47] So every week structured, not always about work like that consistency and then just patience
Thomas: [00:09:55] it sounds
Derek: [00:09:55] like you’re saying, yeah.
Thomas: [00:09:57] You know, they can be out every other week if you have to have them. But the important thing is that they’re happening. They’re consistent and they’re well prepared. I’m just logging into a zoom calland not having anything prepared or any talking points, you know, someone’s not going to feel like they’re growing or developing, or are taking it really seriously.
so I think preparation is probably the most important thing and then consistency.
Derek: [00:10:22] Okay. So you’re part of a big org and you got promoted. Did you end up managing anyone who had been a peer?
Thomas: [00:10:31] I did, several people for sure.
Derek: [00:10:36] This is probably, this is the question that I get, I think the most, is like, how do you go about managing somebody who was just your peer and maybe is still your friend.
Thomas: [00:10:46] It’s a good question. I think there’s two things. First, when you’re in that individual contributor position, you should be carrying yourself as in fear in the next role. So I think that’s one of the most important things and that makes the transition much easier. therefore you don’t have to have these, really challenging relationships.
you know, you’re, you’re playing a step ahead. you know, that, that comes with being a team lead, you know, being really, You know, engaged in meetings, bringing ideas to the table, et cetera. but when it comes to, you know, telling a friend or managing a friend that used to be a peer, I think it’s important that right out of the gate, you actually draw a line in the sand and you don’t avoid being their manager.
That’s actually a mistake that I’ve seen time and time again, where someone is managing someone on their team, but isn’t managing them the way that they should, because they don’t want to be uncomfortable. Giving that sort of information or giving feedback or critiquing the way they’re doing things, you know, upfront, if you have a friend that you’re working alongside of, and you’re going to be their manager, you need to have that conversation and draw the line in the sand and just say, Hey, things are going to be differently and I’m not going to manage you differently than I’m going to manage anyone else on the team.
Did you have any conversations that were like, Hey, me at work is your boss and me outside of work, like. We’re friends or did you have to navigate through anything like that?
When I say I drew the line in the sand, I might’ve been a little bit more harsh than, than a lot of people. I, the outside of the work stuff, if it was a work event.
Cool. but anything outside of that, I didn’t really never occurred anymore. So I probably had some people that were work buddies. That could have become longer term friends, but are now just friendly acquaintances because, you know, I was really adamant about, about drawing the line in the sand and stepping away from anything that kid could impact.
Ultimately not just my performance, the team performance and company performance as well.
Derek: [00:12:52] It’s a hard decision to make.
Thomas: [00:12:55] I agree.
Derek: [00:12:58] but it’s a good one. That’s like, it’s a mature decision. As hard as that is.
Thomas: [00:13:04] Yeah. When I, when I went into Yodle, let’s say, you know, I didn’t lose sight of the mission, which was growing my career and that to me was, was paramount over, you know, the longterm relationship, of a coworker. You know, these are new friends, obviously I want to be friendly, but at the end of the day, if they can’t handle, you know, being, being acquaintances and, or just being friendly peers and, and that kills, you know, any sort of relationship, I think that’s OK.
if you do want to continue, you got to do the right thing. You have to do the smart thing and you got to be mature about it.
Derek: [00:13:41] Yeah. That’s a great example of how to do that. so what was the hardest thing for you about transitioning from, from individual contributor to peer or I’m sorry to manage manager.
Thomas: [00:13:53] Yeah. So pretty quickly you realize a year in a position that you have to make some really difficult decisions and, and ultimately in a lot of cases, especially at some of these cutthroat. companies cover sales organizations, where it’s like, you know, you got three months to perform or you’re out of here.
you’re ultimately, you know, in charge of someone’s livelihood and their success, actually, it really very much depends on your competency, in the role and how effective you are. And at the end of the day, You see so many salespeople fail. I’m pretty adamant. I’m a firm believer that, you know, if someone comes in and they have effort and they have a certain element of grit, you can eventually become a strong performer, but you need a few things you have to put in the work.
you can’t lose sight of the end game. You can’t lose belief. and you need a manager or a mentor at the very least that that has your back. And, and I can guide you the right way.
Derek: [00:14:57] what, what’s your super power as a leader?
You know, a lot of people that know me, if they heard this, they’d probably laugh and, and potentially not believe me. but, it’s empathy. You know, if you want to be effective, you want to keep people around. You gotta be understanding. This is also obviously you noticed Derek, this is a really important trait of a really good sales, professional.
the best way that you can close the deal is being empathetic. So only way you’re going to get someone’s guard down so you can actually figure out what’s actually going on. And, and, and shut it down and move the deal forward. But I think empathy is extremely important if you’re in any sort of leadership position, if you want to be successful and if you want to keep people around, I think the best advice I was ever given the first day I officially started as a manager.
my director of sales, his first bullet point on our, on our meeting agenda was assume best intentions. And, those are words I live by. Those are words I echo to people around me all the time when something happens. And, yeah, I think that is, one of the most important pieces of advice that I’ve ever received as a manager was just to assume best intentions and, you know, ultimately be empathetic.
Can you think of any situations where, like the assuming best intentions maybe sort of saved the situation.
Thomas: [00:16:24] it happens it’s almost every day in some way, shape or form. yeah. Yeah. Thinking about Roe issues that crop up, you have one, a furious at another aid because they think someone’s stealing their leads or crushing on their territory.
Right. And they’re furious. They come to you that they’re pissed off. Assume good intentions. You cool them down. You investigate all of a sudden, that’s not the case and you cool things down and those peers are connected and fine again. Right. That’d be one example as a manager, you know, there’s various other examples, you know, so, and so has X, Y, and Z going on in their personal life, they miss three or four days, and haven’t been as effective as opposed to getting pissed off at them.
Just ask them how they’re doing, what’s going on, what happened? you know, As opposed to jump into any sort of conclusion. So it’s a that I’ll tell myself on a regular basis if you know something. Yeah. It gets my bloodline a little bit. You take a step back. Yeah. That’s in good intentions and you know, people, you know, if you hire the right way, should have genuinely good intentions in the first place.
Derek: [00:17:38] Yeah. It reminds me of, I had a similar situation with. It was an AA who came to me and said, Hey, this rap is just like, is, did this thing for unknown reasons. That’s what he said to me. This is my Slack. And I was like unknown reasons. Did you just, did you ask him the reason? Well, no. Do you mind doing that before? Coming to me about like, it’s probably a perfectly good reason. Like he probably just doesn’t know.
Thomas: [00:18:04] That’s funny. You just brought up the. The biggest one that comes up every day in today’s world, as we’re all working remotely Slack, you can misread messages as in Slack and take them out of context so easily that I’ve had a cooldown multiple situations because.
You don’t understand where someone’s coming from via Slack, you get a short message. You can turn around and be like, you know, what the hell does that mean? Right? It’s like, there’s no, there’s no emotion behind what the other person’s saying. And they could be generally they come in front of a good place.
So shoot. Yeah. Slack is one of those places where I would advise everyone to, to assume good intentions. And it’s probably, someone’s trying to get you there.
Derek: [00:18:53] It’s dangerous, anything written, it just, it removes the tone. It removes like there’s so much more information, like embedded in tone and body language. Let’s make sound so easy. Yeah. Alright. So what is something the thing that our listeners could do today? To improve their chance of getting promoted to their first manager gig
Thomas: [00:19:24] perform, always perform. Okay. no, I, I joke, but, you know, step one in getting promoted is being, you know, a strong performer, right? Yeah. But beyond that, is not just perform, it’s perform with quality and. You know, it’s really important, especially at early stage companies, you know, sales performance is great, but not doing so in a way that’s aligned with the company’s expectations, the process in place and ensuring that you’resetting proper expectations for your clients.
That is everything I’d rather sacrifice deals all day, and lose out on some, some revenue. If I know we’re bringing in quality deals, And the reason is it’s so important for the company from a branding perspective, to ensure that there’s a strong reputation there, and it will make or break you, when it comes to, you know, longterm success within the company.
So it’s not just performance, it’s performing with quality. I think the other thing I would say is being engaged, being engaged with your team, sharing ideas, helping people around you, That is, that is really everything. Those are the traits and characteristics that any director or VP or CRO wants to see, when they’re thinking about who is that person that I want to promote, you know, no one wants to just promote the lone Wolf, you know, high performer.
That’s, that’s never engaging with anyone or really proactive in terms of how they might better the business,
Derek: [00:20:55] right? So you get promoted you’re in their role and now your job is to help people. That’s the first time you’re helping somebody’s steep learning curve.
Thomas: [00:21:05] Yeah, exactly.
Derek: [00:21:07] is there anything else that stands out to you when you’re looking at somebody, you know, that you might be considering promoting?
Thomas: [00:21:16] Yeah. It’s really important to me that, you know, this person is now going to share, you know, let’s say if I, if I’m stepping up and putting someone in. Under me, right. This person is now going to be my voice. Therefore I want their actions to be very much aligned with my general strategy. Now they can make tweaks and, and have a different perspective and, and, you know, Take their own stance on certain things, but generally speaking, I want their process, their framework on, on how they get stuffed on and how they mold people to be rather aligned with how I think about things as well.
So what I would say is, you know, get really close with your manager, get really close with your director and make sure you understand and make sure you understand very clearly. their general philosophy on how they want things done. because without that, I’m never going to feel really warm and fuzzy about putting someone in a managerial role.
Derek: [00:22:14] Right. So this person’s going to be an extension of you, so you’ve got to be able to trust how they’re approaching the problem. Exactly. Cool. That’s great. alright man, that’s everything I’ve got. Thanks so much for coming on and sharing your experience and your wisdom with my audience.
Thomas: [00:22:32] Cool.
