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AI Can Finally Kill CRM Data Entry. That Might Be the Problem. · Selling AI

• Warren Kucker: Hey there and welcome to another episode of Selling AI. Today we're diving into the world of rev ops, the death of CRM data entry and what 15 years of Salesforce implementations taught Eddie, my guest here, about why AI is finally ready to unlock everything we've been waiting for. We have Eddie Reynolds on the show today and Eddie is the CEO of Union Square Consulting. They're a go-to-market strategy and operations firm that's been working with B2B SaaS companies for nearly a decade. He also hosts another podcast on his own called GTM Science, which is a great dive in. to a lot of the surface level topics we'll get into today. Here's what makes the conversation interesting really. Eddie has a great mathematical approach to how GoToMarket should run and a strong thesis on how to leverage AI in the process. Came up with a finance background and now he runs his consulting firms and he brings a statistical data-driven lens to GoToMarket that oftentimes is a lacking one. So in today's episode, we debate whether a processor behavior is a real driver of sales performance. Talk about a little bit about what headless sales force means. and how he uses sample sizes, cac math to make bets in his own business. All right, let's get into it. Hey Eddie, thank you so much for being here today with us to talk about bots and AI. Welcome to the show. Eddie Reynolds: Thanks for having me and what an awesome introduction. I'll just add one thing. I've also been carrying a bag and selling since I was 16 years old. So hopefully that adds some color to our conversation for today. Warren Kucker: I love it. I have a different background, so that'd be a good contrast. was just founder, read books until I figured it out. Now I'm a slightly below average sales guy. Now I'm after a decade of doing it. So, awesome. Well, let's dive into that background. First job out of school, you were selling cars at Beverly Hills Porsche. Every sales origin story starts with something like this, which is excellent. You dove into finance, capital, equity, raising, and then you spent some time at Salesforce and now you're kind of like go-to-market engineering expert. What pulled you in that direction? Give us a bit about your career arc there. Eddie Reynolds: Yeah, sure. So I don't talk about selling cars very much. First of all, it doesn't always have the most positive connotation, but it was a long time ago. And I actually paid my way through school selling cars. I wanted to own a Ferrari dealership at some point. I always wanted to own my own business, and that was the dream. And everybody I talked to that ran their own business said, go learn to sell. And since I wanted to own a Ferrari dealership, it made sense to sell cars. So I did that all the way through college, paid my way through college. and then did that briefly after college, getting a job at Beverly Hills Portia, which at the time was my dream job. And I think the thing that I gravitated towards was always process. So when I worked there, I was 20 years old. By some miracle, the manager hired me without realizing how old I was because I had worked with him in a previous job, like over the summer when I was 18. And I think he just had no idea that I was only 20 years old. And everybody else that I worked with was 35. And they were able to sort of carry the conversation and have this gravitas with the type of people that were buying Porsches that I didn't have. And so to overcompensate for that, I literally physically moved faster than them. People would walk onto the lot and I would run out there before they could say hello to the person. And I always thought from an operational perspective, if I talked to X amount of people per day and if my close rate is Y percentage, then I can hit my target. And as I moved from selling cars into banking, where I had access to a lot of data and analytics that I could run on who to call and why to call them or what to call them about, I really leaned into that and it became my competitive advantage versus other people that had been in the job for 10 or 15 years where I was just starting. Warren Kucker: Awesome, yeah, that's a really cool ⁓ story. And obviously like that type of selling is just like hand to hand combat, right? So it really kind of preps you. ⁓ That early stage is excellent. ⁓ Awesome, well, let's dive into some more recent work. We talked prior to this episode and I kind of floated a thesis that we should stop making reps fill out fields in Salesforce in order to drive like good deal health. ⁓ You had a different approach. You think that there's something that companies get wrong when they're kind of like, driving this type of CRM implementation and CRM usage. ⁓ Dive in. Let's go. What's your thesis in that area? Eddie Reynolds: Well, I don't know that I would say that ⁓ companies get it wrong, but I think you and I had a discussion previously about not forcing reps to fill out med pic fields and things like that. And I think it was more just a different perspective on this, right? So let me give you some background on this. I started using and implementing Salesforce when I worked on Wall Street. And as you can imagine, a lot of the people that I worked with were very relationship driven. They'd go out, they'd meet people, they'd remember kids names and birthdays and... all kinds of things that you need in order to maintain a relationship. And the last thing they wanted to do was come back to the office and type everything into Salesforce. And so they like this first job where I first implemented Salesforce, they would literally call their analyst and leave a voicemail and have the analyst entered into Salesforce. And as the person that was trying to build out Salesforce for this team, I was so frustrated. And I remember thinking like, it's like these people want Salesforce to read their minds. They don't ever want to log in. They don't want to use it. And I've been fighting this uphill battle. for 15 years. When I left Wall Street, saw Salesforce did a really good job of this. I worked at Salesforce as an AE for three years, partially because I was drinking the Kool-Aid and I wanted to work in a bleeding edge tech environment. And Salesforce did a great job of this 10 plus years ago when I worked for them. They really picked and chose their battles and said, these are the key things that we need you to update on a deal in Salesforce. And they drove that accountability on a daily, if not hourly basis. They had a culture of real-time all the time. There was no excuse not to update the CRM. And I think at that time with that technology, that was the right thing. But now as we go forward with AI, there's an incredible opportunity to take that workload off of sales reps, to update that information inside of the CRM for them, and to give them more time in their day to do what salespeople do best, which is to initiate and grow relationships. However, what I will say about this is, is that if the AI does all of the work and the rep is never looking at Salesforce or at least never looking at the data in Salesforce, I don't know that they need to log in to do that anymore, then they're not thinking about the right questions to ask and the right steps to take during the sales process. And this is really the core benefit to a sales rep and to management in managing those sales reps in having a systematic way. to remind reps of what they need to do at each step in the process. Warren Kucker: Yeah, that's a great call out, right? Because again, you cut the admin workout of filling out a CRM with which a decent amount of time is about updating the rest of the org about what the sales team is doing, right? Real time all the time also means real time for your boss and your boss's boss and your solutions consultant on the way. Cut that work down, but you don't want to lose the essence of like, how do I manage deals? Do you still feel like the CRM is the best place to do that to drive that like sales process buying journey behavior in this? Paradigms in just any way to kind of get that in front of the rep and have them manage a deal appropriately. Eddie Reynolds: You know, in asking that you're jogging my memory about what I wanted to say that most companies do wrong. And I think the thing that I see companies do wrong is how they implement this idea. And oftentimes what I see is they ask reps for too much information and it becomes overkill. There's too much noise and there's no signal. This is not what I saw when I worked at Salesforce. I worried that that would be the case before I took the job, but when I actually worked there, they didn't ask for much. their asks were very reasonable. was update three or four fields on every opportunity and then as a deal becomes bigger, more strategic and more mature, update more fields, especially as you start bringing other people into the team that are gonna sell with you. So this wasn't management writing me and saying, we need these 25 fields updated at all times for all deals. This was my SE saying, if you want me to prep for this call and run discovery and then do a demo. I'm not gonna have an hour long verbal discussion with you. I expect you to update this information in Salesforce so that I can be prepared and I'm not gonna accept this calendar invite until you do that. These are literally word for word what our SEs would tell us. And then of course if we're bringing in a senior executive from the company or other people, that's the same if not higher expectation. So let's take a step back and ask what does that mean? Well, let's start with the simplest thing. What stage is this deal in? If a rep doesn't know what stage their deals are in, in their pipeline, like that's a real problem. That's not something AI should even attempt to fix. Yes, it can signal and it can say these are the risk factors in the deal and why you might not want it in this stage or that stage. But I think the sales rep, unless we're talking about an extremely high velocity sale, the sales rep needs to ultimately decide what stage that deal belongs in because that influences whether or not they invest time and where they invest time in that deal. And time is the most precious asset for a sales rep. So if you have a sales rep that does not understand the difference between a qualified deal that is worthy of time investment and one that is not qualified, then you are going to have a sales rep that is going to spend most of their time chasing deals they can't close, and as a result, they will misquote it and make it virtually impossible for management to forecast accurately. Warren Kucker: Yeah, that's a really good call out, right? Like ⁓ the key here, I think is like we don't, we're at a point where we could access conversational data, extract information and eliminate work that wasn't really value added for anyone. But in the same token, you don't wanna extract the critical thinking part of the process. With the way we've run CRMs for the past 15 years with the tech we had that was bleeding edge was we can do both at the same time, right? Like this is how reps. keep forecasts updated for management, but also pace themselves through deals. We don't want to throw the baby out with the bathwater, right? Is there something in particular that you think like reps could focus more on when it comes to like deal progression? Like that they have it in the past because they're running around too frantically in between deals to close. Is there like a better use of their time once you kind of like extract a couple of the key non-value added tasks? Eddie Reynolds: Well, I think the next layer of progression from understanding what stage and opportunity is in, and I would extend that to what stage an account or contact is in. Like we literally have these fields in our sales force. I manage a handful or a few dozen, depending on where I draw the line of relationships and private equity and venture capital. And the most important thing for me is to determine where those accounts are and the contacts in those accounts in terms of what stage they're at, where I focus my energy, who's a tier one. Are these people that I'm engaged with that are stale, that are new, that I need to start working? That's a really, really important aspect of the way that I do my relationship management and outbound. But as we take it to the next layer deeper, we need to start thinking about the stage by stage progression and steps. Why is this important, right? Let's just start with qualifying a deal. When I worked at Salesforce, the number one factor that I saw that separated top performing reps from people that underperformed and misquote and ultimately left the organization was the ability or inability to understand the difference between a qualified and an unqualified deal. Reason being because there's so much time that gets invested. Now, as we progress this from a stage zero or whatever we have to a stage one, stage two, stage three, every single stage requires an exponentially larger time commitment from the sales rep. It takes 30 minutes to run an initial discovery call. And even if you're updating Salesforce manually, maybe another 15 or 30 minutes to type your notes into Salesforce and prep for the next meeting. But then the next meeting is an hour. The meeting after that is an hour of prep plus an hour call plus an hour post call. Then all of a sudden we're doing this big customized demo or presentation and it just gets bigger and bigger and bigger at each step. So let's forget the technology for a moment and let's ask what do we want our reps doing? We want them to be crystal clear on whether or not these deals are worthy of that time investment and to have a clear understanding of what the customer's evaluation process is. I mean, that's part of of medic or med pic. and understand how they're going to progress this deal through the funnel. The best reps don't win every single deal that they pursue, but they win a lot of them because they know when to walk away. And when they walk away, they have more time to devote to those deals that actually stand a better chance, as well as more time to generate more of those deals where they have a better chance of closing. And that, to me, is the number one differentiator between great sales reps and sales reps that are struggling. Warren Kucker: That's really fascinating because I don't do a good enough job of this myself. How large of this particular problem do you think is out there? And so let me phrase the question in a way that's a little bit more helpful. We talk about like, so reps are overworking deals that are never going to close or are well under qualified, right? So that's core. They're spending too much time because they're not disqualifying deals when they should. Do you think this is like one of the top problems in sales that like 80 % of reps like kind of like exhibit this behavior? And it'd be like, listen, this is like a core thing as a sales community we should really be focused on. Because you're absolutely right. Logically, what you say makes total sense. it's what should be done. I don't necessarily see a lot of it in practice, which is probably my fault as a leader. Eddie Reynolds: To answer your question, yes. I think the problem is so much deeper than even what I've described so far. So we've talked about how when a rep chases a deal, they waste a lot of time, but it's even worse than that, right? Let's start talking about what stakeholders we're engaging. So this is something I've seen firsthand in so many organizations. If we are engaging at a junior level, then we are gonna have more transactional deals. We're gonna have lower close rates. We're gonna have smaller deal sizes, right? So when we have the ability to go to the senior decision maker and to push a strategic deal, we can have a significantly increased deal size. We have a higher close rate. We also have a shorter sales cycle. All of these things combine and you'll have one rep that's over here closing. I'll just share like concrete things that I've seen. You've got a rep that's constantly closing 50 and $100,000 deals in like S &B mid-market and another rep that can only close $15,000 deals and they're closing half as many of those and it's taking them twice as long. Like that is a multiplicatively smaller outcome, right? The other thing is that you give up leverage. So if you say, all right, I'm going to go into an evaluation with somebody who's not a decision maker, I've asked to speak to the decision maker and they will not grant me access. So I just go through the motions. I give them their demo, I give them the custom pricing proposal, I go back to management and I give them a special discount. I give them a trial, a proof of concept, I put them in front or my sales engineer, I give them everything that they're asking for. Now I'm done with my sales process. I've already spent all of this time. And now I say, could I ask to speak to the decision maker? Could we talk to the CFO about budget approval or an ROI case or whatever it is we need to get our deal done? We've now given that customer everything that they want. And by the way, I'm not advocating that we don't play nice with our customers, but there needs to be some give and take. And so when we do all of that, and then at the very end, we say, hey, could you introduce me to your decision maker? Could I get XYZ from you? they have no reason to even respond to your email. And this is when you see people just go dark. Warren Kucker: I think this maybe like because a question that I, that tactically doesn't matter so much, but I think in terms of like how we look at sales process might, right? ⁓ This is a really ⁓ good call out. So in theory, we'd want our salespeople with some extra time that they may have, because we should be able to automate some things that we made them do in the past. They should be working fewer better deals more deeply, right? In order to win more work for the organization, win more work for themselves, hit quota more often. But also, the knock-on effect of this is when you're getting deeper and deeper into deals, you're also pulling your own internal stakeholders. Now, your CEOs, like, let's say C-suite is talking about forecasting those deals, and they're worse deals. So you're absolutely right. The time commitment snowballs for the whole organization. I guess the question would be, in the midst of... Yeah. Eddie Reynolds: I would even also add on CS, right? So it depends on the product you're selling, but like I sold Salesforce and continue to in a way. And if you don't have senior stakeholders involved with Salesforce, for example, then like the actual implementation of Salesforce fails. So even if you do win the deal, the customer just churns six or 12 months later. So, and that doesn't apply to every product, but for many products, especially bigger, more complex implementations, if the senior leadership is not behind that initiative, Warren Kucker: right? Eddie Reynolds: especially if you need to change behavior and drive people to adopt the system, et cetera, well then the whole thing just fails. And so now you have lower NRR, not to mention your lower new business rate. Warren Kucker: Right, right. ⁓ with all of what's a with this efficiency kind of like paradigm Do you feel like it's like great we should go increase quotas across the board ⁓ or should be like listen now Let's sell like we've always meant to sell right like we haven't we've been half selling because we're chasing a quota with bad deals and let's do it better and Let's actually hit our hit our quotas, but we don't really need to be juiced in the numbers And I know this is a hard broad question to ask But like what are your thoughts on that in terms of like what should be the end result of the productivity gains? Eddie Reynolds: Well, I let's just look at what's happening in B2B SaaS or B2B Tech right now. I close rates are for many companies between 10 and 20%. Meanwhile, they're trying to get 3x pipeline coverage. And so what is 3 times 10 to 20 %? That's half of your goal. Meanwhile, that's about exactly where most reps are landing. Now granted, there's a lot of padding in there between the rep and the manager and the CRO and possibly even the CFO, CEO and what their numbers are. And you see many organizations hitting their numbers while They have very low rep quota attainment. I personally think just from a philosophical perspective, that's incredibly demoralizing. My first job in banking, I was at 504 % of my quota, and it just was a fantastic feeling. I didn't want to stop. I wanted to be number one. I don't understand why 100 % of quota has to be the almost impossible goal for people to hit. But let's back up and let's talk about that. a team of salespeople that are closing 10 to 20 % of their deals, then you're facing all of those challenges I just mentioned. You are losing opportunities to close deals that you could otherwise close. You could close bigger deals. You could close them faster. So this is exactly why we have something like Medic or MedPic. I we're literally asking the customer or ourselves who's making the decision, what is the decision making criteria, et cetera. And so the whole point of having a methodology like that is to translate that into a sales process and then ask, like, when and where do we ask these questions and what do we do with the information that we get back? If we are told that their evaluation criteria is out of sync or they're not willing to share it or we can't talk to the right person, are we going to continue down the path with that evaluation or are we going to cut bait and go talk to anyone else that is willing to work with us that we have a better chance of serving or winning as a customer and serving successfully? And I think that this is a massive problem in the tech industry where there's this culture that we just chase everything. ⁓ And when I started my business, it's like the first thing that you hear as an entrepreneur is you need to define your ICP and you need to learn to say no to people. Because if you say yes to everybody for everything, you will end up with a lot of very unhappy customers. Warren Kucker: ⁓ No, it's really prescient, right? Like in a scenario too, where you're optimizing for your cost of acquisition, like continually chasing a number that's not gonna get you there and holding on to deals that are probably not going to close when you should be talking to other folks and trying to do everything all at once creates a bad cost equation. With free cash that was existing in venture capital, this probably was the reason why we were able to do that, right? Like it's like cash isn't the problem. We need revenue and growth no matter what, even if it's inefficient. paradigm has shifted and we should really try to look as like a sales function to make sure that we like do it the right way the next way. ⁓ I would say. Eddie Reynolds: Yeah. Well, if you don't mind me ⁓ pushing us in a different direction for a moment, let's talk about AI. I think that there's incredible opportunity for AI to help. Warren Kucker: Please do. Yeah. Eddie Reynolds: both save time reps and make, save reps time and make them more effective, right? So if we can use a tool to take all the information from our calls or emails, et cetera, update Salesforce, and we've got all the med pic fields in there, we've got all the other important information, we have our stages really clearly set, and we now have a tool that is coaching reps in real time on what they should be doing at what step. Now reps are more intelligent. This is, I'm not even talking about doing account plans, which are great too, and doing customer research. We have the ability to make reps so much more effective with AI, but we need to design the process around our customer and our product so that we can empower our sales reps to actually do just that. They now have better information and more time to leverage that information in meaningful ways to talk to the right people about the right thing on the right deals. And when they're not doing that, to go build those deals through outbound prospecting or whatever motion we have, expansion sales, for example. And I think that it's an incredible opportunity to improve efficiencies and effectiveness at the same time. But in order to do that, we have to really understand the foundational process that gives our real buyers the journey that they really want to make a real decision to buy from us. Warren Kucker: ⁓ I couldn't agree more, right? Like in theory, should, Salesforce should be able to slow down and be more strategic. And let me give you a tactical example that I struggle with. I almost never think about what the buying, the buying committee stakeholders on my deals, what their personal stake is in this. I kind of tangentially do, I just do it for my champion, but I never really truly think about this person, if they bought my software, what's the outcome that would be better for them if they did it, right? I also never go into think about like, great, when they have an internal meeting about my software. What are they going to talk about and how do I drive that conversation? I know I should. I never spend the time on this. How do think we can create an environment for reps to get that information to serve it up appropriately for them so they're spending that time to strategically work through their deals now that they should have a little bit of space and breath to do that? What's a good delivery system? Eddie Reynolds: Sure. So I saw exactly this when I worked at Salesforce. And so for context, I sold into SMB mid market when I was at Salesforce. I have cursory level knowledge of what they did with enterprise, but I wasn't on that team. And let me share what worked 10 plus years ago and what could work today with the advantages of AI. So when you talk about that personal pain, Salesforce, I think this is part of Sandler training, if I remember correctly, they talk about L1, L2, L3 pain. L1 is the... technical, like I need Salesforce to produce a report for me. L2 is the business. I need that report so we can forecast accurately for the business and L3 is the personal. I need to forecast accurately so I lose my job as CRO, right? We literally had fields in Salesforce that said, what is the L1, L2, L3 pain? I mean, it's really in some ways that simple, but it's not. We have to drive people to adopt it and I'll talk about that in a moment. And then I now forget the second example that you gave me. Warren Kucker: ⁓ When they're meeting about my piece of software, like what are they talking about in the meeting and how do I drive that conversation? Internal meeting, yeah. Eddie Reynolds: got it and so I don't remember because this is over 10 years ago so if you get my memory I don't remember exactly what field that might have been but I'm pretty sure there was something like you how's the champion going to sell this internally right so you start by asking that question and keep in mind like I said for context I was selling SMB mid-market these are just a handful of fields in Salesforce enterprise had like entire documents that they needed to fill out for these giant multi-million or multi-ten million dollar deals that they were working and it became this massive project management thing that you can imagine how complex it would get. I have friends that went on to enterprise that sold deals literally over $50 million. So you can imagine how much time they're spending on these kinds of things. So you start with putting the fields in Salesforce or in a document or whatever and you ask people to fill it out. The next thing is you have to have an accountability layer. You have to have pipeline inspection. 10 plus years ago, management would go in and they'd say, let's take a look at the pipeline. Let's look at every single open deal that's going to close by X date. Let's sort it in descending order, starting with the largest deal. And then let's click into the deal and let's see if these fields are filled out. So I go in and I see the biggest strategic deal across North America. I'm talking about my boss's boss's boss's boss's boss at the time, Tony Rodoni, who we've had on the podcast. ⁓ He would go in and look at these deals and he's like, OK, here's the biggest deal across North America. And I see that my sales rep doesn't understand the L1, L2, L3 pain or doesn't understand the risk factors. This is blank. And they say that this is in like a stage five and it's close to closing. Like that's a red flag. And so he would literally do what is now the equivalent of a slack message to the rep. And my boss would do that and his boss and everybody up and down the chain of command. and it created a culture where you knew this was coming. So you make this mistake once or twice, and then you're like, there's scrutiny on my pipeline. So I need to be on top of this. But it's also making this a reasonable request. The flip side of this we saw, we had a very nasty implementation with a customer many years back where we were working with the CFO, and the accounting department wanted 35 or 40 fields filled out on a deal every time the rep got off the phone. The result of this was is that the entire sales team ⁓ revolted. We got fired. The CFO got fired. The controller got fired. Everybody involved got fired, even though we were like, don't do this. This is a bad idea. Because that's not going to work. No sales rep can actually sell when they are being held to that level of admin work. So now let's fast forward to AI. We now have tools that can go into all of our call transcripts, all of our emails. even possibly other data sources. I forgot about data enrichment tools like Zoom Info, Clay, etc. They can go and fill in all of this information for us and then now also coach us and say, here are the risk factors we're seeing in your deals. You were on this call two weeks ago when they said the decision-maker and decision-making process is XYZ, but, now you have a better ability to coach reps, especially newer reps that are still learning. on how they can manage their deals. And that to me is incredibly powerful. Warren Kucker: Yeah, I mean, that's absolutely the case, right? I like the split between keeping it simple, right? Like, your boss's boss's boss's boss at Salesforce isn't gonna look at 40 fields either to determine what's happening at his most important deal. He's gonna look for the three things that he knows he's gonna find to see if you have a healthy deal or not, right? So it's like, what's that up and down view look like that can truly help you assess things quickly? And then everything else kind of like is secondary to that. Eddie Reynolds: say is the SE on a multi-million dollar deal probably would look at 40 fields or a document with 40 data inputs as with the AI. And so one of the pieces that I skipped is that we can now train the AI to say like here are the specific things that we need to do at each step in the sales process. And I want to make a really clear point here. Why do we do this? We're trying to reverse engineer why we win or lose deals. So this is unique to every company. Medic, MedPic is really great. Bant, a lot of people don't like it anymore, but I've always thought it served a purpose. There's many other methodologies out there, but they all need to be customized to an organization. When I worked at Salesforce, for example, our biggest competitor, which is the true for many companies, was no decision. So we've run this entire valuation and then we just arrive at no decision. They didn't buy from us, they didn't buy from someone else, they didn't decide what they're going to do, they just, I don't know, we'll think about it. So when you think about something like, medic or med pick, why do we have that? Well, we're asking what their decision-making criteria is because we are trying to limit the risk that we go through this entire process and they just reach no decision whatsoever. We were trying to limit the risk that there's a person that's going to make the decision that's going to come in at the 11th hour and just say, I'm not approving this, even though everyone else involved in the evaluation wants to move forward. And that is slightly different and unique for every organization. And so we need to look at the deals that we've won and the deals we've lost and the most common reasons why. And we need to reverse engineer our sales process. And then we can coach the AI to say, as you're reviewing the current transcripts and emails, look for these things. Warren Kucker: ⁓ That's a perfect segue into, I'd say, a little bit more of the work you're doing now with Union Square Consulting. When you're approaching engagements now, or people approach you now, what are some of the common themes and new problems that are arising? They're probably asking how to use AI in their overall tech stack and what they should be doing to improve. What's common themes that are coming inbound? And then what's some common things that you're looking at like, hey, we should be doing X, Y, and Z now that we haven't in the past, or that we should just do better than we have? What do those engagements look like? these days. Eddie Reynolds: Yeah, so it's such an interesting question because it's so informed by the marketing that we do. So we scream from the rooftops that we can help solve certain problems. And then unsurprisingly, the people with those problems come to us, right? So I'll just caveat it with that. the number one reason that CROs reach out to us is oftentimes they're entering a new job and these kinds of things are a mess. But specifically, they want to generate more pipeline and to a slightly lesser extent, close more pipeline and forecast more accurately. Warren Kucker: So yeah. Eddie Reynolds: And so the things that we oftentimes see, whether they recognize it or not, is that their pipeline is an absolute mess. It's full of deals that never should have gone into pipeline in the first place, should have been taken out of pipeline months or quarters ago, that are just never gonna close. And it makes it virtually impossible for them to forecast accurately or even manage their team because they log in and they look at the pipeline and they can't separate the wheat from the chaff. They oftentimes don't have these fields that we're talking about. And so when they do look at an opportunity in Salesforce, All they can see is the stage and the closed aid and a series of emails and call notes if they're lucky. And it's very difficult to wrap their heads around what's going on in the pipeline. And then the same thing is true for their outbound, inbound, all bound or expansion motions where we can't always see how many calls are being made, how many meetings are being set, what's happening with those calls and meetings, and how are we driving towards creating actual qualified pipeline. So oftentimes what will happen is a CRO will come to us and they'll talk to me and they'll say, I need to generate more pipeline. And I will uncover that even if we could help them generate more pipeline, we wouldn't be able to measure it accurately because they don't have any clear qualification criteria that is executed consistently. So they go and they do XYZ and, OK, we've generated $50 million of additional pipeline. Nobody believes it. Everybody says, yeah, that's cool. We're not closing the pipeline that we have right now. So what does $50 million mean? Does that mean we're going to close 33 % of that? That's not what we've been doing historically. So how do we know that people didn't just click Create Opportunity more frequently in Salesforce because that was what they were told to do? So for me, it's really, really important that we get at least the foundational aspects of pipeline management down, that we have clear qualification criteria, even if our number one priority is to generate more pipeline, because at least now we can objectively measure it. And then we need to get some visibility into what the team is doing. so that we can see, all right, they've made X amount of calls to these set of accounts, and those are resulting in meetings or they're not, those meetings are resulting in pipeline or they're not, and then we can start to figure out what parts of that motion are working and what parts are not working. So a really big problem that I see this sort of come secondary of this is just a lack of visibility. And that's one reason I'm so excited about these AI tools that now we don't have to crack the whip and tell reps that they need to spend an hour a day updating Salesforce. Instead, we can automate a lot of this data entry and get the visibility we need. Warren Kucker: Yeah, so qualification being big, ⁓ and I would say I'm asking you to broad brush a lot of different engagements. When you think about how you're managing your deal health and your pipeline post-qualification, do you often spend time to map the buyer's journey and try to stage out the sales process? In this, let's say, more minimal way than most organizations, I've been guilty of asking 40 questions in the sales process for a $75,000 deal in Salesforce. Is that a core part of what you find yourself doing early? It can be a challenging. It can take time. You're trying to do some guesswork if an organization isn't working well. Or is something you usually defer. It's like, let's just get qualification correct. Let's figure out what's a good deal and what's not. And then we can figure out what's the indicators of deal health throughout the process and what questions you should be asking to exit what stage. Eddie Reynolds: I think it's a difficult balance, right? I don't think anybody hires us or a full-time VP of RevOps or go-to-market strategy and operations or even a CRO and says, hey, I want you to go and talk to the team and spend the next 90 days putting together a PowerPoint presentation and come back to me and tell me what our customer journey is. No one says that, right? So I get a lot of resistance when I bring up the idea of a customer journey to a CRO. Not always, but sometimes. my pushback will be, look, there are various levels of this. You can go spend $5 million and hire McKinsey to go spend the next six months doing customer journey mapping for you. We could do it for you in an hour. Now, is that going to be as good as what we could do in 10 hours, or 100 hours, or a month, or ⁓ three months? No. But you can get a lot done in an hour or two when you just sit down with the right people and ask them, what does the customer actually want? And I'll give you a concrete example of this. It was interesting how many times I was on a call with a customer at Salesforce where my manager would step in and say, we know that XYZ is very frustrating for you. And I'm sorry that that's the case, but basically it is the way it is. I'm sorry. I'm sorry that we change reps every three months. I'm sorry that we make you go through 15 phone calls before we will even show you an semblance of Salesforce. And this latter one is a real sticking point for me because I finally saw them come around on this. In the beginning, the way that I was trained was that we needed to do, if this was an inbound lead, the SDR is qualifying it, so they have one or multiple calls for the SDR, then it gets pitched over to the AE, then I'm requalifying it, then I need to do full discovery, then I need to bring in the decision makers and requalify them and do full discovery, then I bring my SE in and then they requalify it they do full discovery, and the customer has to go through all of this before they can even get a glimpse at what Salesforce is. And the way Salesforce would push back is they would say, Well, if you want a demo, how long do you have? Like, I could do a demo for 24 straight hours and still not show you 1 % of what Salesforce can do. If I don't run proper discovery, then I can't show you what you want to see in Salesforce. And that is true. On the flip side, you can also put, you can, and we did this at Union Square Consulting, put together a five minute demo video that says, hey, for your particular use case in this industry, here's a five minute demo. We put it up on YouTube. To this day, I think it's like the YouTube video that we've created that got the most views because we sent it to all the AEs at Salesforce after I left. And they started sending it around to their customers because their customers are like, I get it, but I just want to see the thing. Like, what does Salesforce actually do? Can I just see it? And that is an incredibly valuable part of the customer journey. I'm thankful that Salesforce also shares pricing on their website and always has. But I think it's important to understand these key elements before you start to think about like, Well, what do we need to do on the first sales call? Because if the customer is like, just want to see a demo, how can you give them a demo while still running your sales process in a way that results in the outcomes that you want? Warren Kucker: And you talk about the customer journey and getting it done in an hour, sometimes it's a three month process. ⁓ I couldn't agree more and more mainly because if you don't get something in, it's hard to test against what's working, what's not, right? So there's some baseline. This is what makes a healthy deal. This is what not makes a healthy deal. These are the types of questions we should ask that you should iterate on pretty quickly once you have more data. But it's hard to have the data if you don't have anything to kind of mash it against, which I guess it leads me to my next question. You have like a math background, heavily focused on like. let's say analytics from a get-a-mic and engineering standpoint, when you come in, how do you kind of like analyze what parts of the process aren't working, what are working? How do you take that like analytical mathematical approach and apply it to every step in the prospect to customer journey there? Eddie Reynolds: Well, I think it's really hard. And I think there's a lot of people that work in go-to-market strategy and ops or rev ops that have some type of a mathematical background or affinity. And it can actually get you in trouble because we oftentimes go into these organizations where the data is an absolute mess. And especially on the smaller scale, and I'm not even talking about startups, I'm talking about companies that are 20, 30, 40, 50 million, sometimes even $100 million in revenue. They don't have any of this reporting in place. And the CRO is in every deal or almost every deal. And they kind of know in their head what's going on. Now, that's not scalable. But the trap that we have fallen into many times and the hard lesson that I've learned is I go and spend a bunch of time running reports and I go present it to the CRO or my team does, and they just say, yeah, I already knew that. So we actually just published this a couple of days ago, and I can share the link if you want to put this in the show notes. We just created a simple questionnaire specifically for go-to-market metrics and insights to get around this. Like for example, do you have clear qualification criteria documented and do your reps follow it? If the CRO just says no, Well, then you don't need to run a pipeline report because without even looking at it, you already know it's a mess. And you just figure that out in 30 seconds instead of spending an hour trying to build a pipeline report and figure out how to present it to the CRO. And this goes all across go-to-market. So what we really need to understand is do we have the foundational definitions and process in place? And is the sales team and or our automation following that process such that we can actually get reliable data out of the report? If we can't, then running the report becomes kind of a waste of time. The second thing I will say is that at the end of the day, go-to-market is a very imperfect science. mean, let's take marketing attribution as an example, and let's run that through the scientific method. OK? So we have one person that went and listened to this podcast, and then they went to your website or my website, and they filled out a form, and they became a lead. The next person did the same thing, but they've also been subscribed to our newsletter for six months. The next person did the same thing, and then we cold called them two weeks later by some miracle because we just happened to cold call them. We didn't know that they listened to the podcast. It is the most unscientific thing in the world to try to say that this is the percentage attribution for the podcast versus the cold call versus the newsletter. And this is what's driving revenue. It is just plain black and white, not scientific. So at the end of the day, you have to take this imperfect set of data and just make a gut level decision to say, do I want to invest money in doing more podcasting or more newsletters or more cold calls? or do I not? And that is like, I think the disconnect between a lot of folks that work in go-to-market strategy and ops and the people that are having to make the hard decisions in the CRO and CEO role. Warren Kucker: ⁓ I won't piggyback on that marketing attribution thing because our listeners have heard me beat that drum in at least five other episodes. I couldn't agree more. That marketing attribution is silly. Whatever happens last is not what should get attributed along the way. All right, great. Well, last question. We'll try to do a little crystal ball. What do you think, let's say two years from now, we have a new paradigm in tech with generative AI. What do you think either looks a lot like the same, but better, or might look different when it comes to sales process? Eddie Reynolds: ⁓ man. Like you're basically asking me to predict like where AI is going to go in two years. And so who knows, right? ⁓ Warren Kucker: I know, I'll build it. Agreed. Eddie Reynolds: So I think if we just look at historic technology adoption and we think about the dot com boom and bust, I think that we're going to go through that. I wonder if we're going to go through that significantly faster. I see right now that many organizations are buying every AI tool they can get their hands on. They don't have the foundational definitions and process in place. They don't have accurate data. And I do think that AI can help solve some of these problems. But without sitting down and doing the customer journey map and mapping out the sales process and the outbound process and the inbound process, et cetera, you can't just magically sprinkle AI on top of that broken process and expect it to produce the desired output. And so I think you see that coupled with a lot of tools that are being bought like month to month. And I think that you're going to see this massive crash where people wake up and realize this isn't producing the outcome that I wanted. So we're going to back off of this. bought everybody chat GPT licenses or cloud licenses. Every person across the organization is trying to like vibe code their own solution. I don't think that that's tenable. I think what we're going to do is we're going to slowly move towards a place that is more similar to where we've been, where we have, you know, go to market.com ⁓ or rev ops or go to market engineering teams, whatever we end up calling them. This name seems to change every three days. Building this stuff out at an enterprise level and saying like this is the agent or the workflow that we are going to build that goes across the entire organization that every sales rep is going to leverage. They're not vibe coding it on their laptop. This is how we're going to ensure security and reliability and how we're going to debug it, etc. I think what we're going to see increasingly is a CRO that is more tech savvy and AI native, not that they need to be vibe coding this stuff themselves, but they start to understand how to build process and how to think about metrics and analytics in a way that many CROs today are not equipped for. Because many CROs today just were really great salespeople and then got promoted into the and at no point in time did they learn these things. and I think that you're going to see a real separation between the CROs that lead with an operational bent that say, we're going to build a team, we're going to build this technology across the team, we're going to have our process in place, we're going to have our analytics in place, and we're going to be a process-driven, data-driven organization. I think you're going to see that those teams will significantly outpace the folks that are still doing it the old school way. I think that the old school CRO that just personally to help the reps close every single deal and forecast manually with gut feel and makes these gut level decisions across the board are going to be phased out. Warren Kucker: That's a great many forecasts where things are moving really fast and we don't know where it's going. So I like that shift, I that paradigm. think with everything we talk about in this space, a lot of times it seems like AI is going to eliminate some layers of like red tape and actually kind of like bubble up things that we've always been doing. And in your scenario, it's like, you know what? Frontline salespeople are better equipped, but have more responsibility to do the selling, right? Like, the CRO is more about how do you frame the context more and less about the hand-to-hand, day-to-day carrying. reps through a sales process. Eddie Reynolds: Yeah, and I think the other question is, like, are we going to have the 10X sales rep? And what does that mean for the size of sales teams? I think we're already seeing this. If you make every rep 10 times more effective, buyers are not going to buy 10 times more stuff. You're just going to end up with less sales reps. And we've already had interviews on our podcast with CROs sharing that this is exactly what has happened for their sales teams. So think you're going to see that. I also think in the world of go-to-market, strategy and ops or rev ops that you're going to see more going on because I don't think any of these tools are set it and forget it. I think that you're going to see that if you really, really want to perform here, you have to have this ongoing engineering mentality where we are continuously optimizing these tools. And I think that you're going to see organizations graduating where each rep is like an F1 driver and they've got this entire team behind them engineering the car and the system for them. And ultimately, would also say that hopefully this comes back and makes the sales rep more human and more relationship driven because now they've got somebody else doing all that stuff behind the scenes for them and they can focus their energies on what they do best, which is building relationships with people. Warren Kucker: I like that F1 comparison. I'm definitely gonna use that because that's absolutely the way it should look like, right? So much of the preparation and the system design is what should enable the driver to do what they do best, which is go out and win a race, right? So I think we have a new opportunity to do this that hasn't really been possible in the past because we need to do a lot of the other stuff. They needed to also help build the car, right? Like, and figure out the process and tell us what's wrong at a mechanical level. Awesome, Eddie, well, really informative, really illuminating. Where can our listeners find you? Eddie Reynolds: UnionSquareConsulting.com, can find me, Eddie Reynolds, on LinkedIn. And if anybody wants to see our core frameworks, go to UnionSquareConsulting.com backslash frameworks and the go-to-market efficiency pyramid is our main pillar content where we've outlined what the fundamentals look like, what adoption looks like, what optimization and amplification with automation and AI look like. So organizations can think very clearly with tangible specific things that they can do in their go-to-market to build this foundation. so that the AI can layer on top of a functioning model. Warren Kucker: Well, I'll drop that link in the show notes. It's been a pleasure having you and looking forward to seeing what you guys continue to drive and go to market over the next couple years. Eddie Reynolds: Thanks for having me.