600: Vendasta Acquires Yesware | Joel Stevenson

Podcast Cover Image: Vendasta Acquires Yesware Featuring Joel Stevenson
Podcast Cover Image: Vendasta Acquires Yesware Featuring Joel Stevenson

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On October 2022, Vendasta announced the acquisition of Yesware, a product assisting sales professionals in delivering positive buying experiences and building valuable relationships that customers deserve – making the process easier and more effective.

Join us to kick off the new season with Vendasta’s acquisition of Yesware. In this exclusive interview, George Leith chats with the former CEO of Yesware, and Vendasta’s Vice President of Growth, Joel Stevenson, to discuss the history of Yesware, the acquisition, the Hard Sell Podcast, and Yesware’s tool for driving sales growth. 

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 $400 Million in annual revenue. He also ran Wayfair’s UK business and oversaw the FP&A function as Wayfair transitioned into a publicly traded company. Before Wayfair, Joel worked as a consultant at ZS Associates and spent the early part of his career in various 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.  

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Vendasta Acquires Yesware


George: This is the Conquer Local Podcast, a show about billion-dollar sales leaders, marketers leading local economic growth, and entrepreneurs that have created their dream organizations. They want to share their secrets, giving you the distilled version of their extraordinary feats. Our hope is with the tangible takeaways from each episode, you could rewire, rework, and reimagine your business. I’m George Leith, and on this special edition, we welcome Joel Stevenson. Joel is the former CEO of Yesware, a leader in sales productivity software. Yesware was acquired by Vendasta and Joel is now our VP of Growth. He has over 20 years of experience in building businesses, and prior to Yesware, Joel was the general manager and founder of Wayfair’s B2B division, which grew to a 100 million in revenue. He began his Wayfair career by leading the company’s home improvement products division, followed by his role as managing director of Wayfair UK, where he drove the growth of the company’s international presence. Joel then served as vice president of FP&A, while Wayfair was making the transition to a public company. He earned an MBA from the Yale School of Management, a BS in Business Administration from the University of Illinois, and he studied Chinese at Harvard’s Beijing Academy. Get ready Conquerors for Joel Stevenson, coming up next on this week’s episode of the Conquer Local Podcast.

George: It’s a pleasure to have Joel Stevenson here in studio for the Conquer Local Podcast. Welcome, Joel.

Joel: Glad to be here, thanks for having me.

Yesware’s Backstory

George: So Joel, you were the CEO of Yesware, and recently Vendasta announced an acquisition of Yesware, and now you’ve moved into a role as VP of Growth. So congratulations and welcome to the rocket ship known as Vendasta. We have a bit of a tradition here at the Conquer Local Podcast when we bring on senior folks that have been doing it for a while, we like to have them as guests. So we’re gonna spend hopefully the next 20 minutes just talking about Yesware because I need a bit of a refresher. I remember when the sales team, and we were just a couple of sales reps, we started building inside sales, came to me and said, “Can we sign up for Yesware?” And that was nine years ago that we met the Yesware organization. So I’d love to hear from you, where’d Yesware come from? How long has it been around? Just get a bit of the backstory.

Joel: Yeah, well, you were pretty early there ’cause the company is only a little more than 10 years old, I suppose. And the original founding idea of the company, just so you know, I came in about five years ago, so I’m not one of the founders, but Cashman, our CTO and co-founder still with the company, and Matthew Bells was the other founder and CEO, and at the time, there wasn’t really such a thing as sales software built for salespeople, though there was plenty of sales software, but it was more the traditional CRM, which I always think of as like built for the sales manager. You know, like when I did some CRM installations many, many years ago, the whole thing was just like Orum and Siebel back in those days, the whole thing was, well, you don’t want the salesperson to leave with a Rolodex, right? So it was always a bit of a control and what’s the forecast? It was never really about, well, how are we gonna make salespeople more productive? It was really about like, how are we gonna get information, control information from the sales team? And so the idea behind Yesware was like, well, what is a set of tech that would just make salespeople more productive and make their lives better and make them actually earn more money or be more successful in their career? And so that was the idea. And it started with actually a mobile sort of template keyboard, and then eventually sort of got to this idea of taking some of these marketing automation principles around email and applying ’em to the salesperson. So instead of just like getting a report of like, oh, here’s your email campaigns and here was the open rate and the reply rate, you know, bringing that to a salesperson, but then giving them a notification as soon as somebody opens the email was sort of the original, kind of innovation of Yesware.

Joel’s Skills and Expertise

George: Well, it’s interesting that you talk about that magic moment because I’ll never forget the morning that Justin Babiy, who is one of our top sales reps walked into my office. We actually weren’t even in our old building or the new building that you and I are in today, we were in another building they kind of put inside sales and he said, “I’ve cracked the code.” I used this Yesware thing and I phoned the client as soon as they opened the email. Now think, that’s pretty normal today, but think back nine years ago, it was quite revolutionary. And that was where Yesware really started to ride the wave. We’ll get back to a little bit more of the history, but let’s talk about you and your history. So five years at Yesware, where were you before that?

Joel: Yeah, before that, I spent seven and a half years at Wayfair and I started when it was a company called csnstores.com that had three or 400 individual microsites, things like as extreme is allroosterdecor.com. It was very much of sort of an SEO, SEM driven, sort of almost an advertising management combined with supply chain management. There wasn’t much of a brand or much of a retail story there. And over time, as we built that business, we eventually realized that we need to build a brand and bring it all together. So we then became wayfair.com. I ran originally a bunch of websites that had to do with home improvement, you know, plumbing, lighting, that sort of stuff. And it sort of incubated a little B2B team while I was there. Then I went and ran our UK business for a couple of years, came back, and actually ran our financial planning and analysis group while we were going public, which was fascinating and super interesting. And then had a chance to go back to the B2B division, which I’d sort of started and sort of grew while I was away. And that was about, around about a 100 people when I sort of took it back over, and then in two years, we took it to about 500 people and 400 million in revenue, and now it’s a one and a half billion dollar plus division of the company. So it was fun.

Boosting Sales Productivity

George: Yeah, it’s exciting growth. You don’t do too many searches online and not find Wayfair if you’re trying to buy some products for your house. So I’m sure it was thrilling. So now let’s talk about Yesware and in the five years that you’ve been there and we were talking off-camera about all of the sales organizations that use the tool for this phenomenon of inside sales and there’s a lot of tech that’s being deployed there to help make this thing more efficient and help sales professionals communicate with potential customers and existing customers better. If you were to look at some of the highlights over the last few years, what would those be in the five years that you’ve been in the space?

Joel: Yeah, well, we’ve sort of moved from where this was very much a sort of a single-player type of phenomenon where you got some benefit as an individual rep to really the teams that have gotten the most benefit out of Yesware and there’s a whole litany of companies that have started with Yesware when they were small and became public companies, Yelp comes to mind, Flywire, Jfrog. I mean, the list sort of goes on, especially in tech. And what you see these companies do is they have this very interesting sort of test and iterate approach where they sort of see what’s working across the team, they allow for some amount of experimentation and then they take the things that are working and they apply that to the rest of the team. And so if you think about you’ve got one rep that somehow figured out, oh, well, here’s a better way to go from the discovery meeting to the demo meeting. Like, we get more people to show up or we get, drive better discovery that leads to better, that can all then be applied to the rest of the team. And so now if you’ve got a step where you used to go, 8% of the people made it from this step to this step, and now it’s 10%, well, one rep figures that out, and then if you can do that across your whole team, well, now you’ve got a much better funnel, you can spend more on acquisition, you’re gonna get, drive more to the bottom line. So that’s really what we’ve started to see is people taking, individual productivity and then sort of turning that into team productivity.

George: The one dream that I’ve always had over the years, there’s probably podcasts where I talked about it, really excited to put it in place, was a test team and having that test team not be a junior rep because junior reps have gotten the building and they’re learning what they’re doing. Having it be somebody who’s been there for a while, kind of knows how to run the plays. Is that something that you’ve saw over the years in this experimentation where there’s a team that tests these new things? Or is it in general population where you pull a couple of reps out and you get them to run the test? What would be the best practice there?

Joel: Yeah, I think it, I don’t know that I’ve ever seen somebody say that this is sort of the experimentation team. I think sometimes what happens is they just emerge because you’ve got some senior people that are good and they get bored, you know, just kind of running the same playbooks and you can’t just have ’em like do the same thing over and over again. And I think that group ends up sort of becoming like the defacto testers and then they tend to be the pace setters for the rest of the sales organization. And so whether or not there’s an explicit sharing, people are sort of watching what they’re doing. And one of the things about making your sales process more tech-enabled is it does make it more possible for the rest of the team to see what’s going on. And so if you see that somebody, oh man, like this person is killing it, like what templates are they using or what campaigns are they using or like how are they following up? You can start to get a lot of that information as a rep versus before you maybe couldn’t get that sort of thing.

The Hard Sell Podcast

George: Yeah, that collaboration and sharing of information is so important. So I also have been doing some listening recently to the Hard Sell Podcast, which is a show that you’ve created and let’s talk a little bit about that podcast show, and what was the, you know, I remember the day that I opened my big mouth and said, “We’re gonna do this podcast and it’s gonna be every week.” And then probably had PTSD for the next year afterwards going, “What have I got myself into? It’s a lot of work.” Now of course the team does all the work, and I just show up here and talk. But what would you say are some of the highlights and maybe the things you learned in developing that podcast?

Joel: Yeah, well, we’re not as high budget as this one I would say, we’re definitely in that early sort of scrappy phase, but it’s been fun. I mean, the way we approach it is we’re trying to bring people on that have something interesting to say about selling, and in some cases, it’s the CEO of a tech company that serves sales, in some cases, it’s the sales leader, in other cases, it might be somebody that’s like somewhat adjacent to sales like I had Jerry Colonna who wrote this book called “Reboot”, who’s my executive coach and I had him talk about like rejection and so we try to bring in people that are broadly interesting across a number of areas. And mostly I think the way that I keep it interesting is I just bring on people that I find interesting and we just talk about interesting stuff. And so that part of it feels quite easy, and then we’ve got some folks that help get it produced and edited and out in the world. So I don’t know, I couldn’t do that actually, so.

George: Well, absolutely, I couldn’t do that either. The other thing that I’ve noticed over the years, I’d love to see if your learnings line up with this, but the first couple of years always answering the question of where’s the value from this? And you’re producing episodes on a regular basis. And then it felt like in year three, we’d be at a conference and someone come up and say, “I listen to the show every week”, or we go on a cold call and the client would be like, “I listened to that show.” Is that kind of what you’re seeing as well, having that consistency, and what were some of the things that you noticed where it really started to pick up traction?

Joel: Yeah, I would say we’re still pretty early. One thing that’s happened recently is I’m starting to get inbound from other people saying like, oh, we heard about the Hard Sell Podcast or this one episode? So I think there’s something there. Certainly, I think the Vendasta acquisition helped ’cause now we’re like, it’s sort of a joke, that it’s like 150 in entrepreneurship in Canada or something on one of the iTunes charts or something like that. So the way I think about it is there’s probably some exponential where if we keep building good content over a long period of time, eventually someone’s gonna find one of ’em, and then they’re gonna say, “Oh, I like that one. Like, let me listen to the other 30 or 40 or, you know, you have 250”, we’re nowhere near that. But if we keep making every episode good, eventually there’s a sort of a catalog of content that becomes available to people whether they discover it now or they discover it three or four years from now, they can go back, and hopefully we’re doing stuff that’s relevant to folks for that whole period.

Trends in Sales

George: Yeah, what we’ve found is actually episodes from season one and season two are getting as many listens as brand new episodes for that very reason when somebody finds the content. But I always like asking that question of other podcast creators and hosts because it was a little lonely there for the first 24 months. You’re trying to justify the investment in your own head as much as to the organization. And I think really where we saw the magic start to happen was sometime in season three where people were, now they’re starting to be a little bit more forward on it. So we like to share that with our listeners because it is still one of the fastest-growing content mechanisms out there for businesses of all sizes. So in sales, as we look to the new year, not sure when people are listening to the show, but we’re recording this late 2022. What are some of the trends that you’re seeing in sales? ‘Cause you work with some of the biggest and best inside sales organizations on the planet through the Yesware group. I always like to ask that question, what are some of the trends and how could our listeners learn from what you’re learning?

Joel: Yeah, well one thing that we see is the bar continues to go up for personalization. So we talked earlier about the experience nine years ago, sending out an email and getting it open and I think you maybe as much as three to four years ago, you maybe could have gotten away with sending out a relatively half-baked campaign and some people would’ve thought it was really, like it was really meant just for you type of thing without a lot of personalization. I think now there’s been so much more sort of automated or structured emails put out into the world that like you really can’t get away with that as much as you can anymore. Now you still wanna get the benefit of the tech, but you really have to spend more time personalizing those messages and making sure that the person that’s receiving it gets the sense that it’s not from a machine or it’s not automated. ‘Cause I think now like that is the, yeah, that’s sort of the kiss of death I think. And what’s interesting is that if you actually do the work and do the personalization, like actually add some value into those emails, they really stand out because we see a lot of people using tech, like yesware or other tech as a crutch, but it’s really meant to assist, it’s not meant to do your job for you. And so if you can use that tech to be more productive, but then you can also sort of remember the craft of selling and like who are you selling to and what do they want and what’s the value and how can you solve a business problem for them. Like I think there’s actually better chances to stand out than maybe there was three or four years ago because so many people just think they can just hit send and their job is done.

Artificial Intelligence Technology

George: No, if our audience picks up one thing, there is no silver bullet. There are components that can make it a hell of a lot better. So I appreciate you bringing that up. As we look into AI, I noticed in Slack yesterday, you were sending a note around AI. We were just recently at a conference where pretty much every presenter was talking about AI. What do you see in the crystal ball as we look forward?

Joel: Yeah, well, the ChatGPT thing, which OpenAI just launched is really a stunning, in my mind, a really stunning lead forward. And it sounds like they’re even got sort of, this is like an interim model and they’ve got another bigger one that’s sort of coming. And two things that I find interesting about that, one is that they’ve taken this massive corpus of internet data and trained this model on it and you could just ask it the craziest stuff and it’s sort of a bullshit artist in some sense, but like it’s pretty believable and the fact that it can take so many just random unstructured queries and get you part of the way there is really interesting to me. And I think folks that are not really adding value from a creative standpoint, even in selling, like if you’re not really understanding what the customer really wants and rank something personal, like, your job is probably in danger from models like this that are just sort of like wash, rinse, repeat, taking information that’s broadly available and synthesizing it. And so I think this is a real change. And the other thing that’s interesting about the ChatGPT to me is that it’s a much more accessible way to get at it. So it’s like a very comfortable interface where you’re just sort of typing questions, like you’re not coding an API, you’re not sort of getting data back and having to parse it and do something else, whether you’re not writing Json, you’re just like writing free language text and getting interesting responses back. So I think a lot of people through means like this are going to start to understand what the power of some of these models are. And again, it’s not a cure-all, but it’s indicative of where the tech is going. And if you could take a model like that and then train it on very specific data that maybe you have proprietary to you, like people are gonna start doing some very interesting stuff with this, I think.

George: What I found last year when it was called here in Canada where we live, that’s my content time. I was using Writer at that moment and I just found that it helped me to be even more productive, but you’ve gotta go through it and make sure that it makes sense, especially if you’re sending it to a high-value customer. You don’t want it, I don’t think we want it to look like a form letter, but it’s amazing to see the advancements even in the last 12 months.

Joel: Yeah, I forget who said this, I don’t know, Hazimov or somebody was this idea that humans are very good at extrapolating things linearly, but we’re very bad at extrapolating things exponentially. And so you tend to overestimate what something can accomplish in the short run, but underestimate it in the long run. I think we’re definitely starting to get on the steep part of the curve with some of these AI technologies now.

Vendasta’s Acquisition of Yesware

George: Yeah, Amara’s law is at play for sure. So let’s talk about the acquisition and yes, we’re coming together with Vendasta. You’ve got an enormous amount of customers that love the product. We got an enormous amount of customers that love Vendasta. We put the two organizations together. It’s not gonna happen overnight as much as a salesperson, I’d love for it to happen overnight. But how are we lining up as companies in your opinion?

Joel: Yeah, well, there’s, I mean, I think there’s some really interesting stuff, I mean, one great part of the acquisition was Vendasta is a long-standing customer so you understood the tech and what we’re doing and what we’re trying to do. And one thing that people love about Yesware is that we allow you to work in context, like mostly in the inbox, but we show up in some other places like Calendar as well. But that’s where we allow you to work. And I think for reps that are busy in constantly contact switching, like there’s a high cost to go into this screen, then into that screen, then into that screen. And so to the extent that we can sort of keep you in context, people really like that. And so what we’ve done with things like our Salesforce integration is we basically bring Salesforce into the inbox, we take all of that activity, we passively sync it into the right place inside of Salesforce. And so without doing all the work, you get all the value of those systems of record. And so if you look at the Vendasta system, we can do something very similar there where over time we’re gonna bring Vendasta into the inbox and all of that data that you’re gathering from communications with customers like that’s gonna end up in Vendasta now as a system of record versus in some other system of record and all the power of, sort of one to one communications that Yesware powers, we’re gonna bring that in and combine that with automation. So you might maybe, might get a lead in and be able to immediately route it to a person, immediately put them into a campaign which then goes outbound and you start. So there’s some pretty interesting stuff I think that’s possible.

George: Oh, really exciting stuff. And culturally, the two organizations playing well in the first couple of months?

Joel: Yeah, I think so. I think we’re all setting new records on our phones for temperature. I think it feels like negative 50 is a new thing. So we’re having to up our winter clothes even being from Boston, we’re having to up our winter clothes game I think a little bit here. But yeah, it’s been great. Everybody here has been very welcoming and you can tell that there’s a real desire to win here and a lot of energy and excitement and yeah, I mean, to me it feels a little bit like Wayfair was a few years before we went public.

George: So in the five years that you’ve been at Yesware, you’ve been working in one of my favorite cities on earth, Boston is one of my favorite places. You can feel the buzz in that community from tech. What are some of your takeaways from being in the Boston area just to share with our listeners? ‘Cause I know that it’s a very popular place for people to go visit.

Joel: Yeah, it’s great. I mean, it’s got a lot of history. I think it’s a relatively compact city so you can sort of get, I mean, it’s hard to get around ’cause it was built for carriages, not cars, so the roads are terrible, and the transit system isn’t particularly good, but it’s pretty small, so you could, it’s a very walkable city. We sort of, I think punch above our weight in restaurants and there’s, the North End is a bunch of Italian food. Like there’s a lot of interesting stuff there. And what makes the city pretty interesting at the moment is there’s something like 50 universities in and around the Boston area. So you have, obviously Harvard, MIT, you have Boston College, MBU, and Emerson, like the list goes on. And so there’s an interesting thing that happens in Boston is like, it gets a lot quieter in the summer actually while the tourists start to show up, but a lot of the people that you see around that are younger are gone. But it does make the city feel young because it has such an influx of college students. And then you have all the innovation that’s coming out of the likes of MIT MBU and Harvard. And that sort of drives an interesting culture. And on the tech side, you have not only tech, but biotech is very big in Boston and so it makes for quite an interesting set of dynamics for the city.

George: Well, Joel, we welcome you to the Vendasta rocketship. It’s been a pleasure getting to know you and the team over the last month or so and we’re looking forward to some great things coming in the new year as we start to bring these two platforms together. And thanks for joining us in the Conquer Local Podcast.

Joel: Yeah, thanks for having me, and glad to be here as a part of Vendasta.


George: Great episode from Joel. And as you could tell, we probably could have went on for quite some time talking about sales and how the Yesware platform has benefited some of those logos that he was speaking of, like the very large Yelp sales team that calls on local businesses all over North America. It’s all about efficiency, it’s about a product stack that allows sales organizations to be more efficient. And it’s not about replacing sales, it was interesting to hear him talk about that. The automations that can be put in place, the workflow models that can be put in place drive more efficiency so that the salespeople are able to be more productive with the time that they have. If you liked Joel Stevenson’s episode discussing Vendasta and their acquisition of Yesware, let’s continue the conversation. Check out episode 508. Vendasta acquires Matchcraft with Sandy Lohr and Brendan King. Please subscribe and leave us a review, and thanks for joining us on this week’s episode of the Conquer Local Podcast. My name is George Leith, I’ll see you when I see you.