Dave Boyce: Do We Still Need Salespeople?

Welcome to Go to Market, a podcast for RevOps, sales, and marketing leaders to dive deep into industry insights and best practices. Go to Market is sponsored by Fulcast, the go-to-market cloud. My name is Amy Cook, and I am so excited to introduce Dave Boyce, Executive Chairman and EVP of Product at Winning by Design. Dave, thank you so much for joining us.

Amy, it's so exciting to be together on a Friday morning. Let's, let's get to it.

You know, Friday mornings are my favorite to host podcasts because we're all just a little bit more relaxed, right? And we can just have great conversations and talk about things that matter. And anyway, really appreciate you joining me today.

Fantastic.

Yeah. So tell me a little bit about yourself and about what you do at Winning by Design. Okay.

Well, myself, I'm a kind of serial entrepreneur, kind of just naturally curious person. Every time something starts to go right, it seems like I move on to the next thing. I mean, I'm old now, but you know, we've, we've built and sold 5 SaaS companies and some of them for better outcomes than others, but every single one has stories and battle scars and amazing, like, just amazing. I just feel super lucky to have been part of that since the early 2000s. And now winning by design, which is an advisory firm, a growth advisory firm, we work with those mostly scale-up companies, kind of $50 million to $2 billion on those challenges of growth. Like, how do you, you know, you're gonna go through several transformations as you try to get from 0 to 10 and then 10 to 50 and then 50 to 100 and each, you know, and you don't want those transformations to catch you by surprise. You want to be able to see around corners. You want to build infrastructure for it, for your kind of RevOps and go-to-market perspective. Like you never want your RevOps team to be like, oops, now we got to do, gosh, we didn't know that. No, I want to be anticipating that I got to put that in place and that I don't do it too early because I'm wasting time and money. But I don't do it too late because it's going to slow me down, kind of the operational debt of not having addressed that, you know, in advance is going to slow my growth down. So, that's where Winning by Design lives, and my job is indeed around product, like figuring out how to package that, make it easy to consume, make, you know, how much of that is digital, how much of that is advisory, how much of that is hands-on work, how much of that do we do with partners, et cetera.

Wow, that's amazing. So, you really do come in with all of your experience, and by the way, 5 SaaS companies, that is absolutely incredible. It's a record from anyone that I've interviewed on here so far.

I might be record for oldest too. So there you go.

Well, I'm very, very impressed. And it— how awesome that you're now using all of that experience, that hard-won experience, the battle scars to help other people. I think that's amazing. That's one of the reasons we started Fulcast was because we had experienced revenue pain ourselves and learned a few things and wanted to be able to serve the community. In the same way, only through product rather than services.

Love it.

I love it. I have so many questions for you on our own go-to-market. So that's for another time.

Rock on.

But tell me a little bit more about something that you mentioned as we were chatting in our pre-call about automation. So on one side, you know, you and I are both Gen Xers. We know what it's like to have manual teams. We know what it's like before— well, I remember getting my first computer with a blue screen with 64 kilobytes, and we thought that was the coolest thing that was ever done. And now, you know, where we are in technology now is just absolutely amazing. And so I— we both know what it's like to have teams that are just run manually, and we both know from being in the industry the gains and also some of the drawbacks that can come from automating that work. So, I kind of want to dive deep into that and get your thoughts on, you know, what are the pros, what are the cons, is it inevitable? Tell me what your thoughts are.

Yeah, well, you know, from a, you know, from a company standpoint, we're selling services or products to our customers and an automation standpoint, you know, you talked about, and we started off with the Commodore 64, amazing. But, you know, at the time we're using like, This word still exists. I don't think anyone really knows what it means, but we're using like a Rolodex, which is literally like cards that flip on rings on your desk to keep track of like—

I had that. I used to write all my friends down on my Rolodex and like, there you go.

We go from a Rolodex, then we have, then we start to have like these spreadsheety looking things like Goldmine and ACT. These, like, I don't know if you remember this, but you bought it in software in a box and you installed it on your Commodore 64. It was a little later than that actually, and then you kind of then you had an electronic way to manage your kind of your prospects. And then we, and then we went to, and then we went to Siebel. Amazing. And then we went to, and then we got everything kind of out of Siebel and into the cloud with Salesforce. And then we've got, you know, the option of HubSpot. Okay, cool. So that's like helping me keep track of the stuff that I'm doing. But then we add further automation with things like Outreach and SalesLoft for kind of managing outbound cadences. We met HubSpot introduces kind of automation around kind of managing inbound marketing. Amazing. So our life's just getting easier and easier. And now AI is helping me literally automatically generate content, automatically create microsites, automatically process inbound demand, and in some cases, you know, take entire tasks on that I used to do. Sometimes customer-facing, like you can literally have a conversation with a robot about a purchase. Sometimes kind of back office, but the more interesting— so we should talk about all of that, like how much of that's gonna get automated, what are the limits, like, you know, what are the benefits of it? But more interesting to me is just flipping it and saying, well, what does that mean for the buyer? Like, is this good for the buyer? Is this a trend that driven by economics of the seller or convenience of the buyer? And when we flip it, then it's more called self-service. Versus automation.

That's right. So I love the way that you're going with this. And just to kind of like recap the way that I'm— I think that you're positioning this is, you know, at first we're using technology to help store information that we can't in our brains, right? Like we're putting things in CRM, whether it's a little spreadsheety thing. I don't remember that actually. So that I gotta go back and remember that. And then, you know, and then into Salesforce, which we all use, and HubSpot, and then, and And then I think there was a big shift because I come from a marketing background where, where all of a sudden marketing pretends that it's a one-to-one relationship, but it's really not because you're automating it away.

So like Eloqua, Marketo, stuff like that?

Yes. So, you know, you have your personalization tags, you have your cadences, you have— then there's a huge blowback in the industry. Yeah, every bit. And, and I really believe in many ways marketing did itself a disservice by trying— by— because it was inauthentic. Yeah, it was trying to pretend that it's a one-on-one relationship when it's really not. Yeah, right. So now, so now the automation I think went too far in some ways. And then the market now is saying, no, let's go, let's go to a real person event where I can actually talk to somebody face to face and know that we're real people. But in other ways, the automation is so much greater. And one thing that I've noticed is that the shift is that level of authenticity is back. And HubSpot works great for newsletters when everybody knows it's a mass email, right?

When you're not pretending.

We're not pretending. But a lot of— if you've noticed, but there is just an absolute chasm of It where all of the automated prospecting emails that BDRs have been using are going somewhere into cyberspace. And the only way that BDRs can get through right now is highly personalized, real person messages, because the industry is totally sick of the inauthenticity.

Totally. And by industry, that includes you, that includes me. Like we all have figured out how to spot what those things are. We We don't take calls from unknown numbers. We don't like unsolicited texts. We, we, we can tell the markers of a mass kind of mass customized email coming out of one of those spam engines. And so, yeah, we just, we've figured out how to tune it all out.

That's right. And so what I want to explore with you is now, now that we figured it out, what's good automation? And what's bad automation, and how are we flipping this to reposition as self-service? Because to me, the automation to self-service is an authenticity play where we're like, you're right, you're right, you're right, it is automated, but you love it, right?

So, you know, I, um, I know you were going to bring this up, but I'll bring it up now because it's really relevant. I'm publishing a book on this exact topic. And it, you know, it's called Freemium and it's about how companies selling B2B software, like that's normally boring. So, we just talked about, sorry, Salesforce and HubSpot, we just talked, and Eloqua and Marketo, we just talked about a bunch of platforms, B2B platforms that are basically boring. Like they're not, they're not kind of well-beloved kind of consumer brands. They're just boring stuff that help businesses get stuff done. But a lot of B2B software companies in, in the 20-teens built freemium models by giving functionality away. So think about Dropbox, Zoom, Canva, DocuSign, Twilio. These are companies that had real value to add, and then they gave it away and they didn't have a salesperson involved. And once you do that, You don't have a salesperson involved. You have to think more about your customer than you're thinking about yourself. You're not forcing anybody. You're not talking anyone into anything. You're literally saying, oh, you have a problem you want to solve? Cool, take this. And then they either pick it up or they don't. And if they don't, it's because it doesn't— you haven't communicated the value well or it's not solving a real problem. And so you got to make some changes. But everything starts with empathy for that end customer. Like, what does she need? How is she making progress in her life? And how could this help her? Otherwise, she's not going to pick it up. And if she does pick it up, she's not going to use it. And if she uses it and doesn't get to first impact quickly, she's going to abandon it. So these freemium models really were forced to meet the customer on her own terms and really kind of enable what we're calling self— you know, it started as freemium, then it went to self-service, then we called it product-led growth. Now we're calling it Now, and now there's AI helping us with that. But you flip it and you think about in my customer's life and how she makes progress against the things she's trying to accomplish, how could I be helpful? How can I develop maximum empathy and maximum generosity to get that wheel turning? And now, like, I can build billion-dollar companies based on that.

I love that so much because, you know, being customer obsessed, that's a kind of a catchphrase, right? Sure. Customer obsessed, but you've explained so well why we need to be that way from an economic standpoint as a business, right? But why do you think we went to the PLG motion in the first place? Why did we do a freemium model?

Well, it gives you— there's a couple of things. Love that question. I moved, you know, I moved from Boston to Silicon Valley. We had a company that we started in Boston and we were, and we needed kind of high velocity kind of social distribution. This is in 20— 2010-ish, plus or minus 2010. So Facebook has been around for a couple of years. We're using social network to spread kind of our software. We couldn't afford, I mean, it's a little bit of necessity. We personally couldn't afford to invest a salesperson in every single conversation with a potential new customer. We just couldn't afford it. So we had, and if you go back and study Atlassian, which is now a $54 billion public company, Same thing, two developers in Australia, they're trying to build Jira, which everybody uses now for managing their development teams. They couldn't afford salespeople, so they just had to figure out how to make it easy. And once you flip that, dot-com had happened right before that where, you know, where it was all about kind of getting people, getting and keeping people's attention. But now it's getting and keeping people's usage, which is another form of attention, but usage of a product. With no salespeople, with no coercion, with no conversations, with no talking anybody into anything and letting everybody be a tenant at will. So I think we went there because it would open up a way broader market for us. Now we can go— now you can sell to a schoolteacher. Now you can sell to a department. When I've shown up in Silicon Valley, one of our board members said, hey, I think he was talking about Zendesk. He said, people are building software now that a manager can adopt by swiping a credit card. So if it's under the expense level and you can get a manager to solve problems on our own team without you having to get all the approvals, you can just run faster. And yeah, so that's how I experienced it.

I, I love that. I think that, that makes a lot of sense. You know, necessity is the mother of invention, right? So, like that Atlassian story just like set my mind going in 10 different directions. Like that is so innovative, so interesting. And, and it's just, you know, over and over and over companies are showing how PLG-led motions are leading to like amazing outcomes. So do you think that we need salespeople anymore?

Ah, good question. You know, I need to figure out how to pronounce this guy's name. I hack it every time. I need to just like go ask Claude how you say it, but Will Guardia, I think he's an author. He wrote a book called Unreasonable Hospitality.

I have it on my desktop.

You have it on your desk. Yeah. You know it. Yeah. You know, and you know, I think his background is mostly, you know, restaurants and hotels and how do you create kind of that special, unreasonable moment that people will never forget. But he's got a quote in there about that I think tells you how you could afford— I mean, I can't afford to be unreasonably hospitable. He tells a story about a couple celebrating their anniversary at a restaurant. A server overhears it, and at the end of their dinner, they present that couple with a photo album of all their memories from that evening having been surreptitiously taken during the dinner by people in the restaurant. So they hand them the photo album. Happy anniversary. That you can't afford to do that for every experience. So what he says is automate the predictable so you can humanize the exceptional. So when you say, do we still need humans? Yeah, of course we need humans. Like, You know, you can't have robots build personal relationships. You can't have robots, you know, manage kind of multi-stakeholder, big kind of multimillion-dollar decisions. You can't— I mean, maybe we will at some point, but right now we don't. You can't have robots kind of channeling empathy and helping instill courage in people who are deciding whether to go forward on some big transformation effort. But you don't need— so you need humans for all those things, but you don't need humans to process an order, to kind of write the paperwork for a renewal, to teach me how to use the basic features of a product. And yet we still, to your point, we used to schedule a training call every time someone bought a new product and then would walk them through the exact same script. And that can all be automated now.

Interesting. So what about all of the people who have had those jobs? What about all the people who have been the ones doing kind of the manual labor? What do we do?

You know, I'm a perpetual optimist, but I think that is a very tricky problem, Amy. Like, it really is. Like, I've got kids entering the workforce. You know, in some cases they're super lucky. Like, my youngest kid is literally working as a prompt engineer. He's literally building and training digital employees. He's 18 years old and he's got a job at an AI company where he's training the digital employees that are doing the job that an entry-level employee would have done in the past. Okay, cool. So Davey's super lucky. But what about, you know, what if you're not that lucky? What if you, what if you, you know, you don't know how to train a digital employee, you don't know how to be a prompt engineer, and so now you're just getting your job replaced. In the, in the late 19th century, just, you know, this happened with switchboard operators. Like, you know, we were starting to automate all the switchboard, I think early 20th century, trying to automate all the switchboard operators and all of these entry-level and a lot of, it was a job that was considered like a job for women. They were now kind of flushed out of the workforce 'cause you couldn't be a switchboard operator anymore. So now what happens? Did we figure it out? Of course we figured it out. Like we figured out the women are actually capable of way more than switchboard operating and they—

thank goodness for that.

And we, that was a temporary maladjustment and then we all figured out what to do. So my perpetual optimist brain thinks we're going to figure it out. Like we're going to figure out how to be, operate the machines rather than be the machines. But I think a lot of creativity is required there because entry-level employees indeed are not going to be doing the same things that we did in the past.

I was literally just going to say that I'm not worried about the seasoned professionals who can use the who, who can take AI. I'll just give you an example. Yesterday, in 5 minutes, I created a really pretty decent press release just using ChatGPT. It would have taken an entry-level person about 4 hours to do. And now I can just take it and, and, and I can make it better and enhance it.

Totally.

Entry-level people need the reps. And so, and our kids need the reps. And so I'm like, that is going to be tricky, but I love your switchboard operator analogy because it is, it's true. We're, we're gonna figure it out. It's just another level, it's another transformation. It's another way that we're going to move society forward. So my last question for you, Dave, well, I have two. My first question is, what do you do to stay at the top of your game? Clearly are, are just, this is one of my favorite interviews I've ever done. I just think that you were just absolutely phenomenal. So interesting to talk with. So how do you stay at the top? And my second question is, how do we buy your book?

Oh, we'll just— first, it's super easy. Anywhere you buy books, Target, Amazon, Barnes Noble. If you're in the UK, Waterstones. It— I was really lucky to get picked up by Stanford University Press, and they've run all of that for me. Like, so you can kind of get it anywhere. You can order it now. It ships on the 26th of August. I don't know when this will air, but maybe it's already shipped by the time you hear this. Amazing. See? Just make it easy. Just order the book. Top of my game. I don't know, Amy, like I, here's what I don't do. I do not dream about retiring. I just don't think that's interesting. Like I do not try to, I don't optimize for leisure. I know that sometimes, sometimes I get my, uh, sometimes Lisa, my wife, doesn't love how hard I run, but I'm like, I just don't. She's actually the same way. I could say the same thing right back to her. She doesn't think about relaxing either, but I'm not optimizing for time on the golf course. I'm not optimizing for time surfing. I'll do that. Like last week we were in Mexico for a week and I surfed like every day. Amazing. But I'm not like trying to maximize the amount of my life I can do that. I'm really actually trying to stay curious. So I read, I listen to a lot of books, I travel, I took on the challenge of writing a book, which, you know, you wouldn't have to do at— guess I was 54 when I started. You wouldn't have to do that. I was up at 4:30 in the morning writing from 4:30 to like 9:30 before anyone noticed that, you know, I wasn't around. And I did that for like months on end. So just staying in the game, like, that's it. Just staying, staying curious, pushing yourself into, you know, out of your comfort zone, taking on new things. And I am really, I guess I'm a little nervous about the day when I stop doing that, cuz I don't like the idea of atrophy of any kind, physical or mental. And I know I'm gonna be fighting it, but I'm gonna fight it hard.

I love that. Thank you so much for being such a great example of what to do and how to have a wonderful career and how to be at the, at your peak. So I really appreciate you coming onto the show today. Thank you so much. And it is an absolute pleasure to meet you.

Thank you, Amy Cook. Amazing. Be amazing.

Business, yes, that's business.

Business, yes, that's business.