How AI Agents Are Rewriting Sales with Kris Billmaier

John Barrows: Hey, real quick, before we get into the conversation, look, if you've been listening to this podcast for a while now, you know I don't have sponsors, and it's mainly because I know most people, including myself, skip right through them. And I just don't want to annoy my audience with 10 minutes of sponsor spots every single week. However, it also means I don't get paid to do this. So the way I help fund my ability to provide free content and really interesting conversations like the one you're about to hear is through my sales training and coaching services. So if you've gotten value out of some of these conversations on this podcast and you're looking to level up your sales game, do me a favor and go to jbarrows.com and check out the training tab on the Top Nav bar. I have training for teams or individuals, and you can even get an individual training module focused on a specific skill that you're looking to address, like objection, handling, negotiations, and much more. If you're an individual, you can also use discount code podcast for 20% off the membership. Look, sales is evolving faster than ever right now, especially with A.I. uh, and we all need to level up or risk becoming irrelevant. Whether you're an executive looking to train your entire team or you're an individual rep looking to level up, I promise I can help you get to where you want to go in 2026. Send me an email to schedule a call or sign up to my membership today, and let's make it happen together. Now, let's get on with the show. Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with GU, who I truly respect and I think make a positive impact on the world around us. Now, this week, I have Chris Billmare on the show. Chris is the EVP and GM M of agent for sales at Salesforce, which means he runs the largest cloud and one of the largest software companies on the planet. This one is pretty personal for me because Salesforce is where I built my entire Training business from 2010 to 2018. Training, all those reps on prospecting and the predictable revenue model. That's where it all started, my friends. Uh, Chris grew up in the San Jose Bay Area, and he used to go to work with his dad at Sun Microsystems on weekends and absorbed the tech world from the inside. He played baseball at Notre Dame on scholarship, almost hit a.500 batting average in the NCAA tournament, and he carries that team first mentality into almost Everything he does. Before Salesforce, he was at Microsoft during the shift from on prem to cloud. And before that he was at a startup called digio, selling early DVRs into the cable market where the product won back to back Emmy M awards, which was actually really cool. Now this conversation goes straight at the thing that scares me and should scare almost every seller listening. Salesforce's own SDR team deployed agent force agents to handle the inbound leads. They never had capacity to touch. And in eight months it generated over $100 million in pipeline. Their SDR leader now manages 100 humans and the equivalent of 400 agents. We get into what that means for the SDR rule, how the sales rep job is evolving from generalist to strategic relationship orchestrator, and why Chris believes we are headed back to full cycle sales. And so do I, my friends. So I hope you enjoy this conversation as much as I did. Let's make it happen, Chris. Bill Meyer. Welcome to the Make It Happen Monday podcast, my friend. How are you doing today?

Kris Billmaier: I'm doing great. Thanks for having me. Excited to be here.

John Barrows: Yeah, I'm looking forward to this one, man. This is kind of bringing me back to my roots of Salesforce because, uh, you're running agent for us these days and there is a whole lot to talk about with that. But, uh, my, my heyday of 2010-2018, training, all those reps on prospecting and the whole predictable revenue, it's kind of where I built my whole business, my whole ecosystem. So I got a lot to appreciate, uh, about Salesforce and have been following the ride ever since, man. So this is going to be a fun conversation.

Kris Billmaier: That's awesome. You know, it's, uh, it's great to hear your background and so much has changed since you started with us. And I, uh, you know, the journey must be pretty, uh, amazing.

John Barrows: It's fan. It was fantastic to like be a part of, quite frankly, and also fascinating to now from the outside. Watch to see how Salesforce is continuing to lead, quite frankly in this space where it's getting real, real interesting. So we're going to get into all that, but I always start my audience off with the origin story here, my friend. Uh, and you got some, you got some real, uh, interesting Notre Dame baseball statistics that I want to get into. But even before that, before that, talk to me about where Chris comes from. Like, what were some of your influences growing up, parents growing up, kind of what, what can we learn about you without being, you know, that's not on LinkedIn. Let's put it that way.

Kris Billmaier: Yeah. So born and raised in, uh, San Jose Bay Area. Uh, my dad was in tech from the time I was born. Uh, and so I kind of have grown up with it. I remember going with him to the office, uh, on the weekends, uh, at Sun Microsystems, which is funny, it's now the Meta campus, uh, and, uh, and just kind of hanging out and just absorbing it all. And so that's kind of where I started. My. We moved up.

John Barrows: Just real quick, was he on the sales side or the. Or the tech side?

Kris Billmaier: Started out in sales, but I had a computer science degree. So, um, moved into the tech side, uh, and then became a founder, uh, and ran a lot of different companies. The CEO for Paul Allen for a number of years. So, um, I was kind, uh, of kind of born into this. So, um, a lot of good influences growing up.

John Barrows: All right, so that. Because a lot of times it's like adjacent so that. But this was spot on. This was like, all right, dad, like, I'm gonna kind of follow this. But. But I mean, obviously you're pretty damn good at baseball, right? Did you get a scholarship to go to Notre Dame?

Kris Billmaier: So got a scholarship to go to Notre Dame. Uh, was fortunate to do. So I never set foot on campus, uh, before my recruiting trip and.

John Barrows: Oh, no way.

Kris Billmaier: Oh, yeah, it was awesome. Uh, not. Not a legacy guy or anything, but, uh, I hope to build that legacy through my daughter going there hopefully at some point in time. She's only eight. Um, but yeah, love my experience there. Spent four great years playing with a bunch of great guys, uh, on the baseball team.

John Barrows: Love it. You're a Rudy fan? You like the movie or. No?

Kris Billmaier: I mean, that's my guy Cry movie when he gets in every time, you know, my favorite movie. It's a tradition in the Bill Myer household. You have to watch it before every football season kicks off.

John Barrows: I love it because I didn't know if that was a love hate thing for being there. Like, so you might be like, no, that was terrible. But no, I'm glad to hear it, actually. I love it. Awesome. Uh, so. And then you. I mean, you had some pretty good stats, obviously. I saw that you had almost a.500 batting average in the, in the NCAA tournament.

Kris Billmaier: 3 All time all Star, you know, uh, it got hot when it mattered. Uh, a lot about baseball's, A lot about timing, uh, and finding the. Finding the right time to get hot at the right time. And uh, somehow I always did, which was, which was awesome.

John Barrows: What were some of the things that you Took from that experience related to leadership. A lot of the stuff that you apply today, as far as, you know, seeing the field different or leadership or team Mark, what were some of those kind of key takeaways from, from that part of your life?

Kris Billmaier: Yeah, it's to me it's all about the team. Uh, and I, I, I'm one of those that like, I'd never try to put individual success over what the team can accomplish together. Uh, and it's funny when we hire folks, I try to hire what I consider to be athletes, somebody you could put a put on the field and they'll just figure it out. Um, but I think, you know, when you look at it, uh, the greatest thing that was ever said to me is the greatest thing you could ever be on a team is a great teammate. And so that, you know, that's something I carry with me to this day. It's like you build a great team, you work together, you win together. It kind of doesn't matter what you're doing, um, if you have that camaraderie, that teamwork and that win together kind of mindset. So I mean that's kind of the bottom line for me and everything I

John Barrows: do love, um, it, yeah, it's amazing. Like you could have the best product, best service, best fit and all that stuff. But if you don't got the right people on the bus, man, it doesn't very fast. But if you got the right people, you, all those other things might not even be great, but you can do some fantastic things. I always look back at the uh, this, the Sony. I don't know if you ever heard the origin story of Sony where you know, he just got together with a bunch of friends and was like, let's build a company. And they were like, what are we going to build? He's like I don't know, but we'll figure it out. And I think like the first their, their first product was a rice maker that, that burned up and broke and then their second one was like a heating pad and it like that they started to get some traction with that and then one leads to another and it becomes Sony because the core group had built there which was I always find fantastic.

Kris Billmaier: That's amazing. It's a great background story. It's a great uh, methodology for how you go into the world today, I think.

John Barrows: Yeah. So then you kind of got into it, right? So you started at uh, let's see, you were business development after that, right? In Comcast chart, you had some uh, was a Comcast Charter in Adelphi, Time Warner Cable with, uh, Diego. So you managed those accounts?

Kris Billmaier: Yeah. So the company was called Digio. Uh, we built, uh, it was back in the day of uh, early DVRs. So like dual tuner, record two shows at once, video, uh, on demand, all that. And so yeah, our job was to go out and try and, you know, sell into the cable market, uh, which, you know, not easy. A lot of, uh, entrenched embedded players and we were the new kid on the block. So that was a lot of fun. Did that for about three years. Uh, and you know, at that company was it was a startup, you know, about 150 people. Uh, cool thing about that was you're close to product and the, the team had built a really amazing product there that actually won back to back Emmy awards for outstanding user interface and experience. Oh, damn. And so the cool thing for me was I got to see how the, the sausage was made and that's where I really learned about product and design and, and just overall user experience and lessons I learned there. You know, still come with me today.

John Barrows: What were. Because you were selling against some pretty big dogs in a tough market. Brand new, what was, you know, and Salesforce back in the day was the same thing Cloud, nobody knew of. So what were like from a sales standpoint? What was your approach? I mean, obviously the product was great, so that helped. But being an unknown, going into a market with a bunch of knowns, was there a specific strategy that you and the team took to that or was it just like carpet bump, let's go right.

Kris Billmaier: Uh, it was a little bit of both. But the thing I always found that worked the best was get it. If you have an amazing product, get in, get demos. And what we always did was we'd meet with all the execs and then we put it in their house to make sure that they were living with the product and seeing the difference that it made. And you know, if you, if you experience something every day, if you're in it, you really see how it can affect others. And so I'm always product first. If you give me a chance to present to anybody, I'm not showing slides, I'm showing a demo and I'm talking about how this can change the way you operate.

John Barrows: So I mean, that was kind of the origin, like early days of PLG then, right, for you, like getting it, get it in their hands. So what are your, what's your take on PLG these days? Because I think there is a lot of like, I need to see this, I need to use this first before I'm going to buy it. So how's that deal? You know, especially in enterprise sales, that's not exactly the right, you know, the easy play because you can't just get a bunch of users free and then see what happens in the back of the day. So where, where are you at with PLG these days?

Kris Billmaier: So we actually launched a freemium experience, uh, at Salesforce about, I think it was back in March. Um, and you know, we actually, it's interesting because Salesforce, traditionally a sales led company, is trying to move to more product led and adoption focused. And usually it's the other way around. Right, right. Companies usually start product LED and then move it to the sales led. So it's something we're absolutely focused on, um, making experiences for users so users can try a bunch of different capabilities that we have and kind of tip into them easily. But I think we're almost at another inflection point, uh, to product LED growth, which is agent led growth.

John Barrows: Okay.

Kris Billmaier: How do agents and product experiences really unlock those capabilities for users? Kind of guiding you along the path, telling you what you need to do next. And from a Salesforce standpoint, I actually think we're moving to a place where, you know, conversation becomes the new customization and that will be very agent led for us, uh, in product, you know, out outside of product, outbound. Um, but I, I just, I really think it's going to be the center of everything. People need to try and experience conversation.

John Barrows: Because say that one more time. I think, I want to make sure.

Kris Billmaier: I think, I think, you know, Salesforce has been huge in terms of how we customize our overall experience. Right. But I think when you're able to start talking to the product and talking to agents in product.

John Barrows: Yeah.

Kris Billmaier: You're going to get to a point where the conversation you have with the product actually customizes the outcome.

John Barrows: Okay, cool. So where. I guess this is a different question that I was going to ask earlier, but I'm, um, curious now because I'm starting to see the unlock here with Claude and Claude Cowork and these connectors, like these MCPs. Right. Uh, where it's the connector and there was, I mean, I'll say there's been a few real unlocks with me with software. Right. Because you know, a lot of times when you're setting up these cadences and all this other stuff and you know, it's like, oh God, I gotta get in there, I gotta configure this and then I gotta Use it and all where, um, all of a sudden a connector comes in and I can just. Claude knows me. It knows everything about me. And I could just talk into it and be like, hey, could you go into that software, configure it, do all this other stuff? And so now I don't even have to go in there. So where is Salesforce in the. I guess I don't say fight, but fight for the user. I will say fight for the user interface. Because, um, I'm kind of starting to look into this and say, is every pick your AI platform one of the big ones? And is that going to be my world? Right, because we're all fighting for this. And I know Salesforce was kind of cloud and it was system of record. Great. So now we're going to live in Salesforce and then you have these tools like Salesloft and Outreach come out and say, oh, no, no, no, no. You could still keep Salesforce as a system of record, but we want you to live in our platform. And now you have these AI tools going on top of them and saying, no, no, no, no, you don't. Yeah, you can maybe still use those as systems record, but you really just need one interface. It's going to know everything about you and you can just tell it to go do what you want to do. That is agents. So where is Salesforce's strategy related to the clods and the open eyes of the world looking to be that interface that people engage with.

Kris Billmaier: So it's a great, It's a great question. Um, we want to be where our customers want us to be. I mean, we just announced that, you know, we're. We're effectively headless at this point in time. And, you know, customers have been using our APIs for years to build custom experiences with their data sets. And I think that that paradigm doesn't really change. The intelligence layer that, you know, the Clauds and the open AIs of the world have built shifts it slightly. But, um, we're really embracing the whole headless mindset. Uh, you know, I think about M where I innovate, Uh, I innovate enlightening, uh, in our traditional interface, but I also spend a ton of time innovating in Slack, because I think those default Slack experiences, um, where Salesforce is effectively the system of record, but also the system of intelligence returning into a conversation first AI layer is what people want. And we built an integration with ChatGPT as well. We just announced our integration with, uh, Google Gemini. We're going to be doing More and more with all of the different players where sellers live uh, and work. And my hope is that for people or companies who want to configure all of that and do all the work themselves and have Claude code stand up and take all their data and create amazing outcomes, you can do that or you can use the out of the box capabilities that we build on the same surface areas. And throughout this I think of Salesforce returning intelligent results based on a query. And that's what's most important to me.

John Barrows: So fundamental shift here, right. With Salesforce as a business model. Um, you went through that at Microsoft to a certain degree. Right. Because you were there for eight years and I think it was at the 365 to M M M365. Right.

Kris Billmaier: I was lucky enough to hit bunch of great timing at Microsoft where we had a lot of shift. So I started in uh, Microsoft in Office when we were just about to go O365 and that transition from on prem to the cloud was super interesting to be a part of. Um, and then I was there for another shift which was the whole company kind of focused on Azure and platform and you know, spinning meters on Azure with all of the apps moving to the cloud and driving those consumptive um, methodology. So um, yeah, I was there from Office 365 to Azure to M M365 and got to see a lot of it up front.

John Barrows: What was harder, the internal shift or the external shift for that? Uh, and when I say that like the internal shift of Microsoft and how you ran business and the positioning and the messaging and the shifting the sales team and all that stuff versus the customer shift and getting them to shift from on prem to cloud. Like what was more challenging? I'm um, obviously both but I mean that's the answer.

Kris Billmaier: Yeah, well, but you know, I think internally, uh, you know this is the, in the Wayback Machine, but internally for me it was always like we understand the shift and we understand that this business could get disrupted if we don't disrupt ourselves. And I think the best companies do that. I think when these major shifts happen like on prem into cloud and mobile and social and Agentix and Generative, uh, in each one of these phases the best companies adopt understand that they're going to have to cannibalize something but at the end of the day will come out ahead because you've adopted this new business model or this new mindset on how products are built and shipped.

John Barrows: So then let's not relate that to the SaaS world now, right? Because one of the things that you hear all the time is SaaS is dead, right? AI is going to eat SaaS. It's like why, you know, the models run, the pricing model's wrong. It's about consumption now and it's so much easier to build versus buy. So you have these, I think the sales forces and the bigger ones of the world, obviously you have a moat, right from a customer standpoint. You also have the investment in the technology to, to make that shift. But like mid market SaaS, there's kind of a panic going on in Mid Market SaaS right now because you have a lot of these companies who are in a lot of ways putting lipstick on a pig, right? Like say, yeah, we're AI, but it's not like it's just maybe an Interface with, with ChatGPT or something like that. So how do, how does, how do companies make that shift in a real way? And I guess from your standpoint with what you're seeing with AI right now, is it, is it a fundamental shift in like, do they need to rebuild the like in this new way world or is there a transition phase here where they can leverage AI to make this transition into whatever this new model is?

Kris Billmaier: I think it's kind of company dependent, frankly. And I think there are companies that right now you're seeing companies that are adding a dock AI and then there are companies that are embracing AI entirely. And I think if you're not embracing AI entirely, there's a potential for some pretty significant disruption to your business. From our standpoint, the way I think about it is we created great SaaS applications. Uh, I am now entirely rethinking them, um, in an AI first world. And I look at everything we've built and I'm saying, you know, if you're not AI native and AI first in all of these capabilities, you're going to get disrupted. But I look at it as like, there are three things in the sales process that will always remain true, right? You need to grow pipeline, uh, you need to grow ad deals and you need to grow revenue. And the way we've done them in the past has been, you know, sometimes messy, sometimes manual. But those three things are going to persist. The way we accomplish them is going to change forever. And so when I think about the top of the funnel, I think about inbound and outbound. And really what's the outcome that we want? Well, we want to create pipeline, we want to get meetings with individuals, we want, uh, qualified leads, and we want our Sellers to be entirely ready for those meetings to walk in on day one and make it feel like day 100. But as I think about the top of the funnel, all of that can be accomplished agentically. Uh, you shouldn't have to touch that. The old way of booking meetings, I think, going back, I mean, you know this. Like, how many times in your career did you go back and forth with a customer? 4 hours over email to try and book a meeting. What a waste of time. Yeah, uh, just set an agent on it and let it happen. And that's what we're doing. And we're building those out of the box for our customers.

John Barrows: All right, so I skipped, uh, to the questions I really wanted to get to here, back into some other ones, because I agree, um, and that scares the shit out of me, quite frankly, because especially with what Salesforce has created, this model, we talked about it before we jumped on here, you know, the predictable revenue model, the segmentation of roles, the SDR BDR AE segment, you know, se. You know, what you're talking about is the SDR BDR role basically being automated 100%. And it can be. And I look at the inbound specifically as far as speed, delete, you know, speed to response and insights and all those type of things. So if you're a, uh, sdr BDR right now, and you're seeing this trend with this stuff being more personalized, faster, better. Some of these are even making phone calls and having real conversations with people, qualifying them to a certain degree. What. What are you telling your rest? What? Well, let's go direct. Like, what are you telling the SDRs and BDRs at Salesforce? Right. Forget about everybody else. But, like, what are the SDRs and BDRs at Salesforce doing right now to level up so that they don't get replaced?

Kris Billmaier: They're using our agents. So it's really. This is a really interesting story. So we at Salesforce, we have, uh, our lead scores 1 to 5, right? So when we get inbound, um, 3 to 5 are our highest. They go to a human, uh, SDR because they're higher than yours. For years, our ranking of 1 and 2, we didn't touch them because we didn't have the human capacity, uh, to show up and actually handle that leap volume. But that was 75% of our lead volume. Yeah, yeah. So what we did was we said, okay, what we're going to do is we're going to assign our engagement agent to follow up with all of these ones and twos that have never been touched in the past. And it's what it's done. It's crazy. It's generated over $100 million pipe in the last eight months and it's closing ACB, but it's augmenting our SDRs and it's augmenting our SDR leader. So our SDR leader now manages the team of like 100 individuals in the equivalent of 400 SDR agents. So to me, the SDR and BDR role, it's about learning to embrace a team of agents to make your job more efficient and effective and turn you into a 10x seller.

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Kris Billmaier: and, and I'll one more thing. I'll tell you the woman who leads our SDR team, she told me, you know, when SDR comes out of college and they're hoping to make 12, 15 phone calls a day and they're making three. And they're making three because they're spending all their time prospecting or sorting through the inbound garbage that comes in versus understand where to leverage agents and understand that the human to human connection is the thing that's going to matter most

John Barrows: in qualifying those leads and help me clarify qualifying from your perspective, right? Because there's a lot of qualification that happens even before they hit. We have this conversation, right? I mean we could look at intent, we can look at their profile, we can look at all these things and see how they are. So a lot of us, uh, I mean, I think three of the most insulting things you can say to a prospect at this point, tell me about your business, Tell me about your priorities and what keeps you up at night. Those are three of the m. Most insulting things I think you could say to somebody at this point, because it's so easy to figure that out. So talk to me about qualifying and what is that experience? And let's say on the inbound, right, uh, what does that experience look like? What does that rep come to the table? Those three, those three fours and fives, right, that are high qualified, intent driven. Is it. Is the rep now taking that and booking the meet? And the meeting's already booked and they're coming with insights or they're following up, they're doing the research. Help me understand that. That value right there.

Kris Billmaier: So it. It. I'd say it depends. But in the, in the, in the highest value cases for us, we've understood and had a conversation with the prospect via an agent in advance. And so we know enough about that to build an account plan and probably do background research, uh, already through our agents that are actually prospecting to build that kind of. Call it a point of view document or a meeting prep. So that when the meeting is booked, hopefully by the agent and not by the human, that the individual can walk into the meeting and say, oh, here we are. I know everything that I need to know. Um, I know the five questions that I actually need to ask without doing the cold prospecting that you're talking about. Tell me about your business. Like all the things the web knows that you don't need to know, and all the things that the LLMs know that we can just build a document around. And that's exactly how. How we're trying to operate in the best case scenarios.

John Barrows: What percentage. You know, there's a, There's a Gartner stat that came out back in 2022 about how on average, 43% of people want a rep free experience. But they wanted a 23. But they had a 23% higher regret rate when they bought. When they didn't talk to a human. I think that number is now up to 67% of the people want a rep. But when they. I think the new version of this is when they do talk to a rep, it's a 1.8 times higher close rate. So it's a closing. It's not a regret rate anymore. It's a closing rate. Where are you seeing the shift of. Of or where are you seeing the inflection point of people still wanting to talk to a human and, and being like, you know what? I can, I can do this with either the agent or, or Claude or whatever it is. And the reason I say this is because the. The history of Salesforce was, well, the history of the cloud, right? At first the cloud came out. Or like, let's even talk about old school, like credit cards, right? Like, at first it was like, put your credit card on one of you out of your mind. And then it was like, all right, if something's like 10 bucks, M. I'll throw my credit card online. And then it was like, okay, 50 bucks. And then, uh, like, I bought a Tesla online. You know what I mean? So it was like, okay, never mind. Same thing with cloud. Oh, it's cute for small businesses. But then State farm, you know, $150 million broke that barrier for Salesforce is like, no, the cloud is here. Where are we right now in that phase of people being comfortable buying from AI? Because this is my biggest fear of this entire shift that we're going through. It's not the sales automation, it's not the tools that are replacing sales reps. It's when the client wakes up and realizes they do not need us because they can get better information. And one more piece of context. You know, I had. I had this conversation with somebody like, oh, no, no, no, no. You know, good sales reps always know what kind of questions to ask. So, okay, hey, uh, Claude, could you act as the best sales rep from salesforce.com and ask me the questions that I don't know that I should be asking myself? Like, it. It's kind of a hard argument right now. And I know like SMB, there's. There's some personal components to this, but is there a dollar figure? Is there a complexity? Is there a piece where you're just like, no, this is still where the human matters and where people are not comfortable. Just auto buying, whatever.

Kris Billmaier: Yeah, I think. Well, I think it always depends on the human. I think there are early adopters to shift into the. You know, I just want to throw my credit card down to your point. I just want to buy online. I just want friction free experiences. I mean, we've been there for years now, right? I mean, but. But to me, buying online and getting educated is. Is something that, you know, that a lot of people already do. Does it become easier with Claude and chat? Yeah, sure, absolutely does. I think there is a dollar value. Uh, but I think there also is just kind of an overall experience that you want. Like when you bought your Tesla online and you followed up for your first maintenance, you know, that account that was built the Understanding of you. There's moments in every buying cycle where an individual needs to insert themselves. I think whether it's post acquisition of uh, a Tesla or a tool online, there's always going to be that mindset and moment when somebody wants to interact with somebody else. At least that's my point of view. Um, for me, I'll give you my, my personal, like if I'm going to make a big purchase, I want to talk to somebody and I think it's beholden upon the rep at that point in time to make sure that the engagement with the customer is of high value. Because what you're talking about when you're going back to is like, don't ask the canned questions, be prepared, understand who your buyer is. Uh, and I think the tools that we're providing are really enabling that because I, I think that is, that that's the key for sellers. Understand the tools, understand the capabilities and when you get that at bat, have the highest quality experience with the buyer you possibly can.

John Barrows: And, and I'm gonna bring this up, we talked about it before and this is where I, I agree. And, and again, I'm scared. I agree. For guys like you and I, man, you know, we've been there, done that. I, you know, we put in the grind. We, we did the manual stuff, right? All the, all the stuff that gave us the context for you and I right now to have this conversation without a scripted list of questions and you know what I mean? And, and so I can be dynamic. I can look at AI and say okay, yeah, that needs to be automated. But this doesn't. I can call BS on AI when it bold face lies and I know it, even though it sounds awesome from uh, you know, but the 20, I keep coming back to this, the, the entry level, you're hearing all the stuff and still looking about like entry level jobs are over like, and, and it's hard to argue that they're not. So how does, how does that 22 year old kid gain the like Again the question what uh, are the fundamentals anymore? And, and where they come from. And yes, we can use AI to be smarter, but if there's no context of the why, which is what I'm personally trying to train reps is, I'm trying to train them back on the, on the fundamentals and the why behind the outcome output. So when they get that kick ass email, when they get that awesome prep doc that has some great questions, they understand why they're asking them. They're not just asking them. So how Are you enabling that at ah, Salesforce right now for the younger generation to get that context, to understand the why so they can have a valuable conversation that isn't just reading what AI is telling them to read? Because it's a great question to ask. Chris.

Kris Billmaier: I think learning is different now, right? I mean I think if you go back to like how you learn to sell.

John Barrows: Mhm.

Kris Billmaier: I actually think if we, I haven't done this, but I think if we did a compare of like how guys like you and I learned how to sell back in the day, you probably take what we did in three years and convert that into two months. And I think like the context and the insights exist.

John Barrows: I think. You don't think, you don't think the door to door, holy crap. Like walking the streets, getting thrown out of offices, getting, you know what I mean, Sitting face to face with somebody off a zoom, um, reading body language. You, you think that can be truncated into two months versus three years?

Kris Billmaier: I think maybe not two months, but I think we're on a much faster adoption scale of understanding the bad beats and understanding like the why I screwed that up. And I think about like we built a product, um, it's all about coaching. So you sit in front of an AI and you talk to it and you give it your pitch and it gives you your feedback based on the knowledge of the account and all. Uh, so I think the, I think your point about context is very, very spot on. And I think what we're doing is we're taking that context and we're leveraging it to skill our sellers up so they don't have to establish the context themselves, if that makes sense. But I do think it's a, it's a challenging time. Like we're, we're bringing folks in and you gotta learn fast. But we're still hiring a bunch of reps. So I mean that's not changing for us. We just think about our reps being 10x reps. Now

John Barrows: let's go back to the hiring piece that you said before as far as team and what you're looking for. Great teammates. Has the profile changed in your experience from pre AI, if you will, to now AI with the sales. So are you looking for different characteristics now than you were looking for back before AI really kind of took over here?

Kris Billmaier: I don't, it's a really good question. I don't think so because I've always been looking for are people who are curious. We're going to use the latest and greatest tools to their advantage. We're going to figure out how to augment themselves in order to be, you know, A players. And, you know, we, we talk about hiring. I, like, people say, do you want an A or B player at certain times? I was like, I only want A players. Yeah. And so if you can be an A player in this world, understand how the technology around you can affect you and embrace it, uh, like, without fear. I think those are the kind of people we're looking to hire.

John Barrows: What's the conversation a sales rep has to have right now in an interview? Right, Because I had a buddy who was, uh, you know, he was out of work for about a year, right? And. And I, you know, not as, you know, directly connected all the time. So I got caught up on a couple times, didn't know what he was going through, and come to find out he was literally looking for a job for a year. And he was an accountant, um, and he wasn't a cpa, he was an accountant. And he was kind of looking. He was like, yeah, I've sent out hundreds of resumes and, you know, whatever. And I said, where are you with AI? And he goes, well, you know, I use it. Update my resume. Oh, shit, Jeremy. I'm like, oh, God. Okay. Um, I go, here, I know why you're not getting interviewed in jobs. I go, you need to walk in and be like, hey, um, I get it. I've learned, actually 80% of my job is irrelevant. I can automate it all with AI, but the reason you're going to hire me is for this 20% here, because my experience and everything else. And if you can't have that conversation, right, you're. You're not going to get past, you know, the screener at the end of the day. So from a sales rep standpoint, how much of their, like, what do they need to show in that interview for the curiosity and those type of things. But as it relates to their aptitude with AI versus just answering really good questions, you know, that. About how they would approach, uh, an account or something like that.

Kris Billmaier: I mean, I think the being totally prepared and having great answers to hard questions is, you know, that's fundamental and baseline to every table sticks, you know, regardless of AI, uh, when I think about hiring great people, I think about, like, how are you going to show up and tell me something different, uh, than everybody else? And so what's your key differentiation? And in this world, maybe it's, what's your key differentiation with AI? Have you built, you know, your, your own SDR agent? Right? That can handle things for you. Like, are you bringing two of you into a job versus just you? Like, uh, those are, those are interesting conversations to have because, you know, when you talk about, like, how would you handle creating pipeline, I wouldn't ever want anybody to tell me, yeah, you know, I'm going to go on to LinkedIn and I'm going to, you know, do this and that. It's like, oh, you're gonna, you know, you're gonna create your own pipe agents, uh, or you're gonna use a pipeline agent that, you know, Salesforce or somebody else built for you. But going in and having that educated mindset about how the job is actually already been augmented and where you need to shine to me are like the key things that have changed but kind of stayed the same a little bit.

John Barrows: Yeah, true. All right, let's shift to the customer.

Kris Billmaier: Yeah.

John Barrows: Um, and this transition customers are going through right now because the things that are common themes that I talk about a lot and think about a lot are this whole indecision phase that we're in. Right. I talk a lot about Challenger, uh, sale, challenger customer, and the book jolt effect. How I think the book jolt effect, I think it nails the problem we're all faced with right now. I don't know if it nails the answer, quite frankly, but the problem of everybody says no decision is the biggest competitor, uh, of all sales reps. But it's actually indecision. And the reason is because things are moving so fast right now and there's so many options that people are just scared to make decisions. So with that, and you layer on the MIT study and however flawed people might think It'd be like 90, whatever percent of AI initiatives have failed, you look at all these stats that AI, AI implementation has, has a false promise here, right? It's promised all this efficiencies and this revenue, but most companies aren't seeing it yet. So how does a company make a decision right now in this world of AI, to A, make a decision in this very complex, fast moving world and B, do it so that it's, it. It actually makes a difference? Because I, I'm seeing a lot of companies just be like, all right, uh, here's Claude. Giddy up, go to work. Right. Uh, what are you seeing the successful companies do to make this transition with AI?

Kris Billmaier: It's going to sound overly simplistic. Um, it's something we actually went through. It's identifying your key use case, like narrow. It's not. I want to work all my leads tomorrow using an Agent, it's okay, let's get specific. What segment are we talking about? What are we trying to accomplish as an outcome? How are we measuring this and actually treating these agents like a new employee? And how would you train that new employee? So for us, when we look at this, wherever I go in front of the customer, my whole thing is, okay, what's your use case? What do you want to measure? What does success look like? And what's our training plan for this agent to actually learn and be efficient and get the context of your company. And I'll say, when we built our first sales agent, uh, at Salesforce and we deployed it on our website, it was the product, me and the product team, it was uh, representatives from our sales team, representatives from our marketing team and our IT team, all working together in one group to define those capabilities and characteristics. And then it was somebody's job to make sure this thing was learning, was understanding, was writing better emails, was being measured against itself, but against humans and against it. And so I really think it's about like your use case, your discipline, your, your criteria setting, treating this like a new employee who needs to be trained and making it somebody's job to continually train it. And so that those are what have been successful for us. Um, and the onboarding is incredibly important, but the decision making up front is critical.

John Barrows: And where does the, how does the sales rep fit into that equation? When 80 plus percent of the buying decision process experience is, is being done without them and probably 80% of the buying committee is people they don't even know. So, so where like, I guess once they're like, let's call it discovery, right? Uh, you know, okay, we get good discovery, you know, prep for the meeting, you and I have a call is great. Let's try this out. Next steps. All those things that happen behind the, behind the door, right? What is the, what is the sales reps positioning now of value and how they stay engaged in that process to try to add value throughout? Because I think it's, it's really hard to guide the process these days when there's so much that people can do internally. Especially if you give them playing, you know, around with agents, let them to build their own stuff. So how are you, um, coaching reps or how's your team coaching reps on how to add value throughout without being a, uh, hey, uh, I'm still here, I'm still here, I'm still here. And without obviously the other flip side of that is having a very detailed mutual action plan that everybody agrees to which is obviously the best case scenario. But, you know, that doesn't always happen.

Kris Billmaier: I, we like to talk about being strategic advisors. Um, and by the way, this isn't just a seller's job. Uh, I think it's a team's job to like, we have product, we have sometimes for deployed engineers, we have sellers all thinking about what's the customer's goal and how do we help them get there. You know, kind of, uh, I wouldn't call it a mutual, uh, action plan or an agreed to action plan. I would say that you have an agreed to set of scenarios that you're helping to bring strategic insights based on either your own experiences, your company's experiences, or your other customer example experiences to build that credibility. And so I think it's, I think it's about getting in there sometimes not selling, sometimes just advising, uh, and being that expert. Because while a lot of people can play around with AI and trying to build agents, you know, your MIT survey, it's 91 failure for a reason. Yeah. Uh, because a lot of companies try and go it alone versus embracing teams and people who've been there who understand it and who can be that strategic advisor along the way.

John Barrows: Yeah, I think it's that, that's the part. It's almost, you know, I, I went from believing in the past that sales reps can, you know, be the generalist, right? Where it's okay, I, I'm the quarterback. I'm bringing all these pieces together and I'm, I'm helping guys, I. The process and helping you buy. Right. But then when AI first showed itself and I was like, oh, now, you know, 70% of the rep, you know, clients know before they even talk to us. So the client's so much more educated now. We actually have to have deep product knowledge. But then I backed off of that saying, well, actually, not really. We just need to know how to use AI and actually almost learn out loud with the client. So instead of me saying, actually, Chris, I don't know the answer to that question, let me get back to you, or let me pull in, uh, uh, you know, somebody else. You know what, let's just open up the agent right now. Let's, let's ask it some questions, let's figure this out together. Right?

Kris Billmaier: And great statement. I love that. Ah, learning out loud. That's awesome.

John Barrows: Yeah, that's my, actually that's my, my, uh, my whole, uh, newsletter, uh, and everything is called the JB Sales Learning Lab. And it's all about just learning out loud because I know I'm not the smartest kid out there, but I got enough access to some smart people and I'm just going to learn out loud and, and see what happens and, you know, hopefully figure out some stuff along the way.

Kris Billmaier: I mean, I think that's the mindset, right? We're learning out loud together because I mean, there's a lot of depth and a lot of knowledge in these areas, but it's that kind of mutually learning together as we embrace all these new technologies that's going to kind of win the day. Uh, so positioning like that, I think

John Barrows: is phenomenal and it hopefully breeds a little bit of trust, right? Going back to that trusted, you know, trusted advisor, the consultant. So with the knowledge piece, I mean, it goes back to when knowledge is a commodity at the end of the day. And you said you got a nine year old, uh, is a daughter. He said, yeah, I got it. By the way, after this I got to get your address. I'll send you one of the books I wrote with my daughter. Uh.

Kris Billmaier: Oh, awesome.

John Barrows: I wrote it. It's called I Want to be in sales when I grow Up. Uh, yeah, so I'll say. But, but, you know, knowledge is a commodity at this point, right? I mean, it's. Any one of us can have the smartest whatever on our, on our side. So, you know, iq, eq, everything. So with what you're seeing, how are you thinking about? And I know this is a long leap, but we're gonna go backwards. Um, how m. Are you seeing this evolve here? Like, my daughter's 15.

Kris Billmaier: Yeah.

John Barrows: I don't know if college is gonna be a thing in the next couple years here for her. Right. I want the college experience for her because I want the social component to it, the EQ side of it. But to drop 80 grand a year, uh, to get a $50,000 a year job like that is going to be irrelevant like that. I doubt that. Like that ain't happening. So I guess what are you doing now for your daughter? Seeing what you're seeing with all these agents and knowing right now at 9 years old, you kind of have to learn how to learn, right? So AI can take a step back for a minute here, uh, because you got to develop the brain and how critical thinking, all that fun stuff, but I guess what are you seeing the future for your daughter when she gets into this world of ours?

Kris Billmaier: That's a big question. Uh, but you answered the first thing I was going to say, which is learning how to learn. If you can learn how to learn and you can always be curious, uh, and evolve how you think about all the tools that are in front of you that can help you be more effective. Uh, I think that's the first step. Um, second step for me is it's kind of tied to the EQ thing, but it's also encouraging creativity because I think we still need creators, we still need builders who think creatively and can put these tools to use in the absolute right direction. So to me, I think, uh, it's the threefold. It's strong eq, learning, how to learn, and how to be a creative individual. And I think that, you know, it's not. It's a pretty simple answer, but it's the one that I'm sticking to right now.

John Barrows: Yeah. And I mean, look, I agree. And you know, it goes to like, uh, I asked this question a lot is, you know, curiosity, for instance. I believe it's the superpower of the future, Right. It's like if you're curious, the world's, you know, your oyster at this point. If you're a creator, the world is you. I mean, do it right. The challenge I have though is that, uh, I, and I think I've come to this conclusion that you were either born cure natural, like not fundamentally naturally curious, or you're not. I think you can become curious in things, but I don't, I don't necessarily know if some people are actually born naturally. Everybody's born naturally curious. I think there's a portion of us that are. So with that curiosity, like, how do you foster that? Because my fear is. Or here's my optimism, optimism, pessimism, My optimism is for right now. If you are a creator and you are curious, like I said, like, oh, my God, it is unbelievable what you can do, what you can create, what you can build. But for the people that aren't kind of the status quo people, the ones who are just, I just want a job. I just want to do my thing. I'm the B player, right? A B player thing. I'm the B player that just. I am terrified for those people. So how do you address that? Because I think that's a much larger part of our population. And I'm not just talking sales, I'm talking our macro environment here.

Kris Billmaier: Don't you think that, uh. Let me get it back to you real quick. Don't think that. Well, I mean, I don't think we ever stop evolving in how we come to things. And uh, I think the next evolution is to that curious. And it's a lot about how we're raised and a lot about how we think and a lot about the, you know, socioeconomic things that surround us. I think my guess is by nature we become more curious because that's the way that this next generation is going to be raised. Because their parents were, you know, ingrained integration with AI that, that we had to learn. It was thrust upon us. Now my daughter and your daughter, they're like, no, we're born in AI and that promotes that curiosity and just a different mindset and a different view of the world. So that's my hope anyway.

John Barrows: That's my hope too. It's just, it's kind of like we live in the tech world, right? And I mean, I'm at least here on the east coast in Boston, so it's not as bananas as it is in San Francisco. Cisco and always has. But I, but I always joke, you know, for me as a sales trainer and doing what I'm doing in SaaS and tech, and I'm like, oh my God, like, uh, I'm like I'm, I'm getting behind, right? And then I realize if I pull myself out of SaaS and tech, it's like sales 1985 all over again, right? And so, so same thing with a creator. It's like, oh, we're all creators here. Look at all like, look at the vibe that we're all in these, you know. But then you go to, you know, middle America to, you know, the, you know, and it's just, I'm doing my job, man. Like I'm just got the same damn job and doing it for years. Uh, you know, I like my 9 to 5 so I can go to my kids and do my thing and whatever. And the displacement there I think is coming faster than anybody knows because the 1% are the ones that are paying attention to this and how fast it's moving and all the things it can do. And I think that wave is going to hit a lot harder to the mass population than any other wave has. And I'm trying to figure out how to bridge this gap for people to help them understand the urgency and the opportunity without the panic and the pessimism of the Terminator. We're all gonna, you know, universal income, all that crap. So any kind of parting words to, to give comfort to non sas tech leading, you know, people out there that are listening to us being like those guys are crazy, you know, whatever, it's, you know, go from there. So any, any parting words for that group of people to say how, what to do right now?

Kris Billmaier: Well, I think people like you and I are definitely in it. We're definitely feeling it. We're definitely feeling it more than, than most. And a lot of things are moving very fast. I'd say the things that are moving fast and I, I think at times we're out ahead of our customers. But I, I think it's embrace the tools that are around you, uh, and, and don't be fearful of them because I think the tools that are around you and the tools that companies like Salesforce and others ship and that, I mean, our customers are the smallest of the small S and B to the largest, largest enterprise worldwide. If you embrace the tools that companies like us can provide, I think it's going to help you learn, I think it's going to help ease fear and I think it's going to help you do your job a heck of a lot better and give you the time back to make you way more efficient and way more growth oriented. So I think it's an embrace it moment. Uh, and, and yeah, I mean that's kind of what I'd, what I'd leave it with.

John Barrows: It's funny because I think that half the value I bring to the table right now when I do training is literally waking people up to how easy this actually is. Because previously it was like, ah, dude, I don't know, you know, I like, I gotta figure this out now. It's like, turn the microphone on, man, and just start talking to it and see what happens. Like, this is because I, I've trained a bunch of old dogs, you know, like older than me, like 50 and plus. And like, yeah, yeah, yeah. I get this whole AI thing. It's, it's adorable, right? I'm like, guys, can I, I can I just show you something? And I'll, and I'll light the microphone up and I'll be like, hey, um, prepping for a meeting here, here's the company, here's the person. Could you go do deep research on them? Put together a brief and an agenda and some questions that I can ask and my hypothesis on how I can help them. Right? And then, you know, 30 seconds later, boom, it shows this beautiful. And you see these like, whoa, wait a minute. And, and when that happens, it's like almost you got woken up from the Matrix. It's like, wait a minute, what? And I did a blog post about three weeks ago called I know Kung Fu. And it's when I made the switch from open, you know, from ChatGPT to Claude Cowork and then I saw what Claude Cowork can do and I was like, there's nothing I can't do. And I, uh. And that was an unlock for me. And so I'm really trying to get that unlock for people who are sitting on the sidelines right now and just like, hey, just start playing with it. Just start playing with it. Because once you do, you're going to see what, what it can do and then you can use it for good. Because everybody's all scared about what, you know, people are using it for bad and layoffs and it's like, no, there's so much opportunity right now to use this in the right way. Um, it's just we gotta wake some people up to get there.

Kris Billmaier: Don't be afraid of it. And we're making tools that make it super easy. And so that, I mean that's my goal is like, I'm gonna give you the tools to augment you to make you a 10x seller and I'm gonna do so in a super easy way. You shouldn't be scared of it. Just go embrace it.

John Barrows: All right, last question. What's next for Agent Force? Like what's on the. What's. Uh, I mean, you know, obviously, you know, you don't have to spill any beans here as far as what you can't. But any, any what's, what's next because you've, you've up, you know, you figured out the agents and kind of the model and yeah, we got to sell that and transformation of our clients. What's the next kind of big wave for Agent Force and Salesforce? Obviously now pretty much that it is.

Kris Billmaier: Yeah. For our, for our agent for sales product. I mean, I think it's really about sellers managing teams of agents. Okay. And managing teams of agents that they can observe and they could jump in when things are going wrong. Um, but I really think it's about how that whole sales process gets very streamlined. Sellers get up leveled and they become kind of the strategic relationship advisors and strategic revenue orchestrators, frankly. Uh, and kind of that's the world I see us going into and that's the technology that we're building. And I think it's really exciting, um, to where you're not going to spend 70% of your day doing the busy work. You're going to spend 100% of the day on the things you want to do, which is engaging the customers.

John Barrows: Yeah, that. So are we, are we headed back to full cycle effectively? And, and the, the, you know, the desegmentation of roles that predictable revenue created.

Kris Billmaier: I, I think it's going to be dependent upon how the company operates. Um, but I, I'm of the opinion that we're moving m more into strategic relationship managers that have the team that you're talking about right now underneath them and work. Cool.

John Barrows: Awesome, man. Well, it is a, it is a ever moving world and obviously you're right at the tip of it here. So, uh, I'll be interested to, you know, if we reconnect here. And I was in shoot, I was going to say six months, but maybe six weeks and see what happens.

Kris Billmaier: But how fast it's moving. But yeah, we'd love to reconnect. And, uh, thank you for this. This was, uh, a lot of fun.

John Barrows: Yeah, absolutely. So, Chris, tell me, tell, uh, the audience where they can find out more about you, what you're working on. Stay on top of agents, force and, and that type of stuff. Uh, where can we find out more information?

Kris Billmaier: Yeah, if you just go to salesforce.com, uh, you'll see everything that we're working on. We're very transparent about it. You can follow me on LinkedIn. Chris Billmeyer. Uh, and uh, and I'm always posting about the latest and greatest innovation from us. Uh, and yeah, thanks again. This has been awesome.

John Barrows: All, uh, right, very cool. So, been a pleasure, Chris. And uh, let's definitely stay in touch and see how this stuff evolves because I am, I am very curious and again, I'm, um, balancing between optimism, pessimism on a daily basis, almost on an hourly basis of like, oh my God, look what it can do. Oh my God, it's going to replace all of us. Oh my God, look what it could do. Oh my God, I was replace all of this. So I'm, I'm trying to find the balance here and I appreciate your perspective on this because it definitely helps.

Kris Billmaier: We got it. Thank you.

John Barrows: All right, everybody. Well, I hope you enjoyed this conversation as much as I did. Like I always say at the end of all these podcasts, go out there and make somebody smile today, because no matter how bad your day is going or how bad you think it went, if you make somebody smile, you know you had a good day and the world needs a lot more of that right now. So thank you all, all very much, and I will see you on the other side.