Being the CEO of You

with Bryan Elsesser,

VP of Sales at SaaStr

In this episode, Pete is joined by Bryan Elsesser, VP of Sales at SaaStr. The two discussion challenges of selling in today’s climate, owning your effort in sales, the context for hypergrowth at successful companies, and more.
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Key topics in today’s conversation include:

  • What is the biggest challenge of the last six months (0:30)
  • Helpful tips for selling to today’s customer (4:50)
  • Bryan’s journey in sales to where he is today (10:08)
  • What is SaaStr? (19:55)
  • The context for hypergrowth in a company (23:35)
  • How Bryan’s interest in real estate helps his SaaS career (27:32)
  • What does SaaS(ramp) mean to Bryan? (36:10)


The SaaS(ramp) Podcast explores how tech leaders scale from product adoption to enterprise success. Learn more at


Pete Thornton 00:00
All right, welcome back to the SaaS(ramp) Podcast. I’m your host Podcast Pete welcoming Bryan Elsesser to the show today. Brian is VP sales at SaaStr. Happy to have Brian on. Welcome to the show.

Bryan Elsesser 00:17
Hey, thank you Podcast Pete. Pleasure to be here.

Pete Thornton 00:21
I should probably tell you on podcast Pete before we actually jump on and start podcasting.

Bryan Elsesser 00:25
I’m ready to rock and sounds good. Yeah, love it.

Pete Thornton 00:28
Got a very interesting person today. Maybe we’ll do the hobbies and background pieces at some point. But let’s dive straight in and offer some value for our sales leader straight up right thing year we’ve been in, we’re kind of rounding up coming up on fy 23. I saw a couple posts you put on LinkedIn recently about things like, macroeconomic environment, etc. But all that taken into account, what is maybe the biggest challenge you’ve seen in recent times, maybe past six months max?

Bryan Elsesser 00:56
Look, I mean, I think there’s no if ands or buts about it. I still don’t know what I would call. I don’t like using the R-word. So I don’t try to use the word recession ever. Because I think it’s just a bad omen. But that said, I do think that it’s very evident that people are buying differently, right? You know, they’ve been buying differently. So let’s just take a step back and identify the fact that when people are purchasing software, or purchasing anything, right now, they’re taking extra minutes and extra, like moments, to understand what it is that they want to buy first before they even engage. So do a lot more research. Right? We know. But additionally, now and in that macroeconomic environment, you’re not seeing people make spend, without having a lot of thought behind it. And I do think that means that there is more onus on the brand’s right now to make sure that your best foot is put forward before they even engage with your team. Maybe three years ago, I used to train my team that when someone is on the hook, talking about your product, whatever you do not disclose too much before you can get them on a call, I used to like, like, talk all day about it. I’m gonna call Ken, I’m gonna call you want to come on the call, you know, I still think you want to get people on calls. Because when you get them on a call, you can overcome any objection, you can talk through any problem that they may 1 see. But I also think right now you’re seeing a lot of movement on different software that’s out there to try to get the product out at the top of the funnel. And I see that helping educate buyers more, which is actually making the sale somewhat easier, but more educational, more value driven. When someone joins a call, as opposed to saying what do you guys do? They’re saying I have this specific problem I’m hoping you can help me with. It’s a very different buying cycle. And it requires different pieces. So you have a lot of brands out there reprise in Nevada IK. And there are these brands out there that are creating for software companies the ability to get your demo live out and in the open first and foremost, right. And that’s like, and there are just two brands of many they’re doing this, but it’s just an example, right of the type of software that’s necessary, really, for brands to help stand out, and maybe get a little bit more education out in front of their buying cycle.

Pete Thornton 03:17
Okay, so if I’m hearing you correctly, because of what’s happening of late, you’re kind of seeing this rotation over to more customer education on the top end, like trying to offer more value upfront, even if it’s not even on a live call, just like whatever you have to do digitally or the advancement education is never dissipated, right?

Bryan Elsesser 03:35
It’s always been at the forefront. I remember I got started in sales back at TNT like I don’t know, it eons ago. And I remember the first class and sales they taught us is like, you need to educate your customer. But 67% The deal is already done before they talk to you. And then that went into the next training. It was like 81% of the deal. And then the next one was 84% of that. And that leaves the number always seeming to go up right? I could never like and so today I just assume that the deal is done before they talk to me, I need it. My job is not to get in the way. Right? That’s it. Just keep getting away from the deal. I’m here to educate, help overcome any sort of fear, or like potential objections internally, maybe understand how budgets are allocated, and maybe see if there’s some things that we can tie they could benefit from, they’re not even thinking about it. That’s the piece. It’s how do you take one need that they’re trying to fill but then other really sticky things to it to make it so that they just never can lose you. And the best software today is doing things that will make it so their customers can always use it. They’ll never lose.

Pete Thornton 04:43
Yeah. Okay. And just not to like overly stay on question number one, but any like tactical points like if anybody’s trying to make a pivot to more customer education or like, you know, the rallying cry was sales, onboarding, like that’s all I would hear about as high hiring, right and you still hear a lot of that just because the it’s like Series B has a sales we speak to a lot, but but now it’s sales efficiencies like, hey, we have this team, we really want to drive them to quota and beyond. We’re still hiring but we’re not hiring it 3x The headcount like that these things have modified slightly become more sane probably wouldn’t be the word, you know, hypergrowth SaaS, but what kind of things might they want to consider doing? Is it just all about their digital connection with the customer like revamping the website, things like that, or, you know, if there’s a practical tip?

Bryan Elsesser 05:33
From the brand itself, or from the salesperson?

Pete Thornton 05:36
Well, you know what, let’s do it harder from the salesperson harder, but like, let’s put whatever is in their control that will probably be helpful.

Bryan Elsesser 05:43
Like, because we could go on for years about the brands what they need to be doing right now. Honestly, salespeople right now, you notice, right, first off, notice, the brands, large and small, are doing layoffs, let’s just call this out. It needs to be get out there, like brands large and small. There’s no hiding that fact. I don’t think though, that is indicative of SaaS declining, or that this is Going Ape or that we’re in this major hurt. The reality is that during COVID, we were in a booming market where we were also simultaneously hiring Crazy, right? Like it was when we rephrase that, because it’s not exactly true. At the beginning of COVID, there was somewhat of a booming market. Okay, the market took some hits once COVID got started. got underway, right? Like we saw that. But still people were over indexing and hiring, they were reinforcing, VC was high, there was a lot of investment happening. And so when you saw a lot of hires, a lot of hiring a lot of hiring, so a lot of teams grew up. So what we’re seeing right now, right is people making sure they’re tightening their belts, and they’re just making sure that they’re able to succeed long term. So salespeople, if you want to be successful in this market, the one thing you can do is realize that you’re an owner of your day, and you’re an owner of your domain, okay. And I’ll go a step further, you also need to be an owner of your own business. And so, what I mean by on the surface level is you cannot be you cannot be successful right now, in this market. If your ego is attached to the brand that you work for. Right, you need to be attached to your own brand. And what I mean by that is you need to be intact and in check with yourself as CEO of, whatever your name, you need to be the CEO of it. And that should help direct you is that every day when you wake up in order for to be super successful to be knocking it out of the park, what is it that needs to do? As a business to execute? Okay, so like reframes the mind out the gate? Second thing is ownership. Right? So, okay, so if you’re going to be CEO of your own brand, what kind of ownership? Do you really want to be? You want to be a passive owner? Right? The company just hands it in, and I think it’ll work out? Or do you want to be an aggressive, mindful, tactical owner, someone that’s coming in every day, with a laundry list of items that they need to get done, and holds themselves to a certain standard of excellence and performance. Now, the best business owners I’ve ever met hold themselves to that standard, the best salespeople I’ve ever met hold themselves to that standard. And so I think that’s a really big thing. And it goes a step further, I’ve never met a business owner that checked out at 5pm. Right? Like, I’ve never met a business owner. So at least a successful one. I’ve been working business owners in both small mom and pop shops up to, you know, large scale SaaS CEOs. I’ve been working with business owners for 15 years. I have never met a business owner. That was like, five o’clock. That’s the bill. See you tomorrow, folks. It doesn’t work that way. You need to be mindfully obsessed about your craft, and mindfully obsessed out to get and mindfully obsessed about the work that you’re putting in every single day to execute. I need to hear that advice. Right? Like, I need to hear it every now and then. We’re not all perfect. You shouldn’t wake up every day being like, Well, that wasn’t mean today. Okay, well, then, every single day you wake up is another choice, right? You made the first hardest choice, which isn’t good, either. Bad. The second hardest choice is to understand what you’re gonna do that day. accomplish.

Pete Thornton 09:20
No, I was hitting the third person who was like day domain and an ownership business, your business essentially. Yeah. So that that totally loved, love, love anything that comes in threes and that separate them out. But that other phrase that you said, we rolled it all together, and it could be a little bit like, if you know what you’re needing to do if those days and business pieces are already inside of you. And it’s just like that little kick in the pants. It was mindfully obsessed, mindfully obsessed. Is this good? That’s because it kind of gives the duality of it like yeah, don’t go blindly. But like, do go.

Bryan Elsesser 09:54
Be mindful, right? Mindfully obsessed is the right way. I think it’s the right mantra. Anyway, In any way, I come up with a few, that’s at least one that makes sense to me. Makes sense to,

Pete Thornton 10:05
I’ve let go now, that’s cool. That kind of hits that second thing. So let’s, I’m going to roll straight on. You mentioned at&t, so maybe we can go through that but your VP sales at SaaS are now we’ll hear about Sastra in a second. I’d like to know a little bit more about it because it’s different , it’s a community. A little different than just like hyper growth, SAS startup, you know, most people are aware of, but we can back into it. But what about you? What personal and professional experiences kind of bring you into the VP sales role, and especially at a company like Sastre?

Bryan Elsesser 10:33
I think it’s a lot of dumb luck, right? I mean, honestly, vitamins, I think luck is based on work. It’s still it’s dumb luck. I got my start TNT advertising solution selling Yellow Pages advertising and Google ads to local business owners, and did it as a way to actually fund the career that I thought I wanted at the time. So I was an opera singer, was trying to make it and had made it, but it was a thing where you just ran out of money. And so I was like, alright, what can I do to make money, like my degrees are in music and not going to be a music teacher right now. That’s too time consuming to do that and try to be a singer. And so I was like, Ah, I could sell stuff. I’ll just go talk to people. It’s fine. And so that was how I got into it. career, I spent five years at at&t, I spent after that I went to Yext for a little before they went public. And then after they went public, it was my first realm like taking a SaaS product, and building a team behind it and sales development. And I spent a lot of my career in outbound sales and building up an idea and understanding of process and hiring and what works, what doesn’t work, different frameworks for different demographics. And kind of refined this over time. And, and so after Yext went to E marketer for a little bit before their merger with businesses, and then was that aircall for a little while, built their app on program. And then right after the air call, I took a few minutes, a few months to kind of regroup myself and decide what I wanted to do next. And a friend of mine introduced me to Jason Lemkin, who’s our CEO and founder at Sastre, and Jason took a chance on me as a stretch VP of sales. And it’s been, honestly, one of the most rewarding parts of my career.

Pete Thornton 12:29
Very cool. So there’s a couple of cool things in there. Like, my, my cousin does lead a team cybersecurity for 18 t now, and so I’ve like watched her over 20 years and like, kind of like, the training that they receive, like, if you’re hyper growth or like SaaS, or I mean, I start up minded like you, you might not stay there, like you did not stay there. But the foundational programs that they put you through the fact that you could rattle off those statistics. I’m like, I didn’t hear those statistics when I started. You know, they’re like, I don’t know, we don’t know, why don’t you call people and ask them about those statistics, you know, like when you’re hitting the phones for SaaS. And then you mentioned Yext as well. And I only mentioned that because there’s an unusually high number of people who have literally been on this show that have a background at Yext. Yeah, it’s like we get a little mafia happening here. So and then I see that former founder, like putting out a new thing now. And I’m just like, Yep, you’re gonna do it again. So there’s something there’s a culture that brews that kind of seems to spin off these next generation of leaders, which is cool, cool to say, part of

Bryan Elsesser 13:29
culture is a very unique thing, right? I remember being at TI and really wanting to get in software, I met all these. I was working in New York City in Manhattan, and would meet all these people my age, and they would work for this company, or that company. It was like, everything ended in LOI. I was like, Oh, we John Lee, you know, like, it was like, every, all these companies, they’ll lie and I never understood, I was like, why is it all a life, but I was enamored, and you know, and I would talk to people, well, what do you do for them? How did you get into it? No one ever really had a story that was like earth shattering to get into SaaS, and I wanted to get into it, you know, and they like, it was like, how are you doing it? Like I’m trying to get interviews. And I remember making that transition. And Yext was a really natural one because it was helping local businesses. And so it was like, I was already working with local businesses at that transition, a lot of being a real natural step into SaaS and was worked out in that way. But yeah, it’s really interesting. Like when you first look at SAS, that startup mentality is something that I didn’t when I first got into SAS, right, I didn’t know you needed it. I think it’s where some of the grind Dias mofos out there, right. Like there’s just, you really have to dig in. There’s no way to be successful in a startup without digging in. You’re working with brands that no one knows who you are. You’re right. For the most part, don’t you know in some cases they don’t even exist. In some cases they do. And you’re a competitor. In some cases, they don’t, you’re a category creator. And that’s crazy, that’s easy to tell the story of why they care, you know, like that’s. So there’s a lot there. And it’s very interesting. And it takes a certain amount of prudentness for a certain type of person to work. You mentioned the year’s time in the title. And what I think is very interesting is that these days, I go on LinkedIn, I do a lot of recruiting and a lot of interviewing. But these days, I go on LinkedIn, and you see someone’s career trajectories. So far less common now. And the timestamp of you know, over three years, like I, I’ve just a year and a half is what I’m seeing company to come in the company. And I have a whole theory there of why this is awful. But I also have to understand why it’s happening. Right. But I have a whole enormous theory there. That’s awful. Yeah. And, and, you know, in a way, I think, is workers who had regrets. But I think in a way, as workers, we’re getting away from some of the things that have worked traditionally, over the years really well. And that has helped some of the most successful companies in the Fortune 500 be successful.

Pete Thornton 16:14
Yeah, that average tenure, like, you know, it looked at first it looked like it was just a sales thing. And you can kind of understand like, you’re in a ramp year, okay. And then you made it or you didn’t, or something, you understand a little bit more about the company. And then whether it’s a push or a pull, and halfway through that next year, or somewhere along the lines, it kind of seems to dissipate. See it?

Bryan Elsesser 16:34
Yeah, I mean, I see it in engineering, I see in marketing, I’ve seen it, it’s like, it’s whether someone got bored, or they decided to make a change. It seems to be a stark thing, anything that you know, you’re going to spend X amount of time before you transition, I think the average tenure of a VP of sales and SaaS was 18 months or something insane. You haven’t even warmed up before you’re out. And so, but I truly think that my father has been at his company over 30 years. And, you know, and I can’t imagine he’s always done the best work. And I can’t imagine he’s always done the worst work, right? Like, there’s going to be ebb and flows here, ebb and flow years, right. But the one thing about that company that he works for out here on Long Island is the people that they have, they value them, and they do what they can to retain their people, so that they don’t go elsewhere. Because they need their teams in order to be successful, the company and for them. And I met their founders a couple times, through my, you know, upbringing and growing up, was that they, the founders came to my grandfather’s funeral. Okay, like, they’re right. And I’m like, I went up to him, like, you know, thank you so much for being here. And they’re like, Are you kidding? You guys are family. And that’s, what’s that? What’s the power and that’s tremendous. I mean, I’m a kid, I’m not, I’m removed from it. I can’t even do what my father felt. Right. And that’s what I think is super powerful. And it helps me shape my frame of mind about that brand even though I want to talk now. Right? Remember, the founder of that company called My, the original owner and founder of that company call my dad on weekends back when I was a kid and my dad got so frustrated about something? And I have this memory in my head, but at the same time, I know my dad wouldn’t take back the time. Yeah. So

Pete Thornton 18:27
do those are yeah, those are different. This highly contrasted to fast SaaS, and then remote and then this transition where you never maybe even saw somebody or so much shook their hand in a location now that is very much that is very much different. As in as in like, it’s just, it’s an hour north of Charleston. And so a lot of the people who are working nearby are actually working in a kind of like a, I don’t know, it’s a lot like building and construction and things like that. And that’s the mentality behind it. When I tell them what I do, they’re like, where do you go? I’m like, to me, to a guest bedroom on it, or like an office, you know, so it’s a different thing altogether.

Bryan Elsesser 19:04
Yeah, I mean, you know, I go off to Dunkin every day. I’m a Dunkin drinker. This episode has been brought to you by Dunkin Donuts. Dunkin drinker. And every day I go up there and you know, they know me My name’s and every day and they’re like, Hey, Brian, and I mean, they’re in like, you know, this is type of sweatshirt, but wear a hat and a sweatshirt to work like, this is what I wear to work. There’s nowhere else that really works, right? Like I talk to people that still have to get dressed up every day. Go to work. I mean, you know, I don’t know. We’ve redefined work culture a little bit here. But it’s anyway, we’re way off topic of what you want to talk about today. But this is interesting.

Pete Thornton 19:43
Podcast Pete hasn’t met rabbit hole, Brian and we’re having a good time.

Bryan Elsesser 19:50
Asked Exactly. A Rambler, the Rambler, they call me so.

Pete Thornton 19:54
So like everybody, not everybody, but my audience will know SaaS Sir, but like, Would you tell us a little bit about Sastre? And then like, I mean, maybe the Genesis where it is today, because this is a massive, massive world largest, as I understand it, are SAS founders, and execs and things like that. So yeah, what are you guys doing now? You just got back from London, just tell us a little bit about Sastra bigger. I

Bryan Elsesser 20:19
I think you nail it on the head. We’re the largest community in the world for b2b tech execs and entrepreneurs, and founders. And we’re founded by Jason Lemkin, who if you don’t know Jason, first off, go follow him, his content is unbelievable. But Jason was the founder of EchoSign, which Adobe then acquired and became Adobe sign. He had been a multi founder. He’s done this several times. And he’s also the founder of Sastra Fund, which is invested in 28 different services that have been successful. And so, you know, Jason’s whole story here is about helping the founder, he started Sastra at a time when no one was helping the founder, right? He wished he had the advice as a founder at Adobe EchoSign. Before doing so, he wished he had the advice, right? And it wasn’t there. But now Jason is that generator for founders and execs, and helps facilitate a network of the best and most likely hottest, unbelievable, big tech execs and entrepreneurs in the business come together and share best practices for SAS founders to be successful in scaling their business from zero to $100 million. And I think that’s an incredible mission. It’s, I’m sure, a thankless mission at times. But ultimately, it’s you who should see the community. It’s the amount of content, the amount of people that reach out with just sheer admiration, and thanks to Jason for the work that he does, and for the team. It’s unbelievable. Yeah, him too, in between that, right, I think, our largest vessels for creation of new content, as well as getting our content out there. And also, working within our community, our events, we’ve had a long tradition of building really, really top top of the line events. Our biggest every year is Sastre annual. It happens in the San in the San Francisco Bay area. In San Mateo. And it’s kind of like a SaaS festival, if you will take a music festival, sprinkle in the SaaS nerds and mix them up really well. Yeah, yeah. So that’s from September 6 to the eighth. And then our second largest show is sastra. Europe, disaster, Europa, you’re right, I was just in London, taking a look at the venue, but it’ll be in London this year, June 6, and seventh. And that’s just going to be an incredible show. You know, it’s, we find that we have so many different countries that come to that show, it’s really amazing to see the reach, right? For the first time, this year, we’re also going to do SaaS Drapac. And we’re doing it in February, in Singapore, and that’s, so we’re gonna, we’ll be out there for about a day and a half of incredible content and networking and meeting our community out there. So we’re, we’re reaching. So my team was responsible for talking to different businesses that are looking to represent those. Okay, and then on top of that, I’ll go a step further, just Yes, the question. Sastra has been a long term, longtime creator of content, listen. And we have different vessels that get that content out there. So our podcasts or newsletters, they’re super, super popular. We generate somewhere in the neighborhood of 3 million impressions every month through our different streams, which is pretty amazing. And so we have a lot of different avenues by which we help companies get in front of the community.

Pete Thornton 23:32
Okay, that’s awesome. Okay, awesome. Yeah, I love that. So like, you do interact with a ton of dives in the space between zero and 100 million. There’s a lot of technology happening right there. So in general, like, when I because cuz Sastra itself, it has this idea of morality, like you have this like community, one person tells another long before I really knew its answer was I was getting like these LinkedIn, you know, like a little, a little ping a little, or sometimes through a text thread of some former buddies of mine from like, my first SaaS organization that we still, because we were in an office together, we’re all still big buddies. You know, like, imagine that. And then, and then it would just be like this little, hey, here’s this. Here’s that from Sastre. So like, I know, it can spread like that. So the companies, you see, like, what’s the context for hyper growth behind it? Like, why is it that a SaaS company might just like, just absolutely blow up? Like when you see what’s happening? You know, why is it that they would get more popular than another thing?

Bryan Elsesser 24:30
There’s a lot of reasons, right? I think it’s a hard question to answer, ultimately, because there’s probably a lot of companies that have that virality, but there’s also a lot of companies that are extremely viable, that can do really well and then don’t. And so I don’t necessarily know outside of execution, right. Some teams are really good at execution. Some teams understand, you know, when they can exploit a gap, right, and how to really take advantage of that within their product, but that additionally getting the right first few hires in place to take that message and bring it to the masses. And that it’s a, it’s a really interesting piece. And second piece to that is like making sure that you have the right partners along the way, you know, if you’re going to bootstrap it, that’s a decision. And how are you going to scale as a bootstrap company? How’s that going to be different from VC? If you’re going to take VC money? Who do you want to take money from? And if you’re going to take money? How are you going to stack the cards in here? Because, you know, you couldn’t, could really hurt you. But it’s a hard question to answer because ultimately, I see it firsthand. There are a lot of different businesses and companies out there that have truly endless possibilities for success and eating and some that take massive amounts of money. And but they either implode or do things that don’t work out. And so, you know, it’s a little bit of a gamble when you’re working in SaaS. Okay, I wouldn’t, I wouldn’t say that there’s one way and look like venture capitalists. Some of it is doing this every day, analyzing businesses and understanding what they’re doing is going to have a more refined answer, right? Well, I think they would say, at some element, there’s

Pete Thornton 26:09
a little bit of guesswork lately, and so many, many variables, so many different things, you can kind of look at FTX.

Bryan Elsesser 26:17
Look at FTX. It’s a perfect example. Right? You like to laugh, but like, someone lost $200 million on that, like it has an investment, right. That’s a large investment to lose. And it’s a company that just imploded. It just imploded. Right? And like, so, there are bets, there are bets in this business. And that’s the thing, and we don’t always get it, right.

Pete Thornton 26:42
Yeah, for sure. Yeah. Okay, then I got something on the other side. So first of all, maybe for context, if enough people check out your LinkedIn profile follower for you have this you already mentioned, like professional opera singer, which is just starting to check people’s boxes of like, oh, we unique

Bryan Elsesser 26:56
volunteer, firefighter, and your fire. And then going through this, you’re gonna make a lot of people feel weird. Oh, like, what

Pete Thornton 27:05
are you doing with your Saturdays basically, like, Yeah, so like, I but then one of them was real estate enthusiast. So I have a question for him. Because I find a lot of people in software. And this is just an aside, this is like an anecdotal, like, I’ve looked at a lot of LinkedIn profiles over the years, mostly as a BDR, early days, but like, now I can like scan them and just like, absorb the information, kind of get a sense of like, I know this person. So it’s okay, if I call them, you know, that I think that’s what I’m trying to do for my soul. But, but like, the real estate thing, like, and this is just, this is like, based on what you just mentioned, is it there’s such a lower return on real estate unless you have these big booms? But is there something like, I have been in the land of ones and zeros all day, but I can go touch this brick and mortar? Is there something about, like giving you a yin to the Yang or anything like that? Or is there something about real estate that you like? And do you think it’s a contrast to what you experience in your SaaS day to day?

Bryan Elsesser 28:00
Interesting question. Interesting question. I’ll put some clarity behind it also tell you how I think. I think if you’re I didn’t go to school for business, I don’t have like business operations, ground or anything. My experience in sales and building teams, that’s my business degree. And in some would say that it’s equivalent to a master’s depending on who you’re talking to. Right. And some would say that’s, you’re not worth anything. So I don’t know, I think my experience in building teams, leading teams, working with businesses, understanding that was ones and zeros, just talking, have helped me understand that, like, one of the best things I can do for myself, is have alternative forms of revenue, right? And like, like, how am I thinking of investments for the future? If you’re a salesperson, and you’re good at your job, you have plenty of capital that you need to think about. How do you invest in your future? Is it just a 401k? Could you do things that are a little bit riskier? Maybe you’d see a bigger return on that you’d be working with a financial planner is going to help you get x returns. One of the things that I’ve always been interested in so take a step back, after I left the X i didn’t i was gonna come to Jesus moment with myself. I didn’t know if I wanted to be in SaaS, to be honest, I knew that. Like, I knew I enjoyed my time at x very much. And I knew that I was excited for what I was for my future, but also like, I was still young enough where I just didn’t know what I wanted to do yet, really. And so I had to come to Jesus moment. And one of the things that I decided to do was go get my real estate license because a friend of mine told me to do it. So I went and did it. Right. It was like, okay, I can understand, I think real estate’s interesting and you know, and Grant Cardones ads just started popping up like, Well, hey, you are rich in real estate, I’m like, oh, no, man, whatever, you know. And so I went and I went and just, you know, dialed into trying to figure out if it was something I wanted to do, what I found is that I love real estate. I think it’s very interesting at the time, it was a great market to get in. start making some investments. Right now, maybe not the best market. But it was the right time then to make some investments. I think what I found is it’s just a way for me to reinvest in myself. And I’ve made some key investments that are both property based and business based that are about, like, you know, what’s the long term return? And how does real estate play in that? And I think, ultimately, the goal there is to call myself an enthusiast, because I just didn’t lose YaSM for that. It’s like I’m spending any part of my nine to five.

Pete Thornton 30:33
Right, right. Right. Right. Okay. I just see it a lot. And I see it, like, posted about a lot. And almost like, the former post was about like, some kind of like, I don’t know, product lead growth, you know, like, monthly active users. And the next one’s about like, Hey, did you know the interest rates are dropping? Now would be a great time to, by the way, that’s not a recent post I’ve seen, but it offers a lot.

Bryan Elsesser 30:53
Yeah, well, look, I mean, just think any posting that you’re gonna do needs to be relevant. So at least when I try to, or just, it’s, what’s that’s it, because nothing I used to post every day, or every other day. And I was like a regiment and it became very tiring. And so when you’re trying to be successful, the thing is, you have to let certain habits go. But whenever I post, it’s very tiring. I think the most important post right now is the want to get an AWS. All right, I put up a post that said, Hey, who’s hiring, right? We’ve seen a lot of layoffs, who’s hiring. And we’re, we see there’s hundreds of comments on there, which is awesome of people that are hiring. And so if you’re listening to this, and you’re thinking about what do I want to do next? It’s, uh, you can go find me on my LinkedIn post as there are a lot of different job postings, and a lot of people they want to help. Yeah, that’s good. That’s good. Because all you do hear about is the rush. Yeah, exactly. It’s also a really good point to say yet, people are going through some downsizing. But at the same time, here’s all the companies that aren’t, here’s all the companies that are reinvesting in growth. And so there’s still for every company that’s downside is love it too. It looks like they’re reinvesting so well, it’s like,

Pete Thornton 32:05
I don’t really watch. I’m not much of a news watcher, unless it’s because somebody will tell me about the news. It’s actually pertinent, like, that’s a good way to like, keep in like, common lockstep with somebody like just a personal relationship, they’ll tell me, and I’m actually interested, because I don’t know. But my whole thing is, is like, because nobody told me about like, nobody told me when I commuted to the office, and I made it alive. It was just like the one wreck there that’s what you see on the news. So we are seeing a little bit of that. But it is an idea for maybe like sales leaders to to pivot some of the message to make sure that it’s not just the bleeding edge of like, you know, reckless, gross, like that you’re seeing your product around, sometimes it’s around maybe some of the sales efficiency pieces, or that seems smart. Anyway, that seems like you could get mindfully obsessed around that topic. And don’t make your 300 dials.

Bryan Elsesser 32:49
I mean, there are a few of those. But yes, I agree. 100%.

Pete Thornton 32:56
So you’ve had a cool journey to get to where you are and as most like SaaS journeys like it is not that you did not like to go to school, but like from the age of six, he was trained as a, you know, like, this wasn’t necessarily the case.

Bryan Elsesser 33:08
You know, streaming was being a Cub Scout and going door to door selling candy bars and my mom is driving along the road as I’m knocking on the door. Hi, would you like to buy a candy bar? And that was me. Like I figured I thought I always won the award for Most candy bar sold. And, I would be out there for hours, I’d wake up with Mom, what’s goodbye, let’s get some more candy in school, we had to raise money for senior trip again, it was like, Let’s go sell candy bars. I was out there. My older brother, okay, benefited from this because he didn’t want to sell any candy bars, and he wanted to do a senior trip. So he hired me to sell his candy bars. And so I sold these new candy bars. And so he could go on a senior trip. So I’m not sure I get the benefit of that deal. But regardless, like at the time, it just was easy for me. I didn’t mind it. And I think that’s what I applied early on. When I was like a man, I knew that I could be a salesperson. There’s probably something wrong with me where I really don’t care about going up to a stranger and talking to them about any random old thing. And there’s no mechanism in me that says that’s not normal.

Pete Thornton 34:11
Dude, so yeah, so somebody else will create the product and you will take it door to door like, rather than to the Yeah. The CRO

Bryan Elsesser 34:20
If that’s, it’s, you know, for me, it’s like, I probably will never be a product founder coding. At some point, if I want to be a founder, I will sell it. Like it’s got to take it apart. That’s the thing is just I think that you know, if you if you’re listening to this, you’re thinking about getting a career going. That’s somewhat in sales. You want to continue your career, you’re wondering if you should continue your career in sales. Just ask yourself people like people, ask yourself if you’d like to talk to people, if you’d like to, you could talk about anything, you know, I mean, if you just like to build relationships, we focus so much on selling the value of the product, how to sell the product. None of that really matters, right? Can you build an authentic model that people can Any, if you can, great because you’re gonna sell to the same people over and over and over and over again your entire career, take a bite and chew on it for a while. Right? Like if you identify that you’re going to sell to the same people over and over again, your whole career, how does it reframe the way in which you approach this job?

Pete Thornton 35:18
Maybe you’re selling arms to make sales. Yeah, a little more honey and less vinegar. It’s more stay in one position.

Bryan Elsesser 35:24
For a while, we were talking a little bit about consultative sales, there’s a transition that’s happening. There’s a transition, it’s you need to be able to build relationships. That’s it, you know, even if, like SMBs like the SMB sales, you know, the transactional, I’m on the phone with them have this product for $100 a month, I’m going to sell it right now. Like that sale, probably still have as much relationship build, they still need to trust you. Right and it’s this other establish some sort of trust on that call. So there’s still some relationship that needs to be built there. But those small SMBs aren’t SMBs forever and some of them grow big and so when they grow big, how did you first jumpstart that relationship?

Pete Thornton 36:07
Yep, it’s a good point. It is. Okay, this will be interesting because SaaS is in the name of Sastra as well. You are a VP sales so a lot of times speak to VP sales, but the name of this podcast is SaaS ramp Podcast. I’m in an enablement, sales enablement. So that means something specific to me but it seems to mean something different to every particular role. So you VP sales at Sastre what SaaS ramp means to you? No Wrong answer by the way,

Bryan Elsesser 36:34
What does SaaS ramp mean to me? Your Brand What does your brand mean? To me? Just that first first hearing is the question. Just verified

Pete Thornton 36:43
gut instinct for Yeah, for you and your particular location.

Bryan Elsesser 36:47
The SaaS RAM Park would listen to this if I was trying to figure out how to ramp a team up, grow revenue or understand how to grow my career. That’s kind of how I hear it. I’m in SaaS, want to ramp on ramp? What do I need? Nate? Okay,

Pete Thornton 37:02
so we went career we went, we went ramp as far as like, maybe like day one to do one kind of thing. And then, and then overall revenue, they’ll listen, I’d say that’s kind of like the three buckets we often hear and you gave them all three at once. So you’ve got the magic in the trees. We got the we’ve got that control your day control your domain, your business, we’ve got the SaaS rent means this dude was a magical right here

Bryan Elsesser 37:22
speaking threes. It’s a habit.

Pete Thornton 37:26
That is a good habit to have. There’s something magical about it. I want to study. Yeah, I don’t know what that is. But it’s just so helpful for an audience. Maybe it’s because you’re gonna jump on London and Singapore and have the will to say something and you want everybody and all the various languages to kind of pick up on it.

Bryan Elsesser 37:42
Remember, there is actually a large study behind threes here, I’ll leave you with this because I think it’s important. But there’s, it’s good for all the salespeople out there, listen to this, too. There’s a study on the power of three. And how As humans, when we listen, we hear things in threes different than we hear other numbers. So if it’s four or five, it’s too many, we won’t remember them all. If it’s one or two. It’s not impactful enough. I’m not gonna I’m not gonna resonate with it. But when there’s three, three of something, for whatever reason that sounds lockstep and delivery is always important, too. But if you can, three moments, three things, three pieces, you know, I just did it right there and three different beats like, that’s a powerful moment to help you or resonate with what you’re trying to say.

Pete Thornton 38:29
Awesome. Awesome. Yeah, intuitively that felt like it. But like, if there’s, I love it when there’s science behind it, too. And like when this gentleman

Bryan Elsesser 38:37
knows, that’s the weird thing. But it’s interesting.

Pete Thornton 38:42
So we’ll throw it in there in the show notes and everything. Like if people want to get in touch with you, obviously, you’re on LinkedIn, saw your stuff from yesterday, used to post daily and things like that anywhere else that people want to contact, you get in touch with you.

Bryan Elsesser 38:53
The best place to get in touch with me is on LinkedIn, I, even though I’m not posting every day, I’m on it every day. And so I’m in there, you message me, you can ping me, you can connect with me, I’m more than happy to help. And I think it looks like the big thing here. Okay. As salespeople, as sales professionals, the best thing we can do right now, for our profession is more like community members, we need to help each other. We need to be on call for each other, and support each other. And if we’re, if we’re, if we are doing that, then we can all navigate whatever waters are in front of us, micro and macro economically or not. We can all grow. And I think that’s really important to understand. We’re a community, and we’ve all been there. So you know, we all want to help. That’s the

Pete Thornton 39:41
That’s awesome. Yeah. Great message. Thanks, Bryan. Really impactful man of many talents. We’ll do another podcast on all the adjacent talents and where you could spend your nights and weekends as well. Ladies and gentlemen, for now, gray SaaS podcast. We thank you very much Pete. Great to chat with you. Thanks, Brian. Appreciate it.