S1E139 - The definitive guide to sales leadership with David Weiss of Outreach.io
7 Sept 2020 · 39 min
This content was created by Coach Richard GPT. This content was uploaded by Coach Richard GPT. This is a podcast episode titled "S1E139 - The definitive guide to sales leadership with David Weiss of Outreach.io" recorded on September 7, 2020. It features a conversation between Coach Richard GPT, Scott Leese, and David Weiss, the Enterprise Sales Director at Outreach. They discuss various topics related to sales leadership, including sales training, career paths in sales, mental health, and balancing work and personal life during the COVID-19 pandemic. The episode also touches on David Weiss's podcast "Psych and Sales" and his book on sales careers.
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Hey everybody, it's Richard Harris and Scott Leese with another episode of the Surf and Sales podcast. Super excited today as we have a really, really smart guy, probably smarter than Scott and I combined because he knows how to take care of a fish tank more than anything else. For those who aren't listening.
It is David Weiss who is the Enterprise Sales Director at Outreach at the moment. Is that right, David?
Yep. That's the official title. We can.
That is the official title. He's also part of Sales rebellion. He's also got a podcast with his wife called Psych and Sales, which Scott and I are now. We have to like go to legal battles and all kinds of fun stuff. Lawyers are involved, but we're. David, thanks so much for joining us, man. We really appreciate you giving us the time.
Yeah, Richard, Scott, thanks for having me on, man. Really excited for the conversation.
Yeah, so just sort of from the beginning, like go back to, you know, just for people's perspectives, aside from being at Outreach, what are, what are some of your other sales careers? Just so they understand as we talk about stuff, this is where your perspectives coming from.
Yeah, absolutely. So I've spent the last about 14 years in sales and if we're going to go really far back, I think I've been in sales for 30 plus years my entire life. My parents said from. I was arguing and negotiating with them from the very beginning. But I've worked for. And this have an interesting story in itself. My first sales job, last four months, burnt out, totally failed. And it's because I didn't get any sales training. So from a very early on I learned that sales training and treating your sales career like a professional athlete would, would make a huge difference. So when you ask some of my background, one of the things I tasked myself with after that first failed opportunity was working for phenomenal organizations from a sales training perspective and how I found them. 14 years ago was a great magazine called Selling Power Magazine, still exists today, lists the top 50 companies in the world to sell for. And I've worked for Aramark, that was on it. I've worked for a career builder that was on it. And then I've also worked for adp, that was on it. So, you know, for me I've tried to task myself by working for organizations with phenomenal sales training because I felt like foundationally that would set, you know, me apart. My career.
What does that look like inside those organizations? For those of us who've never stepped foot into a anything other than a couple hundred person startup before, what are Those training programs look like inside of there. And what could somebody like me, who is working with startups all the time, what could I steal from them and input into, you know, my startup gigs or what could, what could early stage VPs institute to mirror some of those good big training programs that you've seen.
And Scott, you're an expert. This, I mean you, you're a playbook guy, you've helped countless startups. I mean you wrote addicted to the process of everything that you preach and do. It's that refined to the nth degree and done over 50 to 100 years. So it's that thought where there isn't a.
We don't know or we haven't or let's build this or let's refine this. It is, this is how it is. This is how it always has been. This is what we do. And so it's very much teaching people exactly what to say, what to wear, how to talk. You know, there is no off the script or off the cuff or outside the box. Like you are in a box prepared.
For all possible scenarios and know exactly what you're supposed to do next. Right.
At all times. It is the opposite of a startup. It is here, there is no outside. It is, you are going to do exactly the way we tell you to do in the way we tell you to do it. And don't buck the system and don't rebel because we've trained countless people and invested countless millions to building this. So we want you to do it our way.
I think what I heard him say, Richard, is that I have to live for another 50 years.
Yeah. I don't think Scott would have survived very long. I don't know that I would have either. So.
That'S interesting. When did you know you liked sales though? Like you, you know, even as a kid, were you the competitive kid? Were you always sort of, you know, you know, we always ask people, were you selling candy at school against the rules? When did you knew you like, know you liked sales?
I think I was always competitive but I think the where I really found it. It was my first official sales job that wasn't a sales job. I was working, I was about 16 years old working at a local computer store called Speed PC and they, I liked actually building computers. I was kind of a geek. I was back at the house building a computer for a customer and they came into the shop and started talking to the owner about it and the owner called me out and I started talking with the customer about what they were trying to do with that computer and, you know, what they wanted and what the purpose was and what problem they were trying to solve for themselves and all of that. And I listened and I started making recommendations. You need this much ram, you need this size hard drive, you need this speed, yada, yada, yada. And at the end of it, the customer's like, go, build me that.
Is this your first sale?
That was my first sale.
You see, you just walked out of the back, out of the lab, so to speak, with your little glue gun and whatever you build computers with. Walked out and sold something.
Yeah, man, that was it.
Now my question is, how come you.
Have a pocket protector?
There wasn't a pocket protector. No.
Okay, David, so my next question is, how come all the other engineers out there and hardware builders can't just walk out there and sell the way you can? Like that? That's amazing.
I realized at that time, though, I actually liked talking with people. I liked asking lots of questions. I was more extroverted. I may have been a geek at heart, and I still am. I still love computers and games and all that stuff, but I also like solving problems. And I think that's really where it came and came out is the owner said to me, after that, David, you're going to be our salesperson now. And so I now was at the front of the house. Anybody who walked in, I would just try and solve their problem.
And then I'd go build it, and then I'd come back and it just. That was kind of it, man. I don't know why others can't do it, but I like talking with people and solving problems. So that's just me.
That's great. Talk to me a little bit about your time in ADP and what you learned in the outside sales kind of environment and how it compares and contrasts to the inside sales environment of most modern software companies, you know, today. And the reason I'm asking this question is I have recently come across a lot of people who have lost their job in outside sales and are nervous about making the switch to inside sales and want to know how they can succeed at it. What advice do you have for those kind of folks?
And it's an interesting question because there's a lot of people who draw very specific nuances to it. I don't. I honestly have always felt like outside inside sales are very similar. I'm also the type of person that when I was selling outside, I would travel as little as I humanly possibly could. And the reason for that is I have a six year old and I've got a wife and I love spending time with my family. So before I got on a plane or hopped in a car or traveled anywhere, I wanted to make sure it was actually a qualified deal. Because I can't tell you how many times early on in my I would spend weeks of my life on the road and not get any benefit for it. And one of the things that actually changed the game for me was telling people no, was telling people I wouldn't travel, that I wanted to qualify, present, you know, do all of the, what I consider, you know, early stage parts of the sales process. And when I would travel is when we were going to get a bunch of people in the room with decision makers to do almost like a final presentation, then take people to dinner, break bread, build, you know, that strong, lasting relationship and then sign the deal and move on. That's typically when I traveled in my, in my sales career.
So what kind of things would you do to push people to let you qualify them? Right. And I don't mean in an aggressive way. I might have asked that inappropriately. But like, what was the defining moment deeper than are we going to get enough people in the room, like, how did you get them to that stage to say, yes, I'm going to get enough people in the room for you to travel?
So my sales process has always been fairly methodical. We're going to have a first meeting. That first meeting is 30 minutes and we're going to build some rapport and understand pain problem and then we're going to align on a potential solution. Then I was very prescriptive with the next step. Next step, we're going to do a deep dive analysis. We're going to really, really dig in to all the elements and all the questions would be fairly laid out. I'd send them to them ahead of time and then we would go through them together. Then I would present my idea of a solution as well as what I felt like it would cost and what I felt like the business case from an ROI perspective would be that we learned in discovery at that point. That's when it's too often was a chro and a few other people on their team that I would be involved in discovery from there. If they're like, look, we can afford it, we see the roi, we agree on the solution. I've done most of what people would do in person. I've done most of the selling at that point. Now it's, let's get all the stakeholders involved in the room and actually present what, what we're going to be doing for that organization. So I wouldn't, until I got to that point, that's often where I was like, do we have the business case? Do we have alignment? Do we agree if there's a problem we could solve, do we agree how to solve it?
So how do you teach that at outreach? Right. How do you teach a rep to say no in a healthy way that's respectful to you, the brand, but also to the prospect and customer? Because and oftentimes, you know, it feels like you're speaking from this wisdom of skill and years and honing this down. Now you're, now you're having to transition and teach people who are not as you just haven't had as much experience. And that's not their fault. That's just where they are in life. How do you coach people to take that? Because it's a pretty bold step.
So I feel like it's the job of the salesperson to define the next steps.
We as sellers know the buyer journey for our solution better than the buyer does. And the buyer knows how to buy other solutions, but they haven't likely bought our solution in the past. So you speak from this position of here's what we see as the next best action and here's when we do these things and this is what we've seen the most successful. And I actually have a slide that I will pull up at the end of meetings and say, here's the journey that we're on together. And we just had our first meeting. Here's what the next meeting looks like, here's who's involved, here's what we're going to talk about. And at the end of that meeting, it's very prescriptive. Then you know, you can even layer on. This is normally when we come on site and have this conversation. So you kind of just, you know, you prepare them with the journey that you're going to be going on together and you come at it through a lens of we've done this before and this is what success looks like.
Do you have reps who don't get on board and doesn't have to be at outreach? So let's make sure we're not talking about outreach. How do you, I mean, you can talk about them, but you know, I don't want Manny to get upset with you.
How did you coach people in that regards? Right. And I know some of that may have come from your ADP days, but how do you coach those reps who think they're smarter than everybody else.
You know, I've. I allow people to run and manage their lives the way they want to. When I lead people, I'm going to talk about what I've done. But if for some reason they are better in person and this is more natural for them, I want reps to be able to play jazz, especially once we get into the enterprise segment. There are some people who are really, really good in person and they can over the phone, they're not as good, they don't build relationships, they don't connect as well. And so I recommend people to sell the way, play to their strengths, do what they're good at. But if I then start noticing feedback from them where, oh, I can't get these things done, or I took another plane flight and I'm away from my family and it didn't go anywhere, you know, if I start hearing those types of things from people that I've led in the past, and it's like, well, how about you try it this way? This will give you more time with your family. This will give you a better thing. This is what I've learned. So I try and let people do it their way and see if it's successful and see if they can get all their work done. And if they start, you know, struggling in certain areas, then I'm going to layer on, hey, how about you try it this way? And for the most part, a lot of people will come around to it, but there's some folks that are just really better other places, and I don't want to, you know, put them in a box.
David, talk. Talk to us a little bit about this passion project and podcast that you work on with your wife. Psych and sales. Particularly interesting to me since I have a psychology background. So how did you get started in that and what is your goal and where are you taking it?
So that was very start of COVID We were just hanging out one Sunday night, drinking a bottle of wine, having a conversation, and we were talking about how her and I were going to structure.
From home. I've always worked for the last eight years. My wife has two offices. She's always been office bound. My son has always been in daycare or school. So we started looking at how is she gonna get her job done through video therapy? How are we, you know, manage my day, her day with our son home. And we started talking about how we were gonna structure things and like aligning calendars to make sure when I was working she wasn't and vice versa. And here's when we were gonna both help our son and all of that. And so we started talking about that. We were like, man, this is really good. I was like, I bet parents all over the world are having this exact conversation right now. Let's record it. And we did, and we got some interesting feedback. And so we're like, all right, well, maybe people are struggling with other stuff, so let's just record that too. And it started becoming this just fun ritual between my wife and I where every Sunday night we grab a bottle of wine and just talk about what we're seeing out there and things that we think could help. And then that has transitioned to. Now we're having guests on and we're having them talk about.
What are those things you're seeing? Right. What are those? You know, we're at a really critical moment. It's August of 2020. Back to school. It's happening right. People are. We're not where we hoped we'd be in March. Whether we were naive or right. Doesn't matter. What are the things that you guys are talking about that is resonating with people? Because I think we have a lot of parents who listen to this.
Burnout is really big.
I find, and I'm, and I've experienced it personally, most high performing people just work through problems and they just work harder. And what I feel like a lot of people are struggling with right now is that it's very hard to outwork this problem because a lot of you don't have. You've got your, you got your spouse home. There's the things you used to do to decompress aren't happening as much. And then those personal rewards that you have as salespeople of, you know, winning deals and things along those lines are getting pushed out. So you're not getting the gratification that you used to. And then you also have lots of external pressures that are bombarding without as many, you know, releases. So we're, you know, burnout has been a big one.
Depression, of course.
Laying gratification and being able to work through elongated sales cycles, fear of potentially losing your job and organizations, maybe not having your back. Those are all kind of like big topics that we're talking a lot of people on.
So this, you know, this speaks to me. I've written about it about, you know, I made depression my superpower. Been dealing with it long before I was in sales.
What are a couple of things you can give people who are listening, who may or may not want to admit they've got These challenges or maybe they have, but they don't know what to do. What's the recommendation? Aside from just the topic?
Yeah, so some big ones. You are not your number. So many people tie their success to their sales goals and you're not in your number. You're so much more than that. And so that. That's one another one is looking at and confronting some of these things. So it's like physically almost like writing down if you're having a thought. It's fighting that thought in the sense that I'm gonna write down, what does that thought say that's good about me? So if I'm stressed out that.
I'm not making commissions because everything. Well, the good thing that says about me is I care about my family, I care about my well being. I want to be successful. Maybe. What are some of the that that says I'm fearful of my job. Okay, well, if you lose your job, will you get another one? Yes. Will you get another sale? Are other people going through this? Am I alone? Have I had the right conversations? My boss. So it's kind of like.
Reframing that narrative to both understanding the pros and cons that, that you have around it, knowing that there's a lot of people going through it. Go ahead, please.
What about the organizational level? Right. You've seen it in a lot of organizations. Big, small. I know, I know Manny. And he's very big on health, mental health, life. Right. He's a leader in that space, in my opinion. What are some recommendations? Maybe you're the sales leader like you and your company doesn't operate that way, but you want to operate that way. What are some advice for the company leaders who might be listening?
You have a lot of open and honest communication with your salespeople. Tell them where it really stands, where the organization is. Some of the biggest reasons why people get depressed or have fears because they don't have certainty. So give them certainty. Whether it's good or bad.
The known is better than. So let them know about the health of the organization. Let them know about the health of the team. Talk to them about how they're feeling. Let them know that you see them as more than their number, that you understand that this struggle for everyone. So have those communicate, have that those conversations with them. Let them know that you know your job is likely not in jeopardy if you're going through.
So help redefine what good looks like for them. Maybe good used to be closing a deal a week or a deal a month. Now maybe good is Keeping your customers engaged and moving things along the sales process, even though it's taking longer or setting new meetings or more education sessions like help redefine good doing those different types of things are going to have a big impact. Like Manny sends out weekly communications every Friday of how our organization doing. My boss sends out communications empathizing with working parents and letting them know that if you need to spend time with your kids because you're working from home and they're homeschooling and need to take a couple hours a day to do that and then get back to work later and you need to be offline, that's okay. Like it's just, you know, being very transparent and caring about the individual and having conversations about what they're going through.
We were talking beforehand about the book that you wrote. So I got excited because I was like, oh, that's like the prequel to my book even. So talk a little bit about that. Tell everybody what the book is and, and why you wrote it and who it's for.
So it's called your definitive sales career guide. It is for people thinking about a career in sales. There's so many books on like sales process and how to sell. There's not a lot of books on why sales and so many people that aren't in the sales profession fall into it by accident or have this negative stigma around it. And what people don't realize is sales, you have the highest earning potential with the lowest barrier of entry. But a lot of people when they think sales, they still have snake oil salespeople, used car salespeople, you know that the swindlers and grifters, they still think about that associated with our profession. I think they all.
They also think of like the mass scale of failure and frustration and ups and downs that are involved in our profession as well. That skews some people off to and.
Those are people that maybe have some history with it. We surveyed a hundred people before I wrote our book and almost all of them fell into it by accident and.
Had some sort of negative stigma tied to it. So the first chapter of the book is.
Dispelling myths. What to love and hate about sales. Why even think about it? So it's painting a really clear picture of this career path. Then the middle of the book is all about interview techniques, how to write the resume, what questions to ask, how to essentially find the right company and get the job. And then the end of the book is almost your 30, 60, 90 day plan, year long plan of here's how you just ramp up and build a strong foundation for yourself. And then it's a reference guide to all the other books to learn kind of the more selling skills, if you will.
So I've just finished David writing my second book which is all about the life of a VP of sales, basically. So now you need to write your second book, which will be the prequel to my second book. And it should be all about like, how do you know if you want to be a VP of sales?
Right.
You can fill everybody in on that process.
How do you know if you're ready? I tell people that are thinking about going from being an individual contributor to leadership.
Look at when you get excited, get excited about seeing other people win. That to me is the first glimpse of sales leadership. When you coach and develop someone and you see them have success with it, that's your first glimpse. If you still get jealous of other people winning, you're not ready to be in leadership yet.
What is your, what is the first like thing that you do to pressure test whether somebody has the capacity to lead? And I'll give you one example that I do or have done in the past. I've noticed that the moment I start telling somebody, hey David, we've got this sales management spot coming up soon. Are you interested? I'm considering you for it. I think you could be good at it. I noticed that people do one of two things. They either lean super heavily into the leadership stuff and drop the ball on their day to day job still and think that they can win this management job by, you know, showing off some leadership stuff and they fall apart. Or they continue to do their job really well and pick up people pieces and add certain things and help, you know, make a sales leader's job easier and whatnot. That's like. So I sort of dangle this out there to watch people, how they react to it and how they can kind of keep two different outcomes in mind at the same time. So I'm curious how you've, how you think about it and what things that you've done and what you look for.
I look for, do you create followers?
So, and you guys have probably seen this in your, in your sales journeys. Once you start being at the top of the leaderboard, other salespeople call you and they ask you what are you doing and how are you doing it? And the reps will often respond to it in a couple different ways. Some are super guarded.
Some don't really give time or give very loose advice and some really dig in and want to help people get there. And ask them lots of questions and share, you know, best practices and they, you know, create informal mentors and mentees and they, and that just starts happening and those people start coming back to those folks again and again and again. And then those people start telling their boss, hey this person helped me with these things and I really appreciate that because you start hearing it in the shout outs of the deals those people want and when you start seeing more and more of that, those are people that create followers. And if you can create followers, you can lead.
How do you. So let's look at it from the other angle and maybe answer the same question. How do I choose a good sales leader? I'm a rep, I'm looking and I'm like, you know, I can imagine what a conversation with David would be like in that interview process, but what are the kinds of questions I should be asking my sales lead, my potential sales leader to see if it's right for me?
That's a great question. So Richard, let me ask you this. If someone said to you, hey, what are the sales methodologies you believe in? What would you tell them?
I believe in mine.
I created one consulting form of. But you have a methodology. You'd hear things like challenger spin, selling med pick, winning by design. You know, you'd start hearing all these, these different methodologies.
Right, right.
If you ask a good leader, hey what say what sales leadership methodologies do you subscribe to? You should in theory hear the same. Oh I love John Maxwell. I mean there's.
Their leadership and sales are paths. People that have chosen to be good leaders have. They just haven't woken up good leaders. They've studied it. They've studied leadership, worked hard at it. They tell stories about what it's like to work for them. So to me that's how I would determine a good leader is have they dedicated themselves just like a good salesperson dedicates themselves to sales. Have they dedicated themselves to being a good leader? And I try and figure that out the same way I would. If someone's a good salesperson, what's their process? What do they do? How do they work with their reps?
So what, what happens again? So if I'm the rep and manager doesn't know that. Right. Like I've nobody ever told me here the sales leadership books to read right here the you know it. And again I lived in a small world, startup world type place.
What would I do? Do I run to for the hills? Do I what do I ask? Maybe people on his on the team. Maybe when it gets to that stage of like, hey, you're going to interview with a couple of our ease to see what they're like. What kind of things do you ask those people?
So there's, to me, there's some tenets of leadership.
Do people work for you or do you work for your people? So I would ask some questions, hey, what's a typical one on one look like? And if it's highly pipeline and forecast driven, man, that, that to me is a red flag. Is it, hey, I want to understand your priorities for the and see what they are and see how I can help. That to me is a collaborative you and me against your quota approach.
Are you, when you look at deal strategy, I would ask, hey, how often are you going on meetings with people and do you review calls and do you, how do you help people prep for meeting? What do you do during a meeting and how do you help us after a meeting and what's your relationship to our buyers and what do you do inside of my opportunities? So I'd be asking questions like that and then I'd be also asking, how do you help me remove internal roadblocks?
So are you going to bat for me and do you have my back?
That's great. Those are all. It's funny, we interviewed a woman the other day and she defined culture as, you know, not necessarily how much you like the people you work with, but how easy is it to get shit done in the organization? And those kinds of questions show me that at a sales rep level, how easy is it for me to get my job done? Not that my job is easy and what kind of support do I have? And I think that's what you're really talking about. So I really just sort of continue to validate that in my opinion.
I know you talked a little bit about psych and family and those things just shifting entirely. What do you and your wife do to create downtime in this world? Right, Your wife's used to being in an office, being around a lot of people. You're used to being home. How do you support that? Your spouse, how do you support each other in that?
It requires more intentionality than I thought. We tried to wing it when we first started.
We all.
It didn't go well.
So with intentionality and it's funny, both my wife and I were a type, hard charging type folks and we both need to look at each other on the weekends and say, put your phone away, close your laptop, we're gonna listen to music by the pool. And we're Gonna have some margaritas. It needs to be prescriptive and it needs.
And if it's not, we're just onto a lot of patterns because frankly, everything feels like work these days. It's Groundhog Day. We're all home nonstop. We're not most going anywhere. I haven't. We haven't left our house in any meaningful way in like six months at this point. So if we're not highly intentional about it, not reading the news, turning electronics off, spending time like being prescriptive, we just find ourselves, you know, treating every day like any other day.
Just out of cure. What do you. So you. I love that you. You like listening to music by the pool, right? What other things? Like, I'm trying to. Again, I like to give people idea more than just the idea of like, oh, I hadn't thought about that.
We pick what movies we're gonna watch every weekend with our son. So we have conversations about with what. Hey, hey, Ian. What is. What would you like to do this weekend? Oh, I want to do a movie night and I'd like to set up a tent in the backyard. Okay, we'll do that. So we try and make sure it's a good experience for him. So we ask him every single week, what would a good weekend be like for you, buddy? I want to do these things with you. So we make a plan to do those things. Then we. Then my wife and I, hey, love playing virtual reality. We've got really cool, like surround VR setup in our living room. So we will talk about that. Like, we. What do we want to do during the day? We want to grill. We want to cook together. What do we want to do at night? We want to watch these movies. We want these, play these games, do this VR. Like, we make a plan for the weekend and then we execute that plan. So it's kind of just being intentional with what are your hobbies? What do you like? What can you guys do together? And then spending a lot of that time together and putting our fricking stupid phones away for a little bit.
How do you guys again? And then we'll shift back to sales. But how do you guys. And how do you even coach people to, you know, it is Groundhog Day. And if we're not careful, we will be on our devices till 11 o' clock working. But then again, we've also got kids in school and I've got to sit there and be there. You know, I'm thinking of, mostly I'm thinking more of the, of the parents with the four Five and six year olds who just are, you know, the kid just can't sit there and look at a screen all day for three or four hours. What kind of advice do you give to those people, whether they're your employees or to your listeners of the podcast?
Value the time, take the time, know you'll never get the time back. And know your kid is probably struggling with this worse than you.
I know my son feels lonely. He's an only child. He's used to going to school, having daycare, and playing with, you know, 20, 30 something kids a day. He hasn't seen or played with another kid in six months. If I think this is hard on me, it is so much harder on him. So I try and be really intentional about that. Like, son, let's do something together. Let's play together. If he wants to play on his phone, let's find Roblox. There's games called like Roblox and Zumba. He loves both of those. So we can download them on our phones and on our. We will play them together. All right, son, let's go for a walk. Let's walk the dog together. Okay, that, like, let's play blocks or build Legos. Like, I try and find activities that he's trying to do and then say, hey, how can I? Let's do that together. Then I try and immerse myself in his world, not try and get him to conform to mine.
You gotta, it's, it's very. There's a sales metaphor in there about like meeting them where they're at, right? You gotta meet your kids where they're at, do what they want to do, not what you want to do, which is very similar to meeting the buyer where they're at rather than where you want them to be already or what have you. Right? So what is, what has been the most challenging part of being on this outreach? Rocket ship. Everybody just assumes that it's, you know, a beautiful thing and so fun and nothing ever goes wrong. And, you know, what an amazing place to be. I want to know some of the warts of being on a rocket ship like this. So first tell people about that about it. That's hard.
First. It is an amazing place to be. It is a great product.
With the episode titled the Warts of working at Outreach. We're not going to do that, man.
Every place has flaws, man, but sometimes some organizations flaws get glossed over more than others. And it doesn't even have to be outreach specific. I want to know what is the hard part about being At a rocket ship, right?
Yeah, I'll keep it a little broad. So there's multiple applicability. For me, one of the hardest things is being new. I didn't freaking realize how hard it was to be new. I've spent the last six plus years at a Fortune 250 in sales leadership. I thought I'd just be able to jump into outreach and rock it.
That wasn't the case. I had to learn all new products, all new talk tracks, build my brand from scratch. No one gave a shit about what I did in the past. So that to me was really tough. I forgot how hard it is to be new at an organization. And I can promise I'm not going anywhere anytime soon unless they fire me because I don't want to be new again. It sucks.
The other piece of being on a rocket ship or really I'd say any startup. And this was a big lesson for me again coming from 10 plus years in the Fortune 50250 ADP is they don't have everything figured out. Talk tracks do change. Positioning changes, competition is constantly evolving. Outreach kind of created a space right along with Salesloft and so, and there's a few other companies that you know, are trying to do what we do, but we're the players constantly iterating how we go to market. And so that is tough. We are flying a plane while we build the engines and that's difficult for people that are maybe used to all things being figured out for them. So that's been one of the harder parts.
That's a really good point about the processes changing, pitch changing and things like that. Right. Speaks to what you said before at the beginning of the show where you talk to some particular company who's been around a hundred years.
Right.
And they've got this thing dialed in completely, right? Yeah, not like that. Not like that. Even at a, even on a rocket ship that's taken off.
That's been tough for me because I'm used to, here's exactly what you do, how you do it, why you do it, go do it. This is more like what do you think we should do? It's like, oh, let's talk about that.
This has been fun. David, what can we do to help you and support you?
Hey, if people are looking for help with mental health and sales, Scott, you're going to be on my podcast here in a couple weeks. I'm super excited to have you on, man. Richard, you're of course welcome. Love to get your perspective as well, but you know, if you're looking for people that need help with mental health and sales. I think my wife and I have this really unique thing where she has her PhD in psychology and that's what she does every day. And I know one or two things about sales. So, you know, helping people both with mental health and sales process. If someone's looking for that type of coaching, I'd love to be able to support them. If you have people in college high schools that you happen to know that are debating our profession, love to see if sales is right for them. Love to share the book. We sell it for $9.99. We ain't trying to get rich on this book. We're trying to get it in as many people's hands as we possibly can.
Where can they find your podcast and your book? Is the book on Amazon?
Yep, books on Amazon. Podcast is on Apple and anchor. So anybody looking for those things, you know, just want to help them. And look, I coach a lot of salespeople for free, so if folks are just looking for general advice or have some questions. Scott, I know you do this, but you know, I'm here to support the sales community. So if you just want to pick somebody another perspective, find me on LinkedIn. David Weissoutreach, hit me up if you want to build a relationship with me. I will respond to you within 24 hours. If you try and sell me something, I will not respond to you. So please just can be a nice human and just be like, hey, I listen to you. I'd love to have a conversation. I'll give you so much time. It's no problem. I just want to help people.
That's great. Thanks so much, David. We appreciate you spending some time with us and hopefully everybody gets a chance to check out your podcast and your book. And I'm excited to get on the show in a couple of weeks. So we'll talk again soon.
Yes, sir. Scott, Richard, thanks for having me on. I appreciate you guys.
Yeah, no worries. We actually gotta give a quick shout out to lead 411. We forgot to do that beginning of the show. One of our sponsors who, if you're looking for intent data and direct dial phone numbers, please check out Lead four one one. Thanks, everybody.
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