the ups & downs in sales, business development, & executive leadership

feast on some hard-earned wisdom as we welcome our guest, a seasoned professional who’s weathered nearly two decades in the industry's trenches. from door-to-door sales to business development leadership in major startups, his experiences are a treasure trove of insights. he illuminates the harsh realities of the field and shares a real-life story of the challenging dynamics that developed between him and the newly appointed, less-than-supportive CRO.

sales isn't a path for the faint-hearted. it's a rollercoaster ride of intense emotions, requiring resilience and a knack for understanding what your prospects are really looking for. we dig deep into these challenges, exploring why making a great first impression can sometimes be paralyzing. we also turn the spotlight on the enigmatic world of business development. far from being a soft skill, it's a meticulous blend of art and science that's often misunderstood and underrated. we discuss the misconception that the younger generation can excel in this field with little to no training, and why it's crucial that organizations provide the right training and support for their sales development teams to thrive.

leadership is another key theme in this episode. striking a balance between focusing on tasks and people is a delicate art, and we dive into the concept of situational leadership as a potential solution. we also discuss the pressure of wanting to be liked as a leader and how to navigate the complex task of relationship building. whether you're a seasoned professional or a newbie in sales, this episode is peppered with stories, lessons, and tips to help you level up.

transcript

josh: 0:07

welcome to the disaster recovery podcast. i'm your host, josh santo, and this is the show where we reveal the untold horror stories and hard-learn lessons of software as a service startup life as told by the SaaSholes who lived through it. their stories about the managers, departments and companies they worked for will leave you thinking what a disaster. our mission is to help you bring order and sanity to the chaos you will undoubtedly encounter in your own adventures in sass. there's stories and conversations with our guests who have been there and done that in all aspects of sass from sales, marketing, product and more you'll get the tools and insights you need to recover from disaster. today on the show we're digging deep into the realities and hard work of good sales and business development. we're going to talk about how it's not as easy as you or as marketing or account executives or even chief executives might think. we're going to get into why biz devs should be viewed as a luxury by the sales organization and we're going to talk about what happens when the new cro is an ass. our guest has nearly two decades of experience in sales and business development and it started way back in his childhood, at summer camp, where arts and crafts turned into door-to-door selling. he learned value selling first hand at blockbuster of all places, where they actually created a role specifically for him due to his ability to sell rewards and memberships in the stores. now we all know that that didn't help blockbuster change its course. ultimately it shut down, but he did what he could. his time at dell is where he really honed his craft. it enabled him to develop processes and frameworks, to capitalize on his gift of gab, and it taught him to shut up and listen from time to time. since that early adventure into sales, he's led the business development teams at several major startups, helping multiple companies scale past the $10 million revenue mark, which is a critical milestone for startup companies. i'm excited to share his ideas, his perspectives and his stories. but before we get into the episode, a quick disclaimer. the stories shared on the disaster recovery podcast are based on anonymous, individual experiences at real companies. the goal in sharing these stories and these perspectives is to help fellow sassholes like yourself learn from each other, get a much needed sanity check and build empathy along the way. no specific company or person is mentioned at all. if a story feels like an attack on you or your company, well we encourage you to reflect on why you have a guilty conscience with that. on to the show now. you've got a ton of experience not just selling but connecting and talking with people, and it's something that i think you're very good at. you're very naturally gifted at the ability to not just communicate but to, i would say, adapt some of the things that you're saying to the person that you're talking to. i think you have that very naturally. so i'm really excited to talk with you about your perspective in the discipline of business development, sales development and sales, because i do think that you're one of the rare people in which this really comes together naturally for and i'm excited to hear about it- well, great, thank you, i'm excited to talk about it. i don't know if you do that about yourself.

guest: 3:46

i appreciate the sentiment, but i think it i mean it probably just comes from. i love talking to people in general and so just hearing what they're all about and then just honestly having conversations, and then i was like, oh well, maybe i could sell them something too.

josh: 4:07

you're also a storyteller as well, which is something that, of course, comes very much into play in sales.

guest: 4:14

yeah, i mean i have a, i guess, a very different background than maybe most other salespeople their interests in the arts and how to tell a story and then how to communicate that to people and where the points to hit on and what is meaningful to the audience or, in this case, in regards to sales, i was like what is meaningful and what's the value proposition to someone that's actually going to give a crap about it?

josh: 4:48

that makes a ton of sense and it's certainly in line with how i view selling and my time working in solutions consulting, dabbling a little bit in some activities that an account executive should take on, but as a solutions consultant who had no boundaries. i tended to do a lot more than i should have, so put it very much resonates with me.

guest: 5:10

yeah, that always comes with the tier. i mean, it's like the old group project thing back in high school. it's like there's always a one or maybe a few people who just didn't really pull their way and you're like i did everything. that's one thing that maybe people should tell kids when they're getting out of high school that shit doesn't stop. it does not stop. i mean, where do you go?

josh: 5:36

it does not stop. no, it is a tried and true principle of working with other people, period.

guest: 5:43

it's just who knew that people didn't really want to work yeah.

josh: 5:48

yeah, certainly, not me, yeah right, certainly.

guest: 5:50

i had no idea.

josh: 5:52

well, you've got such a great career across sales and business development. i would love to dig into that with you a little bit. i'd love to hear from you how do you personally define business development?

guest: 6:08

the business development was. i didn't really know about it until i would say, halfway through my career because i thought a lot of the actions or the activities that now i know that an sdr or bdr would normally do was just natural for a salesperson to do. but then to have that extension of a sales or is like oh wow, this is an interesting idea for me who's always done these things just naturally, like being basically the tip of the spear for a salesperson, or the sales cycle and the sales journey and then the customer journey. so you're the first impression for the organization. so that's kind of a heavy lift or a lot of weight on the person's shoulders. as soon as you call someone or the first time you meet someone you're trying to sell them and sound like a dumbo. then that leaves a certain taste in someone's mouth all through, like do i really want to work with that company if this guy or this person is not conveying the message very well or i have no idea still what they do? so it's a pretty important thing. but the whole point is obviously just to find potential customers and then to cast them on to someone who's going to be closing them, and then the part of it is that it teaches you one what your limits are in regards to sales, because, yeah, you're the first person, the first impression for the organization, but you're also the first person that gets told no. that teaches you a lot of things about yourself and how to build a pretty thick skin. if you can't take that over time, then you really have to come to terms with yourself. is sales something that i really want to do? this is, i would say, the sdrs or bdrs, normally the junior salesperson getting into, hopefully into their sales career, but i don't think anyone's above it. i remember first time that over time working for a company cole calling somewhere, talking to somebody, and i had a call that was. i ended up selling them and at the end of it they were saying oh wow, this is the best experience i've ever had with a salesperson before. i'm always going to buy this product and stick with this company and you're the best salesperson i've ever talked to. all these accolades, all these really nice things, no reason why this person had to say it well, thank you. next call, right after that, was you're the worst salesperson i've ever spoken to in my life. i'm never going to buy this product again. screw this company, and i hope you die or something like that, and i was like i can't do this. this is driving me crazy. but i was young, i didn't know what i was really doing yet, and so it's a tense. it could be very intense and for anyone not to like, for anyone sugar coated. it's like i was like no, don't be upfront with the people that you're hiring for this job, because i mean, it's so hot.

josh: 9:29

it can suck.

guest: 9:30

yeah, it can suck.

josh: 9:32

i'm curious how did you push through it, like those highs and lows of going? you're the top, you're the best, you suck and personally, as an individual, you should not have been born right or like that type of sentiment, that like the vitriol that comes from some people.

guest: 9:49

how did you push through it. okay, i'll say two things. one, to be honest, i actually quit right after that call. i actually walked out. i was like i threw out my hands. it was like 10 o'clock in the morning on a tuesday. i was like nope. and i seriously walked up and i was leaving. my manager was like well, i was a good performer, but just mentally i don't think i was there just yet. and looking back i think that it was like, oh my god, my life would be very, very different if i stayed with that company. it would just be kind of night and day i think. but i'm glad i did, because one i didn't know what my limits were just yet and i didn't know how to take that kind of reaction to me just yet. and i didn't have the skin or at least i thought i did, but i didn't have it that much just yet. personal things are going that way. when you're young to work for at the time it was a very large company. to be that young to work for an organization like that, you really have to kind of hopefully know what you're getting yourself into. but i wasn't really ready to start my career and do all those things just yet. what do you want? i just wanted beer and money. and so, after years of just struggling to be financially independent, to get a job that actually paid anything, but also, at the same time, really developing my skillsets even further, i thought that the gift to gab was just like i was going to ride that wave until the bitter end. and so, no, there are other ways. i actually do this, and there's techniques, i think, more than anything else actually listening to your prospects and customers, of who you're trying to sell, and really understanding like, okay, what is the value of them speaking to us? to begin with learned all those things after i quit that company, and it actually made me stronger because one then i knew, okay, what was the lowest of low that i can do in regards to sales, and then build my way back up, and it made me, i think, ultimately a better salesperson, because i was stubborn. i'm still stubborn, but i was stubborn enough to challenge myself and put myself through the ringer, which that's how i got through it. i don't recommend it to everybody, but if you want to have a hero's journey, you can go for it, but i don't necessarily recommend doing it the way i did.

josh: 12:45

i certainly crashed and burned in the first couple of tips i had as a business development representative. we had a special project going on at the company and i had no training or anything like that. but i was good at talking with people so people assumed like oh he's good at talking with people so he should be good with that initial, making a good impression. he knew what he was talking about. i knew the value propositions and all that stuff. i had all the things needed to do well yeah. but i had this overwhelming desire to be liked and it caused such a huge paralysis in the actual cold calls. because i personally, as an individual who tries to treat others the way that i want to be treated, don't call me, i don't want to hear it, i don't want anyone to try and sell me on anything ever, period. so, having that perspective and trying to go into cold calling where i'm thinking i wouldn't want somebody to bother me, why am i now i'm going to go and bother them.

guest: 13:51

it's funny you say that, because now i love being sold over time doing really pretty difficult jobs. after that company there was an experience i had with i did door to door at one point. at one point i was managing a team at the time and it was actually my first time managing a team. at that point one of my reps called me, crying. i was like what's wrong? this guy pulled a shotgun on me. i'm freaking out. i was like what? i got so hungry for him and i drove over to where they were, got a car and he was in his car crying. i was like who did this? this first time i became very mob bearish when it comes to any of my team members and i walked up to the house like how dare you? and i was yelling and he got the shotgun in his hand still and he was starting to pull it up. it was like you better get off my property. all you had to say was no, just no, thank you. that's all you had to do. but you had to be a dick and show your shotgun off. it's like well, this is going to be representing your dick. well, it looks quite small now in comparison. and so i was furious. and so i ever since then and i started doing cold calling for another company later on i then always started thinking about it. i was like, well, at least it's not a shotgun in my face. so when someone is telling me, screw you or you deserve to die and all these things, hey, at least you're not sure a shotgun in my face, that's totally fine. it's like now i feel like my skin is so thick that now when people are going ape and telling me i can't believe you're calling me or whatever it is and giving me an objection, i find it funny. it actually kind of delights me because i've heard everything now. but it was like, at least it's not a shotgun. but again, i don't recommend going through literal l and near death experiences to build up your skin. there's other ways to do it.

josh: 16:08

totally agreed. i think it's an important perspective that you're sharing, though, which is have i done things as challenging as this, either in my current role or just in my life? have i dealt with harder times? would i rather deal with this thing i'm dealing with right now or that previous situation? and if the answer is that previous situation, then the thing in front of you, it's not as bad.

guest: 16:32

it's not as bad as putting things through perspective.

josh: 16:35

i think that's a great perspective to have. so, talking about business development, i like how you started it out, with the fact that when you were starting out you didn't know that there was a specialized role focused on the outreach, the cold calling, the setting up the deals. you saw it as a salesperson's responsibility to be a part of it. i think we would both agree, and others would agree, that account executives, salespeople, must be able to do that, must be able to perform that particular function. it is critical in making a deal. i like how you think about it, that you are setting up prospects to become customers by being that first face, that first interaction with the company, by being that tip of the sphere. so i think that's a very good way to call it out. the highs and the lows. it's a tough job. you have to have thick skin and you can't take it personally, and you have to deal with rejection and oftentimes inflated numbers that you have no idea where they came from or why you're being held to achieve them, and so it is a tough role but it is so critical. but i like how you brought it all together with another learning, not just the one about have i been through worse, but the one where you realize that it's not just an art, it is a science. that's a big debate with some sellers about the art of selling versus the science of selling. and that leads me to another question that i've got for you. in your experience, what do people typically get wrong about business development?

guest: 18:20

and what. it's easy. i think that executive leadership tends to not remember what it was like, or if they've ever done it at all, and thinking this they just put your teeth in, they make it very. the way they explain it, or the way that they explain it off, is very blasé. that i've seen, and i think every salesperson worth their weight should have gone through the ringer. it's like you're training for a sport or something like that. you have to start with, you have to learn how to do lifting weights and sit-ups correctly so you don't break your back and all that crap, and so i think that they tend to forget that and then they just write it off as we'll just do it, just do it. i have a very adverse to passing things off. i hate it when people say when someone comes up with bad news or devastating news about something and you're telling someone and they just say, oh, that sucks, that sucks. i know that. i know it sucks. i'm trying to reverse with you and gain some kind of empathy or sympathy at the very least is like what the hell are you talking about? it sucks, does it just do it? yeah, i know it's like chop, of course. i'm just going to just do it. but what does that mean? i think a lot of it comes to successful any kind of like biz-depth departments. you're talking about a wide variety of people who get into that role. people who are trying to either get into sales ultimately and have to start somewhere, tend to be younger people. it's a very stereotypical thing about kids right out of high school or college and getting into a company and blah, blah, blah. definitely these days and i think that there's another common misconception is like oh man, the younger generation, which i also find very demeaning. i'm an older millennial, but it was like oh, millennials just think it should just come naturally. or they expect so much like, okay, hold on one second, screw you, you dickbag, that's not how this goes. they expect more out of you because you're a company that made a multi-million dollars in revenue and is like, yeah, i expect training, some continuous training. hopefully you know how to do these things and how to tell us how to do them. it's like, sorry, if we just our expectations are high, it's crazy, but the good sales development team needs to have that type of training, like teaching the science behind it and then the arts behind it is more of the. that's the subjective sign of how to teach certain techniques, but everyone learns at a different speed and rate. sometimes it takes people a little bit longer, and that's where it goes back to leadership, which is why i think that out of touch executives just things like oh, just teach them how to listen, teach them how to listen are you stupid? like what does that mean? it just takes a little bit longer for certain types of people, and i think that's where you really find good leadership that can manage different personalities and different types of people and also identifying what their i guess training rates are. there was a great leadership training that i took years ago called situational leadership, and again, getting into leadership is like, oh, i just talked to them, like you know they're people and how to make them like me, kind of like how you were saying is like i just want them to like me, because that's what usually like. well, scott, i just want them to be my friends. i was like they'll be short, but also they need guidance. and so situational leadership taught me that there are certain situations that you need to provide the you know less or more guidance or you know attention, and in that really opened my eyes because i always thought that again, out of touch leadership, like well, who's your a player, who's your b player, who's your g player, even though i was oh.

josh: 23:06

i always.

guest: 23:07

i always still thought that was dismissive. i was like, well, why isn't the c player an a player? because he's like you just gave up and you're like, well, they're going to or either going to fire him or they're going to quit it. i always thought that, again, it's just like it's so dismissive and demean and so you can treat everyone differently depending on the situation. i thought that was way more akin to like how i wanted to think about like how to actually lead people.

josh: 23:36

that's the key word, right. lead. yeah, leadership requires enablements of the people that you're asking to perform a particular duty, and often it does come across as a do what i say as opposed to we're in this together, let's figure out how to be successful. i like that. you called it out that there's this common perspective of it's easy and that can come from a lot of different places. right, that can come from. i've done this before, and so you've got a little bit of like survivorship bias, where they've made it to a certain point and, looking back, it's because they did all the right things, type perspective. i think there's also depending on who the executives are. if it's like founders and co-founders who are just super on board, that's not the right word. super enthused, super believers in their product, they believe you just need to show it to someone and they're going to get it and they're going to love it, and that's not the case. it takes work to get to that point, yeah, so i like that you called it out. you can't just take the nike approach of just do it. you have to really work together and build it out what's required. you have to build that training and that enablement and to even get to that point. the leadership team must get past that. just do it. it's easy attitude, because it's not. it's about developing not just the frameworks and processes internally that are required, but the people who you are asking to fill those positions, and that's what a great leader does, and i'm glad you called that out. i'm curious about you know, when we think about this, we think about these common mindsets that we encounter. have you encountered a strongly held opinion about business development or within the role of business development representatives that you completely disagree with?

guest: 25:40

one that and this is your course more of just like other people's perceptions about what this dev or sales development does, which also i love. that industry cannot you know, figure out what to call it.

josh: 25:54

it's either sale or sales to call it.

guest: 25:55

like i, i, i, i, whereas like oh well, this dev is inbound and sales development's outbound.

josh: 26:02

my other company is flip flop and like and then sometimes business development is the partnership side of the house and has nothing to do with inbound, outbound sales.

guest: 26:12

i love it when companies love to play dress up with titles and it's. i always think it's really adorable and funny. and even when it's like a big company, we call them associate sales managers. so the cool callers like, okay, so it's like, just say it when it is. shoot it straight, don't try to be, don't try to sugarcoat it. it drives me crazy.

josh: 26:32

yeah, should, it's straight.

guest: 26:34

but, um, that the biggest thing that i i it drives me crazy is that, um, this dev people end up becoming like almost like admins or secretaries to to aes and i was like, no, that's not what they are. they, like everyone has a function in the sales side. i'm not just talking about sales people and marketing, csm work, implementation, about everything, every part of it, the whole company, the whole company and, like you're just a different role and function in this sales cycle or this, this customer journey. and, um, and sales dev or biz dev is again, like we were saying earlier, is like the tip of the spear, so, like they're not here, like to to bend at the will for the ae to either, like you know, do r and d research and develop the, the pipeline and find, like god almighty, like there's the one thing i want to say to customer, any company that is, either has a sales development team. like please, for god's sakes, invest in a data management person. like, if you don't have a data management person, you're excuse me, i'm like you're fucking idiot. like it drives me crazy because it takes away time from biz dev and sales dev teams, because they, like you, know executive leadership, but they're like whoa, why are they cool calling all day? it's like because they have to find who else to call. like because you know that person doesn't work there anymore and now they have to get a hopefully referral or just go back to the drawing board, go and linkedin or zoom info or whatever else tool that's out there to find data. and it drives them crazy. they wish in a lot of ways, they wish you could just do their job. it's kind of crazy, right, and so they're not there and like in only biz dev. if a biz dev team exists at a company, like that should be. i mean, i don't want to like again diminish what they do, but that's like a luxury. that's like, and don't like take it for granted, like that is a very specialized team that is doing the hardest work possible that they in an ae should view a biz dev team as that kind of luxury. there's like, oh my god, because, like the biggest hassle for an ae to do is to to understand how to forecast for their month, quarter in year, okay, and if you don't know how to do that, then your manager is not telling you how to do that and so they are forecasting it. that's extremely important. so if, if a sales rep in ae is unable to forecast really showcase that they have at least three to four x their pipeline to actually let only close for a year. because i mean, that's the point is that hopefully you have about a 20 to 30% close rate at least that's traditional industry rates. if you have that then you should be good. so if you're lacking on your own pipeline generation for an account executive, then hopefully this sdr can actually start to cover that gap. maybe you're at like 2.5 or maybe 3x. well, if this sdr can hopefully get you another one x of that pipeline, then you should be good and like you should be thanking your lucky stars, because one you probably don't want to do that kind of hard work again. so like it should be like the other way around. like the ae you're like how can i help you do your job? it's like you're a you know again traditionally a quote unquote junior sales rep getting into this world. like what can i teach you? what can i help you with to find more out there that i just don't have the time for. i mean ae's dillow's discovery golf actually closing the damn business is like it should be flipped on. the mindset of like how they're working with an sdr or vdr, and and and also again, ae should be willing to do what they're doing at any given moment. i mean definitely in this day and age, right now, i mean a lot of sales teams and just people are being laid off left and right. i mean sales development, business development, kind of like the first things to look at in the sales org to be let go, and so like ae should be ready to rock and roll at any given moment. and because i think also and i've been in the account executive and i know i can be just lazy in general, but ae's can be lazy as shit to their job and and just like sit back and watch the leads roll in, if you, if you do that and you feel that way, then quite frankly it's like you got. you got a whole lot worrying still left to do. because if you can properly partner with another person at the organization, especially with someone that's actually feeding like buffet, but feeding you more, god almighty, like i've never had the luxury of having an sdr or vdr to generate leads for me, and so it's like to have someone else do that. like what, what can i do for you person. i'm going to help you out, guess it's going to help me, and that's how i also view like leadership, like your success breeds my success, and that's how an e should look at it as well. with the bdr and sdr is like your success will breed my success. what can i do to help you out?

josh: 32:04

and that's a concept that's true between any relationship within the company internally and prospective customers and current customers externally is what can i do to help you out? because the more i can help you, you know, the more you're able to be successful. uh-huh, ideally, that turns into a mutually beneficial situation for all parties involved. yeah, i like how you called it out that business development is a luxury, and really, especially the smaller the company is, this idea of specialized roles are, in fact, a luxury because there's so much involved in, let's say, sales, for example. right, you have to. you know, ideally you're working with the marketing team and ideally the product works and is something that solves a problem that people are wanting to pay for. let's assume, like all these ideal situations have been set up, you have to find who you're going to reach out to. ideally they've reached out to you, but not always the case and then the whole sales process, depending on what you're selling, of course, takes a significant amount of time. you have to make it trackable and traceable so that one, you know what is going on and what needs to happen next, and your boss knows as well. so that's often updating salesforce, for example which is a pain, a time consuming activity. it takes away from doing the actual job. like how you brought up the example of cold calling. how come people aren't making more calls? well, it's because they have to do all this other work just to prepare to then make the cold call. and so the more that you can have specialized roles who take that off and pass it on, almost like creating an assembly line right, and like that's the nice flow of work that you want to be able to happen, to process that. i agree with you that they should not be looked at as secretaries. some of the worst aes that i have worked with sit back and just expect the leads to roll in without taking an active role in it, and i think that comes from their previous experiences of working with way more established companies that have that assembly line process already in place.

guest: 34:20

right, yeah.

josh: 34:21

and that's not the case for these smaller, scrappier startup organizations. so i think that was a perfect thing for you to call out. i have seen very successful aes and bdrs working together to be strategic, like here's the division of labor, here's the division of responsibilities. i'm gonna do x, y and z. i need you to focus on a, b and c. my goal is to get this piece of information so that we can go to this person and do this thing, et cetera, which is a totally different scenario, one that i'm sure you would approve of. so i think it's a great thing to call out.

guest: 34:54

yeah, i mean, why wouldn't you want it? from my point of view, why wouldn't you want to be that way, to be one, to be a team player? but, like you know, here's a tip for you aes. i mean, if you're kinder to your peer and you're trying to help them out, one, you see a much slower burnout rate from sdrs and bdrs. because, i mean again, if you haven't been told to go screw yourself a hotter times a day and you're just not used to that, i mean, the burnout rate is a lot faster than other types of roles. so, like, if you're collaborating but also showing, like what else they do after they graduate, let's say, from an sdr, bdr role, like that means you're also helping the organization retain them, like that's the biggest thing too is that you're all apart. so you're still kind of internally selling, like working for the company too, like a lot of people just don't realize that and as like, well, it's either make or break it and, like you know, you don't have to think that way. you have to go to like a goblet and it's just like whoever comes out through the meat grinder is like oh, they're okay, there's still people that could be taught and develop these techniques, even though for how difficult it could be and like and ae's a part of that too, and it's unfortunate when and i've seen this, like you were saying too is you know, i've seen ae's develop great partnerships with sdrs and bdrs and there's nothing more fulfilling to see that because it's just like they're also human. like what are you treating like shit. but then sometimes they just completely take advantage of bdrs and sdrs and i think those salespeople like one, my initial reaction, like that moment bearer kind of aspect, is just like i don't want them to work with you at all and you can go screw yourself. it's like then go back to the drawing board and develop yourself, or like self-generate. i was like cause. all i have to do is tell them not to colk off for you. that's all i gotta do. it's quite easy and i've done it before and you're like what do we do? it's like well, that's because you're a dick and you were trying to take advantage of the person and they're just trying to start it in the sales career cause now all they're knowing is like oh so ae's are bastards. it was like what's you doing? and like do you realize that your actions are affecting this person's like one perspective of like what a sales career could be? and then they're just going to perpetuate that when they become an ae themselves. it's like oh, i guess i treat like sdrs videos like shit, you idiots, they drive to be crazy.

josh: 37:41

yeah, that's why i can't get on board. you know, with the workforce issues that you hear a ton about in the media of, and you hear this quote people don't want to work anymore. right, like how? how frequently does it come up? and i hate that because i'm a big believer in extreme ownership, which is that concept popularized by jocko willink, and i think that that is such a prime example of not taking ownership. people say people don't want to work anymore because really it's, people don't want to work anymore for you, for you exactly, for your company, for your industry, for your department, for your management team, for your ae's. and that idea of extreme ownership, of really coming together and understanding, okay, but why do people not want to work? it's not government handouts i mean, look, some people are going to be in that camp, sure sure, but it's it's much more.

guest: 38:42

it's not going to be the majority. no, not at all. they just like i'm sorry. i guess people just don't want to be treated like shit. it's crazy right.

josh: 38:51

it's almost an abdication of responsibility. it's like, well, there's nothing we can do because people don't want to work, instead of looking inward and doing that self reflection of saying, well, what you know, is it enjoyable to work here? cause that's the thing. it has to be enjoyable, like it just does. you have to be willing to put up with and deal with it, and for so long that just hasn't been the case.

guest: 39:14

and he like you start to ask people and it's like do you enjoy your job? and a lot of people say no because they're just having to like grin and bear it. and it's like, why does it have to be that way? it's like, why do?

josh: 39:30

you people.

guest: 39:33

it sucks so much that, like you know, leadership or some companies just don't get it and they're coming from this like 1982 mindset. he's like, well, you just have to go through helen back to make it to the top and then you know, you'll go through helen back and then someday you'll make $100,000 a year. they should not talk. they're like, why, why can't i enjoy what i do, even if i'm making 30, 40 grand a year, but still enjoy it and still want to challenge myself to then progress in my career, in this case sales? because why do i have to go through a literal shitstorm every day for the next like three years? it doesn't have to be that way. when people are happier, they sell more and the customers are happier. so that idea is the dumbest way of approaching how to lead and how to them, you know, develop your team members. it's horseshit.

josh: 40:33

and this is something that i personally think has been brewing for years, maybe even for generations, but it was the covid pandemic. that really kind of sparked the mass amount of like yeah, why, you know, like anything could happen in life, why wouldn't we spend it doing? spend that time that we have doing the things that we want to do right, and i think that's an interesting topic for us to get into, because this is where your story of disaster starts right. yeah, sure, yeah, yeah, you know setting the scene. you know you and i had talked. this was right around the covid pandemic that you know that your story that you're about to share comes into play. so tell us about your story of disaster.

guest: 41:21

well, the organization that i was working for right before covid was seriously, at that point in my career, the best company i've ever worked for. it was. it was fantastic. i loved the culture, the people, the product. i thought was great leadership for you know all it's like. you know blemishes here and there was pretty solid. and the person that was leading the organization one of the founders of the company he was still very actively involved. he would still get on. i remember he got a customer call with me. the guy was like so many runs up on the sales totem pole. i was like, oh my god, i can't believe this guy's doing this. and this was like a fairly established company and i appreciated that. and so the pandemic hit and it was funny i, just because i was leading another i was leading a sales team at a full sales cycle team and then i had a chance to develop a sales development team at a company that hadn't had one in years and it was like, oh man, 2020 is gonna be a good year. i'm gonna hit like the first couple of months we were doing crazy business, like we were making tons of set meetings, discovery calls, like it was the most money i'd ever made on a commission check in my entire life and leading a team, that's the other thing too. i don't tell you when you get into sales management is that. i remember the first time i got my commission check and you do see what your team members are making too. one of my team members who was just destroying it he made more money i did on his commission check. i leaned over my mentor, who was a manager too. he was my previous manager and i asked him. i was like what the hell is this? and he just like welcomed the fucking shell. i was like wait what and so, but leading the sales development team, i was making money. henry fisk, like they had to get like the cfo involved just to make sure it was doing their reports correctly. he are. so then this funny thing happened in march, in 2020. and, of course, covid broke out. they sent us all home and then, about a month or so later, they furloughed everyone and then, three months later, of course, the ceo had to be optimistic, like i think in august everything could be fine. well, so we about third of the company was laid off, and which included myself and a lot of my team members, and so i was out of job and have great recommendations for video games inno lacrosse was awesome and so i then had the opportunity, through my network and then people that i had previously worked with, to work for basically a direct competitor for the same industry, and so i inherited the sales development team and i was like, okay, so this is kind of the first time i was doing that, and also i, you know, we were doing everything remotely, but i had a chance to do that actually with previous company because two of my team members were based in state, and so i was like, oh, this could be weird. i'd never had to converse with people, just only via zoom, and it actually became easy. it was like, oh well, just keep up the same cadence of you know, during one-on-ones, team meetings, standups or whatever it is, and, you know, be readily available on slack if they need you for whatever reason. but just set those expectations. and it's not, quite frankly, that different from managing people face to face. you lose that, you know, little personal touch here and there, but you could still manage well, even relatively. i learned that very quickly. and then the pandemic and now i inherited this team was like, oh, this is not that different. so but these team members, these strs, had worked all throughout the pandemic which i was like i don't know how you guys did this, like this is nuts, and but a lot of them had been there for a while where they're wanting to take their next steps into an ae role and i've been very, you know, vocal about career development and wanting to like you know you do your time, you're hitting your numbers. then i've always told my team members like i want you off my team in a year. i like that, i want you to take that next step, cause i mean, if you're an str manager or leader or whatever it is, i mean you got to be prepared to like get them off your team, even though if they're kicking a lot of ass for you, that's one that's insanely unfair. if you just like, well, but they're my best person, i want to keep them on my team. it's like then you deserve to be fired. if that's the way these days, i fundamentally believe, because if they're that good, then they need to get onto, hopefully, a sales team to make more revenue for the organization. crazy concept, right? and it's like how do you not think that way? either way so.

josh: 46:29

it's not a common thought process among managers, among leadership, and i think it's really related to what is the culture that's been set and who's teaching them how to be a certain way right, because this is not. you know, we can get down to kind of the previous topic of the art and science of sales. well, there's an art and science to leadership too, and that perspective of you're a top performer and i want you off my team, assuming that your personal goal and development and growth is whatever these next steps are. but i do think it is the responsibility of a leader to help, guide and shepherd people to where they want to go. 100% yeah. so you covid hit, you were furloughed, then laid off and then you landed at a competitor. so the industry, the same industry, yeah, and this was an industry that was decimated by the covid-19 pandemic. so this was like, just to make sure everyone understands the challenge that you were taking on of making a team successful of building a team in this timeframe for this industry with this type of product. it was quite the undertaking and i wanted to make sure that that's the gravity is understood.

guest: 47:42

i appreciate that. i mean i was, you know, i think about like don't make excuses, but, like you know, that was a very special situation. i mean none of us had been at least for us have ever been in that situation. what do you do? no only from the individual standpoint. we're like that's a company and like how do you not go? i mean, plenty of companies went under and i mean people were fired and laid off and shit, yeah. so it was very difficult. so we and since most of my team members were looking to become aes and they were not hiring charlie just yet because they were basically just trying to like hold on to every customer they have from either canceling or hell, just trying to like hopefully to have them not go under themselves and just retaining as much as they have. so they weren't internally hiring yet. so i lost like good 60, 70% of my team within the first like two months, because they were like i gotta move into an ae role and because i had this other opportunity and i was very you know, i was very empathetic, but at the same time i was like i was encouraging, like we're not doing this right now, we're not hiring for it. so you have two options one, you stay here and we will work together and not only making you still very successful in exceeding your targets here in this role, but hopefully within the next six months. if we're gonna be start hiring for, you know, smb aes, then we'll have that opportunity. but if you need to take this leap right now because you need to either make more money or this is the opportunity you wanna take now that's presenting itself, then i fully encourage you to do that. like i'm not gonna tell someone like stay here, it's gonna get better. like i can't in good conscience do that. so i lost about five of my team very quickly and i was like i get it, i totally understand, but i was also tasked with two xing my team within whether i started in like november 2020 and like march or april, two xing. i was like well, i just lost most of my team and i had that as like i had to rebuild it, but i did. i mean we had to be very creative and nimble how we were approaching the marketplace anyway, because, again, the country was still shut out and industry that we were selling into was still just utterly fucked from the pandemic. and like we do, and it's not to be super creative and figure out ways to like kind of double up sdrs on particular territory, cause it was a territory based go to market strategy and which, in an odd way, actually helped us out quite a bit, cause at least, like you know more, let's say, the central time zone was a little bit more laxed on covid restrictions. so they're like. i will say, in a very horrific way, thank god for some states that just didn't, i guess, give a shit about covid, cause it kept us afloat a little bit, but that still was kind of devastating. kind of states that way more restrictive, that also were california's and new york's that were, i would say, have that industry they were selling into, supposed to be a lot more profitable anyway. so, but we did it, we, through thick and thin, we got through it and we were still struggling to hit our target and it was also. it really tested me on how to set expectations, and i mean even down to like kpis, like what do you, how do you do that when, like you know, when most of the people that you're calling it, just like we're struggling to keep the lights on, which i could clearly understand is like, how do you set? like okay, you need to make 50 calls a day, and like, and you, you're talking to people that can't do anything right now? yeah, it was just, it was straight. like i didn't know what, fully admit, i didn't know exactly how to approach it and, and a lot of people just also assumed that i would, which i, you know, i've done these things before, but again it was a very special circumstance. so it was very difficult, to say the least, to figure out how to get this whole thing going and to still set up my team for success but also hopefully set up the aes with enough to still sell. and it was no matter what, it was, just it was going to be difficult, every struggle that we were like running into, and still difficult to hit our targets, which we barely did most of the time.

josh: 52:39

it was a tough time. there's no overlooking that. it was a tough time, not just professionally but personally, for everyone, and no one knew that it was going to last for years, right as well. so, and there's nothing wrong with you acknowledging that the, the, the, the obstacles were there and just, it's still an objective approach to say this is what we were dealing with, this was our goal and i, like you, know that you still explored creative ways to try and meet that goal. yeah, but you know, it sounds like, despite the efforts, it was still a time of turmoil, still struggled to hit some targets.

guest: 53:18

yeah, but you know, for everything we were going through, we was able to still, you know, build off team to the full eight you know headcount and then to exit. but by when i was getting to like 13 or 14 headcount, we finally i told the leaderships we got to get another manager in here. so i had the first opportunity to manage a manager and then manage a much bigger team all around and that was great. i mean, i've been doing sales development leadership or just sales manager or sales leadership for a while, but my next step was becoming a director to oversee managers. because, like you know, as we've been talking this entire time, there's been so many things. i'm just like i want to shake a manager like we can. we don't have to just like well, i had to go through hell. like they need to go through. like we don't need to do it this way. like you need to think about what we're doing here. we need to think about, you know, again, retaining these people, because interviewing and putting people through training on onboarding and then training man like i like doing it, but it added that's a tough thing that people don't talk about. i think enough managers like and it costs so much money for a company to like find and hire someone and then you know, praying to god, that like just that they're gonna work out. because, like back at my, when i was 21, went through i did a month of training at that big company and i remember the first day on the floor i had a buddy that was like my buddy there. we went through training together. we were both very excited and they just pushed us in the deep. all right, go get out there and be somebody. and i was. i came back at the end of the day with my manager. i was like that was rough, but i think i'm getting it. and then my buddy, he was like yeah, that was it for me. and he quit right there. i was like wow what? and he's like, yeah, i don't want to do this. and he went through a month of training and the first day on the floor, quit, whoa and. and my manager was like, yeah, makes sense. and it was like, oh, and i was. i was shocked because i was also coming from. you know my background, you know being, i would say, from humble means. maybe that was just like you have a job, what are you talking about? you can't quit and so, yeah, i never quit a job before. i always just had to like, yeah, leave, for you know i moved or whatever. um, so um, you know it's, it's not talked about enough to her. like, man, you, you gotta approach this by. you know you want to make this a place to where your team members want to work and also be successful. i mean, you're not getting into usually sales just to be like mediocre. that doesn't make any sense. it's like you're not gonna make any money that way, right?

josh: 56:18

right? no, i think that's a great call out. you were tasked with managing and developing a team during a very tough time and had retention problems for factors outside of your control. yeah, i appreciate that your focus was on what was best for them and, being real, i think that that's all you can do, yeah, as a leader, and and there's going to be those situations where it's like, look, there's just not an opportunity for you to do that thing that you want to do here and i can't guarantee that there's going to be one in the future right, so your options are to continue doing what you're doing or look to change it up, and i think that's such a great thing for you to call out. it's not for everyone like this. this role is not for everyone, but it is a tough situation. yeah, so the you know, in at that point, you were trying creative things. you're trying to keep the team afloat. you were trying to lead them to develop these deals that aes could then take and close. things weren't happening. what happened next?

guest: 57:16

well, the i mean we we are building up the team enough to where then we had, you know, manager, and we were about like 14, 15, 16 strong, like head count wise. so we had full teams. but you know, we were still struggling because it was still at that point. it was still in the middle of like 2021 and then getting past q2, getting into q3. i knew that the organization and you know when that happens or when a company is trying to focus on that, that's when they really start to try to bring in the big guns, you could say, and then bring in people that are more or less going to make it happen, like now, and and so they brought in a new cro and this person they came in and i, you know, i didn't necessarily have, you know, any expectations. i've worked with a cro in the past, back at previous company, and what i knew about that cro i knew. i knew him, i knew how he worked and how he looked at things and the transparency that he needed. it was one of the best like piece of advice that my my previous company at that time gave me. who are the? my director gave me is okay, you go into those like the leadership meetings and you're it's like a revenue ops call and you're like this is where we are for the week, a month so far. he told me, like all right, you go in there, full transparency of where you are, what are the issues going on, how you're going to try to resolve them and if there's any requests or asks of executive leadership to help you out to either resolve those issues and you come up with those ideas of what they can do, you go in there. but if they have no questions for him, because the first couple of times i went in there i was like i was. maybe i was a little too like salesy of like you know, you know how we're, you know, approaching an issue or something like that we're asking too much of them like i don't know, i didn't want that they.

josh: 59:35

they were like what are?

guest: 59:36

you going to try to do and then, once they gave me that advice, i'd go in there and give them. give them all the good, the bad and the ugly and how i'm going to hopefully try to cure those bad and ugly and uh and then move on from there.

josh: 59:51

that's a great framework by the way yeah like to use consistently for sure.

guest: 59:57

and then i and i was like i was always in a like five minutes. i was super sweetly clean and i i was very animate with my team members like you update your shit and sales force. i told them from day one. i was like i want us to be the standard of a few things. one, i want us to be the standard of how to use sierra i'm a huge proponent of sales force, it's not difficult how to use it and but i want us to be the gold standard at this organization to help me have how to use this damn thing and how transparency can work on our favor and we work. i love that and. but i knew how that's cro worked and we were good. we're good. this year i came in like bull in a china shop and i the the second conversation i had with him. uh, this was, um, this i. i knew something was very wrong with how he started the conversation. he's like hey, so i've heard a lot of bad things about you. nice to meet you.

josh: 1:00:57

i was like wait, i'm sorry.

guest: 1:00:57

oh my goodness uh, i was like, excuse me, hello, and um, and uh, you know, i was like, oh, uh, whatever do you mean? and um, he, you know, explained that that with not hitting our numbers consistently, that, um, we're, you know, doing a bad job. and i was like, oh, did you not hear about this thing that was killing hundreds of thousands of people, that also decimated and destroyed practically this industry that we're trying to sell into? and but also, this person came from a completely different industry, which, again, is completely fine, and i think that you know, not necessarily having a background in the industry and you're getting into a new one, it's not like completely, just like, oh, that's, that won't work. i mean, there are. there's a reason why they're in that role. is that they, hopefully, are malleable enough, uh, that they are taking their best practices and skill sets to that new industry to hopefully rework it and make it even better. there's a reason why he was hired, um, but i'm assuming from that first conversation, like, oh, your interpersonal skill sets are not the greatest. so, um, he's like, yeah, i've heard nothing but bad things. so here's the deal. uh, i'm gonna re-interview you for your job and i was like nice to meet you, my name is blah blah blah i was like. i was like wait what? i was like, oh, and man, i immediately started thinking about the shotgun in my face thing. i was like, okay, remember, there was a shotgun in your face. don't forget that, because this was testing me. uh, on it like on a professional level and a personal level, basically telling me like your dog shit. so i want to see if you're like, you're worth your weight of anything. i was like, oh, my god. i was like okay uh, i understand, um let's, let's do it. and he's like um yeah, let's do it tomorrow okay oh, my goodness, and so like next morning, like eight o'clock in the morning, i had to read interview for my job that i had already for at that point a year and i was like, oh my gosh, this is happening and that's a terrible experience it's. it was, it was so intense. i've never had my anxiety personally and professionally tested that much, um, in my entire life. it was just, it was so intense, and so i, i prepared, uh, like i, you know, set up a whole deck, like i wanted to really try to wow him and and i was internally selling myself, which was, and you, had you had no context for this interview, just like tomorrow you were going to re-interview with me. was there any direction provided of like i want you to come with this or speak, speak about these things uh, yeah, maybe a little bit, um, but i mean i wanted to, you know, you know, go the extra mile and showcase, you know, everything that i had done and what my team has done at that point. you know what we've accomplished with. you know what's obviously been going on in the industry, of course, and with all the failures as well again be transpired, but also transpired with the, the good things that we have done. at that point, well, uh, it was like i trying to get to know them. even initially it was just like i i've had a root canal before. i would take that root canal over, talk with that person without anesthesia or like numbing or anything like oh man, this is this is rough, like painful. yeah, this is very painful. um so, of course, the interview was like an hour long and i i i have never done like stand-up comedy before, but i was like, oh, this is bombing, it's like. i was like man, i'm not getting anything across the audience like this is just like only in deaf years, um, and so you know i'm going through it. it was, it was a lot. he was giving me like objections to like literally everything i was saying and you know it gave me some kind of well, okay, and um, you know, give me some leeway here and there. yeah, i mean it. you tell me how to do it, like how i was supposed to call us this, and. but also i thought it was, you know, pretty demoralizing when he told me that, um, the rest of the leadership lost like respect for me or lost all hope that i was going to do a good job. and i was like what and? um, because i to be and this is not me just play like dumb or anything, but like i had not gotten any kind of feedback from my leadership, but also any of my peers say like wow, you really shouldn't have bed, what are you doing? and, uh, like everyone's be like hey, you know it's a brian at his struggle right now. like what can we do to help out? you know, everyone's very collaborative and so this is the first time i'm hearing it's like, by the way, like you know, other than chilling yourself, like you know, you should really think about what you're doing in your life. and it's like god almighty. and so he then asked me is like, well, okay, i see everything you're presenting and i just don't really buy it. i was like, okay, uh, i was like, yeah, i, you know, i see what you're saying, but you know, i just, i think you really drop all and everything, blah, blah, blah. and so my, my last question to you is you know, if you, you know, interviewing for this job, and if you don't get it, if you don't retain this position and someone else gets inside of you, i wonder what is that going to do to your ego? and i was like, what, what? i was like, yeah, what is it going to do to your pride or your ego? and i never even personally been asked that before, let alone in a professional setting. and it was i was interviewing and i was flabbergasted.

josh: 1:07:26

and this whole situation seems like an hr nightmare. well, yeah.

guest: 1:07:31

i mean it definitely was. i mean i'll explain it in an ultimately what happened. but i looked back at what i said and how i responded to it. i was like, man that's, i thought of that shotgun and i was like how to take the shotgun right now instead? wow i was like shh. so i told him one. i don't think that matters of what i would do to my ego, because all that would mean is that i need to prove to you and the organization that, while i can do this job well and exceed your expectations and goals to where, then i can earn that role back. that's all it would do to me. and of course his response was like yeah, whatever. and he was asking that question to break me because i was just so stunned by how brazen his question was and of course we end the call. he's like all right, dude, good job today. i'm like okay, and that was like that's how i began my day. that was at eight o'clock in the morning.

josh: 1:08:47

wow.

guest: 1:08:48

i was like go out there and be somebody, oh my god. so next day he calls me up early. hey, he calls me up and he's like, hey, good news. i was like, yeah, i was like you do get the job. i was like, oh great, okay, he's like, yeah, someone else did, but you're going to be just a manager instead of leading the other manager. okay, and quite frankly, i looked at it and i was like there's a silver lining to everything and my first initial thought was like, oh, thank god, i don't have to talk to him. someone else has to deal with him directly. and that's how i looked at it and, honestly, it made my work-life balance much more positive in the end. and you know, granny, i was technically demoted, which was a pretty big drag. but now i just had to manage my team members and i was like, okay, i could do that. i mean, i've done every year and this is something i can definitely handle. and again, i don't have to go through like walking on eggshells around this person all the time, which was not fun at all. and i was actually pretty good. my team was excelling and exceeding goal and i was like, hey, and then i started thinking about okay, wasn't i even ready for that just yet? and it was like, well, i was. it was just again the situation itself. it's just like time is, you know, heal everything. but what was happening at the time when i was being successful, what was it? the country starting to open up again, like, oh, okay, and it's crazy, right, like things are starting to be better because, just naturally, the industry is healing and the states were finally opening things back up again. so, naturally, i was like, oh, i'm starting to hit my numbers again and exceed them and we're doing better in this. and i and the other thing was that when i was managing the other manager and their team, i was still managing my own individual team too. so i was like managing like basically like 20 something people all on my own. it's way too much it was a lot and, and so this person finally just got to manage us two managers, and then i got one of my team members that actually came promoted.

josh: 1:11:16

so they're now their three managers.

guest: 1:11:17

it was like you know, 20 something, 26 strong headcount for individual contributors. so the problem was is that that director went on maternity leave and and then that meant that we had to like, oh, oh, spaghettios, we have to work with the cro directly again. and, luckily and unluckily, one of my colleagues manager. they were like the de facto, they were the interim director and man, it's just like i could. i can imagine like what, like hardcore hazing for fraternities, just like how much, just utter shit that this might park with my peer and good friend went through during those three months that the director was on maternity leave. it was just like hell, literal hell on earth. we had to do like qbrs the three of us and just go through it. and this, this cro, was just man, it was. it was as if it was the first time i talked to him again. jesus christ, it was just so utterly intense. and then we just started to learn more about how this person worked with people and like the way that they viewed the world. they were very, you know, they. they diminished the effect of what covid did and like didn't think it was that big of a deal. i don't know what evidence you need.

josh: 1:12:51

and.

guest: 1:12:52

i would say those you know, 600,000, maybe more now that are dead was good enough and so it was just dealing with him was so just awful. at any given moment. it was like anytime he would call. like i started to develop like a fear or anxiety when i saw like the green bubble pop up on his name on slack.

josh: 1:13:16

oh god, that means he's working, see it anyway.

guest: 1:13:22

so you know, we would spend days and nights, the three of the managers, the three of us, just working together, just making sure that all of our numbers were airtight. we knew what we were talking about all the time and we just still just like getting our kneecaps blown off at any given moment and she's like this is so fucked.

josh: 1:13:46

so, yeah, you're you know you already had a tough situation. this guy comes in and seems to make it worse. yeah, and i love that you still are trying to make the best of it. you're still trying to find what can i learn, what can i do, how can i develop myself, and how you took that as an opportunity to you know, once it once again go back to, we're going to be this standard of a team, we're going to be the you know, the gold standard that people think of, and you started to lead your team to success. it helps that the market was shifting back into a more favorable position. yeah, the, the person who took over your role that you got demoted from, went on maternity leave. a colleague stepped up as the interim director, but it was back to you dealing with this guy, this guy who so far seems to have not really contributed anything to it being positive to the company.

guest: 1:14:40

no, no. and to go back again, i don't want to seem when i've always thought myself as a team player. now did it. and then this like my colleague, they were chosen to be the interim director, not me and did that hurt for like a minute? yeah, of course it did. i was just like oh shit, like wow, they really fucking hate my guts. and but what that meant, though, was no, we are here for you. i was like no, we're going to. i like, if that is their time to shine as much as possible, then me and the other manager that was there, who was on my team previously, like we are here to make you look like a badass as much as we can, and like that was the role that i was playing and it just it wasn't my time and that's. that's completely fine, and i'm not going to be kind of like the type of person like that would look like shit. so then it makes me look like a badass, like that's not what i'm here for. we're all here to make each other look great as much as we can, and to build each other up, and like you're, you're selling ourselves still, and if i just i wasn't here for any kind of like vindictive, or or, or, to perpetuate his kind of negativity towards us, like well, we're all fucked, i guess. like no, no, and besides, i appreciate, in a way i liked the challenge to basically prove him wrong and i mean again, like i said a lot earlier, i mean i, i could be pretty stubborn, i was just like i want to be, if not more stubborn than he was, and it was. it was a lot to prove daddy wrong. so what happened?

josh: 1:16:39

i mean this situation. it sounds like you were kind of stuck. yeah, there's not really a successful so i was not looking to leave.

guest: 1:16:49

i liked the company a lot, i liked the people that i worked with, i believed in the product a lot. i i loved every facet of it, except for working. and i wasn't looking. now, when you're in leadership, and if you've been leading a certain and i'm talking about just sales specifically if you're, if you're leading a like a specific part of a sales organization for a number of years yet spoiler companies, your, your managers, are getting hit up by recruiters like left to right, and i would care if they're like that good or if they're great. i mean, they're just getting hit up. and so i was costly being hit up by recruiters and i was turned away. i was like, no, i'm going to prove daddy wrong and i'm going to continue to do this. but then there is something that finally broke the straw, that broke the cams back with. just like how intense the sierra was doing in my my you know work-life balance was off kilter like crazy and i was pretty low and just really, really struggling to build myself up still and also keep optimistic. for the rest of the team too. it was just, it's just hot. so this company reached out to me and it was definitely in an in an industry, one finally out out of the industry. i've been working, you know, with the past like basically six years at that point, and then to an industry that i was really interested in, which was sales enablement and sales engagement tools for saas, and i was like, oh okay, and they, we talked. also, by the way, if you're remote, it's way easier to apply interview than having to figure out like, yeah, i have to get enough time, i have to go to my automatress for three hours to interview face to face. so it was. it was kind of the right place at the right time. it tickled this, this interest that i've had for a number of years. now i've had a few of my colleagues and mentors go into that industry as like this is really cool service and product. i like the people that i'm talking to, and it was all very quick and i mean seriously, from soup to nuts it was. maybe it took like a week and a half and yeah, and so i was like i'm doing this and so hey, and the funny thing was that the director was still on maternity leave and i had to call them. i was like i have to talk to you and i told them that i was leaving because i accept the job offer, and so they understood. but i was very, very clear. but this i want to be explicit here i am not leaving because of you, i'm not leaving because of the organization, product people on the team, no one else. i'm literally leaving only because of the crl. i need you to know that. that is it. and at that point five other or four or five other sales leaders i'm talking like vp level, two vp director, two directors and another manager and maybe another manager or something like that they all left and cited him specifically why they're leaving. and so well, it was the fifth or sixth person doing that now and it was funny, this guy. he found out, of course, and i told my colleagues first i didn't tell the team just yet until, honestly, about a weekend, until like two weeks, because i didn't want to slow anything down. i think it was like the end of a month or a quarter or something like that and he said he was going to call me to talk to me about it. he never did. i didn't speak to him towards that last two weeks at all and i don't know if he knew that. i cited him specifically. but during my exit interview i was also very explicit to hr and it wasn't like. i even said, look, this is not a thing about like it's either him or me, and i'm like i doubt that i could choose me. that's crazy. it brought him in to help sell the damn company. i was like, yeah, but what's his face? we should keep him. i'm not going to do that. but i said my concern is is that i don't think i'll be the last leader to leave because of him, and that's something that you guys have to figure out. that's all on me. anymore can't do it. and so the last day that i was there and it was very emotional because i was very close with a lot of my team members and other two managers, just like everyone there, like we came very close. i mean, when you go through, like you know, i think that the other thing that the pandemic also showed us is like how close you became with people because you're all going through hell and back and it's like you know you're going through the trenches kind of shit. you develop like special bonds you will definitely not forget you're, you know, professional and sometimes even more than that, to where you become like actual friends, and it was. it was a lot, it was very emotional at the time and so, like when leaving, i i just wanted to say like one last goodbye via zoom or whatever, and the whole team showed up. i was just inviting my whatever that i was managing at the time and they all showed up and i just, like you know, i wanted to say you know, this is not like goodbye forever, like please always reach out to me. do you ever have any questions that you just want to? i don't care and you know, i just hope that you know, you two are in fantastic hands with the other two managers and the director that's still here. it's like you guys are not going to fail because, like i, i wouldn't feel 100% ready to leave if i knew that you guys were not in good hands or whatever. and then they did something that i was like, oh my god, i've never felt this before. is that they all like saying, saying really nice things to me and like what i had done for them, but they all like had posters that says, like we love you, like you know, break a leg, good luck, all these kinds of things. i was like what the fuck? i i'd never experienced that before and because i i really wanted to change things for that team. that was like they gave me this opportunity to have a lot of creative control over how to develop this biz dev team and to build it out and to take it to the next step of where they wanted it to go. and i thought we did an admirable job with the state of the world that was in at the time and we gave a lot to these people that weren't. we gave a lot of like trust in them and and build up their confidence. and like i think i had like at least like six or seven people on my team get promoted with two other roles. like i had one person that was they were amazing. they went to become a marketing manager and there was one person that i convinced not to go and i because they were going to leave and become a sales rep somewhere else like i it was the first time was like i don't think you should do this, i think you need to stay here. and i immediately went up to my other colleagues who were overseeing the sales teams full sales cycle teams like you need to hire this person right now and they're now still with the top sales reps on the company and they're incredible and we talk all the time still and it was a very humbling experience that i definitely never forget and i have all the things.

josh: 1:25:12

that's here the silver lining. yeah, sure, right. so you were stuck with this tough situation. industry was decimated. you started to really rebuild the team, even though people were departing pretty quickly for a lot of valid reasons. new cro comes in who is going to make sure that the company does extremely well or whatever they sell themselves on? and comes in and just really, like you said, bullet a china shop, destroys the place, comes in and makes you re-interview for your own job and asks you some pretty bizarre questions during this interview. mm-hmm, stuff that there's no way that hr would have appreciated hearing. you took it like a champ. you were still down for the cause. you decided to refocus and really control what you could control. yeah, that was the performance of your team. to a certain degree, you saw success. it helped that the timing of the market was starting to do better. the director that took over your role goes on maternity leave. so then you're back to really having to deal with the cro, because now you're supporting the interim directors, who needed a ton of help just dealing with this monster of a personality, yeah, as well as ridiculous demands and expectations, and it sounded like you were just resigned to going through this, until this way out presented itself and you found a new opportunity, one that got you excited, which is certainly something you deserve, and i'm so glad to hear one that you got it. got this new opportunity. you were able to get something that you deserve, but you saw firsthand the recognition and the appreciation from the people who you had served through your entire time there. i think that's such a great up and down. overall, it sounds like you won in the end. i could.

guest: 1:27:25

yeah, i do appreciate that. i mean the whole my mindset around managing anyone really in the end and leading them is that i want them to be well, hopefully by the time i'm finished with them, well rounded, individual to where that they can proceed and most cases with sales, dev or whatever follow their sales career, whether that be here or elsewhere. like we can't i'm realistic people will leave companies i did but i want them to be prepared for anything and knowing also what they want. that's one of the things that i think that it's not talked about enough. with definitely that role it's like you know have hopefully start to develop an idea of, like what you want to do. and i have a goal i want to take the next step in my leadership position or role into managing managers and to a director role, because i find it like fascinating i don't think that managers get a ton of guidance as much as they need and to develop them still, because i mean it doesn't stop. it doesn't stop until you're. i don't think it ever stops, but tell that to the cro. but they it was again very humbling to see it's like okay, my efforts weren't in vain. and i mean they could have just said, you know, like in that movie tombstone, towards the end, where like powers boost just says all right, well, bye, they could have just said that to me, but like they didn't and i knew it was like not to say it's like i made an impact here, but it's like, okay, i feel good. i feel good with what i did, even though i had to go through a lot of only first year personal turmoil. but i also didn't bring that to them. and because that's the other thing too is like i've seen it in the past, like when a manager is just getting shit on from their leaders or whatever it is, they bring that to, like they bring that home to their team members and just like it's like you, motherfuckers, you need to do that. and like they just like treating like shit and like i didn't want to do that, like that's not fair and also that's what you have to pull back. you can't just you grant it like yeah, you have to set goals and expectations and put people on action plan. it's you can't be like. it's like you, piece of shit, you're not doing this. i'm gonna have to make you re-evaluate for your job. no, you don't do that and they showed that grace to me that i hopefully showed to them and it was it started like for how much like the worst professional experience i was going through with that crl. that moment right there showed me like maybe one top street best experiences i've ever had in my own professional career.

josh: 1:30:45

yeah, i think that's such a powerful moment, especially someone who's in a leadership position, to have those you are leading just show that appreciation that you specifically made the difference. i think that's great. looking back on this entire experience of yours, what would you say were your top takeaways?

guest: 1:31:06

well, the i you know, even through all of the i want to be as introspective and you know, or reflect objectively as much as possible, because i mean there's a lot of subjective view, even the way that i'm telling this story about, like you know, that sierra was a dig bag, but like i think that what i did learn is to, no matter the situation, i mean, really be as firm as you can on setting expectations of for your team members, even through, like, the craziest time that humanity was going through at the time. i mean you have to do it cause i what i really thought about, what, like even what kpi's are really there for? it's just the measurement to success. that's really what it's supposed to be. it's not to be, like you know, hold your feet to the fire. if you don't make a hundred calls a day, we're gonna fire you. like no, that's not what it is.

josh: 1:32:14

there is actual, it's not the goal.

guest: 1:32:17

it's supposed to be a specific science. okay, if you make 70 calls that day, 70 calls a day, what it's supposed to lead to is x number of positive conversations that you have, and then those x number of positive conversations lead to a meeting set for a discovery call. same kind of idea of, like, again, forecasting for accounting, and i really, if i thought about it that way initially which i don't think i did, quite frankly then it would have put hopefully i put in you a place to where the sierra wasn't completely horrible to me and we granted, we would have probably lost more people, we would have seen a lot more attrition that way, quite frankly. but thing is, though, we would have been at least in a objectively better spot. we would have had more of a foundation to where, yeah, even though the world was on fire, at least like, well, at least we got cement to stand on. but you know, that's what i learned from is that, even through thick and thin, like, you need to have those expectations in place, and it's kind of the idea again being transparent and just covering your ass how, playing the game, you gotta do that for yourself, and i wasn't holding myself accountable for it as much as i probably should have and because i think i assumed which was saying sales. i think i assume i had much more of a longer grace period than i probably should have had, and that's on me. but you know, i also assumed that, even being a leader, that your leadership would hopefully give you some kind of mentorship or guidance. and like. franklin before and the aftermath. you know that director, who was a great person. they were great and the director took over my role. they were great, ed, and we were being successful, but like i was not getting the mentorship or guidance to take even my own steps, next steps into my career. and plus, i also saw like the glass ceiling was like way through my friggin' rick cage. at that point i was just kinda like i'm not getting through this and because the cro hates my cutscene. so there's a lot of things i learned objectively, but like i don't think i would have changed any way that i felt about it and how i was approaching my team at the time.

josh: 1:35:03

well, like your original shotgun story, this sounds like a new, very tough, a hard experience that you went through. that is now the threshold for pain that you know you can go through, and i love, just in general, how you're always taking the responsibility to find the good, find the lesson, learn, find what you can control and capitalize on it, as well as your thoughts on leadership. throughout the conversation, what's come through is that you've got a very strong and natural focus and approach to leadership, one that certainly resonates with me. you know, a lot of things you were sharing resonate with me personally as far as my approach to leadership as well, and, at the end of the day, i love that you're taking it on you to understand what are the things that you can do to make the outcome best for everyone involved. and that's a team player, that's teamwork, that's what the company should try to do. that's gonna leave me on a side tangent where i think, true sales enablement is really done through company enablement. yeah, because it is the entire company coming together to make all this stuff happen. i would agree. a lot of great takeaways. i really appreciate your time. i appreciate your vulnerability in sharing some of your thoughts and perspectives as well as such a frustrating story, but one that i'm glad you were able to come out on top of.

guest: 1:36:31

so i appreciate you saying that. i mean, i've told this story to a number of friends and colleagues, and mainly friends who are not in sales or in the industry. they're kind of just like oh my gosh. and when i talk about with sales people or in sales colleagues they it's usually the same reaction. it's like the hand over the overhead kind of thing, or hand like the face palm, just like got them mighty, like they, you know, when you're telling a story about, like you know, a good sale that you had, they just like it's riveting. and when you have it a bad sale, they're just like they're right there with you, they're sharing the cup of coffee, just like oh god, i know what you're talking about. and this stuff is like, oh my god, that like that's how bad it could be. it's like, yeah, but you know saying that, the natural parts of leadership or wherever. i appreciate that i don't know if i'm necessarily like a natural leader. it's just more about again, what i've learned from good leadership and also from bad leadership, basically what not to do. and i've taken those two things and molded into the you know my natural personality that i have and put it to where i think is the best, not only for the company or like for the individual, but for the company, and that's how i lead it, because i always feel extremely grateful that anyone has given me an opportunity to work for them ever. so i was like, no, if you got me, you got me. like i'm here for the long haul. i'm not thinking about like what's the next step and how do i? i'm not thinking about that. i'm here to win it as much as you're investing in me.

josh: 1:38:20

and that is exactly what i expect a natural born leader to say so you're just proving my point. really appreciate your time today. thanks for joining, of course. thank you, man. so much to unpack from that conversation. i expected us to talk about bizdev, which of course we did, but i was surprised by how much we delved into leadership. bizdev cold calling, it's hard, it's very hard work. it's okay to call that out internally and externally and if it's not working, be a part of the solution. don't just dismiss it as just do it. it's easy, it's your job. figure it out. that's not gonna help. that's not enablement and, like we talked about on the show, the best sales enablement is company enablement. that's where you're helping the company and the company is helping you. now, a good leader partners with their stakeholders to enable them not to dictate to them, and she's. what a disaster story. let that be a lesson to all listening. a bad executive will destroy an organization and, potentially, the entire company. i am not being dramatic. people ruin companies all the time, but no matter the circumstance, it's always what you as the individual make of it. i love to just focus on what he could control and how he could become better as a result of it. that's hard work, but it's hard work that pays off in the end. now, before you go, take a second to subscribe to the show. let us know how much these stories resonate with you by leaving us a rating and a review in apple podcast or spotify or any podcast player of your choice. and share these lessons with a coworker or even a boss who's going through it with you. who knows, maybe your story of disaster could be next.