Voiceover: What does it take to stay ahead in B2B SaaS? Welcome to The New Go-To-Market Playbook. I'm your host, James Kaikis, Chief Revenue and Experience Officer at Testbox. In our interview series, I sit down with go-to-market operators, leaders, and industry experts who are defining the next era of go-to-market by winning in the margins. These leaders are focused on incremental innovations and non-obvious advantages that drive big results. The goal of this interview series is for you to take action in your business. So sit back, grab a notepad and enjoy the episode.

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James Kaikis: Jesse, it's good to see you. 

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Jesse Dailey: Yeah, nice to see you too. 

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James Kaikis: I'm excited for this conversation because we've known each other for quite some time. You've been very influential in my career and my PreSales Collective journey. But also you're doing some really great things at People.ai. And one of the funny things is when people talk about solutions engineering and solutions consulting and some of the things I talked about at PreSales Collective, I am glad to say that I borrowed the term “co-pilot” from you. 

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Jesse Dailey: Yeah, I mean that's like, I've always been a big advocate of the PreSales profession and like, SEs need to have ownership of the process and that's why I use the term “co-pilot.” Like the thing that bums me out is when you have SEs that are basically like paper pushers, like technical support answerers. So like I've always sought to like uplevel my teams and the profession as a whole. 

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James Kaikis: Yeah, I appreciate that you've done that. And I really like calling it “ co-pilot” and I think that it allowed for a change in methodology of like I'm not an assistant to the sales person, right? Like I'm a partner in crime and sales and I love that you've called it that and it stuck with me. 

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Jesse Dailey: Thanks for that. Yeah, of course, happy to give it to you.

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James Kaikis: Let's talk a little bit about you.You've been in solution and profession for quite some time. So tell us a little bit about your background, but really, you know, your current role, your title, and let people get to know you. 

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Jesse Dailey: Yeah, so I'll give you a quick overview of my career. So I spent 10 years at Salesforce. I was an SE over there, kind of worked my way up through the ladder. Later on in my career at Salesforce, I was running the demo engineering team, so responsible for all the go-to-market demos, which was honestly a really transformational thing for me because I was able to understand the mechanics of running a large go-to-market SE team and how you scale all this stuff. I was just at Dreamforce. And one of the things my team built was the scheduler for all the people at Dreamforce. It's like all the SEs and all the booths, it's like 300 demo stations, three shifts a day. It's like 1,500 - 2,000 shifts throughout the entire time that need to be staffed. So like, it's all these like little things you don't think about that like with larger companies, there's a lot of scale that you have to get to. And that led to solve the demos too, as I'm sure we'll talk about. 

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James Kaikis: That's awesome. And so after Salesforce, you made a couple of stops at a couple of great companies. Where else did you go? 

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Jesse Dailey: So I ran the North America SE team at Mixpanel. I ran the SE team at Talkdesk and most recently I've been at People.ai for the last six years. So yeah, I've had quite a run over there and the story is I started out running the SE team. We were a million dollars in revenue, just barely getting started as a company. But I really believed in the vision and like I still do, it's a very compelling vision. Sort of like a little early and then all of a sudden at the right place at the right time. Throughout my career at People.ai as there's been changes throughout the organization, I've also had the opportunity to take over customer success, customer support, customer training and a lot of other functions. So I found myself running a lot of different parts of the company. And I think it's because I proved myself as an SE leader, gained the trust of the leadership team and was able to expand my scope and sort of, when those opportunities come, you have the choice. I can take this risk, or I can stay with what I'm comfortable with, and I almost saw myself as a risk taker, but my career didn't show that. So I wanted to prove to myself that I could jump into other areas and run it, which I think I've done and I've done it well, I would say. I hope you would feel that way. 

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James Kaikis: Yeah, I love that. And we've talked about risk a lot throughout these conversations but I really appreciate that you've just said that because you have been part of like my research and my research study on this aligned function because you are one of the first people that I've talked to that took over that type of role and learning why you took it over and what impact it made on the business was always super intriguing to me and I have a lot of people who've reached out to me because I actually did a presentation earlier this year and I quoted you and then and quoted some of the function, and people are like, let me get an introduction to Jesse. I'm like, I can't give any more introductions to him, but I'm going to record an episode and talk about this. So I want to dig into this. So, you know, I appreciate that you are a risk taker and you said your resume didn't show that, but what did you do within People.AI where they were like, you know what, Jesse's been in solutions, but he can oversee these other functions? 

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Jesse Dailey: I'll tell you what it was. I think there's one key thing to this. Well, I actually don't get to do two things. As soon as I say that. Okay, I think one key thing is I really understood our customers. And when there was something that had to be done with our customers, they’re like we need Jesse and the SE team in our customer base. So I did not focus purely on PreSales. I understood that, and this was contrary to some of the models I'd seen deployed, but at a startup, and I think in general there's a shift, we'll talk about some of the shifts that are happening, I think there's a shift towards teaming on accounts cross-functionally. And the SE's job is not done when you … Or at some organizations, and that’s People.ai included, your job is not done when you close the deal. You'll just throw it out to a partner and walk away, it's like you need to stay with that customer to some extent. There's a load balancing that happens in there. So my team and myself, we were coming in, helping our customers if an account started to turn red, we'd be there to help turn them back to green. So I started to really understand the customers. I think that was one thing that earned the trust of my leadership team to give me more responsibility. I think the other big thing is I hired good people. I hired people that were, when I expanded the scope of my role, I could look at my team and be like I have an heir apparent. Everybody knows it. I have a team that can run itself sufficiently without me being there. Which takes, it takes strength of will to do this. I think people, it's an obvious thing to say, but when you're hiring, there is that part in the back of your mind where it's like, hey, I'm going to hire somebody more junior to this role. I'm going to coach them, build them up. But if you just do that, you also need to balance that with people that could take your job. With people that are better at your role than you are. And I’ve always said and I told my team, I don't want to be the best SE out of people.AI. Like, I really don't want to be. I need other people to do that. So that, but that allows me to expand the scope of my role. 

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James Kaikis: Absolutely. I love that you said that, and I absolutely agree with you, right? Because I went through a little bit at Showpad where I was one of the first SEs, or the first SE in the business, and grew through that business, and everyone relied on me to do demos or tell stories, right? And it was really hard to scale the team. And so the fact that you're thinking about that type of mindset is really, really important to scale. And I love that you've talked about you being able to oversee other functions because you have those heir apparents and good talent in your business. One of the things that is really top of mind for solutions leaders that are gonna oversee this function is, you know, how do I manage customer success team? How do I manage a support team, right? And one of the things that we've talked about is just value and value orientation. So how do you, in your own personal philosophy, think about value? And how have you been able to scale that methodology to the other functions that you oversee that have been thinking about value differently?

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Jesse Dailey: And this was one of the key advantages I had, sort of moving into this role. So there are organizations that have kind of a wall between sales and post sales. And it's like, there's supposed to be some disagreement and conflict in there. And one of the first things I think in order to be successful in this capacity, you need to really focus on customer outcomes and the account key. So just in general, when I look at my organization structure, I partner with sales very deeply to the extent that I model my organization off of the sales organization. I know where the bread is buttered. It's so much easier to model off of that than to like create different systems and things that are not congruent with the go-to-market team. And then it's about the account team. So like when we do a deal review or a forecast call, you pull everybody in. It's really about bringing the account team together, the AE, the CSM, the SE, executive sponsor, the other folks. And it's so important now as we, like, and the reason why you hear a lot more people talking about customer success is it's much easier, grow your existing customer base than it is to find new customers. Sometimes the detriment of new customers and that's there's some load balancing that comes into that. But back to the value conversation, one of the things that I have observed in a lot of companies is the sales team has like an ROI calculator. It’s like hey we just need ROI so it's like come in, jot down & fill out the spreadsheet, then we spit out ROI. And that's kind of preserved in amber in the PreSales process somewhere. And then the consulting team takes it, and what happens is you hand it off to your consultants. They're implementing, right? The implementation team, they go down to your admin level people, your operators, and they implement the solution, and nobody's talking to the executives anymore, so you miss a value checkpoint. And then the consultants implement it, the implementation team deploys your software, and you hand it off to customer success. And that relic of ROI is still like over here. Nobody's talked about it for six months now. And if you were to dust it off, it would lose relevancy. So here's, here's what we did, which I think has worked really well. We basically went back to the customer journey. And we, I created a customer journey, worked with my team, we collaborated on a customer journey. So we have activation, launch, adoption, value realization and renewal. So these are the five steps. And I want to go back. So activation is the actual implementation of our solution, right? Launch was a new step that we added in, and that's the value step. So as you come in with activation, you're kind of wiring things together, standing up your solution, that's a really important part. We added in the launch step because it's like, hey, we need to get back with our executives, back to the value proposition. and like realign with business objectives and also celebrate what's happened during your, the value checkpoints you've already hit. So we went through and mapped out the entire customer journey and put a value checkpoint in each step of the customer journey. So in our document down at the bottom in green is value checkpoint. And then there's like documentation behind it like, what are we doing there? This is really about threading through pre-sales to post-sales in a material way, and I'm glad, I had the advantage of this because I could get my fingerprints on everything and run orchestrated all together. It's a real challenge for go-to-market teams to align across. People that can figure that out, they'll be really successful. 

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James Kaikis: Yeah. I love that you've done that. I want to dig in a couple things there. Tell me a little bit more about what that launch phase means with getting back to executives. The reason I asked this I 100% would agree with you, the ROI in AMBER, and then, you know, teams are working with admins on admin perspective and not going back to the executives and keeping them up to date and letting them know what's going on. So what does that launch process look like at People.AI? 

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Jesse Dailey: Yeah, so it's like, we call it, like the term we have internally is a launch party, but it's actually where we get, we schedule some time with the economic buyer, the person that like signed up for this. Because I've worked with vendors, I'm not gonna name them on this call, but like I've purchased software where the customer journey feels like this. It feels like activation, renewal. And that's your customer journey. They call me two months, like I activate it, I don't hear anything. They call me two months from the deployment of the software, from the renewal coming like, hey, how's it going? It's like, well, I don't, I haven't really gotten a value. I feel like, I hate to say it, but there's a little bit of ego in here. Cause like, I signed up for this. I put my name on this and like, you disappearing. It doesn't feel good to me as a purchaser of your solution. So I don't want to create that sensation for our customers. And that's why it's so important. Like I, we actually have, we use People.AI to track this. We actually track touchpoints with our economic buyer and they have to be done on the regular in a material way. And I want to just draw a distinction because like you hear the term QBR thrown around in post sales a lot. Like QBRs are kind of dead. What you need to do is you need to deliver value. If you just schedule four reviews in the year, you show up with the same content, it doesn't matter. No, this is a touch point of realigning with business initiatives, and then talking about the value that your solution is delivering. Back to the launch step, this is where we re-engage the sales team. The AE gets back involved, the SE gets back involved, we review the deployment, make sure the deployment was set up correctly, and then we're moving into the next phase, which is actually enabling the teams and realigning with the economic buyer on is this the initiative that we should be solving for. 

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James Kaikis: I love this. I absolutely love this because you said so many things that have been my hot button generally, right? And the thing that resonated with me the most right now is like you said, sales teams build all this trust in the sales process, the AE, the SE and the deal signs and they say see you later. 

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Jesse Dailey: And there's sausage making. 

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James Kaikis: It's just ridiculous that I think it's, I'm no stranger to say it's like, it's kind of like a clown move that like the AEs pop up at the final hour and they're like, "Hey, how's everything going? Are you ready to renew?" And it's like, "Where have you been?" Right? And I think this is why at TestBox we're running full cycle account executives, solutions architects, and programmatically bringing more people in to deliver value. But if we build all this trust with you in the sales process, we should stick around and stay with you to make sure that you find value because I think the common misconception is that the deal is done when the signature happens, right? It's just the start of a process, right? And that's where more and more companies need to focus on value and a term that you use that I want to dig into is value realization. So what we've actually done at TestBox is we don't have a dedicated customer success team anymore because we have full cycle teams. Customer success is a company-wide initiative, right? We're early, small companies, so we can make these changes with a value realization team, right? And that is a programmatic approach to making sure that you are finding value against the like, “let me put a meeting on your calendar to check in with you” type deal. So what does value realization mean at People.AI? 

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Jesse Dailey: Yeah, so at People.AI, first of all… And I like this, you're like the Frank Slootman, no customer success. Controversial take. But actually I like this and I'll tell you why. Even if somebody that's run a customer success team before I like that approach. Maybe not taking away the customer success team, but I like the mentality that the customer’s success is everybody's responsibility, job. So if you give it to one person in the company… and SEs as a profession, we tend to do this. We look at the customer success team, they're like, why didn't you figure this out? It's like, well, we probably didn't have a proper handoff. The business justification got lost a little on the way. And I have the unique experience of being on both sides of the fence, so I can see this happening in my organization and all around. So what I've come to realize that, and I think I alluded to this, is that ROI that you created, the $1.2 million ROI or whatever it was, that's actually, it's really important you should review that. The business initiatives are changing so quickly that you constantly have to stay on top of like what are the business initiatives that we're tied to at the executive level, at the board level. And that's really where you could re-articulate your value as you go. Because the reason why that person bought three years ago and you got that old ROI, that person left two years ago. Like there's been three leadership turnovers. So you kind of have to stay on top of the value conversation constantly, which is why you need all those value checkpoints. And if you're not realigning to it, then you're in trouble. The other thing I'll say is value has to be driven top-down. But by that I mean you can go to your, and I've seen this, and I think every software solution person sees this. I can go to you and say you have 70% MAU and I go to the operators and the admins and they're like, "Awesome, 70% MAU, solutions being adopted, everything's great." What does the CFO say about that? And the CFO is like, I don't care about usage of the solution. I want to know the numbers that it's actually driving. And the way that you get to real numbers is you don't operate without … drive adoption. You have two plays, you have your adoption play, your bottom's up, drive adoption with your end users, but also have a value play top down. If you don't line up both of those things, you just have one component, you're going to be in trouble. You need your operators, admins, and practitioners to love your solution. But here's what really matters. When the CFO walks into your economic buyer's office and they say, "Do you want this? How is it going with this solution?" That person you say, "I cannot live without it.” If they don't say that, then you're in trouble. And you're at risk as a vendor.

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James Kaikis: Okay, Jesse, like light bulb moment, right? Because I love that you said that because the reality of software right now is even if you're not competing in a certain category, you are competing for budget. And at the end of the day, whether it's the concept of above the line, below the line, or stack ranking tools and products, unlimited resources to buy as many products that you can utilize and you go to a market team doesn't exist anymore, right? And so, how are you making sure that you're delivering more value or as much value as other adjacent technologies and the stack? And I think you nailed it by saying, you know, it's People.AI, it's TestBox, these solutions that, you know, teams cannot live without. And that is really important to the future. And I think that just core concept is why I think a lot of software companies are not necessarily set up for success over the next couple of years because they haven't had that mentality, right? 

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Jesse Dailey: Yeah, you can't rest on your laurels right now. 

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James Kaikis: You cannot. 

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Jesse Dailey: The bean counters are out. 

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James Kaikis: Yeah, and you brought up earlier like selling in the install base because I've done some research and seen some VC studies where companies, you know, VC portfolios for the first time in a long time are seeing more new coming from current customers than new logos, right? And you can't go and sell to your install base if you disappeared at the handoff and you've struggled to deliver value in the implementation. So that's something that we see already in our business, I assume that you're seeing the same. 

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Jesse Dailey: Yeah, I mean, the good news is People.ai has phenomenal NRR.  We’re hitting the numbers from that perspective. And I think it's because of the value checkpoints that we have with our customers, and we see a lot of growth in our customer base. But it's interesting, you wanna balance that. And I think this goes back to the pre-sales conversation a little bit, because one of the things that I look at with my pre-sales team is where are they spending their time. And this is back to kind of the CFO question as well, and the AEs. So I have customers that come to us, and they use People.AI for this analysis. One of the things that we help our customers with is let's call it hunting versus farming, right? Where is the organization spending their time? These are big levers that you can pull, big dumb levers, but it matters. So all companies come to us and be like, hey, people.AI, we're not, our pipeline is dried out. We're only expanding our customer base, what's going on? It's like, well, I can tell you that your team is spending 80% of their time with their customer base on recurring calls, on these value checkpoints. This is good stuff to do, but at the expense of new business. So you have to be very careful as far as balancing that because new customers grow those numbers. Like you can't just milk your existing customer base.

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James Kaikis: Yeah, that's a good call out. And I think it's, you brought up the concept of load balancing a couple of times, and I think that's really important to org structures and reorg-ing and then think about where your team spends their time and energy. And that's the way that we think about at TestBox, because I mentioned the word “full lifecycle.” So I know that if I simplify this, the most basic term of high, medium, low, that when my solutions architects are in sales process, it's typically, or pre-signature process, medium level of effort when we're actually implementing, it's a high level of effort. And once we've deployed and we're go-live and we're in value realization, it's typically a low level of effort unless it's an expansion motion where it goes back to medium. And we've been trying to figure that out from a load balancing perspective because we want to focus on building and maintaining that relationship. But what is the capacity of any certain person on the team? 

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Jesse Dailey: Yeah, and you need, in order to really have these conversations, do you have data. I think it's jarring for most companies when they like lift up that rock. They're like, "Oh, well, no wonder our pipeline dried out. We're actually not working our pipeline. We're not working our prospect base right now, to the extent that we could be. 

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James Kaikis: Yeah. And one thing I want to go back to that resonated with me is this concept of just like team selling and like the pod structure essentially is what you have is, so I kind of want to take a flip side approach is you took over these other functions of customer success, support, you know, customer training, how did the teams respond for you coming over to own that function and be like, hey, we're going to think about things a little bit different.

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Jesse Dailey: It was different. I didn't have a customer success background. I admitted that coming into it. I'm like, hey, I know our customers really well. Like that is the advantage that I need, and this is the exact play, I need to find good people in the organization, they could, they could do a better job at it than I could. Same policy applies to expanding my scope of responsibility. I hire people and I find people in the organization that I trust. Yep, they give you really good advice on how to run the team, and you learn from them. So I'm not going to pretend to be an expert on well, now I will pretend to be an expert on this stuff, 'cause I've done it long enough where it's like ingrained in me. But like to start, it's like you just have to go out there, you have to learn, you have to listen, you have to get good advice. From people they're better at it than you are. So I think that that's probably part of the question you were asking.

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James Kaikis: Yeah, I appreciate that because I think that a lot of leaders aren't willing to admit that they don't know something about a function, especially when they take over something that new. You wanna come in and be like, hey, I'm the expert, I know what I'm doing, we're gonna make these changes. So I like that you've leaned into things that way. 

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Jesse Dailey: Yeah, and like humility, I just wanna say like, like when you're moving into a new role, like it really takes humility. 

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James Kaikis: I agree with that. How have you used humility in this whole process? 

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Jesse Dailey: Like I said, like I went to the team of like, I need your help, like I need your help to make this work. And this jogs my memory about the rest of the question. I will say it was a different way of looking at things. Like they're just like SEs that are out there as a support function for sales. There is customer success, which is out there as a support function for customers. And that's not what I think customer success is. So I will say that. And I went to the team and I was like, "Hey, this is, we're now all in a sales role." And what I mean by sales is like, We're not like on a quota. It's not like we're like selling used cars over here, but maybe it's talking about value in a different way. But if you're not aligning to the outcomes that customers try to drive in their business initiatives, and having value conversations, this is not the right role for you. 'Cause we're not spending our time on ticky tacky admin things all the time. You need to address those, so that's a big part of the role. But if you're not elevating the conversation, it's not a good fit for you. I think that was jarring for people to have that conversation. 

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James Kaikis: I believe that because even in my own experience, I think sometimes I've seen customer success managers doing work that doesn't really seem necessary because they've been told that they need to do these types of reports or they need to do these types of check-ins. And it's just like the day to day of the job versus reorienting around value for the customer.

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Jesse Dailey: It's so much more fun to have that type of conversation. It raises the morale of the team, that everybody's respected more, your customers get much more engaged, and then you have these moments of the dopamine rush of a great customer interaction, where it's like, I'm just lighting somebody up right now. I'm sure this is like, wow, this exactly what I need right now and like in order to get to that you have to understand what's aligned with the business initiatives that they have. 

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James Kaikis: Yeah, love that. Let's talk a little bit about the challenges, right? Like what kind of challenges have you personally experienced and the team experienced in this new organization function that you've already talked about. Like you had to make a shift, you're treating customers different, you're thinking about value realization different but like where were the challenges and how do you navigate through those? 

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Jesse Dailey: I mean, I think it was just like for me personally I was just learning the ropes and how the organization worked and then sort of like realigning everything to have it be more customer-oriented. I was just really focused on customer outcomes. Yeah, so it is getting ahead of everything like you have to review and understand your customers very deeply And this is where I'm thankful that I work at People.AI 'cause I was able to use our dataset to get ahead of this stuff. So when we look at a customer that's coming up for renewal, we have our key KPIs. I know, has my team engaged the executives? Has my internal executive stakeholder been involved? Have we had in-person meetings? And in this world, and we're gonna get to the AI stuff, I think at some point, but what's happening is like, we've got a crashing wave of email cadences, avatars, all kinds of AI BS, right? And the people that are gonna be most successful outside of that crashing wave are the ones that may take really strong relationships with their customer base. And you do that by picking up the phone, scheduling meetings, interacting with them in ways that's more human. And understand the network of relationships in a company. This has been one of the things that we've really focused on is getting to know our customers, understand what they care about, and aligning specifically with their business outcomes that we're trying to drive. 

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James Kaikis: Yeah, the human relationship and this era of noise is more important than ever. And one of the things that you just alluded to that we've talked about is AI, right? So I'm curious, as a company who's building and focusing on AI and as an executive who's trying to introduce AI into your own go-to-market motion like what's top of mind for you? 

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Jesse Dailey: Oh there's a lot so I think that the big shift right now is into agents and I think that the industry has basically come to grips with the idea that tasks will be automated. I know we've been talking about that with AI for a while, but like just coming out of Dreamforce, seeing the announcements, all the big companies are basically talking about like, hey, we're automating tasks. And that impacts workforce, right? That impacts talent. It impacts how you manage teams. And that is coming and everybody's sort of moving in that direction. I don't think it's apocalyptic though. Like there's that narrative out there. I kind of mentioned the human interactions of like getting in the room. Like I still, I generally believe in the, and I mentioned this earlier, but if you're not in the room talking to an executive, somebody else is. I promise you it's not an AI avatar, it's a real human that's having those conversations. So I think that's where GoToMarket will continue to thrive, back to having a really good understanding of the account team and how you're organizing, like what are the swim lanes of your account? So there's a lot of interesting trends going on with AI, back to the agent stuff. I think what's happened here is the the shine is off of the the LLM, chat bot, wall of text. And you can kind of see this coming. if I see one more demo of somebody creating a better email or like a blog post, like that's like the most rudimentary use case for AI. And what I'm seeing out there is customers are starving for like, give me a real AI use case. Somebody give me real AI in my go-to-market. Like, yeah, I don't know what it is. And then we kind of like, we jumped out of the gate, everybody's investing, thinking about AI. And we're still creating emails and blog posts with it. And better written content. 'Cause like LLMs are fantastic. So here's what's happening next. And Andreessen Horowitz just had a really interesting article on this. Now, I'm not going to be the person that's going to predict the death of of CRM. I think that's like happening every year continuously. 

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James Kaikis: Yes, death of the salesperson. Death of CRM. 

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Jesse Dailey: But there is like a, but there is like a tectonic shift that's happening here. So I'll give you one example. Something that I think is really absurd. Sales reps, updating sales stages. Like that is, it's over. It's a thing of the past and I'll explain why. And we actually had, People.ai customers come to us and like, "Hey, can you help us solve this problem?" We've actually solved this for customers. So you have a sales stage, right? A sales process document. And every organization has this where it's like a laminated sheet, they give it to you. It's got like 700 data points on it, like exit entry criteria, all this stuff, right? It's like, "Okay, so I'll go out and memorize this sheet." And like, tell which where this is and the managers have their own process every other fifth job in four years like it's a whole mess so AI can actually do a phenomenal job with this. So what we're doing is we're combining AI assisted that actually looks at your methodology so one of the stages that you have exit edge your criteria what should you be doing in a deal and then we combine that with the people.ai data set which actually has like who have you met with what are you talking about every single key moment of interaction that's happened and we're predicting the sales stage across an entire forecast. So we're updating sales stages for our customers and we're doing it more accurately than your sellers ever could. So these problems that we've been suffering with with CRM for the last 20 years, they're going away and AI is going to pick up the ball. 

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James Kaikis: And I think it's about time, right? 'Cause if we were to think about the solutions, consulting role, the AE role, there's so much admin work that's happening and it's taking away from customer-facing activities. 

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Jesse Dailey: You know, I still talk to SE leaders that have people log activities. I don't know who that is, but I heard it happen somewhere. 

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James Kaikis: Yeah, it's like, why does it matter? And I understand it, but there's so many ways to automate this. There's so many ways to use technology, and I think from a solutions profession, just to go back to the solutions engineers, if I'm an SE leader, my ratios are not scaling like they once were, right? So I have to make sure that my team is doing as much as they can customer facing at all times. I cannot have them doing admin work. I can have them doing demo maintenance or demo builds, right? I need them focused on customers to maximize that. And so then also if the account executives have less admin duties themselves, that means more customer facing time and they're going to need more solutions to help do that. And so I think this is a necessary shift because we probably created this unnecessary evil on like CRM management of the past. And it's just become the standard but it doesn't need to be the future. 

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Jesse Dailey: I understand you need data to run the SE organization. Like at the bottom line, and you have two options. You can automate that data and fully automate it, or you can do manual logging. So in my experience, the reason why I'm at People.AI is probably 'cause of my experience with this. When I was running SE teams, I would come in, I'd be like, "Hey, how's everybody tracking your time? Like, what's everybody up to?" The basic question. And they're like, "Oh, we tag our name to an opportunity in Salesforce." So like, I'm like, "Okay, you have worked out 40 opportunities. Like, are you busy or are you not? Like, I see you're busy." But I can't take that data point to the CFO. It's like, I need you to log activity. So what would happen was my best SEs were the worst at giving me data. So everything was perishing. And like, I'd take it to a report, I'd be like, I don't know, my worst SEs are at 40 hours, my best SEs have three hours. Like, I can't justify this, nothing ever makes sense. So the trick is you have to fully automate. You have to fully automate data, you have to attribute time to opportunities and then you can get a sense for where an SE’s spending their time. And without that you can't run an SE organization, in a clear way. So I think that's the first step to this whole problem. You can tell I’m animated about it, because I’ve been down the bad path before. It’s seen the light where it's like, okay You don't have to log stuff. Yeah, it should be done automatically is very profound.

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James Kaikis: I agree and so I’m curious as we talk about AI and your go to market motion and automating some of these tasks for AEs and SEs, one of the things that I understand that you're doing at people.AI are like AI workshops. Can you talk about what those are and how they've impacted your sales motion? 

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Jesse Dailey: Yeah, so this is our AI maturity workshop and what we've found is there's, I mean this goes, this is obvious to people, but it's good to have a framework for it because like all the high tech companies, AI startups in San Francisco, they get the AI vision. Like they're already through the race on that. Like you're paying for GPT, you're like, oh, what, strawberry, like running around with all this stuff, right? Most people are not having these types of conversations. They really aren't having it. They don't know the use cases for AI. They just don't know. And I think that's why it taps out at emails and blogs right? We didn't innovate beyond that. And so what we're doing with our customers and we're walking through the AI maturity model and you can take any business process, take like account planning, right? Like a lot of companies have an account planning initiative. If you plan against your accounts, then you will grow the revenue in that account in theory, in practice. But it's like the first level is a spreadsheet somewhere or a PowerPoint. Second level, it's a bunch of fields inside of Salesforce, but you can move through the levels of automation and actually move to true automation of an account plan. So this is one of the solutions that peopl.ai has developed, we're helping make a quantum leap for our customers. But it's like, we can actually generate account plans based off of your first party data. So the conversations you're having with a customer, combine that with their 10Ks, 10Qs, public generating account strategies. I kind of joke about it, but like an account plan, if you've actually encountered an account plan, it's sort of like that high school essay where it's like you write your name and the date. And then it's like … And then you have the problem. You're like, all right, here we go. I'm gonna start writing this. I'm gonna write my thing, but nobody's there to guide you along and provide best practices. What does good look like? What's working elsewhere? but AI can do that. You need the data. You need the underlying data set to get there, and then you can actually coach your sellers and your SEs to have better strategy.

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James Kaikis: Yeah, how have your buyers resonated with this workshop? 

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Jesse Dailey: They love it, because people will like, when we sort of plot it out every business process, and a lot of companies are looking at tool consolidation right now and like what are the things that I actually need in my organization. And it really helps with that because we over the last 20 years there's been proliferation of tools like interfaces that people log in to perform like different functions. So with AI, the cruel reality is a lot of these things have become irrelevant and pretty fast, so it sort of helps you like inventory where everything is. And then there's also like the not apocalyptic scenario, but there is your competitors are going to come, they're going to figure out AI before you do if you don't move. And one of the stories that we tell like major telco company we want to scale our agent workforce and when our competitor's network goes down we want to contact everybody. It's like how many people do you want to contact? 50 million We're contacting 50 million people today. It's an extinction level event. If you don't start scaling your AI capacity or be ready for that, they're gonna come for you. So it's also like, you have to start future proofing yourself today, like navigate your organization through that because there's AI councils, there's security concerns, all this other stuff comes with it. So if you're not deploying AI solutions, you know who is? your employees are running back home to chat GPT and they're putting stuff in there and you got shadow AI running your company. If you haven't bought AI then your employees are doing it. They just don't tell you about it and that's risky. 

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James Kaikis: Yes, that's absolutely risky. This has been a fascinating conversation. I feel like we could continue to go on I did want to ask a biased question because as we do all AI and tools and and making team more, your solution team and your account executive team, less administrative. People.ai is a TestBox customer, right? And so I'm curious from your perspective, like what role did purchasing TestBox play in this consolidation, but to the AI aspect of your business?

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Jesse Dailey: Okay, I love this topic. I was so excited to be a TestBox customer 'cause it's all for like a big challenge that we were having. So as an AI company, you kind of need to encounter a new question, which is like, how do I demo AI? How do I bring it to market? It's non-deterministic. I need big data sets to fuel it. I still want to tell narrative stories that make sense for different verticals across my customer base. These are like big challenges and big data challenges. And this is where it clicked for me, where you're like, oh, just send them a TestBox. I'm like, what do you mean? It's like, oh, just send them a People.ai environment to a customer. And that's why I was like, oh, that's it. 'Cause people still want to get hands-on. They don't want to sit over zooms and ask questions. They want to touch it and feel it. And I think this is what's so profound about being a TestBox customer, 'cause we can send it to a customer and basically simulate their environment and do it at scale across our customer base. So it helps with a very dangerous thing, which is a free POC. Everybody loves a good free POC. I know we all want them. Like there's a lot of commitment on both ends. And like it's costly for us, it's costly for you. Are we here, are we committed? Can I get you closer to that commitment stage before we jump into the POC? That helps tremendously.

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James Kaikis: Yeah, I love that. And like the time, right? Like time kills all deals. And like to get buy-in on both sides and go through security and compliance, it could be a lot. 

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Jesse Dailey: Yeah, and now you're like three months away from a signed order, you could be six weeks, who knows? 

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James Kaikis: Right, it would faster.

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Jesse Dailey: Changing that outcome with TestBox has been really, it's been amazing for us, so it's solved for two problems. Just how do I demo AI at scale? Which is like tricky, 'cause I can't just HTML fake stuff. You know, it's like you gotta, you need data to do that. And maybe I'll give my customers hands-on experience with people.ai, those have been profound for us. 

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James Kaikis: I appreciate that, I love hearing that. One comment I'll make is that I feel like sales motions will change with AI, right? Because I've talked to so many customers and even worked at companies that hard code the AI, right? The AI is, like you said, HTML coded to ask one of three questions and it's going to give you a response. And I think more savvy buyers will say, let me ask an AI question, right? And so if people.ai is using an environment that's simulating a best in class customer, you know, I think it's a great way to build trust to tell the buyer, ask it a question. 

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Jesse Dailey: Oh yeah, and we do this, and we won't let our customers go crazy on it because like, that's where the static fills the room, that like real energy where it's like, wow, I can't believe it's doing this. I've never seen this happen before. And you need to get off the rails a little bit to do that. You can tell these static demos, they're not compelling. People, our customers are demanding more. 

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James Kaikis: Yeah, they're definitely demanding more and I think it goes back to all the overselling and the sales team and solutions team leaving the relationship after the contract signature and technology not delivering value. So I think we're going through this new wave, right? And that's why I think the product tours of demo automation on our website are great, but nothing replicates live demos and nothing replicates real POCs like the actual products, right? You've got to be able to do it and you've got to let buyers get hands-on for them to trust your solution, we'll do what you say it does. 

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Jesse Dailey: Yes, exactly. 

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‍James Kaikis: Jesse, it's been awesome having you. I really love the conversation. Always great talking to you throughout the years. I appreciate all your guidance and love what you're doing at People.AI.