The First Guy to Lose to Salesforce (And What He Did Next) with Kris Lawson

[music] >> Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between. We guess who I truly respect and I think make a positive impact on the world around us.

Now, full disclosure on this one, Chris Lawson is the founder and CEO of Ruby at hey.ruby.ai, and I sit on their board of advisors. So, Chris and I do work together. That said, this conversation went way [music] beyond Ruby.

Chris was one of the first of four employees at Salesforce Canada, where he helped scale that office from four to over 800 people. He was the first hire at Snowflake Canada and took it from zero to 35 million in ARR and was there for the IPO. And he's got a co-funded investor syndicate called Snow Angels, backing data and AI startups. And he's the father of four, including spontaneous identical triplets, which we absolutely got to do this conversation.

So, as always, we start with the origin story, and he talks about how he was selling newspaper subscriptions at 12 years old, uh, raking in about 500 bucks in tips, and that's really where he got the [music] real uh hook for sales. And then landing, actually landed a $250,000 national contract for sign letters at at Cineplex Odeon at 17 years old. So, I can't imagine what the commission check on that one would have been. But, at 17, are you kidding me?

Now, he was also the first person at Oracle to ever lose a deal to Salesforce, and it was [music] absolute like shock because, who is this company? What's going on? So, he got asked to do a competitive intel presentation for 150 field reps. And then he got cold-called by a Salesforce headhunter two weeks later and joined Salesforce Canada.

And then we got into spontaneous identical triplets. Like, are you kidding me? He had this, he went to the doctor, and you know, they had one kid [music] and they were expecting another, they thought. They just wanted two. And the doctor was like, "Uh, you got three in there, and they're identical." And he got out, obviously, in shock. There was like this Tears for Fears moment in the car that really just uh solidified where they were at this point, but, you know, obviously changed his life forever in all the right ways. Moved the family out so they could have a little bit more of a room and around his uh parents and stuff. So, that was a real life changer, but all the blessings all the way. [music]

And then he talked about, you know, then we got back into business and talked about this build or buy fallacy right now that's going on with AI, 'cause every idiot now can like me uh can develop apps and they think it's a lot easier than it actually is. So, you know, he's, what he's building with Ruby is this ecosystem for sales professionals to have access to every piece of information they need to sell more effectively. So, this is kind of one of those questions that I have a lot, which is, "Hey man, I could probably build the vast majority of this just in Cloud, but why would I now, you know, go purchase [music] it?" And I think that's a huge objection that most reps are, I don't think, I know that's a huge objection most reps are faced with right now.

And the one question that came up at towards the end, which I was really curious about and I wasn't planning on asking, was what AI does to all these sales methodologies. [music] You know, Sandler, Miller Heiman, MEDDIC, you know, Challenger, all these ones. And I've, I've never been a methodology guy. I've always tried to take the best of all worlds [music] and I think AI now is is the best of it because it can pull the best of all worlds and you can create your own sales methodology. So, we got into all this stuff and a lot more. I hope you enjoy the conversation as much as I did. Let's make it happen.

Chris Lawson, welcome to the Make It Happen Monday podcast, my friend. How are you today?

I'm great, John. Thanks for, thanks for having me. I've been looking forward to this for a long time and listening for a long time. You're, you're a legend, man. I'm, I'm glad to spend some time with you.

Thank you. Yeah, I think I've just been around the block for a little while and people getting familiarity, I think, is a good thing. So, I don't know about legend, but I appreciate it, man. Um, I'm looking forward to this 'cause we, we are going to talk, you know, a lot about what you're, you know, what's going on right now, specifically from the buyer perspective, um, and it touches on something that I've been screaming about, right? All these AI tools and everybody's scared about automating sales reps, and that's not what I'm worried about. I'm worried about when the client wakes up and realizes that they don't need us. So, we're going to get into that. But as always, all these shows that I start, I always love starting with the kind of your origin story, my friend. Like, what made Chris, Chris? And and, you know, parents' influence, all that fun stuff. I know you were selling pretty much since you came out. So, you know, where did that bug come from and and how did it evolve? And then we'll get into kind of the decisions you made for school and and everything else along the way.

Sure. [snorts] Yeah, definitely. So, uh, well, first of all, I'm a nice friendly Canadian. So, born in London, Ontario, Canada. Um, and I grew up in a pretty middle-class family where we had enough to be comfortable, but not enough to go beyond, uh, you know, more than like a, a trip a year. And I didn't really, I didn't go on my first airplane until I was 12, and I didn't again until I was, um, 19 and paying for it myself. So, I always wanted to to to kind of get out there and kind of do more with with, uh, my life and, um, had a, a really early inkling of of of selling and like being, having kind of a, a natural, um, interest in in working with people, um, but also, you know, natural interest in in getting people to agree with me.

>> [laughter] >> And so, I kind of, kind of followed on this path, right? And I realized early, even in selling, um, like newspaper subscriptions, which was my, uh, first sales job, that if I was personable and I had great, great, uh, conversation skills and so on, I would get this $20 tip at Christmas. There you go. You know, when you're 12 years old and this is, you know, a long time ago, and you're 12 years old and you're raking in, uh, $500 in Christmas tips, uh, selling newspaper, you're like, "Oh, this, this whole sales thing is..."

Yeah, you're rich. You're loaded, dude. This whole sales thing is really interesting. So, over time, I started to do, uh, more selling. Uh, sold door hinges. So, I, I, I basically worked at the desk, uh, man at selling door hinges and, uh, sliders and things like that to contractors, uh, at a company for, for a year. Um, I was a, I was a field rep. Get this, I was a field rep at 17 because someone I knew in my network thought that I could sell sign letters. He's like, "I'm going to give you a cell phone." Nobody had a cell phone back in 19, uh, '97. Like, I had got a cell phone before any of my friends. And he said, "I'm going to give you a cell phone. I screen print sign letters. I want you to go and sell sign letters all over Ontario." And so, I basically in the summer just drove around in my 1986 Toyota Supra with the, the targa roof off, right? And I would drive around. I would go to these sign, sign companies. And I realized, I'm like, "Who buys the most sign letters?" And it's like movie chains. I'm movie chain, right? They have, at the time, like they have these obviously signs putting up new sign letters about movies that are happening. And I'm like, "I'm going to go to Cineplex Odeon, uh, which is the largest movie chain in, in Canada. And I want to go get their sign, sign letter business." And so, I got a meeting, um, at, uh, at 17. Got into there, brought my, brought my boss, the owner of the company. When we won the contract for sign letters for the national theater chain of, of, uh, of theaters in, in Canada. It was crazy. It was like, uh, it was like a $250,000 contract, and I was 17.

>> Holy smokes. Yeah, so that's, that's where I'm like, "Okay, sales, good to go." You know, did some other stuff like Gatorade and Snapple and merchandising, but when I got, by the time I got to university, I was like, "Okay, I, I think, I think this is what I want to do for sure."

Love that. And you, you got a, so you got a BA in economics at, it was at, no, where did you go? Sorry.

Laurier. Yeah, there's a great, yeah, great business school in Canada at Wilfrid Laurier University. Yes.

And what was the, like, what was, what did they teach you there? 'Cause I, like, I'm, I'm struggling with college these days and and I've never been kind of an undergrad fan because I think it's a social education, not an actual education. But were there things that you pulled from your experience at that college that that still stick with you today, or was it kind of your typical, 'cause I have a similar upbringing as you, like, kind of middle class, those type of things. Love sales, got into it. Kind of got through college just because, right? And I, I don't know if I, probably things that I look back on college and say, "Okay, foundationally, maybe some of those things made a difference." Learning how to learn, that type. But I think it was a lot more of the EQ stuff of me going out, meeting friends, engaging, you know, fraternity stuff. So, what was your kind of, what was the value of college for you?

So, I think there's two parts to this. So, so one is like the, the typical learning, right? The, I, I did a business degree, which is a pretty, pretty generalist type role. So, you, you've got, you learn marketing, you learn organizational behavior, you learn, uh, finance, all these types of things. Uh, no sales course, as in post-secondary, right? We've talked about this before, I think, in, in the few conversations we've had. It's like, there's no, there's no formal sales training, um, that you get in university. I knew I wanted to be in sales, so I kind of picked other courses that would round me out from a, from a sales perspective. So, psychology. So, I minored in psychology. Um, understanding cognitive psychology and how to deliver messages that actually stick with people, so that, that you're appealing to the human brain and how they learn. Um, and then of course, like social psychology and persuasive psychology. Cialdini, I think, is his name. The, the guy who wrote it. Robert Cialdini.

I've recommended Robert Cialdini, probably 50 times in my career.

Oh, you got it? Yeah. Yeah, that's right. Exactly. Yeah, talk about door in the face, facing the door. Um, love that, love that book. I think it's a, it's foundational to, to what we do in the sport that we, we were in. So, that learning was big. But the reason why I picked Laurier and I wanted to go to this school was because of the co-op program. So, they actually had a, a co-op program, um, where you would get placed into businesses and work within those businesses. And I think it is, I, I look at that with my kids. I, I have, I have, uh, four teenagers that are going to be going to school down the road, and I'm looking at co-ops and saying, "How can these people, how can, like, these people, how can my kids get on-the-ground training?" It was crazy though, John, I got to say, 'cause I, I experienced one of the most interesting, uh, co-op terms, I think, of, of, of anyone. Um, I was, uh, I became, I was in a sales, they created a sales position. So, I interviewed with this company called Picstream. They, they created a sales position. They said, "I think we could should put this kid in sales, uh, and we're going to just make this position happen. Work there for the summer." And this was, we were selling, um, telecom equipment that allowed you to compress video feeds and put video feeds over twisted pair, like telephone, uh, lines, so that a telephone company could become a cable provider, right? That was like, that was the, the confluence at the time of, of those services. And at the end of the co-op term, they got bought by Cisco. For, was it 300 million or something like that?

>> dollars. 300 million dollars. And 300 million in, in, uh, in 2000 was obviously like a significant amount of money. And I saw these, these, these three guys, um, uh, Brad, Mark, and, and, and Ed, they, they had started this company three years earlier, and they just pocketed 30 million dollars. I was like, "Oh man, tech is the place to be. Tech is the place to be."

Okay. But then the other part of that story, which is funny, is though, so I go back to school for four months, and then I go back to Cisco, right? I go back to Cisco because now I'm working for Cisco. My previous company had been acquired by them. And at the, that the end of that term, uh, on the last day of my work term, they fired everybody. They brought 250 people into a room and they said, "I'm sorry. The internet bubble has crashed. You are in more of an exploratory, uh, technology. We want to focus on routers." And I saw 250 people get fired. And so, I saw, in, in, in, in university, before my third year, I saw the highs and the lows of the tech industry, like, right, visceral, in front of me. And I think those are, like, you know, from a college perspective, like, you can't get experience like that, um, without, without finding co-op positions. I think over that, and it's just an, it was a bizarre situation, but I took so much from it.

That's amazing. That's, I mean, that's an education all in and of itself, right? That's worth the price of admission for college to that experience and be on that ride up and down. Phew.

Yeah, 'cause I, I remember, you know, I had something similar when Xerox. I, I think the one wake-up call for me was when I worked at Xerox and I got, and it was right in, it was like 2000, you know, '99 and the boom, you know, whatever. And then all of a sudden I got in and like Xerox's stock was like 120,000 or $120, right? And then then all of a sudden the market started to crash and then went down to 60 and people like, "Oh my god, it's never been this low. You should buy. You should buy." And I'm like, "I don't know about that." Uh, you know, 30. And then and I watched people who were lifetime Xerox people who had had all of their money, their 401k, all of it in this, and it, I watched like people who were about to retire look at everything evaporate 'cause it went from 120 to 60 to 30 to 15. And it, and then, you know, obviously it rebound, rebounded after that. But I was like, these people were decimated. And so, that to me was like a corporate wake-up call, like, wait, okay, I can't put all my eggs in one basket and and, you know, whatever. But that was kind of the, the early learning lesson for me. But nothing like rocket ship sale, you know, fired 200 people. So, that's fantastic, man.

'Cause then after that, you went to Oracle, Salesforce, Micro, I mean, your, your resume here is pretty impressive with all the different logos here. But Oracle was the first one, right? Is that, was that the first job out of college?

Yeah, the guy, the guy at Picstream who I, I admired the most, he's a, a sales leader named Bill Jaycox. He was amazing. He was my, he was my coach there. Um, and I said, "I'm, I'm going into sales. What should I do?" And he's like, "Just follow the margin, right? The more margin a company makes, the more likely they're going to pay you higher commissions, so because they're making more profit." And he's like, "The, the best margin is in software and make sure it's direct. Don't sell for, for reseller." And so, um, I found this opportunity at, I was like, "Okay, well, Oracle, like, that checks all the boxes." And I was hired at Oracle for, uh, what they call the BDCs, outbound BDR, cold calling there. That was the, the first job that I had. And fun fact, like, they were actually looking, it was the first BDR organization they ever built for business applications. So, this was ERP and CRM outbound, not database. Yep. And they were like, "We need to hire MBAs. We need to hire people that have, uh, deep business understanding and can talk to CFOs because we want to sell Oracle financials." And they hired me, like, 22 out of school. Yep. And again, this comes back to like, I'm so adamant about the co-op experience and like, Yep.

Finding schools that have that co-op experience because I, I came out fully baked with, uh, experience that they were like, "Oh, cool, we could, we could put this kid on the team." And I was, um, you know, 22, working with like 30, 35-year-olds and and just hitting the phones and getting that amazing sales academy that is, uh, Oracle.

Oh, yeah. Yeah. Getting that. That's why I always tell kids coming out of college, I'm like, "If you don't know what you want to do, just get a, get a logo, you know, go work for a logo." Um, and the reason for two reasons, usually they have a training, you know, and and you go through the process. But also, when you go look for your next job, like, you're not explaining what that company was. Like, "Oh, Oracle, [clears throat] great. Check box." But if you work for some small-ass startup that nobody knows, you spend half the interview telling, you know, explaining what the company did and what the, you know, whereas like, "Oh, like I got, I got lucky. I was DeWalt's, you know, and Xerox." And so, everybody knows what both of those. And I had Xerox be like, "Oh my god, the 8-week sales training." Right? So.

But then you, you, I think you noticed that you were starting to, like, there's this little company, Salesforce, that was starting to eat your lunch here. And this little SaaS thing was, was starting to fly. And I, there was something in here that I was reading that you, let's see what you, competitive intel presentation you put together. Because it seemed like you were, did you put together a competitive intel for, did you say, like, "All right, you know what? Oracle's kind of like, I got to go with my risk profile. I got to go with the Salesforce 'cause I'm seeing them all over the place." Walk me through that transition, 'cause in, in how you did your kind of business plan, if you will, or competitive analysis.

Yeah, so I'm, uh, so I did the BDC role, right? The outbound BDR. And then they moved me to inside sales. So, I was actually running my own, my own deals. Um, and I'm the first guy, I was the first guy at Oracle to lose to salesforce.com. First guy ever.

>> No way. Oh [ __ ] That's an interesting distinction. I like that. I like it.

>> Yeah, ever. I was, I was the first. I was the first guy. And, um, my bosses were like, "Who is this company? Like, well, well, what, what is this company? How did they possibly steal CRM business from us?" And they said, "You got to go investigate them. Go, go find out everything about them." And then we're going to actually ask you to do a presentation for 150 field reps, uh, in Boston, like, you know, two weeks from now. And so, I just, obviously, uh, young guy, I'm, it's, it's a huge career opportunity for me to tell the story. Yeah. Do a deep dive into S1. Deep dive into all the stuff. They just recently gone public. And I'm like, "Whoa, this company is like solving all the problems that our customers, um, throw at us." Right? Like, every, every barrier to saying yes, they, these, these guys have, have solved it. And so, I did the presentation and so on. And then, um, ironically, like two weeks after I do this presentation, I get a cold call from a headhunter and they're like, "Hey, uh, ever heard of this company Salesforce? We're opening up our first, uh, remote office. We're going to put it in Toronto. Um, is this something you'd be interested in?" And I had to be real, I still had to be talked into it, right? I still, the Michael Basch, who hired me at, at Salesforce, amazing leader. Um, Michael, Michael and I had, he, he and I had probably three, four conversations and, and I, thank you, Michael, for continuing to, to, to chase me when I was probably a naive, uh, youngster. But he got, he, he said, "Hey, you got to, you got to get over here." And I, I agreed, moved over. And, um, and then I just started to see the cloud happen, right? So, I think that is a bit of a lesson learned, I, in terms of career development, is like, you should take the call, right? You, people, people get headhunted. You should take the call. You should do your due diligence. Um, and you should have an open mind when these, these opportunities come by because they could be special companies like that. Um, not all companies are special, but you got to, you got to talk to them and see which at-bats, uh, you're willing to take.

Well, and that's interesting, so, 'cause you seem to have a, a lens for like, "Ooh, good opportunity." And, and I've always said for me, you know, I'm a, I'm definitely an opportunist, right? I don't overthink things. I, I usually with two or three pieces of data, I can be like, "Mm, you know what? That makes sense. [ __ ] it. Let's go." Right? I had a similar thing with Salesforce where I worked for Basch, you know, right? We were training. And, you know, 2000, it was, it was a 2007, right? When things were, and Salesforce was Salesforce, but they weren't [ __ ] Salesforce, right?

>> Yeah. And we had, we had been training Oracle, uh, you know, SAP, Gartner, Forrester. Like, the logo list of Basch was off the charts. But, you know, and then it went belly up and the, you know, fired everybody. And, and it was me and two other trainers. And I vividly remember sitting in the, the boardroom with the founder 'cause I went to the founder. I said, "What are you going to do? All the training?" Like, 'cause he fired everybody and he was just going all in on software. And he's like, "I don't know. What do you think I should do?" And I was like, "Shit. Uh, what if I started a company and delivered on all that stuff and then paid you a res?" He was like, "Yes, do it. Make it happen." So, I was like, "Holy [ __ ] Who's coming with me, right?" And, and I had, like, there's two other of the trainers. It was the three of us. And we put all the logos up on the whiteboard. And we debated on who was getting what, right? And they were fighting over SAP and this type of thing. And I pretended like I gave a [ __ ] about any of those companies. I'm like, "Oh, I've trained SAP. I should." But I only cared about Salesforce 'cause I knew that they were a rocket ship. And even, [clears throat] in this economy that was getting murdered at the time, I'm like, "There's something. There's something about this company." And I knew if I got them as my key marquee client and over-serviced them, then the rest of the SaaS industry would be like shooting fish in a barrel. And I just had that, at, you know, whatever, 25 years old, that lens of, "That makes sense." What are, what do you think your lens is that helps you make pick these winners, if you will, um, from, you know, pretty stable, right? 'Cause there's a risk profile of a lot of people that's like, "Why the [ __ ] would you leave Oracle, man? You only lost a deal or two. Like, that's a huge company, big commissions if you score big, but [ __ ] Salesforce." And then you kept picking winners as you went. So, is there, do you have a, a specific lens that you look through when you look at opportunities?

Yeah. So, there's a few things that that I look at. Um, one is just the, the, the market opportunity itself. So, TAM, right? So, if you go into a company that has a large, uh, TAM, lots of selling, um, kind of infra, uh, space, uh, what I want to say, selling, selling area, right? There's a lot of selling area that you can go after when there's a large TAM. Um, if the company has the ability to expand the TAM as well, so they're getting into more potential selling areas, uh, that, that's interesting. And of course, if, if that TAM is growing. So, like chasing the market is, is ultimately the first part of, like, where is this market going? Um, like when I joined, uh, Snowflake, the market was moving all of their data into the cloud, and that space was, was moving very, very quickly, and, and Snowflake was grabbing onto different parts of the TAM. Same thing with Salesforce at the time, right? They were going into Service Cloud, they were going into Marketing Cloud, and they were growing. So, looking at the TAM, I think it's really, really important. Um, the next thing you look at is, is really like, nice-to-have versus must-have technology. Um, and it's got to be really, really, really, really nice-to-have to make it a must-have technology. But if you really want to find, like, safety, um, then, then it is finding the must-have technology. So, like, you can't run a business without a database. Somebody's going to buy something, right? Even when we were at, uh, Salesforce back in the day, it, CRM still wasn't, wasn't a must-have technology, but now it is, right? And, and it kind of developed over time. So, I think leaning into to must-have technology or at least nice-to-have technology that has irrefutable ROI is, is a great place to be. Okay. Um, another thing I, I look at, too, especially when you look at smaller opportunities, like, uh, like startup opportunities, is do you have a partner ecosystem around you? Do you have a partner, partner, um, army that you can build? Because it, there's so many interesting startups, there's so many interesting startups that are building amazing technology, but they're all by themselves, and they're telling their story by themselves. They might be going after a big market, but I've always found that if you can find companies where you can create ecosystem environments and have a lot of people sing your praises, that's another really good indication. And then after that, it's, it's, it's people, right? I think it's, it's obviously it's people, it's great leaders, it's people that have done this before. And if you see all of this happening, then you check your ego and you take whatever seat's available. Yeah. 'Cause you're like, "I think something's going to happen with this type of company when they have all, all these, uh, kind of green lights," and you take, uh, demotions, right? You take a step, step down in a role just to get yourself in there. I think that's, uh, that's always the right, right play. And then you probably know within 18 to 24 months if it's worth your time and if you kind of need to know if it's going to be worth, you need to make a good call and not, um, you know, have that sunk cost fallacy of making that decision. And if it feels like it's going to be a frog and not a prince, you just, you, you look for the next prince.

Yeah. So, Ruby was your next prince. I want to get to to that. Well, not next, but you had a long journey to get there. But, uh, when on this arc of your career, in the chaos of tech SaaS boom, uh, when did you get married? And then we got to talk about the, the triplets, man, uh, 'cause that, like, I got to figure out where that fits in this arc here of your story, 'cause that to me is a curveball that, of all curveballs.

Yeah, so I met a, uh, I met my wife, Alicia, in 2004, so we've been on this journey together. We're almost going to cross over into spending more of our life together than than not, right? So, we're, we're pass, passing that moment. Um, yeah, so we met in 2004, and, uh, we had our first child in 2009. Um, so, still at the boiler room of, of Salesforce at the time. Yeah. And we were going for our second, uh, second child. We're going to have one more. We're going to have one more. And we went to the ultrasound, and they were like, uh, yeah, you're, you're, I, I see one, I see two, and then a few, few minutes later, they're like, "Sorry, we see three." And they're, they said, "Baby A, Baby B, Baby C." And, um, you know, everybody asks, like, "Is this planned?" Like, obviously, you don't plan it, but usually what people are trying to say is like, "Was it IVF?" It was not IVF. It was just spontaneous. I had, I had out of nowhere, John.

And you don't have triplets in your family? She doesn't have triplets in her family, or?

No. No. No, not at all. No, no multiples. No multiples there. Um, and it's funny, you'll probably like this, 'cause because I know you like music, but, uh, we, you come out of the ultrasound, you're stunned, obviously. You're like,

Yeah. Ashen, 'cause you're like, "Everything changes in that second. You're like, every plan [clears throat] you had is just blown up."

>> Yep. Like, our house changes, our car changes, my job probably changes. Like, all of this stuff changes. And, um, and we got into the car, and we turn on the radio, and the first song that's on is Tears for Fears, "Everybody Wants to Rule the World." And the first lines in that is, "Welcome to your life. There's no turning back." And we're like, "Well, that's appropriate."

'Cause this is like, that's a sign. Yeah. So, Tears for Fears holds a very special moment, uh, in our, in our life. And I tell my triplets this all the time. I'm like, "This is when we found out." They're like, "Yeah, I know, Dad. I know. I know." They always hear that song, and then they know what Dad's going to say. So.

Of course. >> Yeah, that was that was wild. Like, that was, um, that was a huge change. Like, it was, it was a, a dramatic change. It was the most, it was the most challenging thing that I think we've, we've ever dealt with. Our, our, our oldest was only two years older, um, than, uh, than our, than our young, than the triplets. Um, they arrived, it was day nanny, night nanny, weekend nanny. Uh, the funds we were spending just to survive, uh, it was survival tactics, right? It was survival tactics. You had, you had to do this. And you had to survive also because you have this two-year-old whose life is completely blown apart as well. So, it was a ridiculous amount of like resources, and, uh, we ended up, uh, leaving the city and moving out to the suburbs just to have more space, be around our family. I ended up leaving, uh, Salesforce at the time, too, because I found that Salesforce, still in 2013, was a ridiculous boiler room, um, and it was still like new logo hunting, and I'd done it for, at that point, close to nine years. And I was like, "I need, I need to find a little bit more balance." And so, I went to, uh, Microsoft, and I ran Dynamics for, for Canada. Um, because we had, they just, I mean, they didn't even have an in-office culture. I'm like, "This is amazing. I can have a little more flexibility, right?" Like, it was, it was, uh, it was a move we made at the time. And so, yeah, I mean, triplets are like, uh, Fight Club. It's like the volume, the volume, you know, after Fight Club, the volume's turned down. Yeah. That was triplets. And, and also, it's like, it's, we, we talk about networking and stuff. Oh my gosh, John, like, best net, best networking, uh, drop mic drop ever. Like, you can, you can, you can bond in, before with everybody when you happen to have spontaneous triplets. And they are identical, too. That also blows people's minds. Jesus, right?

>> [laughter] >> Yeah. So, I mean, kudos to you and your partner because, you know, for having that thrown at you, it's just on a personal level, though, obviously you guys are stunned. I think I always say that the most important decision you'll ever make in your entire life is, is your significant other. Just period. I don't, it dwarfs in comparison to job, to career, to any of that. And, and so, how did, did you kind of sit down and have a, like a come-to-Jesus meeting and say, you know, like, "Hey, look, okay, this is what we need to do. Like, were you in lockstep with, 'I'm going to leave sales, I'm going to get more stable, going to do this stuff,' or was it just like, 'Hey, we're, we're trying to survive here, and we're both kind of doing what we're doing?'" 'Cause I'm always, I'm always fascinated about the partner side of, you know, of the equation. 'Cause I know for myself, if I didn't have my wife doing what she was doing when we had our daughter and taking the sacrifices that she took, there's no way I could have been doing what I was doing. There's no way I'd be where I am right now. And we did, weren't as, as, as deliberate as mapping out a plan and, and, but we were in line from a value standpoint, from an approach standpoint. I think we got fortunate. And I just, for those people who are on this journey, I think it's an important piece of the equation to identify of like, how you choose your partner, but also how you communicate with your partner as you're going through this chaos.

Yeah, communication's key. I think I, I have a very fairly simple, uh, relationship, uh, at the, kind of mantra or or philosophy, and that's that every relationship can be broken down into common interests and core personality, right? And I think a lot, I, I think when you, when you're looking for a partner that's going to be on the journey with you, it's finding, finding alignment in core personality. And so, I think a lot of people get stuck with common interests, um, like the same music, movies, sports, right? Like, um, those types of things, I think are, are very common and be like, "Oh, we love hanging out, we love going to nice restaurants, uh, uh." But if, if you have fundamentally different core personalities around, say, extroversion's one, right? So, you could be extroverted, but if you're with a partner that's deeply introverted, you're going to have conflict. You're going to have the, it, you can, you can make it work, but it's just going to be a challenge. You, I think a core personality is liking to travel, liking to stay at home, right? Like, those are really fundamental things that are going to create a ton of tension in a relationship if you can't see eye to eye on that stuff. Um, and then also ambition, right? Like, some people, I think, I think, um, what, how my, my wife and I fell in love with each other is we both had a similar upbringing, and we both had ambition to chart a new course and accomplish new things that we hadn't been able to experience until getting together. And so, yeah, I think that those things are all super, super important. And then, um, if you're going to be in a relationship with somebody in sales, you're, you're going to have to understand like the, the economic up and downs, the psychological ups and downs. Um, yeah, like sometimes I think the sky is falling, and other times I'm like, "Everything's great." And, and then it'll, the sky will fall again. So, your partner has to kind of understand that journey. Yeah. And, and my wife's been great at that. That's what it's been, it's been amazing. I, she's just an incredible person, and she's the mother of dragons, right?

I can, I can imagine. Yeah. So, she's, she's amazing. Yeah.

I think that's the one thing that my wife still hasn't really, uh, you know, from a budget standpoint, like when things are good, things are good, and we can buy whatever we want. When things are bad, I'm like, "Super cheap," and, you know, like, "That's, that's 50 bucks. We're not going to do that." And she's like, "What the hell, they, you know?" So, I'm like, "Yeah, I'm looking at my forecast every day." So, [laughter] right now we're good. Other times we're not. So, they, they, that understanding of the mentality of those, uh, she gets it. But it, we, every once in a while, it rears up like, uh, "You just, you know, two months ago, you just dropped X on Y, and, uh, now we can't go out to dinner." And I'm like, "Yeah."

I don't know why you do that to yourself. Um, I, so, make a joke in our house. I'm responsible for for debits, and she's responsible for credits. And I, I literally, John, I just don't look at, I don't look at the bills. I don't, I, my wife, I, I economically trust her. Yeah. Um, and I find that it's, it's just unnecessary noise for me because even if you harp on, um, day-to-day bills, it's a, it's probably a rounding error at the end of the day. You're really not going to make the biggest difference in the world. And, and, um, your lifestyle will generally stay where, where it's at. And so, if you get into these, the, you just end up inserting, like, domestic strife over something that really, in the long run, isn't going to make a big difference.

No. And so, I don't even look at the, I don't even look at the bills. People might think I'm crazy. My friends think I'm crazy. But I trust my wife and, um, I, I know it's almost like it's not worth it. So, I just focus on making sure there's enough money to do, you know, the credit side of the, the equation.

Well, that's why I've always, I've always had the mentality of like, you know, saving money, you know, to your point, like saving a few bucks here or there. I'd rather figure out how to make money so that we can afford whatever it is as opposed to cut expenses to figure out a way to live the way we want to live. So, but every once in a while, it kind of rears its ugly head depending on, you know, again, the business forecast is really for me what, Oh, yeah. I'm the sole provider. You know what I mean? I'm not the provider. I'm the sole entrepreneur. You know, my, my bank account is the company's bank account. You know what I mean? So, I'm looking at like, I'm like, "All right, we're doing good. Oh, [ __ ] that I just lost that contract. So, uh, we got to be a little bit more, uh, thoughtful here."

So, you went, so you've had some great exits, some great companies, you know, started zero, brought it to millions. Uh, 2024, you, you started doing some advisory work. So, you know, you kind of had your arc of, of kind of the, especially the tech world. It's like, "All right, cool. You get in, grind, you do your thing, get a couple of exits, be an advisor." And that kind of ends up being like, "All right, cool. Now I'm an advisor. I get to play around with it." What in the world made you want to jump back into the world of startups now? Like with Ruby, right? So, you, in the world of AI, with as much chaos as there is right now with with products and solutions, uh, uh, starting, executing, and dying in months based on what Anthropic or OpenAI releases. What, what was that lens that you took, right? 'Cause if you, if you look at stability, if you look at TAM, if you look at all these things that you just mentioned before, that is almost damn near impossible to judge at this point because of how fast things are moving. So, what did you see, first of all, that made you say, "I, I need to do this?" And, and what was the kind of lens that you used to then do it? Right.

Yeah, so, so I think the, the first thing was, I, I spent a lot of time with entrepreneurs and working with, uh, companies that are moving from founder-led sales to to to building their first sales organizations. And that was one kind of experience of kind of seeing where that, that, that market was at. Um, the other thing too is, um, uh, business partner of, of mine, who's also co-founder of Ruby, we started Snow Angels, which is a Snowflake investor syndicate. So, we, we, we, and a pool of, um, Snowflake alumni, we invest in data and AI startups. Yeah. Primarily obviously AI startups. And so, seeing what these companies are building and what they're doing and all the opportunities that exist, it's, it's fascinating. And I, and I do believe we're still very much in the, the early innings of, of this whole journey. Yep. Um, so started to think about, uh, potential AI use cases and, uh, the combination of, of, kind of working with these AI entrepreneurs, but then also working with, um, the SMBs and, and kind of mid-market companies I was advising, I was starting to realize that, that AI was too hard for the sales reps. It was too hard. And, and, and what I mean by that is, uh, there was very little way, and there still is, very little way for, um, the average salesperson in a small company, in a large company, and so on, to have AI help them through the entire sales cycle. Right? AI just, it doesn't have the context, it doesn't have the memory. You have to generate all the action yourself. You have to know how to prompt it. You have to organize all your thoughts and and chat and try to figure it out. And, and it just reminds me of, you know, back in, in the, the Salesforce days where CRM was unusable for a sales rep. It was unusable, right? Siebel, uh, GoldMine, Act, it was unusable. It was like, yeah, crappy information, uh, no good insights, no good outputs. Um, from a sales leader perspective, it was a black box. And so, so Salesforce made this, made this decision to make a, a highly usable application that then became widely adopted. And I think that most of the AI applications today in sales just, they don't have that usability. They don't have that complete, uh, works like a sales rep, uh, kind of, kind of world. And they also require a lot of, you know, set up and, and so on to, to use it. So, I just felt like there was an easier way to take the power of AI and, and, and put it in the hands of, of sales people. Um, but I got to say, but like, before talking about all of Ruby, we have to talk about like the imperative of AI, right? The, the imperative of AI for, for sales. Yeah, for sales people today. Like, what I think a lot of people don't fully appreciate is, is that your competitor is often your buyer's AI. Yeah. Right? If you think about that for a second. So, you are competing to win the hearts and minds of your buyer's AI. Because what, what's happening is, and again, like, I, I'm, I'm, I'm certain people don't fully appreciate this, but imagine a scenario where, where your buyer, even before they, they decide to take a call from you, they're checking in with Claude. Like, "Oh, Claude, should I, should I talk to John?" I don't know. Claude is going and searching the internet for every little piece of, of information on John. And it also knows everything that you need to know, right? So, it, about your business. So, it already has an appreciation for what the buyer is doing. And it's making the decision on behalf of the buyer. And there's, there's, there's cognitive offload. You can call it cognitive offloading. You can call it cognitive surrender. The, the buyer is, is deferring to the, the AI on, on these decisions. Mhm. And we have a customer at, at Ruby, amazing, amazing tech company, um, doing some pretty, pretty incredible things in, um, in, in billing and in configuration. And they've sold to, uh, both OpenAI and Anthropic. And in both cases, both companies said,

"Just send me all your documentation." Right? Just send it to me. Send me all your documentation. Tell me what you think you can do for us. And we're going to feed our LLMs and we're going to let them have their opinion. Mhm. So this is what's happening today. And I think there's there's two problems with that. One is um you have to make sure what you're putting to the customer is is impactful and highly personalized. Mhm. And then the other problem with this is is you have to earn the right to stay in the room and be in the conversation because if if if the buyer's AI is answering a lot of their questions on behalf of you, then why would they talk to you? Right? That I can't wrap my head around that. And that's like you and I are on the same page with this this the five-alarm fire that I think we're looking at right now. Because everybody's looking at these AI tools that are replacing sales reps and they're automating the sales, you know, parts of the sales process and oh, we're not going to need BDRs. I don't give a [ __ ] about any of that stuff, man. I care about when the client wakes up and realizes exactly what you just said that I don't need you. Because most sales reps, and I and I say this because I see it. And and I think that we have turned I I did a presentation at Pavilion uh a few a few months back uh called Anything but Predictable. And it was basically how the Predictable I feel like the Predictable Revenue model. And and by the way, I'm I'm the biggest offender here. Like I've made a ton of money on the on the Predictable Revenue model. I've trained the entire model. But I I fundamentally think it broke sales because the segmentation of roles turned it into a an assembly line. And we taught these kids way more on process, way more on tech, and we didn't teach them how to sell. We didn't teach them hand-to-hand combat, going out knocking on doors, those type of things. That skill, at least in SaaS and tech, is gone. And and so we turned them into these robots, and now they're getting replaced by robots on the sales side of the house. But when the client wakes up, man, and cuz all I look at as a sales rep is friction. And and I look at myself, you know, people are like, "Oh, well, no, John, people are always going to want to" Yeah, if there's value, right? If there's value in that conversation. But they're like, "Oh, the best sales reps ask questions that the client that that the client hasn't even thought of." Oh, really? Hey, Claude, could you act as the best [ __ ] sales rep and ask me the questions that I'm not even thinking of right now? So so with that, how does a rep, outside of the legacy buyers who aren't there yet, in that scenario, the [ __ ] does a sales rep do?

Yeah, so you you you have to arm yourself with AI first, right? You it's an it's an arms race. So you've got to have the same kind of advantage and intelligence advantage that your buyer has. And so you need to know as much about their business as they know about yours, right? You have to find gems, you have to find insights that they that they may not know about their own business. And you have to do it all the time. All the time. I'm not talking about like, "Hey, up front we figured out these things and we go for it." It's like you have to do it all the time. You have to be at every meeting having hyper-personalized discussions about their business. Hyper-personalized. Um at every in every interaction, every email you send, focused on you, focused on you, right? You should be able to be prolific with personalized ROIs, personalized proposals, personalized POCs that are based in the reality of your customer, and you should you need to be prolific with that all the time. Right? Like it it it I struggle to understand a world or see a world where a customer's going to want to look at a data sheet unless it's about them, right? So we have the technology now to consistently issue a data sheet to a customer that's about them, not just about us. Mhm. And and again, you go back to the situation where these customers are going to go and they're going to put it into a an AI, and the AI is going to make the decision. And so what an AI does, and again, this is something that that the industry is still learning and appreciating, is the the AI has its own cognitive surrender. So what I mean by that is an AI actually loves to be given the answer, right? And so that's is why AIs will go and recommend things that are somebody's written up on like the the top 10 ways to do this or the top 10 solutions that do this or I've compared this solution to this solution, this one wins. The AI is like, "Cool, I agree with that." Mhm. And so what what people need to do is they actually need to give AI the answer. So what what a buyer is doing is saying, "Hey, is this good for my business?" And if you give them the evidence, give the AI the evidence that this is yeah, conclusively what we understand about your business, why it's good for it, Mhm. >> that AI is going to recommend you. And so if you're if you're a vendor and you're up against a competitor, and that competitor is giving generic information to the buyer AI, and you're giving specific hyper-personalized information, that AI is going to be like, "Cool, you figured it out for me. I agree with you. Let's go with you." Right? That's that's that's the thing that people don't fully appreciate. So we're going AIs to AIs here, right? And that's why I'd like that's one of the things I'm seeing, even with me, quite frankly. Like, you know, I'm giving these kids, you know, I trained in Salesforce, and I'm I'm like giving them a prompt to do some prospecting, and I tell them like, "Use it to get close and then do your thing." And then they send it over to me and I put it into my AI bot, and I say, "Review this and give them feedback on it." And I give it back to them. You know, and that's a basic, you know, I that's fine, right? It with some context there, okay. But help me understand how Ruby or any tool out there gives great intel, okay? Um you and I, I forget I don't know how you I'm 50, right? We have the scars, we have the context, we have the business acumen to be able to call [ __ ] on a AI when we see it, to use the information and articulate that the right way in a conversation. How does the 25-year-old kid who didn't go to a co-op, who is really just trying to figure out business and make their cold calls these days, how do they use it to build their business acumen, not just have it have the answer for them that they then port over to somebody else's You know what I mean? Like that's that's where I'm I'm nervous. It's it's not for the guys like you and I. I think the guys like you and I who've got 20, 30 years in our in our back pocket, and we know when to call [ __ ] we know how to have conversations without scripts, we know how to engage with people, and ask like thoughtful questions, get people to think. Mhm. I'm not worried. [clears throat] I think it's a superpower for us. Super [ __ ] power. But it's like these these kids like because they've all been kind of short-cutted like, "Hey, here's the answer. Here's the answer." And it's like, "Oh, great, there's the answer. Good, go." Mhm. >> How do they use AI for the business acumen so they can even have the conversation at that level with all this insane information that AI can present to them?

Yeah, it's a it's it's There's a There's a lot there that you have to work through. I think I think the the first thing that I would recommend anybody does is that they're going to get an AI output, right? They'll get an AI output. They'll It'll be their It'll be their research. It'll be the recommendations of the AI. And then at that point, you're going to want to do something, right? Take those insights into some sort of action. You're going to want to plan a meeting, you'll want to create a a meeting deck, you'll want to create an ROI, etc. And so the best way that you can actually use AI then at that point is to tell the AI what you're going to do and what you want to do. Right? And so there's this aspect There's this thing called like like transfer memory. So you can learn more you learn your yourself more when you explain something to somebody else. Yes. Right? And there's this thing I read about recently. It was like the the rubber duck the rubber duck coding or something, the rubber duck exercise where coders what coders would do is they would explain their code to a rubber duck. Like literally literally, John, a rubber duck sitting on their desk. They'd be like, "This is why This is how I did my code. I did this. I did this. I did this. This is what I was thinking." And just the art of explaining what they want to do to something Mhm. really really dug it in and really gave them a lot more insights about what they're going to do. And I think the best way you can use AI in that scenario is to say, "Hey, you know what? I I did all this information. Here's the meeting I'm going to run. I'm thinking about doing this. I'm thinking about doing this. I want to ask these questions and do this. Um what do you think? Do you have any feedback for me? Um anything I'm missing?" Right? And so now you're you're learning it, you're giving it to somebody that who's who's listening to it, and then they're coaching you. And that's it That's the piece that I think that that we have this amazing ability to do is like you you need to have an interaction with with your with your AI and try to figure out a way to have it start to coach you and give you that that thinking partner that's going to make you really really successful. If it if it's a you know, a kind of like one-sided thing where I'm just going to take from the AI and then I'm going to spit it out without actually interacting with it, it's it's it's pretty challenging. Now, I'll say there are some amazing technologies happening around like role-playing coaching out there today. They're still pretty generic, right? They they they actually aren't coaching you on that meeting or coaching you on that deal. They're coaching you on like philosophically how to compete with Databricks if you're at Snowflake, right? And so I think those those tools as those develop, then that that forced curiosity, that that interactive learning, the the thinking partner, right? I think that stuff will become more more regimented, for sure.

So let's get into Ruby now. For context, let's let's understand what Ruby does. So and then I got some questions about the the challenge I see right now a lot, which is the the hey, I can build it in Claude. Why the [ __ ] would I buy this? You know what I mean? Cuz there's the idiots like me who are using like Replit and Lovable to build these [ __ ] apps when I can find code it, and it looks pretty badass. I don't know anything in the back end of security or any of that [ __ ] but man, I built I just built this kickass app. So that looks fine. Why can't I just go So first of all, give us some context of what Ruby is, and then talk to me about how you're dealing with that specific objection to people right now, cuz I think everybody is going to be dealing with that objection. And I know everybody is right now, which is why can't I just build that. Which is back in my day, when I was selling IT services at the infrastructure level, I faced something similar cuz we would go into companies that had software engineers, and the engineer the software engineers would be like, "We can manage our servers and work, you know, like why the [ __ ] like why would we hire you to do this?" I'm like, "Yeah, but that's not what you get paid for." Like it was a little bit of an easier talk track because it was a technical person that I was like, "You really want to deal with the boring infrastructure [ __ ] when you're creating software that's going to make your company millions?" But now you have every [ __ ] like me in a company saying, "Look at this Hey, boss, why would you buy that? I just created a custom GPT for us to go do the you know, extract some information." So with that as context, help us understand what Ruby is so that people have that, and then how are you combating that objection specifically in the market right now?

Yeah, like um I think everybody's going to deal with that objection. Like no matter what you're selling today, the LLMs are coming for you. So it's it's sales AI, marketing AI, uh uh CRM, what have you, everyone is going to need to compete against those those solutions. Um but but yeah, about Ruby, the problem we're looking to solve is really ensuring if it's ensuring a sales rep can be excellent in every moment of a customer interaction. And so that that that's been the the traditional problem in sales is like you can't necessarily win every single customer interaction because you have too many accounts, right? You you you don't have the ability A sales rep generally does not have the ability to exceptionally manage and exceptionally run dozens of deals across dozens of accounts. They they probably just joined the company and are learning the account. They just if you got salesforce, you just you've just received 100 new accounts for for the the annual shift. You've got new products that have come out. Um and your customer's changing over time. And then within your customer you got the five to seven stakeholders you have to appeal to. And so all of this information is is available to a sales rep but you're unable to synthesize it and execute on it consistently, right? You just you just can't. You'd have to have this this unlimited brain power, unlimited uh storage uh and automation to truly be able to do that. And so this is where uh we feel that Ruby is is down going down the right path. So what we're trying to do is we're trying to create something that has full context that is that is essentially zero calorie effort from a sales rep. So what I mean by that is we're we're perpetually updating information about your company. We're perpetually updating information about uh your customer, right? Creating organizational memory and and customer memory. And a lot of the solutions out there that they don't have that today. Like uh if you look at some of the the conversation intelligence solutions that are out there, they might be able to give you information about what happened at the meeting but they really don't tie in any information about like how you sell or how that company buys or or any of those nuances of and rounding out the picture. They can just say, "Hey, this is the problem I heard on the call. I think that's it." But what what a great AI would do is like, "Hey, this is the problem that I that I just heard on that call. Um this person mentioned that problem in the last call. I think that this champion might be able to help that person with that. Here's why it matters in this this organization. Here's the customer story you should tell them. Here's the ROI that you should tell them." All of that context is what AI should do. And today AI doesn't operate with that degree of of intelligence. And so I think the first thing that we do is we gather the context, right? The the organizational context, the the customer context, the meeting context. We bring that all in, automate it, it's there, right? It's generating it's sitting it's sitting and available for use. Um then we automate all the AI after that. And so the second problem with with the AI if you get past building all the context and feeding the beast with context, the second thing is it's user-operated. So you have to know what to ask. You know you need to know what you should do next. You need to basically uh drive drive the the engine yourself. And really AI should know what you need to do next, right? AI should have some insights and be like, "Hey, this happened, this happened, this happened. Now I think you should maybe do this, maybe do this." And so what we also do is we automate the actions throughout the deal cycle. So we we basically act as bait all those agents and and all that underlying prompting on your behalf so that it's it's there proactively assisting you as opposed to you having to go and call and respond uh to it. And then the last thing that we think about a lot is just those outcomes and delivering those outcomes. So delivering those ROI materials, the ABM materials, the the follow-ups, all of that stuff grounded on the reality of those two prior steps, right? Grounded on the reality of full context, grounded on the reality of of all of these agents working together to come up with McKinsey-level insights that are ready all the time. They're there ready to go. And and I think um the I guess the the last thing too I I would say is it's also organized the way that you work. And so I just have this fundamental belief that the chat interface will not uh exploit the true benefits of AI for the average sales rep. So there's there's there's 700,000 sales people in B2B technology in North America. 700,000, okay? Mhm. You cannot tell me that 700,000 sales reps are going to use Replet are going to use Claude Code going to use a chat interface and accomplish all the things that we've been discussing on this call. It's not going to happen. It's not going to happen. And so fundamentally there there has to be something easier for sales reps. And one thing that we also focus on with with Ruby is that you can go use it on your own. So this whole thing is designed to be is low friction, right? In in a in a life of selling I I try to build things and I've wanted to sell things that are low friction for somebody to buy. Anybody can go to the website heyruby.ai and you can basically run run accounts out of the gate. So all of that context building, all of that is done on your behalf and a sales leader can go buy it for their sales team or sales rep can go and use it for themselves. We have companies that have just logged onto the website and they sell environmental remediation. Great, right? We have companies that have that have gone on the website and they they sell event space for corporate events. Mhm. And they're using it, right? And that's what AI should do. AI should be able to go and figure out all this context for you, activate the insights, activate the outcomes and just kind of guide you along the way. And it it's a novel approach and yes as we as we go through and we we we did a round of fundraising, we had to answer a lot of VC questions about about Claude. And I think that it just it has that fundamental uh usability gap that I am certain in having seen this through the whole you know, world of of CRM and was at Gong as an advisor in 2017. Like I've seen all these adoption challenges that that are coming up. And people um I think they AI just needs to be easier. And so you look at what's out there today um and you look at Claude and I love what Claude's doing and it's I use it every day and it underpins a lot of what we're building at Ruby. But you've got to have the the sales workflow layer and that experience built on top of it because it in itself is like using Claude instead of something that's purpose-built for for sales is like saying, "Hey, I could just build my CRM on Oracle." You can. You absolutely can build your CRM on Oracle and you can build that yourself and manage that yourself in your organization and it deal with all the change management, all that stuff yourself and be locked into that database. Or you can buy something purpose-built like CRM that that or salesforce that somebody else takes care of. Right? And then that's the other that's the other thing is I think we're headed down this this fallacy of of build versus buy. Like we're suddenly going to build everything and manage it all ourselves >> Yeah, no. and and deal with all the [ __ ] that we've been trying to get away from from cloud and now we're saying, "Oh, well, actually I could just build it all myself." Well, what happens when the person builds it that leaves, right? What happens when you've built it all on Claude and you know, you deal with an odd decision uh federally that puts your LLM provider in in jeopardy, right? Like you have to have portability of these AI solutions as well. So Or what happens when Claude if Claude goes public and all of a sudden needs to actually have like and raises their token rate by, you know, 100% and all of a sudden you're paying a million dollars to run whatever you just built. Like that's a real problem. >> they got to make money, right? >> Exactly. And I I I believe that there's there's a world where people uh lean on providers like Ruby to actually token max and actually say, "Hey, like I'm going to run I'm going to run efficient tokens for you so that you don't blow up your budget and have everybody on on uh you know, Claude max running 400 bucks a month." Like I I think that there is there is the responsibility of of providers like Ruby to be able to help people with those types of efficiencies, absolutely.

Yeah. So So you don't think that there's a world where cuz you know, if I leap very far into the future not well, at this point who knows. Um but each one of us having a personal assistant basically, whether it's our iPhone or the the chip in our head that allows us to just be like, "Hey, I I got a meeting coming up with Chris here. Uh do me a favor, go through look through all this stuff, you know, and tell me what I need to know about this business and you know, put it into a little podcast for me on Notebook LM and you know, let me listen to it before I have this conversation." I'm ready to You don't think we're in the world where it's going to be a basically whatever I want is a vibe code as opposed to the the execution layer of a specific skill set.

Yeah, I think you're going to have to you're going to have to have the execution layer, especially something as as intellectually complex as as sales. Like there's a lot of things that need to be figured out. There's a lot of layer layers of understanding that need to be figured out. And especially your your the the jobs change over time too, right? So it's like sales for health care, sales for med device, sales for for for pharma. Like all of those things have their own inputs, their own data sets. Mhm. They have their own uh workflows and language. Yep. And all of those things are are going to be uh specific to to that. And so could an individual vibe code it? Maybe. Could a company vibe code it? Maybe. But I really believe that they're going to defer a lot of that provided the economics are sound. They're going to defer a lot of that to experts in that domain Yeah. to be able to execute that, right? Like domain expertise is so critical. If you say, "Hey, I'm going to vibe code it." So okay, so how do you establish domain expertise to to vibe code it? Are you the domain expertise? I know this is your business, but are you the domain expertise? Should you be building it this way? Are you going to continue to innovate quickly on this as as things evolve over time? Like we see the pace of innovation of what's available through Claude and the LLMs. Are you the company to distill that innovation down into these vibe coded applications as quickly as your competitor is, right? Like I I just don't see that I don't see companies being able to to keep up in this this like age of acceleration. So I think that it I think that these guys all become marketplaces, right? Like I think that you know, Salesforce went to AppExchange, like Snowflake has their data marketplace. I think there's going to be purpose-built applications available to be inserted into the cloud experience or the the OpenAI experience. They've already moved in that direction. And um people will be buying modules, App Store type modules, and they're not going to be building everything themselves. I think it's just it's it's it's too difficult for a thousand different reasons.

What does AI do to sales methodologies? And and the the context of that is you know, a lot of people choose like MEDDIC and you know, Miller Heiman cuz they they got their approach. And I've never been a methodology guy. I just I love tactic structure tips, you know, agility, right? But there's these quote-unquote methodologies. And and one's not better than the other. It's all about how it So, does AI effectively even the playing field when it comes to quote-unquote methodologies? Because most of these tools, right? These platforms, whatever it is, that they can put every methodology in there and then figure out, you know, the best components of all of it. So, it's so it's your custom approach to selling versus you know, off-the-shelf type of thing. So, you know, random question, I think, but what do you think AI is is now going to do to sales methodologies and how they're implemented?

Well, I think I think I think one, you just said it, right? Is like there's methodologies are are are um like too broad and too vanilla in in many cases. And so, there could be more bespoke methodologies for uh particular industries. Um but I think what AI does and you know, something like like Ruby for example is that if it it levels the playing field to for any company to execute like they have a massive sales enablement team. Yeah. >> And so, like even if you you walk into an organization, you're like, "Hey, I want I'm a you know, I'm a sales leader at a Series A company. I got a team of six." And now I come in and I want to deploy MEDDIC, right? That's great. Congratulations. That's wonderful. Now you got to figure out how to train everybody in MEDDIC, but then stay on every single deal to to make sure that MEDDIC is truly executed. Yeah. And it takes a lot of effort to do that, right? It takes a lot of management. It takes ongoing uh monitoring of things. And what something like like Ruby does and and potentially other AIs is it helps you drive that kind of change as if you had a full-time sales enablement person doing that on every single deal and every single account. And so, I think for sales methodologies, they probably uh become more more bespoke, um but they become more consistently applied because AI is helping to monitor that uh more consistently. That's that's what I think. And and yeah, I think your your take on it is is right, which is it's probably going to be amalgamation of all the best stuff, right? Like personally, I like MEDDIC, but MEDDIC doesn't gather any great information without Sandler, right? MEDDIC is is kind of like the lagging information. And and Sandler is the leading information that you have to get. So, you do need both. Yeah, for sure. Yeah, and then, you know, the gap selling and then the challenger sale. You know what I mean? And they're all applicable at different components and they can pull in like for I could I could envision like you know, John, in this scenario based on who you're about to meet with in this like you have to actually pull the challenger sale on this one cuz that's like that guy's a high D over there. And if you don't punch him right in the [ __ ] mouth with your opinion of something, you they're they're no way going to do it. So, I I could see this actually being great for organizations who can finally customize their own process as opposed to trying to, you know, rely on one methodology to to run their org, which It's funny you say that. Like with with Ruby, we we create discovery questions and objection handling as per Sandler because I'm a big Sandler fan. Love love Guru Ganesh. I've I've seen him many, many times. >> to him I just talked to him just the other day. Yeah, yeah, brought brought him into many companies. Um Yeah. He's amazing. So, you know, I ask questions like like Guru Ganesh. Uh qualify like MEDDIC. Uh provide challenger insights like challenger. Challenger customer insights around the buying committee, right? So, we we do actually, funny enough, I haven't really thought of it this way. We do amalgamate a bunch of different approaches uh within within the product as is cuz I've I've seen it all, right? Like I've seen every single sales training and I've cherry-picked what I think works best during different parts of the sales cycle. Yeah. Um so, yeah, it's a great it's a great point. Yeah, thanks thanks for that. That's very inspiring positioning for uh for Ruby. Yeah, there you go, man. And and I think that's the best case scenario cuz you know, that's why I've always been like when people ask me like, "Well, what do you know, we're looking for a methodology." I'm like, "Really? Are you? Do you mean like a soup to nuts, you know, top-down everything integrated from one vendor?" I'm like, "You're out of your [ __ ] mind." You know what I mean? Like you should take the best of this, the best of that, the best of this and put it all together and make it yours cuz no one sales training vendor has the answer to every single problem that you're going to try to face here. So, Yeah, completely. Love it. Awesome, man. Well, we got to tie this one up. So, where can people find out more information about Ruby, about what you're doing, and all the above?

Yeah, thanks thanks, John. Um yeah, hey ruby.ai is the website. You can go on there. You can check it out. You can try it, right? Which is which is a nice thing. Just >> [snorts] >> sign up and and put one of your favorite accounts in there and let's see what kind of gems we can find. Um and uh feel free to follow me on LinkedIn, uh Chris Walker Lawson. Um happy to connect, happy to have conversations on this. And then, I'll be at SaaStr um as well. So, um I don't know if this we're going to we're going to put this out there before SaaStr or not, but that's something people can reach out to me. Love love to meet in person. Awesome. Awesome, my friend. It was a great conversation as usual. And uh yeah, appreciate you coming on. Awesome. Thanks, John. Appreciate it, too. Have a great day. You too, everybody. Thank you. And thanks for listening. As I always say, uh go out there and make somebody smile today cuz no matter how bad your day is going or how bad you think it went, if you make somebody smile today, you know you had a good day. And the world needs a lot more of that right now. So, thank you all very much. And I will see you on the other side. Hey, thanks again for listening to the show and for all your support throughout the years. This is one last reminder to check out my training programs at jbarrows.com or leave a five-star review on your favorite podcast platform or G2 if you've already gone through my training or sign up for my newsletter. Any of those will help ensure I can continue to bring [music] you free content and great conversations like the ones you just heard without having to annoy you with sponsors. Again, let's make it happen in 2026 together.