232: Kris Rudeegraap on The New Path of the SDR

Hey everybody, what's going on? So in this podcast, it's a continuation of the previous podcast that I had with Doug Landis on my curiosity now about product-led growth and the structure of sales organizations. If you remember my conversation with Doug, we talked about how SDRs, instead of going into the AE, they go to account management and learn the product and then move up to account executives. And that coupled with product-led growth is a real interesting new format and structure for me. So we dove into that in this conversation because Chris actually founded Sendoso and they do have a slightly product-led component. They're actually getting into it now, whereas before they started on the enterprise.

And so he's seeing the trends. And we also talked about culture in this remote world and how to stay motivated and all that stuff. So I really hope you enjoy this conversation. What's popping y'all? It's your man, James. Say What Sales Buckley. And this is your weekly Make It Happen Monday's episode with your host, John Barrows. Big shout out to our partners, Sales Loft, Proposify, Gong, Vidyard, Chili Piper, and Salesforce Sales Cloud. Sales Loft, our original sponsor, is the premium cadence platform for all things outbound cadence to drive results. Customizable in every way and with APIs for your additional technology, Sales Loft's value is unrivaled in the sales community. So visit salesloft.com to see it in action for yourself.

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Make no mistake, Salesforce Sales Cloud will be the last CRM that you ever have to buy. Learn more at salesforce.com and dive in. The water is fine. Good afternoon, everybody. This is John Barrels. Make it happen Monday. Hopefully you had a fantastic weekend. Mine was pretty good. Mine was pretty good. Weather's getting better in Boston here. Not hating it. Hopefully you took some time to rest and relax and are looking forward to Mondays and kicking off right. So we are kicking off this Monday with a good friend. We've actually partnered. We've known each other, done a couple of webinars together, but now we're getting to know each other a little bit better. Chris, CEO over at Sendoso. How are you, my friend?

I'm doing really well. Thanks for having me on the podcast. I appreciate it. Yeah, thanks for coming on, man. I know, like you said, we've done a couple of webinars together here at this point. We've got a great partnership going. You know, I'm excited to talk today about this, you know, I'm starting to unpack some new ideas around sales models and what does the future look like? And I think you guys fit really well into this conversation. But before we get into there, tell the audience a little background, where you're coming from, what you're up to these days, and then we'll dive into it. Yeah. So I'm CEO and co-founder of Sendoso. We're a sending platform that helps sales teams and marketing teams send out direct mail, swag, handwritten notes, you name it.

Prior to starting the company five years ago, I spent about 10 years in sales myself, mostly as an account executive. And so I was, you know, in the trenches doing a lot of the handwritten notes, sending gifts myself, you know, up late in hours of the night, packing boxes and really dreamed up of this idea of, you know, clicking a button inside of Salesforce and magically things getting sent out. And so I decided to quit my job as a salesperson and, you know, the rest is history. Nice. I love it. I mean, everybody's got their own path, right? Let me ask you just off the topic we're going to hit on today. Did you always have that entrepreneurial itch? Did you always have that kind of like, I think I want to run my own show or did it dawn on you a little bit later in your career?

No. So I always did, I'd say. Even in college, I started a company that got some funding and then I sold it to another company in San Francisco. Right after graduating. So I already had that kind of taste of entrepreneurship and kind of already crossed the kind of conviction of figuring out how to go from zero to one. But I think I didn't have enough or a big enough idea after that to really want to jump back into it. So I'd say I kind of went back into maybe learning mode, working with other entrepreneurs, seeing companies scale in San Francisco. Meanwhile, I was really good at sales. So that was a benefit there. And then when this problem that I found, you know, hit me firsthand, I said, hey, this is something big enough that I want to do.

Yeah, nice. I think that, you know, what is it? Invention, necessity is the mother of an invention or whatever. Exactly. Like, you know, when you're feeling the issue yourself and you're like, there's got to be a better way to do this. And then you say, screw it, I'm going to go do it. So are you, are you a pretty risk, like, what's your risk scale here on a risk tolerance level? Like super risky, like live on mom's, live in mom's basement and eat ramen noodles and I got nothing versus calculated risk, need some stability, make those decisions. Where do you fall on that spectrum? I'd say I'm probably more up until like the seven, eight of the risk tolerance. You know, when I quit, luckily my wife was making some money, but I went from, you know, a nice kind of mid 200,000 salary or OTs into zero the next day.

So that was quite risky. But, you know, my longer term was really, hey, if I can make this payoff, I'll make way more in the long run and really be a founder and what really what I dreamed about. So definitely risky, but was benefited from having a bunch of savings and a wife to pay for some of the bills. So I wasn't, you know, sleeping on the couch or anything that helps. Yeah, that definitely helps. I think, you know, in your twenties, you, you have a lot more flexibility to take some risks in a lot of ways because there's not as much responsibility. But once you get into your thirties and you, you know, you got some bills to pay, you got, you become less risk tolerant. So awesome, man. Well, look, um, I've been, you know, wrapping this around my head.

I had a, an executive, um, round table the other day that we did and it was like, I think six or seven executives. And we were just talking about the future of the sales model and product led growth where I'm seeing a lot of money go these days and how this, this predictable revenue model that we're in right now is definitely, at least from my perspective, broken in a lot of ways from a scale standpoint. I think it's still pretty beneficial for organizations to build their sales org where they got SDRs. You got them in relatively cheap and then you move them to AEs and go from there. Um, but I just like, we're seeing such a high failure rate of SDRs go to AEs. Somebody brought this topic up, um, and they said what they actually do is they take their SDRs and they move them to, to account management first.

So instead of going to, you know, AE full cycle sales, they put them over there and they're, they're responsible for renewals, cross sales, upsells, that type of thing. So it's, it's still a sale, but it's not as like scary of a sale, if you will. It's like, Oh my God, I have to run full cycle here. And what that does is that educates that. So first of all, it gets them into selling full cycle, but second of all, you know, product knowledge, they get to see what the client, how the client is using it, what their priorities are and what the leverage points are. And I thought that was a brilliant approach to address what I see coming here is a really, really big challenge for SDRs as far as where do they go.

Right. With all the automation that's happening with all the, you know, those tools, it's like, uh, you know, I think we got about five years here and, and, and Sandoso, did you, so this product, product led growth piece, first of all, I want your opinion on that, but I want to start with, you know, Sandoso and, and how did you start, right? Did you start with a seed and grow approach and just getting in people's hands just to get feedback? Or did you go like kind of top down and you were looking to sell either enterprise or mid market first and then get the people to use it? What was your strategy on that and why? Yeah. So when we first went to market, our strategy was really more of a tops down approach.

I think I grew up in more of a tops down approach. So it was what I knew, uh, out the gate. Uh, and, and, and then also, you know, in the early, very early days, we had a product that, you know, was a newer category so that it wasn't ultra obvious how to use it at times. Um, so having a human assisted kind of selling process and a human assisted onboarding and success process was really helpful. And so I think in certain early categories where it's like a new thing to do, it's, it's, it was helpful for us to have that human component. Um, but I, uh, I would say that we've been kind of baiting, uh, kind of a more product led growth approach now that we have, uh, you know, tens of thousands of salespeople who've used us before.

Now that it's more obvious on how to use us. Um, and we see that kind of the, the self-service channel as a, you know, another avenue to drive demand gen and leads in outside of the other channels, like the SDR outbound or your traditional, you know, B2B marketing inbound. So, so you started top down now you're actually going with, and is that in response to the market, uh, or is it in response in some ways to the downward pressure that you're getting from investors to grow, you know, so to grow faster, right? Cause sometimes we see a shift in the market and say, we, okay, we need to address this because we're seeing the data of our existing customers and we need to make this decision. Other times it's, we got to find another channel here to figure out how to take this to the next level.

So is there a mix of that or is one over the other? Um, so definitely not really the investor, uh, approach. So it really, I think there's two things that I think about with that. One is I'd say it's the, you know, there's, we've seen data where, you know, SDRs or AEs are requesting demos and we know that they're not the end buyer and going through a demo request flow for an SDR. That's just not going to work. We, they get DQ'd instantly. And so one, we wanted to capture kind of that interest and intent. Um, and so that, uh, made sense for the kind of getting the end user to the few clicks, getting into the platform, using it, sending it, getting sticky, telling their colleagues, and then seeing that kind of groundswell there.

And then I think the second part is, you know, I'd agree with you, John, I'm seeing more product led growth conversations. I'm seeing more, you know, uh, the buyer's journey thinking about how do you, uh, lead with, or how do you have a product led component? So I think that it's, it's partially the future. And so we want to kind of get in early because it is a new, uh, muscle for us. And so how do we kind of early beta and learn from this? Yeah. And I think that's, you know, we go back to agility being like the number one competitive differentiator for today's day and age. So how do you, uh, you know, one of the things that frustrates me about SAS in general, right. Is that everybody seems to follow the same playbook just because it's the thing to do, you know what I mean?

They follow the predictable revenue model. They hire their SDRs and they go through that. And, and I mean, even doing, you know, events and webinars and, and, and those types of things, it feels like so many people do them just to do them because everybody else is doing them. Not really to think about, is this actually working? So how do you as a CEO, um, balance the learning from others, right. And, and, and, you know, what got us here, but then keeping yourself and your org constantly re-evaluating the effectiveness of whatever the structure of the approach is. Like, how do you look at that from a CEO standpoint of a, of a funded company? What I forget, what series are you guys on at this point?

Uh, series B. Series B, right. So funded series B, a lot of momentum going here and some real uncertainties in the marketplace as far as what's happening right now. I mean, literally nobody knows. So how do you as a CEO balance that? So I'd say a couple of things come to mind. One is, you know, uh, from learning from others, I've actually put together a pretty sizable advisory group. There's about 200 folks in this advisory group. Um, so it's probably more unique than you've heard where people have a couple advisors. And so that gives me access to really smart people around the globe with different backgrounds that I will, you know, once a week ping somebody to get their feedback or to kind of do a, you know, a deep dive kind of thought leadership piece.

So I think that gives me a really good ear to the ground on what's new, what's exciting. Um, I, I, I find myself like demoing new software out there or being open to like, Hey, how do, what's the newest and greatest software tools? Like pitch me, you know, anyone listening, Hey, come pitch me on this cool new thing. Um, I love being a part of some of these like angel investment groups or these other kind of funds where you see these, you know, early stage seed companies creating the newest tech. So I think creating, um, you know, giving yourself the ability to say, Hey, what's the newest tech and being open to being early adopters versus, you know, maybe some CEOs are like, Hey, that, you know, let's not buy new software.

We've got enough kind of mindset. I think those two things. And then I think I'm unique and coming from a sales background as a CEO. Um, I think, uh, there's a good amount of, uh, at least the Silicon Valley is more like thought of as being like a product or engineering type founder. And so my sales background, I think lends me to wanting to be more sales focused at times and being more open to new sales tactics and trying to keep an eye on that too. Yeah, I, you know, it's funny when I left back, when I got fired from, from staples, right. Um, you know, I had been, you know, going through it and I had had this singular focus and, you know, when I got fired, I kind of had to wake up and realize like, what do I do here?

And, and with like, where I guess what I'm trying to say is like the adaptability factor of, of being able to have a different lens on to, to be that growth mindset was, was a shift for me, at least. How do you coach your reps on how to look for that in C-level executives? Cause we look for early adopters. We look for people, you know, you have a pretty good story about those early adopters at Sendoso. So how do you identify those that are a little bit more like want to be progressive and that type of stuff versus I'm good here. Right. And, and because I think we go back to ICP and personas and who we should go after to get those first few customers, whatever. How do you coach your team to look for that or is it questioning skills or is it there something they look for?

Yeah, it's a good question. I think, you know, I think a couple of things come to mind. One is I think as a, as, as good reps are, you know, you're always kind of playing with messaging and seeing what works. And so I think that, you know, creating a, you know, a sequence that has, you know, geared towards that type of ICP. And, you know, specifically this is the early adopter messaging versus the, the laggard messaging is a great way to kind of differentiate, but, you know, always, how do you find that person at the end of the day is, is tricky too. So I think you can identify sometimes by what current tech stack they're using. You can get indications like, okay, they're, you know, they're more modern in their approach because they're using these four tools.

Like they're much more likely want to use us. So I think that's important or seeing, you know, doing research on the CEO or other people, seeing them on podcasts or other areas where they're, where they're more outgoing, talking about their strategies. You can tend to get an idea that they're more progressive that way as well. I think I was, there's a site called listen notes.com where you can search people, search like a podcast search engine. And I like, I like doing that at times. I tell my reps to like use that as a tactic because it's a great way to get insider information that maybe it wouldn't be written anywhere. And so I think you just got to do a little bit of your homework. And if you, you've asked the right questions, do the right research, you can get a few like leading signals.

Yeah. And I think, you know, you had brought some, as far as being a sales leader, the difference between that and being an engineer leader. I actually think that makes a huge difference because, and where I was going earlier was, you know, when I, I was in tech sales and I was, our CEO wasn't like, he was more technology. I mean, there was kind of a three headed monster there. Um, and then, but then when I got to Basho, this training organization, right. It, from the top down, they all supported sales. Like it was sales all day, every day. Even the CE, I remember the CTO coming up to me and saying, Hey, everything about this company is sales. We support the sales team with everything that we got.

And I was just like, Holy shit, what a different environment this is. And it, and it was more, let's try different things. It was more growth oriented. So, you know, a small tip I always give kids who are in sales and want to go work for, you know, say what company I should work for. I go, go look, go look at the background of the CEO and see if the CEO's background was engineering or if it was sales. And if it was sales, that's a place I would probably focus on more than not, because those are going to be the ones who are probably more progressive, who are probably more willing to try things that especially align with top line growth. Right. And, and you can kind of profile that. So it's, it's, did you take that approach when you first started Sendoso?

Were you very selective with your first few clients so that you could get some feedback and maybe give a little bit more away than you did afterwards? For sure. Yeah. And I think in the early days, you've got to do that to build up your, your roster of clients and really get people talking about your product, get the early advocates out there. So I think that's a really important part of like kind of the first year in business. Yeah. I think the, you know, a lot of people want to grow a little bit too fast, you know, and it's, it's crawl before you can walk, you know, you obviously need product market fit, but those first few customers are gold. And did you ever chase, I, we had this problem.

Did you ever chase bad customers just because they were giving you revenue? Yeah. I would say, um, maybe we wouldn't, we weren't chasing bad customers. I'd say we would, uh, uh, maybe we, we just chased a lot of different customers at once. And we, I think our early mistake was maybe we didn't price it right day one. And so about for like the first six months, we were, we, we feel like we were priced on a very like low monthly, you know, user cost. And we realized that that wasn't really a sustainable model. It was easy to get people in the door and it was like, oh, this works really well. Everyone wants it. Um, but then when we did the math with the new CFO that came in, we're like, we need to 10 X our pricing in order to actually create a sustainable model.

Kind of going back to your, you know, predictable revenue model where you've like need SDRs and AEs and the system that gets expensive. And so we really, uh, with that, you know, said, Hey, let's 10 X pricing. We, you know, no customers flinched at that four years ago. And so it was a great decision, but I think in the early days, maybe there was maybe false positives or as I got, you know, getting people signing up, but they were paying pennies to use it. So it wasn't a perfect indication of product market fit. I like that because I, you know, the, the focus on, you know, even though there's revenue to be had, there's, there's good revenue and there's bad revenue, there's good customers and there's bad customers.

And the death of any smart startup is getting bad customers with bad revenue that end up being a boat anchor for you. So you can't really go explore what you need to do. Yeah. I have heard horror stories too, where you get customers that are just ultra demanding on your product. And you basically turn into like a solution, like, uh, for that customer and you're end up just building custom stuff for that one customer. And then it doesn't build your whole product infrastructure. You're just like, you know, the one-off like tech shop for their feature needs. And so I think we early tried to stay away from that a little bit more and said, Hey, everything we build needs to be for everybody. And that really helped us, you know, build value for everyone instead of getting pigeonholed on like a really unique use case or something.

Yeah. I mean, my CFO, my first startup, he, he had some, as much as I hated it, cause I was bringing in some big customers. He was like, we are never going to have one customer that's more than 10% of our revenues. Yeah. Like period. Uh, he's like, because then we are beholden to them. They're going to, you know, they're going to think they own us basically. Yep. And then they're going to let us force us to do things that we probably don't want to do when we could go out and get a whole bunch of other customers. So I, I, as much as it pained me, cause there was a couple of times I brought in some whales and I was like, dude, my C, you know, my CFO was like, no, that would be literally 25% of our revenue.

And we would have to go staff up just to get that client. And then if they fire us, we're sitting there on that staff and all those expenses and we're screwed. We need to have that as a five-year customer if that's going to be the case, right? Yep. How do you see, so with this product led growth, um, you know, let's go back to just the, the evolution of sales and SDRs. And their role within the sales process, how do you look at the SDR role outside of just getting meetings, right? With, you know, the, the, the typical get meetings with your main ICP and your personas, where are the other areas that I think companies are missing on as it relates to leveraging what SDRs are capable of doing at the stage that they're at?

Yeah. So, you know, I think a couple of things that we've done for, and this was with the career progression with SDRs too, or just, you know, complimentary to their skillset. Um, we've looked at where, what they're good at and where other places in the organization that they could thrive. And so we've seen career progression into our partner organization and, um, you know, uh, given them a, a different, you know, more heightened title, but still some of it is kind of breaking into new partners. Uh, we've also seen that from our current customer base where we have a unique kind of land and expand opportunity because we sell into SDR teams, AE teams, CSM teams, HR teams. And, and some of those act or different business units in the same companies.

And a lot of those act very differently. So, uh, rather than an account manager having to, you know, break into all those themselves, we have kind of SDRs that are, that are account managers with again, different titles. But their goal is to work hand in hand with the account managers to help set meetings and break into new use cases into current customers. Um, and then on the, uh, the kind of product led growth example, we've done some testing where we've, we've kind of promoted an SDR into more of like a, a product specialist where it doesn't feel salesy. But the goal is, is for people using our, uh, like our product and a more like trial, you know, product led growth environment. It's more of a, Hey, how can I help you?

Uh, versus like, Hey, let me get you a meeting and book. And so they're looking at, you know, the product usage data they're looking at, um, you know, is that person expanding and what are the, you know, the product levers that, that are product usage levers that they're hitting. And how can we get them to those usage levers and be more consultative, um, and let them kind of boil up to the top, raising their hand that they are ready to kind of, uh, get into a full annual, uh, commitment. Um, so I think that's kind of a, a unique way, uh, and it goes really to your point of, of how SDRs are progressing in more of a product led growth environment. Yeah. And I, and I love the, I love the whole concept of SDR to account management or working with in tandem with a CS to learn not just how to sell in a safer environment, but also to learn the product, to learn what, how companies use it.

Right. So that when they become sales, right. Or they decide to go up there, you know, to, to the AE role full cycle, they're so much more well-rounded and well-versed to have conversations with people as opposed to pitching people. Yeah, I agree. And I think that when you're in that account management and CS environment, you tend to hear stories of how customers are using you. You tend to help, like you said, dig into the product and you learn the feature sets. So all that becomes super valuable when you then want to become an A and you have the stories to tell, you have the product knowledge to answer. You know, you're not always dependent on your sales engineer because you can be a little bit more hands-on with the product.

And I think that extra effort and learnings, you know, are not always the case when you're just a pure SDR and you're just like, Hey, my goal is to, you know, dial, dial, dial email, send out so blah, blah, blah, blah, get a meeting. You're not always thinking as much outside the box in terms of those other areas. Yeah. I think it's, I honestly think it could be the new model moving forward. It's, it's an alteration on predictable revenue, but it's, I think it's a pretty significant shift and an important one because it goes back to like everything now is customer focused, right? Everything is, is the experience and, and that type of thing. But like, if we talk about giving away stuff, a lot of this product led growth is literally don't, don't give them the free version.

It's like the elevated of the freemium, right? Where the freemium was, I'm going to give you some basic bitch piece of shit software that pretty much does nothing. I'm going to see if you download it and then I'll call you to upskill you there. Whereas product led growth is, I mean, pretty much giving them the product. So where's your threshold as, you know, again, as a CEO thinking about this, as far as how much you give away versus how much you hold back, right? Cause I mean, you, you hear the, the old adage that, you know, anybody can get a Harvard degree, right? It's all online for free. Yeah. You just got to put in the effort, but the reason people pay a hundred thousand dollars a year or whatever it is, is first of all, to get the, you know, Harvard degree stamped on their, on their thing.

But you know, they get walked through it, right? Yeah. So that's why Harvard still, you know, people still go to Harvard, even though you can legit get all their stuff. So I do believe in the pretty much give it away and they will come if they, if they really like it, but where, how do you evaluate that as you're looking at strategy and investments and growth and profitability and all that stuff? Yeah. So what I would say is, you know, depending on what your product is, there's going to be different answers to this. For us, I think it relates down to, you know, how much of your product or how simplified can you get to where it's completely easy to get onboarded and using the product. There's some really advanced software out there that, you know, certain features in the, in the platform, you know, could be overkill and could actually negatively affect someone trying to get in there and as an end user and start using it.

And so, you know, we, I think that's something you got to consider is this enterprise product that you spent, you know, five, 10 years building that has all the bells and whistles, you know, are you going to get people in there and get lost? And then they're going to, so I think it's a mix of what's the kind of least amount of features that they can have to be successful, but also maybe, maybe not lock, but maybe educate them that other features exist, but, you know, are more for advanced usage. And so I think that's kind of the, the middle ground is how do you get, come in there, show success, get success, do some virality. Like how do they invite other people, how do you, you see stickiness, but not opening up the, you know, Pandora's box.

I think, you know, Slack did a good job of this in the early days where I remember when you, after like 10,000 messages, you couldn't search anymore. And so like, cool, I can get going for a few months. I can search. It doesn't matter. I'm never going to get there. But if you needed that advanced, you know, functionality to search back for something like from six months ago, you're probably more of an advanced user at that stage. And you'd probably be more open to having a conversation about a, you know, an enterprise plan. So definitely. And I wish like, I wish back in the day, Salesforce had done, I wish they do that now, for instance, because Salesforce, I always kind of joke around about the problem with Salesforce is when you light up Salesforce that you light up everything.

So every field, everything, right. I mean, you don't get the add-ons like the marketing cloud or whatever, but Salesforce, just the CRM specifically. And then it's kind of like a house, right, where my wife and I, when we, our first condo was, you know, 800 square feet, right? That's, it was it. It was two bedrooms, tiny, 800 square feet. We moved to a 3,000 square foot house and we had one room that we had fit all our stuff in, right? So this little part of the living room, like I fit my couch in there and the rest of the house was empty. And I remember us sitting there being like, oh my God, like, what do we buy this for? Like, we don't have enough furniture for this place. It's way too big for what we need and all this.

And shit, six months later, guess what? We completely filled it up. And I was like, oh, we need a bigger house. You know what I mean? So it's the same thing with Salesforce where you give me a field to put some shit into and I'm going to put that shit into it, right? And then all of a sudden I've got this rat's nest that I got to reverse engineer and figure out and spend shit loads of money to clean it up. All right, y'all, this has been a great conversation with Chris. He was risky and I think that's an interesting characteristic that we don't talk about much in sales. Think about where you might fit on that risk spectrum. Where SDRs are headed has been a huge focus for us here at JBSales for some time.

And the insights in the first half of this episode are pretty legit. There's a ton to consider when predicting where the sales industry is headed over the next few years. So what do you think? Is product really leading the charge at this point? Send me your thoughts. I want to hear your reaction to this at james at jbarrows.com and I'll shout you out on the next Make It Happen Mondays episode. Today, we want to give a big shout out to Martin LeClerc of Care Simple. Martin had attended countless trainings that he felt might be, quote, stuck in the 90s. He became a member of JBSales and since then has become one of the 10% that apply our techniques and concepts to achieve goals consistently. During this process, authenticity, process, and relevance became a part of his sales culture as an individual contributor.

Since becoming a member of JBSales, Martin has remembered why he loves sales to begin with, and he's driving toward becoming a top performer. Way to go, Martin. We got you covered. Gain the skills and the tactics that you need to become a top performer like you deserve to be. Sign up and become a member at JBSales at ondemand.jbarrows.com today. Let's throw it back to JB. So it's almost like, give me what is the least amount of features with the highest amount of value that allows me to get shitloads of value out of whatever it is. And then to your point, monitoring the usage and then being like, okay, well, here's some add-ons here. Do you want that? Do you want that? Do you want that? So it's not just, I'm not giving that stuff to you.

It's I'm giving it to you in a more strategic way so you can learn how to use it. Is that fair? Exactly. Yeah. And I remember, I think it was, oh man, it feels like four or five years ago, but the Salesforce bought RelateIQ. And I remember RelateIQ was this like super simplified CRM tool that was like, kind of like what you're explaining. It's just enough to get shit done, not enough to like really break your mind over all these different bells and whistles. And I think it was, I don't know if Salesforce ever did anything with it, but I think it was a smart path for them, at least at the time when I saw it, to be like, good. You have this like a product that kind of easy to onboard, easy to implement, easy to kind of get adoption on, and then let people grow into the bigger features that you pay for.

What's your take on platform versus point solution? So I say this in that, you know, a lot of companies start in a niche, right? They do one very specific thing and they do it really well. And sometimes the exit strategy is I'm looking to sell, like I'm going to sell to a bigger platform. Other time the strategy is no, I want to be the platform. So as we roll up, right, we kind of look at, I look at Salesforce as an example for this, where, you know, they're growing, growing, growing, and they'll start to see something in the market take hold, like conversational intelligence or whatever it might be, right? And so they'll kind of cobble something together because they can, they got developers and whatever.

And it'll be like 60 to 70% as good as said product that it's specialized on that. So as a founder, you know, what's your whole thought process on building a very specific solution to solve a very specific need and just going deep on that versus coming out as more of a platform play that, that is, that kind of plugs into other things. So you're, you're not, you know, like, see where I'm going with that? Yeah, I do. So I'd say a couple of things. So first, I think most founders end up trying to solve a very specific problem, day zero. And so I think it's really like you're, you're a point solution day one. And ultimately you might even be a point solution on another platform. Like you build on top of something that integrates in the Salesforce or something.

And I think that as you get market traction or as the category that you're building into actually grows, you then look to say, Hey, could this be bigger than this one feature? Or, you know, and generally have all these ICP type users using us, what, what else would they need to use? And then do we want to kind of turn our, our feature into a platform? And, you know, what is, what does that even mean? You know, does that mean people can build on us? Does that mean that we are now like a system of record or a system of truth? And now we have this, you know, precious data that people want access to. And so I think it's, you know, I think it's tough for a founder to want to be a platform day zero because there's just so much to do.

But it's important that I think as you evolve as a company in, you know, year three, year five, you kind of make that decision. Are we going to stay down this niche path? We're going to own this till the end. And our exit strategy maybe is, you know, we're going to sell for 500 million or a billion. And our goal is just to get into sell to these players that we know could benefit. Or are we kind of going for the, you know, the super grand slam IPO and we're going to pivot into more of a platform approach and, and use that as a lever to drive more growth. Yeah. I mean, that's kind of where I'm trying to think because there's so, or it turned from a seller's market to a buyer's market pretty quick as far as employees are concerned and the amount of talent that's out there.

And if you're good right now, you know, you can kind of pick and choose where you go, but who do you, who do you pick and choose for, right? Like what, what characteristics do you look for to go start your next journey of your career? And, and, and I want to shift a little bit to the, the, the culture side of the house, because obviously culture has, um, kind of come to the forefront here, uh, for organizations, right? We going to a seller's market and going remotely, you know, it was the, the loyalty is much less because the loyalty, you might've worked for an okay company, but if you had a super cool team or a super cool squad that you kept going out and drinking with and whatever it is, you'd stay for a lot longer.

So there was a lot more connectivity to the organization based on the face-to-face interaction that we were having or the in-person interaction even more clearly, but now that everybody's sitting from home and basically doing the same job, right? As I'm an SDR for Sendoza, I'm an SDR for what, you know, Zoom, I'm an SDR for whatever. Um, so what, what are some of the things that you're doing differently now, uh, with this remote environment for your team to create a culture that people want to be a part of, as opposed to, uh, you know, let me see if I can get paid more here versus there. Right. Is there, is there some specific shifted shift that you've done in your mindset of, of building culture around?

A hundred percent. I think you explained it perfectly. Like you, if you're not thinking about culture, you're going to, you know, you're going to be behind the game and you're going to lose employees. So we are, I'm a hundred percent focused on culture. I feel like that's, you know, one of the biggest things I do, which is either trying to attract new talent or trying to keep current talent, uh, happy and going. So, so one of the things we do, you know, is really, um, and this comes from me too, is how do we be more transparent and visible and show showcase, you know, metrics, growth, things like that, that they can say like, oh, wow, this company is growing. This is exciting. This is interesting.

So giving them a little bit more taste of, you know, and in our all hands, maybe a product will go deep on something. Maybe finance will go deep on something. And for an SDR, I think that's interesting. So they can get a little taste of what else is out there in the company, uh, versus just being so narrow in their scope. Um, I think that's one thing. Um, I think another thing is we've done some more pairing AEs with SDRs in more of a pod structure, which was before more of a round robin structure. And so it gives you another person that's kind of your, you know, BFF that's there for working accounts in the trenches with you. So, and so I think that's been helpful. Um, we've, uh, we've thought about career progression outside of just AE to, or SDR to AE, um, or AE to, you know, enterprise AE.

And so we've opened up tracks and partnerships and account management and recruiting and, um, other roles. And I think that's helpful because someone might feel like they're getting burned out, but they're a great person. How do we, you know, give them a new life at the company because they've built, they understand our product, the industry so much more. So I think it's, you know, taking a chance at a different career, but on a person that we know is going to be successful already. Um, and then I, you know, I think some of those things outside, we do a lot of, uh, you know, uh, kind of virtual events or, you know, sending things to employees, trying to instill kind of more of a community vibe too.

You talked about the burnout factor of certain roles, right. And, and seeing what the options are. I'm, you know, the Simone Biles thing came up and it got me thinking a lot about, you know, the, the, the push through it, the mental health, the, you know, but also like, what is that line of an excuse right now? Simone, I I've now completely retracted any question I had about her personally. I just wish her PR department would have done a much better job. Like if she had come out and said, Hey, I got the twisties, it's like vertigo in the air. If I do another flip, I could land on my neck and kill myself. So I'm going to take this day by day and I'll see if I can do it. Like if she had just said that fucking there'd been no problem at all.

Nobody would have been like, Oh my God, she's a quitter. She's a loser and all that other stuff. But before we find out, found out that it was the twisties, I was a little bit conflicted with it. Right. Because I was just like, she knew the PR, she knew the pressure going into it. She knew what the expectations were. And, and it seemed like she bailed on those at the time. And again, I'm completely retracting, you know, my even questioning her. I didn't question her drive. I didn't question her commitment. She's done enough for the sport and us to be able to earn the right to do whatever the hell she wants to do. But it did get me thinking about this, the patience issue for sales reps and reps who are in roles.

And they're like, eh, I don't like this anymore. So I'm going to go do something else versus I should probably stick this out a little bit and grind through this. Not in lieu of my mental health, not in lieu of my, my, my health itself, but I need to push through. So what are you seeing right now? I mean, everybody talks about how, you know, I think every generation talks about how, oh, you know, I earned it and, you know, walked both ways uphill and fucking, you know, and all that other stuff. And I do feel like I'm sounding more and more like my dad these days when it comes to that. But how do you walk that fine line with these reps who are very eager to, to take that next step in their careers, but you know, that if they spend a little bit more time mastering, whatever that craft is, it's going to be way better for them long-term.

So how do you and some of the management team over at Sendoso deal with that progression growth path, if you will? I for sure feel you in that, the whole grass is greener syndrome for, you know, people are, it's like higher than ever. Like, oh, let's just do, let's, let me just do this again at another place. And that's going to be different. Like, so I think some of the things that we do, we put a good emphasis on like learning and development. So is there, is there training that we can do? And so we bring in, you know, outside trainers or, you know, things like that, that really make people feel like they're, they're learning and growing. So I think that's super important. And I think now is the best time ever to invest in, in learning and training because it feels like your company's buying into your future.

And so that's something that I think is key. I think that also can come with, with mentors and advisors too. So when I was in sales, I had a couple of sales mentors and I would go to them from time to time to check in. And I think not enough salespeople do that. And so for me personally, I have a big network myself as a CEO that I've developed these advisors and I open them up to, you know, my team. So an SDR and my team could talk to a CRO that's been enrolled for 30 years and can really, you know, get that executive type of conversation going. So where you get a, just a little bit more inspiration or you're like, oh shit, you put a lot of work into this. Like I've been doing this for six months.

I'm going to quit. Like maybe I'm, you know, I'm second guessing my decisions. So I think that's important. And then I think it's, you know, having good management and again, management training, but also good managers that could set up expectations and track against that. Like, hey, you know, this is not your, you know, the only role you're going to do for your entire life, but hey, we, you know, let's put, let's put out a six month and a 12 month plan in place. Let's track against that. Let's check in and do, you know, one-on-ones and, and, and see how you're progressing. And let's, you know, let's shoot for that end goal. You don't need to, you know, quit halfway in. Yeah. And it kind of stems from this.

There was a data point that the bridge, Trish Bertuzzi and the bridge group put out a little while back that said, you know, if you're the, failure rate from SDR to AE, if you stay in the role six months or less, the failure rate is something like 72%, some ridiculous number, like 72, 73% fail as an, as an AE, if they spend less than six months as an SDR. If you, I think it was, if you spend a year and a half, basically like 17 or 18 months, the failure rate goes down to like 12%. So just like that year of mastering that craft. But I think to your point, like we got to make it interesting. And that's why I don't blame like, especially SDRs for wanting to flip because nine times out of 10, they're doing some just straight up shit work that doesn't create, that doesn't have any creativity to it.

That doesn't stretch their brain. They're literally just pressing play on cadences and stuff like that. And, you know, at the end of the day, I don't care what job you're in. If you don't feel challenged, if you don't feel like you're learning, you're going to want out of that job as fast as you possibly can. And, and you can hold them longer if you, if you educate, but how do you balance that though with the average, you know, and do you think of this? I think the average rep now is like, you know, spends a year and a half, maybe 18 months or something like that in their job. So it's, you look at that as a CEO and say, well, kind of chicken egg here syndrome. Like I want to invest in my people so they stay, but average, you know, career, you know, is 18 months.

So why should I invest in them or not? Right. Like how do you balance that as a CEO? I think you just got to have to really hope that you, you, you know, are working with a players that will stay past that 18 months. And those people that you invest in will stay, you know, some of our early AEs are now managers been here for three plus years. And so, you know, some of them, uh, some of those shining stars will come through and will be worth their weight in gold. And so developing them, developing them early on and investing in them, I think pays off that way, but, uh, it does go back to your point. And I think there is something to be said to around an AE that has a good SDR background too, could be more self-sufficient at times.

And, um, maybe it's even better for their mental health because they're not like, you know, you know, I've talked to some of these in the past who like, don't know how to prospect if their life depended on it. And then they're like, you know, Oh, they're the round robin slows down or their territory is slowing. And then they're just like, Oh shit, what do I do? Am I I'm fucked now? And so I think they don't even, the SDRs might not even be thinking about that. And that if they perfect the craft and then in two years, they're like, perfect. I'm in a position or maybe they join a brand new startup when they're the first day and there's no SDRs yet. Cool. That's a really good background. I got this.

I know how to set my own meetings versus you'll talk to some AEs or field reps who are like, I don't know how to set a meeting, but I can close a meeting. And so it creates a mismatch at times. Yeah. I mean, I always say, I don't, I don't understand anybody who wants to leave their success up to somebody else. You know, like, I just don't understand that mentality. And I kind of joke, but I don't like when I, when I do training sometimes with AEs, senior AEs who think their shit doesn't stink and all that other stuff. I go, I'm just, I'm here to tell y'all that if I was your VP of sales, and an AE came in and said to me that the reason that they missed their quota this month was because they didn't get enough leads from SDRs or inbound marketing.

Before that sentence was finished, they would be fired and walking out of my door. Right. Because I mean, that's where those skillsets and I mean, prospecting is one that I mean, as a CEO, right, I mean, starting your own business and all that other stuff. It's an, it's one of the most invaluable skills that you could possibly have at all aspects of, of your career. So it just blows me away that most people don't kind of think of it as like, oh, I got to get through this, you know, let me get to that next step. And, you know, patience versus speed. I get it. I was kind of that way too. You know what I mean? I remember the reason I quit Xerox was because I was getting so much smoke blown up my ass about how good I was at what, and I was just doing my job.

I thought, but, you know, it was my role, then the next role, and then the next role. And I was like, all right, apparently I'm pretty good. You guys are telling me that. So here's what I'm doing now. That's the next role. That's like, when can I get there? And they said, well, you got to do two years doing this and two years doing that and two years doing this. And I was, and it didn't jive with me like the big corporate America, because I was like, wait a minute, that kid over there, who's my peer, but you make fun of because he sucks so bad. He's going to get the same opportunity as a promotion as I am. Yeah. And it was like, yeah, I'm like, all right, I'm out. You know what I mean? Because it wasn't challenging.

I wasn't learning anything and I was really eager, but I think I was putting those pieces together. I look back and I wonder, you know, was I too eager? Was I too aggressive with, okay, I don't want to do this anymore. I want to get there. Or was I just, to your point, not challenged, to your point, not learning anymore? And I think if I really reflect back on it, I wasn't really learning much after, I mean, even a year and a half, you know what I mean? I was like, okay, I kind of, I got this figured out, like next. Yeah. But I think that, you know, I think for some people like, you know, like you and I, maybe the journey was moving into a role where we were leading our own destiny. And I think that's actually something too, that's maybe less talked about in sales where it's like, what's your career goal?

What are you going to do next? Like, would you be better being the CEO of your own company or leading, you know, your own venture? And that is a path that you could take, but you don't have to go from AE to, you know, senior, to director, to VP, to CRO. So, you know, you know, mentally know what you, you want to do. And if, you know, you feel mundane and you, the AE role is, you know, not it, then like pivot. Yeah, exactly. And I think if COVID taught us anything, it's, you know, the, really the opportunities are somewhat limitless out there if you apply yourself. Right. I mean, you could start your own business doing a billion different things, whether it's on Instagram or whatever. And so, you know, the whole really reassessing life priorities in a lot of ways, I hope people are taking this opportunity to kind of sit back.

You said they have more time to kind of evaluate products and those type of things, which is good. But I think we should also take that time to kind of evaluate, like, should I, you know, is this what I want to be doing? Like five years out, you know, I look at things change so fast right now. It's impossible to look, you know, five days out right now, but if you have at least have a vision here of where you think you want to be, you can make the adjustments along the way, but it makes this a lot easier to make decisions based on a bigger picture. Right. Totally. And I've talked to great AEs who've been gone into sales enablement or, you know, revenue ops and these other channels where they can still be, you know, close to sales, but they, you know, challenge it themselves in a different fashion.

So I think that, um, I think like we go back to how do you retain those best employees? It's like, how do you give, how do you allow for some people to kind of take chances in their careers with you too? Yeah. I love it. Yeah. Cool. So let's do our, we're coming up on time. Um, but Chris, what, what are some other things, uh, that people should be paying attention to, uh, with what you're seeing from, from your level, right? Like market trends, anything that you think is really something that an SDR AE, it doesn't matter, uh, should really be paying attention to right now to make sure that they're future proofing their careers. Yeah. So I'd say some of the soft skills, like, uh, like creativity, I think we mentioned earlier where people are, uh, how do you prepare yourself to be more creative?

How do you talk about that in job roles? How do you get good at being creative so that you can spend your time more wisely versus, you know, in some cases where things begin so automated, where you're just good at clicking buttons. How do you get good at, you know, creatively testing sequences or adding in a creative gift into the sequence or all these different things. So I think, you know, maybe reevaluating what are those soft skills that you have? And should you brush up on some of these other ones that are unique? Um, I think it's also, you know, for some of these AEs that have been in the field for a long time, for decades, it's, you know, there's a lot of sales tech tools coming out and that is, I don't think that's going to slow down.

I think we continue to see tons of funding go towards sales tech. I think maybe a decade or five years ago, it was all MarTech, MarTech, MarTech, and now it's sales tech, sales tech, sales tech. And so I think for AEs, they need to get good at sales tech, um, and be open to trying new things, to adopting new things. I feel like instead of the, the enablement and ops teams and everyone else saying, Hey, here's a new thing. You have to use it and fighting back. Like I'm good at sales. I don't need that. Like, you know, embrace this. Some of this cool tech is making you better and making you, you know, so I think it's really embrace this new world of tech. That's, that's hitting. I think that's a super crucial skill to have.

Yeah. There's no question. You know, and we all fight change, right? Cause we're used to something, but when you are, are growth oriented and you're open to change, you, the amount of cool shit. I mean, you, you said you take calls from reps these days just to see what's out there. Yeah. One of the things, one of the reasons, uh, you know, dream force is always a nightmare, obviously. Um, but one of the main reasons towards the end, cause I had gone to like, I don't know, eight dream forces by the time it stopped. Um, one of the reasons I, I continued to go to them was actually to go walk the, the floor, but not for the main booths, the way corner ones. The tiny little ones that are just trying to get out there and, and are willing to give their shit away for free.

So people can test it and get feedback on it. And I would just go to each booth and be like, what does that do? How do I use that? Like, is it free? Can I play around with it? Again, product led growth, right? Can I play around? And that's where I started finding, I mean, half the train, it's funny, half the training that I do, half the value that I think I bring to the table for a lot of people when I do training is obviously the structure and the tips and the techniques and all that other stuff. But I try to stay as, as up to date as I possibly can on the technology. Right. And I, and I'm bringing stuff like crystal nose and all these different things that people like, holy shit, I haven't seen that.

I'm like, yeah, you just gotta be, keep your eyes open for it. Yeah. I'm a, I am a hundred percent. I remember going to dream force, looking in the very back for those little like standup booths and being like, this is so much cooler than that. Like mega booths over there. Yeah. Way better. And, and I think that's that, the mentality right now. I mean, look, I think if you're in, if you're in sales and you got, you know, say you're 60 years old or something like that. And you'll, you got a few years left and you, okay, you might, you might be able to ride this wave a little bit further. Right. Based on your relationships and whatever you've developed over the years. But man, if you're, you know, thirties, forties, even fifties in a lot of ways, and you're not paying attention to this shit, somebody else is going to get there first.

And, and the, and the, the question isn't, are you a better salesperson than the other person? The question is, is who gets there and who gets the conversation? And if you can't get there and get the conversation, it doesn't matter how great of a sales rep you are. You're going to get smoked by some kid who can bring in an engineer and have that talk with them without having to worry about it. So exactly. It's a, it's a, it's an interesting world out there, man. I genuinely appreciate being in the tech space because I just, I think it's, it's so fast paced. It's so innovation, right? In a lot of ways, in, in, you know, cause a lot of challenges, obviously too, with, with companies. And now you got analysis paralysis with all the tools that you're using.

But man, uh, you know, I think consulting wise, if you could consult with a company that says, Hey, let me look at your tech stack right now and let me consolidate and give you some recommendations. I mean, to me, that's like a career waiting to happen. Just a tech stack, a tech stack consultant. I'm going to come in, I'm going to analyze your sales process. I'm going to marry it up to, uh, the, my best practice is tech stack. And there's three category, you know, three vendors in each category that are going to recommend to you. And I'm going to take a cut of every referral that I give you. And I've, you know, win, win. And I'm just going to be the middleman there. Like there's a, there's a business right there.

There's a multimillion dollar business right there just for somebody to do on their own. I would totally agree. Awesome. Chris. Well, look, I love talking to you. Um, where, where can people find out more? Uh, and, and where do you want to point them these days with what you're doing? Yeah. I mean, uh, add me on LinkedIn. We'd love to pick up the conversation. Email me. It's Chris, K R I S at sendoso.com. Um, check out our website, sendoso.com. Um, and yeah, I would love to continue and chat with anyone. A little bit. Yeah. I think next time we chat, I do want to dive into kind of the future of, you know, direct mail a little bit more with what, um, you know, what you're seeing as far as trends.

And, you know, I'm starting to see cool stuff like people sending video, uh, indirect mail. So it's like a, you know, it's like a little tablet or something that I can record a prerecorded video and send you. And so you physically open it, but it's still digital. So we're starting to see the mix between the digital and the physical world here, which I think is neat. And then I'd love to, again, you know, let's, let's talk even further about like virtual reality and how you're, you're changing the experience here with where things are going. So let's do that as a part two for this, but maybe in a couple months, uh, when things settle down. All right. I'm in. Awesome. All right, everybody. Well, look, hopefully you enjoyed this conversation as much as I did and got you to think a little bit, just a little bit, right?

Business acumen, those types of things. We all got to level up here. Be different than the reps who are just going out there, pushing the buttons, going through the motions, asking the stupid questions. Be genuinely curious, focus on business acumen, elevate yourself here so that you can stay and you can actually leverage these tools as opposed to getting replaced by these tools. So awesome. All right, everybody. Look, like I always say, go home, make somebody smile today if you can, uh, cause no matter how bad your day went or you think it went, if you make somebody smile today, you know, you had a good day and the world needs a lot more of that. So thank you all for listening. I'll see you on the other side.

Let's make it happen. Cheers. All right, y'all. That's a wrap. As always, we encourage you to become a JB sales member and gain access to the JB sales team. Our training, our courses, tips, webinars, and replays are all available for you at on demand.jbarrows.com. Follow us on Instagram for daily sales techniques and tactics at JB sales training, all one word, and we'll catch up with you on the gram. Have a great week, everybody get out there and serve those clients, catch up with those prospects. Be sure that you are asking the right questions, doing the right things and serving people to the best of your ability. Get out there and make somebody smile today. It'll make your day and theirs. We'll see you next week when we bring you another stellar guest to help you sell better.

Make it happen, everybody. Thank you.