March 13, 2023

Episode 199: Joel Stevenson, Former CEO of Yesware, recently acquired by Vendasta

Joel Stevenson is VP of Growth at Vendasta which acquired Yesware in 2022 where Joel was CEO. Prior to Yesware, Joel built Wayfair’s B2B business from scratch to $400MM in annual revenue. He also ran Wayfair’s UK business and oversaw the FP&A function as Wayfair transitioned into a publicly traded company. Prior to Wayfair, Joel worked as a consultant at ZS Associates and spent the early part of his career in a variety of sales roles. Joel has an MBA from Yale, attended the University of Illinois for undergrad, and has a goal of being #1 for humor endorsements on LinkedIn.

Julian: Hey everyone. Thank you so much for joining the Behind Company Lines podcast. Today we have Joel Stevenson, Former CEO of Yesware recently acquired by Vendasta. Yesware helps. High performing sales teams do meaningful email outreach at scale. Joe, I'm so excited to chat with you and, and not only, you have a wealth of experience in startups and technology and, and especially you have, really I think popularized history at, at Wayfair being being what you accomplished on the B2B side.

So interested to, of course, dive into that and interested in seeing kind of your strategy of how you think about scaling and building. Not only at at Wayfair, but also at at yes. Where but just to jump right. , I heard or I've seen that your strongest skill as a founder, as as, as a person in tech is your humor.

So, I wanna know what's your go-to joke? What's, what's something that, that you kind of, what's like a go-to joke that you have for your team? Anything come to mind for you?  

Joel: There, there's, you ever hear the one about the, the salesperson? Nope. . I'll try, I'll try to tell it fast. It's good. You could tell this in a very long way. I'll try to tell it in a fast way. There's these guys that go on a hunting trip and, and the, the hunting lodge gives them a dog to go with them to shoot the goose. And the, the dog's called salesman. Salesman great. , he goes and he gets the dogs. He hustles super hard.

He brings all this stuff back. They love it. And so they, they had a great, they had a great trip, so, Next year, they come back and and they, they wanna get the same dog again. They're like, oh, can we have salesmen again? And they're like, yeah, actually you, you, you can, but the problem is we, know, we change Salesmen's name to sales manager and now all he does is sit around and bark all day.

Julian: I like that one. I like that one. That's a pretty good one. It's, it's, it's funny, I was on the sales side for a long time and. Hearing that and, and thinking about my past experiences with sales managers and, and, and, and, and I don't wanna say the barking, but, but the encouragement on their previous experience and skillset is funny because it shows the evolution of those orgs.

But I'm super excited to, to chat with you in, in terms of a scaling mindset because we've had a lot of founders on the show and obviously, One of the biggest issues is going from zero to one, but from one to to 10 and on. It's a scaling problem and, and meaning that identifying different strategies to go to market and, and maybe make partnerships.

I'm interested in terms of, back at, at your experience at Wayfair, thinking about connecting, businesses and, and scaling and going upstream. How did you devise a process? How can other founders kind of think about ways to know that, their go-to-market strategy has some validity and, and has some say, data that that will back up their trajectory.

Talk about kind of how you've thought through that and, and where a lot of the success that you've had had, has come from.  

Joel: Yeah. Well, the, on the, in the Wayfair side, it was a, I suppose it was a little bit. Following data and a little bit about following instincts. Mm-hmm. . And on the instinct side Wayfair for me was a little bit of a diversion where I'd spend most of my career more on the, the B2B software side.

Yeah. And, Wayfair was primarily b2c, consumer e-commerce. And so, as in those early days of Wayfair, we didn't, we actually, we were still CSN stores back then, so we had all these individual microsites. I was responsible for a set of ones that had to do with home improvement and that type of thing.

Mm-hmm. . And, we would, you could just get the order stream in your, you would just get sort of copied of the transaction confirmations that were sent to a customer. And so you'd make a folder for it, it would fill up your inbox every now and then you'd sort of go look through these things and be like, oh, what do we sell today?

That's interesting. And just, just from sort of scanning through that. You could start to get, and there were, I wasn't the only one that did this, or other folks on our team that, that had this insight about, there's these other people that are coming through that are like, we see the same people again and again.

Like, we might see a designer or we might see contractors or builders or electricians buying lighting, that sort of thing. Yeah. And so we just, it just seemed to me that there was a, a different level of service that we could provide to those customers that would end up allowing us to get a larger share of wallet.

Yeah, and so it took us pro from that, initial. Hypothesis and then, staffing some people on it, doing a bunch of cold calls, doing a bunch of experiments. Many, many things failed before we finally kind of got into a model where we were finally able to prove out that these cohorts that we applied this service level to were meaningfully better than the ones that we didn't.

Because before that, the idea was like, well, you're just taking money outta one pocket and putting it into another like, are you actually creating value here? So it took us quite a while to, to really prove that out definitively. And then it was sort of a question of, okay, well how do you, how do you then scale this?

How do you build top of funnel and then how do you support 'em? And we had the luxury of having the whole Wayfair database to sort of cull through. And in the early days we would write SQL scripts and get a result back with say, all right, call these people. And then eventually that became data scientists and all sorts of, advanced analytics, driving stack rank stuff and like being very specific about who was gonna call who and when they were gonna call.

But, we, we had that as a, in some ways it was a product like growth motion because we had, Wayfair was sort of the product. And then we were taking all these people that were sort of, not really hand raising, but we thought could hand raise and then we would, we would sort of get into this motion of, of a different level of service.

Yeah. So that was the front end of the funnel. And then, we were, we were able to sort of juice that with Facebook and some other forms of advertising. And then the back end was really pure account management of, how do. How do you give somebody a book of business? How do you structure them in such a way that they can grow that book and, you're reward 'em for that.

And then it's just kind of a washed rinse, repeat.  

Julian: Yeah. And how did that change in terms of the supply side? I assume if you have larger contracts with, say, contractors or people building company or building certain, certain whether, whether it's homes or, or other types of s. What does that do on the supply side?

How much did you have to ramp that up and, and was that up to speed when you were signing contracts? That I think a lot of times we'd go for user data and, and, and or capturing customers and clients and then fulfilling orders. But it seems like you kinda have to, you have to raise the, the supply as you're, filling out orders.

How, how did that affect the supply side?  

Joel: Yeah, well, it was, yeah, that part of it did very much look like a sort of a two-sided marketplace where mm-hmm. . Mm-hmm. , yes. We were getting, builders in, or we were getting interior designers in, but a lot mean, particularly in those days this was before Wayfair had this brand called Perold.

We, we didn't really have a lot of the higher end selection. And so eventually you would reach a point where somebody would say, okay, well, you're fine for these Fillin items, but like the, I'm not buying. The, the buy the inch sofa from you or I'm not buying, custom stuff or whatever, and.

Part of it was going back into our existing supplier base and in educating them about this customer base. And many of them had these capabilities, but they hadn't offered 'em to Wayfair before cuz there was no point. Yeah. And so a lot of what the, the account managers ended up doing was being the bridge between this very large and capable supply base and what the customer wanted, which, like in, in, in a lot of those projects was not.

You couldn't sort of render it in, in an e-commerce engine, if you will. So they, they sort of worked in, to fill in the gaps between what the customer needed and what, Wayfair could sort of translate in terms of self-service. And then over time we were able to convince a bunch of higher-end suppliers that we had a sufficient demand for them on.

On the buyer side and that they were, they were missing out if they weren't part of this. And then, mm-hmm. , some of 'em were concerned about brand perception, and so we then built an entire portal. Where, we would credential these designers to come in and they could only see these suppliers if they were credentialed and could log into the site.

So like you would never know that we have, I'm not gonna name the names, but like we had some real high-end suppliers that, they, most people would be very surprised that you could buy 'em on Wayfair, but you could only buy 'em through this sort of password protected experience. .  

Julian: Yeah. And you, you've had a lot of experience kind of, going into vertical markets and growing accounts and things like that.

Where do, where do you, have you seen some businesses say, I don't wanna say go wrong, but, not maybe take into the account all the necessary pieces that that takes to go up market, go, working with your, your current customer base and expanding that, that's, that's obviously one direction, but going upmarket, if, if you're looking for a higher value or larger order.

how do you approach that? Or how have some, have you seen some companies approach that say, not accounting for all variables or, or not doing it the right way?  

Joel: Yeah. , i, this is sort of, this may be just more of a personal preference, but I kinda like this, this idea of being pulled into the enterprise versus pushing your way into the enterprise.

Mm-hmm. . Mm-hmm. , the enter, the bigger companies are typically gonna have many more requirements. They'll have, security requirements. They'll have, custom development requirements. They might have certain, contracts or covenants that you emphasize, like everything's just a little bit more complicated.

And some companies start. In very large companies and they're sort of built that way. But if, if you, if you weren't sort of built from the beginning to be able to support very large customers, there's a lot of baggage that comes along with that. And it's, it's nice to be able to approach it from the point of, you, you get somebody into your funnel that's a lot bigger than, than what you were typically accustomed to.

And you sort of take an opportunity to understand what their needs are, understand how they're different, and. Sort of intentionally plan for how you're gonna support those customers. So if, if there's a lot of non-engineering, that non-recurring engineering that's gonna be required, like how are you gonna build that into your into your delivery mechanism?

How is that going to live with your sort of regular feature product development roadmap? How are you gonna support that code over time? Like, how, how are you gonna service these customers? Like, these are all questions that you have to start to answer as you get into, into bigger. Accounts and it, and sometimes what happens, we've certainly made these, these missteps over time and in my career as well, is you don't really think through the answers to all of those things.

And so, in some cases you might. You might just sort of say, well look like it's money. Like we gotta take the money. And, and, and maybe you, maybe it's just a bluebird where you, you don't act. You can't actually repeat that same big customer intentionally because it was just some, some strange, so now you've made a bunch of changes, but you actually can't replicate it.

The flip side can happen too, where I think sometimes people get scared of these big customer. And you just decide like, oh, it's too much work, it's too hard, we're never gonna get it. Right. And instead of trying to come up with a sort of, arranging a resource in such a way where you can actually do that, it's yes and, conversation.

I think sometimes people maybe close off those those conversa those conversations too early. But I've certainly, I think been guilty of. Both sides of that whole time. So it's a, it's a, it's a tricky, it's a tricky balance. The other one that you see sometimes is people just declare, like, we're going into the enterprise and they hire a bunch of, very expensive sales reps that expect to make, hundreds of thousands of dollars every year at quota, but you don't really have a plan to feed those reps and you don't really have a product strategy.

And so then everybody, know, that just ends in 9 99 times out of a hundred. I feel like that ends in.  

Julian: Yeah. Yeah. It's funny, you, you something you just said is, is feeding those reps and, and what do you mean by feeding those reps? Is that part of the marketing funnel? Is that bringing organic leads in?

Is that supporting them with, with, say, SDRs or what in particular do you mean By feeding those reps and, and in, in regards to that system? .  

Joel: Yeah, it can be different. I mean, I think in the, in the very early stages, a lot of times what you want is that missionary sort of rep that can build his or her own pipeline and also kind of figure out how to translate the founder's vision into mm-hmm.

Actual, kind of repeatable sales at least, at least the first couple to kind of prove out the model. So in, in that case, it might. You might have to have a very clear idea of like, okay, well here are the 10 companies that are really gonna benefit from our solution and here's why they're gonna do, like, you just have a very strong thesis around that, and then the right person to go execute on that.

I if you're, if you're maybe a little bit further along and perhaps you have more resources, then you can start to look at, yeah, how are we gonna build, marketing funnel demand or, whether that's through paid advertising or it's trade shows, or. Old-fashioned outbound SDR work, but they're, if, depending on who the account executives are and what their capabilities are, some of 'em are very good at outbound prospecting.

But I think, increasingly with the specialization and sort of the. Assembly line methodology that we've started to put into sales right now. I actually find that there are fewer full cycle reps that exist anymore. And, and so you like it, it it's a combination of who you're hiring, where you're at in the process.

And are you, and I think in general, I think as you're really scaling a sales team, you've gotta account for some amount. Warmer marketing driven demand. It's, there are sales teams that can sort of really do it by themselves, and those, those leaders and those sales teams are, are worth their weight and gold.

But it takes the right kind of product market fit and the right type of sales team. And that's, it, it's uncommon. .  

Julian: Yeah. Yeah. And it's fascinating. I I, I love the point you made about sales teams in terms of full cycle reps, I feel like everything's becoming a little bit more systematized and, and people are, are more specialized in exactly what part of the function that, that they come in.

But it, it's interesting to talk about the, the sales motion in regards to translating the vision of the, the, the founder. In, into the prospects and or into the customers that you look to gain. And what, how do you do that? Is it instilling culture? Is it, is it, structurally meeting with your team, going through different, strategy planning sessions, doing, say mock calls or things like that?

How does a founder feel confident that their sales team is going to translate their vision and they're gonna be in, in the same direction that, that the company is going?  

Joel: Yeah. Well, I think the, the most important part of that journey is actually hiring the right type of rep that can, that can work with the founder to figure that out.

Like there's, there's different reps that are good at different things and the, the rep that is the one that shows up first that really tries to. Figure out how the, how the founder doesn't have to do every deal him or herself is, is a particular type of rep. And they're usually not the ones that end up becoming the CRO of the, of the a hundred or 200 person company.

And, and often they're not, they don't even stick around, always be like just the best account executives. And sometimes they do, but, so I, I think the most important thing is just, is trying to find that type of person where like they're really curious. You know how things work. They want to, they, they, maybe they're a little bit may maybe they sometimes have a short attention span where they want to kind of try to go do different things, so they wanna sort of conquer it.

And then once they conquer, they maybe want they maybe wanna move on to the next thing. And those people tend Have a pretty good business head on their shoulders and they can go, they can go speak to an executive with credibility just like the founder can. So I think that that's really a big part of it.

So if the founder can get that type of a person, then the ability to then translate the, the, it's kind of the founder working on the whiteboard to now the, the first rep working in PowerPoint like that. You can, you can make that bridge, but if, if you get the wrong person in, it doesn't matter how good the founder is or how hard the, how hard the founder tries, it's, it can be, it can be hard to make that leap.

And the founder ends up doing all the work. Maybe until you've, you've got enough capital, you can raise a big round and then you can bring a bunch of people in that you sort of know how to do these things.  

Julian: Yeah. I had another founder. Yeah, I think it was, it was a couple days ago. He was on the podcast talking about looking for that sales hire, so, For, for them out there.

Where do you go find that talent and, and how do you evaluate to make sure that you have the right person? Is it, obviously we have intro calls and we have discussions about making strategy, but what, what are some best practices that, that you've seen not only in finding those types of people, but also attracting them and, and then validating or, or vetting that they are they are who they say they are.

Joel: Yeah. Well, ideally they have some proof that they've done it before. And so like a lot of things, if you can get a reference on somebody Some network that often is, is the best way to do it. There's also companies that, that specialize in this. One called J Jellyfish, uh mm-hmm. Outta New York City, where like that, that's all they do is they try to, they try to take founders from the point of like, Hey, I, I'm pretty sure I have product market fit.

And then validating that, figuring out some of the first sales motions that could be passed on. To another foot. So there, there's, there are creative ways to to potentially go about that. But yeah, I think, ideally you want somebody that, that has done it before. I think if you, if you can't find that person and you had to take a little bit of a risk on somebody, I would say you maybe you maybe don't necessarily look at somebody that has a, a strict sales background, but you might wanna look at somebody that has.

Maybe some sales, but maybe they did something like consulting. Sure. Or they did something maybe a little bit more analytical or something where they had to face off against executives for, maybe banking is another one that, it could be kind of interesting for that. Yeah. For that type of background.

But you want somebody that's had, That's worked in a little bit more of an unstructured type of environment. Yeah.  

Julian: Yeah. That's fascinating. And, and I like the, the kind of somebody who's been in, in, I guess, on the other side discussing with executives and, and kind of building relationships and accustomed to.

Speaking with in, in, in that room, in that realm. But describe your experience or, or your journey with Yesware Talk to, talk to us about what inspired you to join the company and, and then of course, most recently the, the acquisition, how that has kind of changed the dynamic of, of the company a little bit.


Joel: Well, Yesware was one of, one of the ways that we were able to scale the, the B2B business so quickly on the Wayfair side was we made pretty big investments in tech to drive sales productivity. Mm-hmm. . And as we, as we started to look at the various landscapes out there, what was available, I mean, it turned out we actually.

An investor in common between yes, we're in Wayfair battery Ventures and Sky near Jagger wall. I was on the board of both companies I knew at near a little bit, and he introduced me. I I was eventually gonna leave Yes, Wayfair, because it got too big and there's nothing wrong with Wayfair's, great company and like the people there, but I realized that I liked the early stage more so than the, kinda later stage, public company side of things.

And so I, I was looking for something new. I, I. The Yes, we're team. And so it was cool to be able to kind of almost switch sides from, being a buyer of tech to being a seller of, of, of that type of tech. And so we, I joined and, eventually we, we raised an initial round of capital.

I took over a CEO at that point and, we've. We've worked, we, we operated in a pretty competitive market. There are a lot of people that have raised a tremendous amount of capital in our space, and Covid really kind of threw everything for a little bit of a loop. We have a lot of the, our primary go-to-market is product led, so we, the majority of our revenue is self-service.

Actually, that comes in new. Sales is kind of ironic for what we do, but that, that's the way that we, that we built a company and so as a result, we have a lot of individuals. Mm-hmm. , COVID happened, a lot of individuals lost their jobs. And so like right away we saw a bit of a hit of of revenue and, we, we, we were building back.

But it struck me that we, it, it would, if we were really gonna win. It'd be better for us to kind of be a little bit more vertically integrated, and so we were actually starting to work on. Building more and more CRM part of the stack. So we kind of started in the inbox communication stack. We're kind of starting to work our way backwards towards a lightweight crm.

And so ultimately the full expression of that would've been competing with people like HubSpot and Pipe Drive, et cetera. We, we just followed that, that was the better strategy, and Vanta was actually one of our customers and they had a similar strategy, but they were starting from a different side.

But a lot of their customers are digital. And other people that are selling to small and local businesses, they have sales teams. Theasa platform is increasingly relied upon by those customers for core CRM types of activities. Even, even sort of, getting into into the ERP a little bit.

And so they had a big desire to try to make that, that part of the platform better, to better service their customers. And so we were sort of coming at it from one direction. They were coming at it from another direction. The roadmaps just lined. And I felt like this was gonna be a good opportunity for us to sort of be, a disproportionate winner in a particular space.

That's, that's big and meaningful and, and interesting.  

Julian: Yeah. Yeah. And what was the transition from going to SEP of sales to, to CEO and, and what was the need of the company? Or I guess, what was your drive to make that decision and, and how has your job changed? Day to day?  

Joel: Yeah. Well, I mean, I think the, the biggest thing for me as, as part of the, as part of the journey, I mean, I, I was, when I took the role, the, the idea was that I would take over as ceo, but a few, we had to get a few things kind of. Rolling downhill for the company before that happened so that we could raise additional capital.

And so I, I had, that was actually one thing that was super helpful as part of the transition because the the original CEO and founder, Matthew Bells and I were sort of working together on this, and so we were able to make the transition smooth. I was able to kind of observe what was happening, knowing that I was gonna take the whole thing on.

So it wasn't like I was in a silo. I was already, you know mm-hmm. , I was able to, to understand. The, the workings of the, of the company. I think that the biggest change for me and the biggest ramp up for me was really getting up to speed on the product side of things. Like I knew the product because I would, I was a sort of a buyer and a user of that type of tech for a long period of time.

But the, the, the difference was really like becoming a product CEO and really sort of like really understanding the product roadmap and in many ways having the courage to sort of, This is what we need to build. That was, it took me a while to, to get to that point, I sort of leaned on more of my strengths with more of the, the distribution and, go to market, marketing, sales, that type of stuff.

Julian: Yeah. Yeah. And tell us a little bit about the traction now that you've, you've been, been acquired and, and now that you, are a part of the Verdo team. What has, not only what has that changed, but how has that increased, say the amount of users on your platform and, and also what are you in particular excited about the next journey, the next stage of the journey moving on into this year and, and where are you kind of planning to take the company?

Joel: Yeah. Well, we're, we're just actually, we're just about in towards the mid, like the end of March there's a, there's a big event where we're gonna be kind of unveiling Yesware as part of the VTA suite. So if you're a current Exta customer and you're on a certain subscription plan that we're gonna give, yes.

For freed all of these users. And so that, that's going increase the user count very, very dramatically. And it's gonna add, I think, a, a ton of value to, to those, to those partners. And, and ultimately for Vanta, because the, the go-to-market today runs through the channel, if we can make the channel more effective and they can sell better, like that's gonna only help Vanesa drive more product revenue.

So we're super excited about that. All, all their customers, if they're not using a tool like, like a yes where they should be using a tool like yes or. , that's a great fit. And then over time we're gonna be working on deeper and deeper integrations really, taking some of the, the best parts of yeah, what we think the best parts are of yes, we're keeping people in context, working out your inbox and bringing, vta, into the inbox as well so people can enjoy those, kind of, those productivity and time savings advantage.

Julian: Yeah. And how do you think about, competitors Obviously with, with, with sales enablement tools and, and email marketing and, and email outreach. There's so many tools, there's so many tools and players in this space. How do you think about, or do you think about the, the competitors and when you do think about how, how you differentiate?

Are you listening to customer feedback? Are you seeing what the markets kind of going in, in one direction or another? But I guess overall, how much time do you spend on com on thinking about competitors and, and how do you differentiate within your space?  

Joel: Yeah, I mean, we, we certainly, we think about 'em. I mean, we, anytime we lose a, a decent sized customer, we, we try to find out where they're going and what their reasons were.

Sure. And, and we try to be thoughtful about that and, and take the feedback and, and use that to, to prioritize what we're, what we're doing next. It's interesting in a, in a product-led. , sometimes that feedback is a little bit harder to come by or to, to, mm-hmm. because you have, you have a lot of smaller customers, and so it, it's interesting to try to gather that information from a, a smaller group of customers than a big set of customers, but we have both.

And so we, we end up gathering that, that information from both sides. I mean, I think for us, we've tried to focus on a more narrow ic, like ideal, customer profile for us is a full cycle account executive that spends some of their time prospecting but not a disproportionate amount of their time prospecting.

And as we've done that, and that can sort of extend into account management as we've done that and really tried to refine the, the icp, we've, we've really tried to build towards. Making those users as happy as they could be with Yes, we're, and, and we've lost some, some folks as a result of that.

And, and that's certainly a, a, a part of the market, but our, our, our business is competitive enough. And and especially because you're competing against other people that sell sales, they tend to be pretty good at sales. And so for us, the answer has been to. More focused on who the, the more narrowly focused on the, the personas and the types of companies that we're really trying to serve well.

Julian: Yeah. Yeah. What are some of the biggest challenges that Yes. We're faces today?  

Joel: Well, there, there's a constantly shifting market for for, I mean, particularly on the email side, , there's various, privacy things that are, that are happening, which could, which could impact us.

We're for our users, they're, a lot of the struggle is like, well, how do I, how do I cut through all the noise? Mm-hmm. and, and how do I stand out? And I, my sense is that's gonna get worse before it gets better with the rise of AI tools. And, and we're, we're currently working on, building.

What we think would be like very practical use, useful features right into the platform. But you know, there's, people are chat, e b T, whatever. It ends up being like there's a lot of stuff out there that I think is you can use to. Crank up the volume of what you're doing. Maybe not in a, in a health in helpful way all the time, but I think what what you're gonna find is, is people are gonna be able to do more with less.

And there'll be a period there where the more is like probably a bunch of crap before it actually, all that's kind of settles out. And then people start to really use this technology to, to, to drive like very smart targeted high value outreach. And so there, there's a, there's a bridge period there where.

We're, I think it's gonna be maybe a little bit harder to get people's attention. Yeah. But over time I think these are gonna be great tools for for reps or for entrepreneurs that are basically serving as a salesperson to be much more productive.  

Julian: Yeah. Yeah. We'll, we'll probably see the, cold calling come back in, in full force with email messaging being so probably inflated, like you said, with a lot of content coming out there, and it's just easier to generate, I guess highly targeted, but semi, semi-personal content.

I guess thinking about the long term strategy, if everything goes well, what's the long term vision for the company?

Joel: Well, the, the long term vision is we're gonna, is we're gonna take the core yesware tech, and that's gonna be more and more deeply embedded into the Vanesa platform. So that for folks that are, are effectively running their business on Vanesa, they're gonna have, best of breed sales tech kind of under the hood that's gonna allow them to, win more customers and service those customers better.

Is, is part of the platform. So, That, that, that's kind of where we're heading. We're gonna continue to sell. Yes. We're a standalone as well. We're gonna continue to improve the platform. We've got a lot of exciting developments that are coming, but we're, we're increasingly pointing this tech towards making sure that, ve DAA is gonna be best in class for, for what they're doing.

Julian: Yeah. Yeah. I would like this next section, I called it my Founder faq. So I'm gonna ask you a few rapid fire questions and we'll see where we go. But first question is, what's particularly hard about your job?

Joel: Right now it's, it's a little bit of drinking outta the fire hose cuz we have, all of our, all the, all the Yesware stuff that we're, we're doing and now we're part of a bigger company where there's a lot to learn and there's a lot to figure out.  

Julian: Yeah. Yeah. What are some ways that you, I guess, one piece of advice for a founder that you learned or you know now, but that you wish you learned earlier on in your journey?

Joel: I think, I, I, I had sort of lucked out. I had this guy John Pepper as a mentor for a little while, who was the, he used to be the CEO of Proctor and Gamble and Chairman of Disney for a while, and he used to talk about, go for the big win, and be on the offensive. Yeah. And I think it's sometimes hard.

I mean, I think founders are a little bit wired that way to begin with, but sometimes it's hard with cashflow constraints and other things. It's like, how do you, how do you change the rules of the game in your favor so that you. , you can, you can go take big swings at stuff mean. It's, it's what typically what VCs want.

It's typically what, what entrepreneurs are in there to, to do it for. But you know, Entrepreneurship comes with like a, a very healthy mm-hmm. helping of failure and, and setbacks and challenges. And so sometimes it's hard to maintain that mindset.  

Julian: Yeah. Yeah. Very true. For, for, for founders out there thinking about, who, who say have a product led, growth kind of motion currently, but are maybe looking to interject a different type of go-to-market strategy or something.

Maybe a little bit more cater to their audience. How would you help them kind of strategize or consider a strategy, whether it's a freemium model, whether they're going through kind of influencer. How would you kind of, I know you mentioned their data was a huge a huge tool that you use at wafer, but thinking about the founder now what ways would, would they kind of, should they look at creating a go to market strategy considering their product is a product led vision?

Joel: Yeah. Well, I think, I mean, I suppose you gotta start with where your customers hang out and like where, where, how can you reach them? I think for, for some folks, an easy, an easy addition to product led growth is actually adding sales people. At the right time. I think, I think in the early, in the early days, sometimes people used as an either or, like, I'm either going to be product led or I'm gonna be sales led.

But the best teams, like,, who's a, who's a Yesware, we're a customer. Like they've, they've been very, very effective with taking a product led motion and then using sales and customer success to really supercharge that. Yeah. There, there's many, many examples of that and so I think, something to look at is, if, if you don't have a sales.

are you starting to get bigger customers through? Are they starting to ask questions in support or other places that, start to look more of like, Hey, there's opportunities here if I have a salesperson in, and then if, if you even get a salesperson in, like, can you start to feed that salesperson's signals such that they know the right time to contact the customer?

Or can you feed the customer signals so that they know the right time to then get a to sort of ask for a salesperson to, to get involved and, and help .  

Julian: Yeah. Yeah. I always like to ask this next question because I think it's, it's always exciting to listen to how founders kind of extract knowledge for, from things that they ingest.

But whether it was early in your career or now, what books or people have influenced you the most?  

Joel: I've always been a huge fan of David Allen's getting Things Done. That's one that that I seemingly always recommend. Yeah, there, there's a lot of good ones. I like some of the Warren Venice stuff around leadership.

There's, there's a book called Leadership is an art by the the original founder of Herman Miller, whose name is currently escaping me. But that's, that's also a good one.  

Julian: Yeah. Yeah. I love that. And Joel, before we give you a, I know we're coming to the end of the episode, before we give you a chance to give us your plugs on where to find you and, and you know where to support Yesware, is there anything I didn't ask you that I should have or that you would have liked to share with?

Joel: No, I think I, I think that's pretty good. The only thing that I, that I was gonna mention earlier, we were talking about cold calling. Is the cold calling's interesting now because for a lot of businesses, unless you answer the phone as part of your business, it's very difficult to call somebody.

Yeah, right. Like with remote work and covid, like people don't have office phones so much anymore and so now you're kind of going people's cell. and cell phones have better defense mechanisms typically than the old office phone did. And like when I started my sales career, we used to figure out like, oh, how do you get to the assistant and work your way through the switchboard?

And like, like all that, I think pretty much out the window these days. And so, I think certainly getting people on the phone or in a live conversation is, is the best way to do most forms of selling. But it's, it's tricky these days. It's, if you're, particularly if you're calling into tech or something where people are largely remote at this,  

Julian: Yeah. Yeah. I love that. Last little bit is where can we find Yesware? Where can we, as, as an audience member and as a fan of yourself, where can we find you? Give us your LinkedIns, your websites. Where can we be a part of the product? And, and maybe if a customer, where can we start playing around with Yesware and, and the tools that you've all created for?

Joel: Yeah. is the, is the place for all that stuff we have. If you go to our blog, we've been writing sales content for, data-driven sales content for a decade. There's a lot of good stuff there. It's all free. If you want to try Yesware, we have a free tier free tier of Yesware, which you can sign up on on the website.

I do a podcast called The Hard Sell which you can find at and yeah, I'm, I'm on LinkedIn. Joel Stevenson, I think it's Joel Stevenson. GM is the, is the is the URL for that. And, happy to, happy to chat.

Julian: Amazing Joel. It's incredible. Not only learn about your journey, but how you view kind of sales and, and go to market strategy and also building a sales team, especially, a lot of early founders kind of struggle with.

They, they may have an inclination or an idea, maybe a frame of reference, but thinking about it in, in the way you've thought about it, using data, using, the really important pieces of your product, listening to customers, it's been exciting to, to, learn all that and, and also to share with my audience.

So I hope you enjoyed yourself, but thank you again for joining the show today.  

Joel: Great to be here. Thanks for having me.  

Julian: Of course.

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