Joel Stevenson shares his insights on being a global citizen and how it can make you a better leader, transitioning from sales to executive leadership, and creating a culture of accountability. He also discusses his experience starting the business-to-business division at Wayfair and the importance of an entrepreneurial spirit in a large organization.

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πŸ“ŒTALKING POINTS

03:31 - The Importance of Being a Global Citizen

10:31 - Transitioning from Sales to Executive Leadership

15:41 - Developing Communication Skills

18:15 - Creating a Culture of Accountability

25:04 - Starting the Business-to-Business Division at Wayfair

30:22 - Entrepreneurial Spirit in a Large Organization

34:58 - Lessons Learned from Failure

πŸ”—CONNECT WITH JOEL

πŸ”—CONNECT WITH TOM

πŸŽ™οΈABOUT THE PODCAST

Every week on the Talent Empowerment Podcast, Tom Finn, the dynamic Co-Founder and CEO of LeggUP, ventures into the minds of trailblazing CEOs, HR executives, and talent development savants from various industries to dive deep into their career paths, dissect their strategies for growing people-first culture in their organizations, and uncover how they’re driving talent innovation.

Tom Finn (00:00.566)

Hello, my friends. Welcome in to Talent Empowerment. Today we are learning from Joel Stevenson. Joel, thrilled to have you on the show, welcome.

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Joel (00:09.574)

Thanks for having me. Great to be here.

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Tom Finn (00:12.202)

Well, it is great to have you. Uh, I cannot wait to learn from you today. Joel is the CEO of Yesware, a leader in sales productivity software. And before he was at yes, where he was the general manager and founder of Wayfair as business to business division, which he grew t2o several hundred million in revenue, pretty amazing. And before joining Wayfair, he held a variety of sales and marketing roles at a Reba in Ovis and Verizon. Uh, he was also a consultant for a few years at ZS Associates. He has an MBA from Yale and studied Chinese at Harvard Beijing Academy. I cannot move on from there without asking the question, what is the Harvard Beijing Academy and why did you choose to study Chinese?

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Joel (00:58.882)

Yeah, it's a summer program that Harvard runs. And one of the professors there started it. And I like to say that I'm a straight A student at Harvard, because that was the only class I ever took there. And I don't know if they grade inflation or whatever, they gave me an A. And the way that came about was my second year of grad school. I don't know, I've always been a, you know, I'd been a grad school student sort of a failed attempt at German in high school, but never really spoke any other languages, but I've always been, I've liked travel and I sort of try to see myself as a global citizen and certainly want to raise the kids more that way. And so I thought, well, here's a good chance. I go, I'm never going to probably be in an academic setting again. Like, why don't I try to do Chinese? And so I, that was an undergrad class. And I was, since I was in grad school, you had to go talk to the professor to convince them to let them in your class. And this guy read me the riot. He's like, nah, like you grad students can't hack it. It's too, like it's too much work. Like you're not gonna do it. Eventually I convinced him that I would do it. So he lets me in the class. And it was, that was the hardest class I had in the two years, like not even close, the toughest. And, but it was great. And, but by the end of my, this is a first year Chinese class, my teacher was like, wow, you know, you work pretty hard at this and you're gonna lose it all if you don't, you know, do something to to kind of reinforce it. He's like, you should do one of these immersion programs. There are a bunch of them that prints and runs one and there are a variety of them. He's like, well, there's this new one at Harvard. You could go do that. So you have to like record a tape and they let you in. So I did that. And actually it was, the timing was a little bit interesting. And I get to thank my wife for this. So the day I graduated from Yale, our second child was born on the same day. So like… got the diploma and then that night, we were at the hospital and it was pretty wild. And then basically three days after that, we drove down to Florida where her parents lived and then I got on a plane and went to Beijing for the summer to study Chinese. So it was really cool and great experience and learned a ton. I think I probably would have needed to stay another three to six months to really get it to where I wouldn't lose it. I've basically lost it all now, unfortunately, but Very much of a mind-opening experience. I certainly understand China and the Chinese people much better living there and interacting with them. And people would take pictures with me because I was like one of the only white people. I was certainly one of the only tall, blue-eyed white people around. So it was fun.

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Tom Finn (03:31.114)

Yeah, it's pretty entertaining. I've been to Beijing. I actually did on a grad school trip. We did a project, MBA at USC. And part of the graduation requirement is you have to go, depending on which classroom you go to Shanghai or you go to Beijing and you do a week and you go to all these different businesses and you actually interact with the CEOs, senior leaders, they tell you about their perspective of Americans in China and business relations and that kind of stuff. And it was super interesting. And, but I remember the same thing as you, Joel. I remember being, uh, on the great wall and having people come up to me and just kind of hand sign if they could take a picture, because I don't speak English and they're trying to get you to take a picture with their family. So I'm standing, I'm not that tall. I'm six feet tall, you know, but I'm just the only, you know, there's this group of white young people running around, right. And, and, uh, and it was just hilarious, um, uh, to be in that scenario, but let me ask you this, why did you think that being a world citizen or understanding different communities and context was important to your own kind of leadership development?

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Joel (04:46.018)

You just see the world, it's hard to envision, I mean, maybe this will end up happening, but it's hard to envision a world that becomes less connected over time. I think if you look at the broad expanse of history, we're getting more connected versus less connected. Certainly things like the internet have massively accelerated that. And from like a little bit of, I didn't, I grew up in kind of a… what you might call a lower middle-class family, like my family had never traveled outside the country, like barely even made it out of the state. And so it was never really part of my upbringing, but I always was interested in it. And then as soon as I started working a little bit of money and started to travel a little bit, my wife had traveled more than I had, like we got it over to Europe and a bunch of other, all of a sudden it's just really like, oh, this is different.

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And there's this whole wide world out there that's not America. And, uh, I, I just remember feeling like, you know, I, I don't want to just be an American, like I'm proud to be an American and all that stuff. Like, I just don't want that to purely define me. Um, I was hoping for something a little bit bigger than that. And, you know, it's, uh, you know, the classic kind of stereotype of, you know, the American cruise ship tourists, like you get off.

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You go eat somewhere, you buy a trinket, and you get back on the boat. Like you never figure out anything about the country. Like I didn't really want, I did not want to be that person. And through experiences like that, and in programs like the MBA program where you got classmates from all over the world, all of a sudden you just feel a little bit different level of connection. And I didn't know if I would ever leverage any of that from a business perspective. I had a...

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fork in my career where I basically could have become the China person, which I chose not to take. But I, you know, at least wanted the option. And then, you know, we had later in my career, one of my stops at Wayfair was I ran our UK business. So we moved the whole family to London for a couple of years. And that was, that was incredible. So.

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Tom Finn (06:43.754)

Yep. What, what was the takeaway from moving to the UK for a couple of years with your kids that you can share?

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Joel (06:53.55)

Well, they were smaller at the time. They remember a little bit of it. I probably didn't set it up ideally as an expat. One thing I'll say is that there's, we were at the time we're homeschooling our kids and so we homeschooled them over there, which actually made it super easy to go. But the challenge with that is a lot of that expat community comes from the school system. And so I had a community, because I was leading a part of the company and had all these new people that I worked with and we were pretty social but my wife didn't necessarily have that. And the kids didn't necessarily have that. And so there was an aspect for them which was a little bit more isolating than the way I drew it up. And I think if I were to do it again, I might try to devise it in a situation that worked better for everybody than just for me. But that said, we had some of the ways that these things work financially a little bit different over there. We had a great au pair they ended up actually living in her tiny Spanish town for a month where they were the only people that spoke English other than The mayor and so they had all these neat experiences. We got you know, it's easy to travel around Europe when you're in Europe so we had a lot of great experiences there and You know two years went by in a flash I think we only I only feel like I scratched the service of the UK, you know from being there for two years But yeah, it was it was awesome and I hope the kids, you know, they every now and then they talk about and they remember, you know sort of bits and pieces of it, but I hope that it's deep in there somewhere.

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Tom Finn (08:24.63)

Well, I'm sure it is. Uh, and I lived in the UK till I was eight and then came to the US so I did kind of, kind of opposite. So I think I understand, um, some, some of this, but I think what's really important to listeners here is that you've really taken a global approach to your career and you've taken sort of a, Hey, I'm yes, I'm a US guy grew up, you know, middle-class, but my whole goal was to enhance and open up my mind to what else is going on around in the world. Do you think that's made you a better leader?

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Joel (08:56.098)

I think so. I mean, there's just very different perspectives on things. Like if you were to take the, you know, sort of the Eastern versus the Western perspective, even on something like, you know, negotiation, like in China, face saving is very important. And that's a key part of the way that you approach certain things. And like, you know, here in Boston, like, we don't care. Like, we'll just, you know, swear to your face and call you an idiot. Like, that's cool. Like, that's a valid way of negotiating and communicating here. No one, you know, no one… no one minds it too much. And so I think, yeah, you pick up different perspectives, different points of view, different ways of doing things. And I think, you know, maybe more than anything, the ability to relate to different people where they are and, you know, very quickly try to get to some sort of common ground, versus if you're always in sort of the, whatever your monoculture is, I think it gets to be more difficult to just relate to people. And, you know, it seems like we've got you know more issues with that lately in the world especially with you know social media amplifying you know though in many ways I think the worst of us.

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Tom Finn (10:02.582)

Yeah, I think that's fair. And look, the reality is we all need to enhance our open-mindedness. We all need to work through understanding each other a little bit more, be a little more kind to other people's cultures and feelings, and be a little more sensible about the way we communicate. I think that's critical in the path for so many of us as we're developing ourselves and trying to be better global citizens. So let me ask you a little bit about Yesware. So you came in this organization, accelerated yourself to the CEO. Tell us about the business.

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Joel (10:37.434)

Yeah, Yesware is a sales productivity tool. So we have an application that sits deep inside the inbox and helps you figure out things like who's opening your emails, helps you take series of communications and structure them together for structured outreach. We'll do things like take all of that information that you're generating in your inbox and we'll pass it. We sync it back into Salesforce if you're a Salesforce CRM customer. So generally speaking, what we're doing is we're saving salespeople time and we're giving them information that they need to sell a little bit smarter, whether it's who's interacting with your content or what types of content works better. And so we, and we're generally speaking used by, uh, you know, the most of our customers are tech sales people, but we've got all sorts of people that are in a sales orientation. Entrepreneurs, sometimes people use it to job hunt, um, all kinds of stuff.

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Tom Finn (11:29.102)

Interesting. So when you started there, you had a career, you did some consulting, but you had a pretty deep career in sales and distribution and revenue development and those types of things. And when you made the leap, it looks like you came over in a kind of similar sales leadership role. How does one go from kind of a sales career to jumping into executive leadership? Because there's a lot of people that are in… verticals, marketing, sales, technology, whatever it is, accounting, finance, and they wanna make the jump from a practical role to a leadership role. How did you do that?

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Joel (12:09.914)

Yeah. Yeah, there are a couple of things that I think were the ended up working well in my favor. One of the things that worked well in my favor was, you know, I was sort of coming up in my career, we had the sort of the dot com boom and bust, and then we had 911, and we had, you know, sort of the great recession of 2002. And that's the I was out of work for a short period of time. And I think it was eventually my wife convinced me to go back and get mad. I was dumb. She convinced me to, to do it.

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And through computer error or whatever, I ended up getting accepted to Yale. And I used that opportunity to, in some ways, reinvent myself. So I had always been customer-facing to that point. But I was reasonably quantitative. But I'd never, and I was a finance major for a while in my undergrad before I switched it. But I felt like there was an opportunity for me to go back and, I think MBAs are really great for that. And I'm not necessarily a b----. an advocate or, you know, for or against MBAs. I think they're right for some people in certain times. But I think if you're trying to do a career switch or a reimagination of who you are, MBAs can be great for that. So I did that. I got a finance concentration. Then I came out and worked for ZS Associates, which is a sales consulting firm, but very quantitative. It's mostly engineers that work there. And they go into, you know, sort of famous for going into massive pharma companies and figuring out how big their sales force should be and what it should look like and who they should talk to what drugs should you talk about first? So they're very, you know, how do you maximize the potential of all these different territories? Started by a couple of Northwestern professors years ago. So that was great. So that kind of gave me an opportunity to then be a practitioner of those things where, you know, I was like, had to build narrowly spreadsheets and all that stuff and explain these things to customers. Then I sort of got bit by the startup bug again and got back into… startup life, the first one didn't work so well, that eventually brought me to see to what was at the time CSN stores later became Wayfair, which we can talk more about. But yeah, at Wayfair, I had a chance to do a lot of different things. But I think probably the biggest thing that prepared me for senior management was just doing stuff, you know, and the ability to actually go and make a difference in a business. And so I had the customer facing skills, I had the quantitative skills, but then I had, I had, was able to prove the execution skills of going and you know, making, you know, scaling a business or bringing an idea into the world or any of those things. And that was really what made it possible for me to make the transition to CEO. And when I joined it, yes, where the plan all along was that I was going to be the CEO. Nobody knew that other than me and the founder, original founder of the company. But that was our plan if a few set of conditions happened, which they ultimately did. And then I ended up taking over.

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Tom Finn (15:02.082)

Yeah, I love the way you talk about your career because you're, you're right on that you had a particular set of skills, uh, in customer-facing roles. And then you had to go learn quantitative skills, uh, which I think is really, really important, which what you didn't mention is I imagine during your, your time as a consultant, you had to learn some pretty deep communication skills, some candor, right? Way to deliver information, um, that may not be appetizing for somebody that you're, you're delivering it to. Right? That, that is a particular skill in and of itself, that communication piece. Did you notice yourself actively working on your communication style as well?

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Joel (15:41.658)

I suppose a little bit, I think I benefit from the fact that early on in like even in my high school and stuff like I was pretty involved in performance art. So I was, I did acting, I was in a, you know, the glee club and the show choir and I was in the glee club and in college and played sports. And so I was always, there was always a little bit of like being in front of people and

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In many ways, I made up for my academic laziness by being pretty good verbally in many cases. So that was something that was always a little, in many ways became a crutch for me. And in the consult, that works pretty well in sales, oftentimes, depending on what you're selling. But in consulting, it doesn't necessarily work as well, where it's like in consulting, oftentimes the numbers have to do the talking and then the story that you tell with those numbers to perhaps convince a client to do something or help them come to some realization or some conclusion. That is a different style of communication. And so that took, I think probably the biggest difference there was the realization that preparation is critical to the communication. And really, the best salespeople actually prepare very well.

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I didn't, I would say I was not best in class at that when I was doing it, but it's very difficult to show up to a client presentation and consulting without really understanding the data and the numbers and being able to express those clearly. So it was like the prep aspect of that I found to be, it was very difficult to fake it.

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Tom Finn (17:22.954)

Yeah, that's a key takeaway for everybody that's listening. Uh, you gotta be prepared. You've got to know your numbers. You've got to show up with a communication strategy that's been outlined and you feel confident about. That's the other part. If you don't have confidence in what you're saying and you don't actually believe it, it will come across that way. So you've got to really be confident that you've got the numbers, right? You got the plan, the strategy, the tactics, and you can execute whether you're a consultant or you're a salesperson, uh, or you're in marketing, trying to grow your career really doesn't matter.

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You have to go through the same pre-work before you show up to a meeting. Um, what did you do when, when you were growing the organization and you saw people that weren't prepared? I, you know, this one's hard for leaders. When somebody comes into your room, they've been invited into your leadership meetings, whatever it might be, and they are just not prepared.

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Joel (18:15.694)

Yeah, I mean, I don't think, you know, I would like to think of myself as not that much of a confrontational leader. And so like, I'm not necessarily the one that's going to call somebody out in the middle of the meeting and say like, hey, you're not prepared. I try to be the one that, you know, maybe after the fact would try to debrief with somebody to say like, hey, that didn't go so well. You know, like, why do you think it didn't go so well, more of a sort of a, you know, an asshole or whatever. So I think that's been effective over time. You know, oftentimes, at least in sort of an executive team setting, I find that even more so than the CEO, it's like the other executives and what their expectations are and the, you know, sort of the culture and the way the team operates, oftentimes that stuff gets kind of self-policed, you know, you get a bunch of people that are ambitious and want to do well and are trying to get better. And the culture that emerges is one of like, well, I don't want to, you know, not only do I not want to look bad in front of the CEO, but I don't want to look bad in front of my peers either. And I know that if I show up not prepared, like someone's going to call me on it, or I'm going to, or someone will ask me a question that I can't answer effectively. And it will be obvious to everybody in the room what just happened. So we didn't, I think I've been mostly fortunate in my career to not have to deal with that a lot, but I think much of it ended up being more the culture, creating the conditions for that versus sort of me personally.

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Tom Finn (19:55.746)

So how do you create a culture that has those type of conditions where people are not being called out meetings, where people feel empowered to do good work, where they are focused on the other peers and making sure that they're delivering for their coworkers, not just the CEO? How do you create a culture like that?

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Joel (20:16.122)

Well, hopefully you first, you model the right behaviors yourself. And so, ideally you're meeting people where you are, like, hopefully you're the one that's working the hardest in the company or close to the hardest and people can see. I mean, there's sometimes that can be, there's sort of that stereotype of the pace setter leader, which can burn everybody out. And maybe it can be not helpful, but in general, hopefully you're modeling the right behaviors for the company. And I have often found that the people that end up being the best, it's actually not that different than sales. It's like the people that end up being the best salespeople are often the ones that are the most curious and ask the best questions. It's not necessarily the ones that are the most pushy. And I find that the same is often true in management where the people that end up, and I've had a lot of first-time managers that have worked for me over the years. And oftentimes you get, the people are nervous about it and they're like, I'm gonna be a bad manager or whatever. And it's like, well, like I'm pretty sure that you care about people.

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And like you're generally interested in this person and helping them because that's the kind of person that you are. And so like I'm not worried about you being a bad manager because you know, you actually care and you're smart and you're going to ask the right questions and you, you know, you've gotten to this position because you've worked hard and you're good. So, you know, and that it doesn't always work that way. But I think often, you know, if you're promoting the people that are generally interested in other people and helping other people, that that's going to be a natural that's going to be a natural byproduct of it. And that doesn't mean you're not confronting, you're not sort of saying like, hey, you got to do better here. Like, you know, our expectation was here and you met us here. But that's also part of the process of caring about somebody. And if you can start from a place of like, well, you're judging the action, not the person. So what's the old saying of like… you know, be tough on the results or the actions, not the person like, I think you do that enough times and people start to get the idea like, okay, well that's kind of how we operate here.

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Tom Finn (22:13.738)

Yeah, look, that is so well said. I think we can play that clip back for people over and over and over again. And here's how you sum that up. You look at the action, not the person, and you try to be human in everything you do as a new manager or as a manager who's been in the job for 20 or 30 years. You have to look at the actions, not the person, don't make it personal, and try to develop people along the way. If they miss something, help them, help them figure out why they missed it and how they missed it and what the process was and how we cannot miss it in the future. And I think those types of behaviors start to create a really amazing culture where everybody feels valued, their voices heard, they're, they're allowed to make mistakes and then you rally around them to support them through their career. That's just the best way to operate a business.

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Joel (23:05.53)

Yeah, and I think, you know, one, I mean, an experience that I had earlier as a manager that I think many people go through is it's like, you know, everything has a yin and a yang. And, you know, I think if you tend to be, you know, on the nicer side of culture, oftentimes you maybe aren't as direct with people or you don't give them the feedback they need. And like the, you know, you really only have to go, hopefully you only have to go through the experience once where you end up having to let somebody go and they're shocked.

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You know, and there's one or two reasons they're shocked. One reason is maybe they're just not self-aware and they were just weren't listening or paying attention. But the other reason is like, you screwed up as a manager and you were not clear with them and you didn't tell them the things that they needed to know and that's on you. And you should feel bad about that. Like the first time that happened to me, I felt very badly about it. And I resolved that would not happen again. And you know, it's no one's perfect. And we, you know, we have our good days and our bad days. But in general, it normally only takes one of those if you're really kind of a self-conscious person to realize that you've got to do better.

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Tom Finn (24:05.718)

Yeah, I couldn't, I couldn't agree with you more. You have to be honest, non-confrontational, but honest with people about their performance in a private setting where you can say, hey, here's what I see and here's how we can work on it and how do you feel, right? And get their feedback on what's going on in their lives. So many times when I saw poor performance in my career in corporate roles, it was related to something outside of the job or some sticking point inside the job that they just didn't know how to deal with, and they just needed a little help, uh, to get over that, that kind of sticking point that was holding them back. So I think if you just listen, be empathetic and, and try to understand people along the way, you can really get through those difficult conversations. I want to, I want to turn our attention to, um, something that was in your introduction, which, which I found fascinating and it's this idea that, uh, Joel, you went to Wayfair and you really started the business to business division.

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So can you talk a little bit about sort of what you did and how you started an entire division in a large company and what that looks and feels like?

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Joel (25:15.266)

Yeah, I think it's a fun story. Hopefully other people think it is, but it's, you know, like many of these things that sort of happened by accident where at the time we were this company called CSN stores, we had all these micro sites. So we had hundreds of these sites that were SEO, you know, search engine optimized. So, you know, think of things like, you know, luggage.com and cookware.com. And we had, there was one site called allroosterdecor.com that all it sold was Rooster decor. It's hard to believe that was a real website.

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So, and I was responsible for 20 or 30 of them that had to do with renovation, home improvements, so lighting and plumbing and tools, that type of stuff. And in those days, the company was a lot smaller and so we would get carbon copied on all the order confirmation emails that would go out to customers. And occasionally I would sort of look through them and you'd start to see some patterns emerge like, oh, electrician shows up again or designer or this or that. And we had a couple of folks that were working for me at a bit of the company for a while that also had some of the same instincts that indicated to me, hey, there might be something here. And so I had a B2B background. And so some of these patterns looked pretty familiar to me, whereas most of the company was B2C e-commerce. It wasn't a thing that folks spent as much time sort of thinking about. And so what I ended up doing was basically convincing the guy that was running the customer service organization to give me a couple of his reps.

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And then we just started cold calling people with the idea that, well, if we could convince these customers to just call a rep, we would give them better service, we would give them better pricing. Would that then lead to better long-term revenue and profit for the company? And so we started with that. It was a complete disaster. We just made call after call, got hung up on, like, what? Like, it did not go well in the early days. But eventually, you know, we started to figure some things out. We lucked out this woman joined the company who understood that business. And we ended up, a recruiter knew what we were sort of doing. I was like, hey, Joel, I think you might want to, you know, pull this person into your group that's trying this thing. So we pulled her in, Katie, and she like, all of a sudden the world changed. Cause like she knew what she was doing. We started winning deals and then it started to look real. And so we then sort of went to this, this idea like, I was convinced. I'm like, oh, this is going to be great. Like I'm going to go, like we're going to go do this for real and I'm going to convince everybody this is a great idea.

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Joel (27:40.982)

Well, you know, so I convinced my boss and my boss reported to Nouraj, the CEO. And so we're going through this thing. And he's like, I'm going to talk to him. And so he goes and he talks to him. And Nouraj is like, Well, the only thing you've succeeded in doing is proving that you can take money out of one pocket and put it into another. It was sort of the idea was like, we sort of are intercepting customers that have already been acquired. And like, maybe we're doing it better. Maybe we're not, but it wasn't that wasn't that clear. It's like, well, go back and I don't believe it, but you're welcome to try to prove it. So we went back and we spent more time. We sort of figure some more stuff. And then I thought we had proven it. We've made another run. We sort of didn't get approval. But then finally, after months and I don't know, probably 20 different ways looking at the data, we finally had a view that was incontrovertible that this was working and this was generating net profit for the company. And so then we finally got the approval to start to spin it up. And so we hired some more people. We started to put it, we had no budget, of course, so I had to like bribe an IT guy to install the CRM. And we did it under cover of darkness and all this stuff. But you know, we started to grow and it started to work. And it was a real business. And so then we, that was at the point at which Wayfair consolidated all these little websites into Wayfair.com. And that was when the opportunity in the UK also opened. So I… I sort of gave this up, which was sort of a side project anyway. I went to run the UK business for a couple of years, came back and ran our financial planning group while we were going public. But then this thing just kept growing and growing and growing. But it sort of had gotten sprawled throughout the organization. At this point, it was probably about a hundred million dollar part of the business, but didn't really necessarily have strategic direction. And it wasn't really clear what we were doing. So...

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Fortunately, one of our investors said something like, hey, I think we should have a GM for this group. And I caught wind of it. And I was like, well, if there's going to be a GM for this group, it should be me. I felt like I've earned that opportunity. And I've been, by the way, I'm terrible at FP&A, and I'm never going to be a CFO. I've hit the head. So please get me out of this group. So it was a little bit of running away from the current job and running to a new one. But anyway, so they let me have this job. And so we...

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Joel (29:48.39)

we kind of set a new strategic direction for what we were doing. We had way more resources. We started to hire a lot. And, you know, we were just able to, through, you know, through a process of, you know, systems and sales productivity and strategy and technology, uh, and, and some pretty good vertical targeting, some really good, um, work on, uh, paid search advertising site. We grew this thing, you know, from a hundred to 400 and like, you know, two years, and now it's, it gets, you know, approaching two or plus two billion actually. So it's like, it actually worked.

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Tom Finn (30:22.162)

Wow, that is a great story. You started with this is a great story and it is a great story. The word that I kind of think of is entrepreneur. You, you almost act like an entrepreneur inside a large organization. Did you feel like that was some of the behavior that you were taking on through this process?

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Joel (30:37.634)

Yeah, for sure. And it, you know, having now been a venture-backed CEO, it mirrors that process a lot where it's like, you got to sort of prove it out before anybody's willing to give you any resources. You get a little bit of resources, you got to prove it out a little bit more. And then eventually you get to some point where it's proven out enough that you've got to go scale it. And that requires, you know, a good vision. It requires great execution. It requires an awesome executive team, all that, all that kind of stuff. So I think it is, it is quite similar in that respect. And

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You know, for me, I had always wanted to start a company, but, you know, circumstances in life were such that it didn't really make sense for me to do that. And so this was sort of an opportunity for me to in some ways scratch the entrepreneurial edge, but within the, I don't know, you might say the safety of a larger organization where I knew I was gonna get a paycheck and benefits and, you know, we had a growing family at that point. So there were a lot of benefits to that. Where it was like, now I'm at a point in my life where

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I can take more risk and I'm starting to do that.

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Tom Finn (31:39.106)

Well, I think it's a really important lesson for people that are in large organizations because there's this sense that you can't be entrepreneurial. You you're stuck. You have to do what the man tells you to do. Uh, and I don't know that that's always the case in organizations. I think organizations for the most part are looking for some level of innovation from their internal employees. And if you can come up with a great idea that yes, it's going to have to increase revenue and increase profits.

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And not have a huge drain on resources at the same time. That is the magic. It's fair that that's going to come up, but if you can kind of put pen to paper and figure that out, I think people are willing to listen. Do you, do you feel that way?

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Joel (32:20.514)

Yeah, particularly after being a CEO now, it's like, I think the thing that you dream for most is you have people within your company that are gonna take initiative and figure things out and just advance the ball without you having to tell them what to do, and whether that's figuring out something new or figuring out an improvement on the thing that you're already doing. That's kind of the dream, and there's no, at least of any public or venture backed or well-funded, private equity backed corporation.

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Every CEO has got to sit in front of the board and try to, and at some point deliver the message of like, here's how we're going to grow X percent this year and in the next year, here's a three year or five year plan. And to the extent that things start to emerge inside of your company that you can start to lean into and invest in that have already been proven out without you having to come up with it all yourself. Like that is the dream. And so I think whereas, bigger companies,

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oftentimes can create constraints and stifle innovation. There are some that don't. And I think if you wanna do these types of activities inside of a company, the most important thing you can sort of screen for is how does a company treat failure? And if the company treats failure in the right way, which is like, okay, you had a good plan, you executed it well for whatever reason it didn't work, that's fine. Like in some ways we celebrate that versus like.

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Oh, well, it didn't work. We don't really care why. Like you're an idiot. Like that is, that is not a good place to, to be an entrepreneur. But there are, there are many companies I believe that have created those conditions and people can do some awesome work.

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Tom Finn (33:59.21)

Yeah, I completely agree. And if you are in a company that you are trying to be an entrepreneur and you've built something great and it just didn't work, but you had all your ducks in a row and you brought in the right resources and you listened, you kept an open mind and it just didn't work out for whatever market conditions or change that happened. It happens. Happens to entrepreneurs all over the world. It happens to entrepreneurs. It happens to big businesses. Things change and you don't sometimes see it. My recommendation is go find a new place to work.

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Uh, because if you have that entrepreneurial spirit and you want to get after it, you want to develop, uh, and you're in the wrong culture, it will hold you back and you don't want to stay. And, and I'm not an advocate for job hopping. I'm not an advocate for, uh, you know, not working through some difficult conversations within an organization. I'm the opposite. I want you to work through conversations, but there is a point that you're just in the wrong culture and that does happen for folks.

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Did you ever feel like you were in the wrong culture, Joel, yourself? Would you always feel like you landed on your feet in the right spots?

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Joel (34:58.254)

Well, at Wayfair, actually, I mean, part of the thing that emboldened me to try the B2B thing was actually like a failure from before. So when we had all these microsites, we were trying to figure out like new categories to enter. And I had the brilli... We tended to be good at things that were a little bit less well distributed, that were big and bulky. And so I was like, oh, the perfect thing is obviously caskets. And so we got... I convinced the company to go into caskets. And I don't forget what the website was called, CSNDeath or something like that. I don't know.

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And so we stood it up and actually like we did a pretty good job Executing it. I think I feel like if it wasn't for the brand police at Wayfair like oh well caskets are off brand for Wayfair It's like I maybe they are But I feel like we maybe could have made it made it work but anyway, it was basically a complete disaster and We sold virtually none of them But the view was that we did a good job. We got into it for the right reasons We actually executed the plan well, but it didn't, it didn't work and so like nothing happened. Every, I was the butt of jokes for years and still am as a part of that, but effectively it was, you know, it was, hey, like, you know, good job trying and like, let's try something else.

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Tom Finn (36:10.258)

Well, and now that we know that the brand police got you, it really, uh, had nothing to do with your execution or strategy. It was mostly the brand police, but I bet you learned that you have to think about that. You have to think about the overarching brand of the organization. How does this tie in? How is this going to map for our customers? Is it going to speak to the market the right way? Lots of different businesses we can be in, but it's just got to be on brand and on target. Yeah. I love it, man. I love what you've done in your career. It sounds like you have really taken every step of your journey and been really thoughtful about what moves you wanted to make. And I think that's an example to all of us that you can bob and weave and have some starts and stops, but just always be thoughtful about the direction you're going, how you're treating people, how you're looking at these experiences from a learning standpoint. And it sounds like you've done that. So congratulations, Joel, on all of your success through organizations and then of course your great success at Yesware and the sale of the organization a year ago or so, congratulations my friend.

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Joel (37:15.622)

Yeah, thank you.

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Tom Finn (37:18.52)

Joel, if somebody wanted to get to know you, reach out to you, come work for you, where could they hunt you down and find you?

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Joel (37:26.234)

Yeah, I mean, best place is probably LinkedIn at this point, I'd say. You can find me, I think it's Joel Stevenson, GM is the tag at the end. You can, you know, we do a lot of work at Yesware that I think is helpful to folks that want to understand sales. So we've got a great, we've been putting out content for years, which you find at Yesware.com forward slash blog. And then I've got a… A podcast that we've been doing for a while in sales topics called the hard sell which you can find it Yes, we're.com forward slash podcast or the normal the normal places. So those are a few places

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Tom Finn (38:06.094)

A few places to hunt you down. We'll put that all in the show notes, my friend. Thank you so much for the work that you do and appreciate you being on the show with us here at Talent Empowerment.

Tom Finn
Podcaster & Co-Founder

Tom Finn (he/him) is an InsurTech strategist, host of the Talent Empowerment podcast, and co-founder and CEO of an inclusive people development platform.

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