About this episode
Eddie Reynolds, CEO of Union Square Consulting, brings 15 years of Salesforce implementation experience and a mathematical approach to go-to-market strategy. His firm partners with B2B SaaS companies to align sales process, data quality, and operations, with a particular focus on how to deploy AI effectively across the revenue engine.
Most CRM implementations fail not because of tools, but because companies lack clear qualification criteria, accurate pipeline data, and alignment between sales behavior and business definitions. This foundational problem persists regardless of how much AI you layer on top. Reynolds' core insight: automating CRM data entry with AI is only valuable if reps are still engaged in the strategic thinking that actually drives deal progression, and if the underlying sales process reflects how customers actually buy.
The episode unpacks the real cost of unqualified deals and poor deal qualification. When reps spend time on deals they should have disqualified early, they miss opportunities to engage with decision makers, close larger deals, and move faster. Reynolds shares concrete examples from his Salesforce AE years: top performers closed 50-100K deals in SMB, while underperformers closed half as many 15K deals at double the cycle time. The difference was not effort, but the ability to walk away from deals without executive stakeholders or clear buying processes.
The conversation then explores how to use AI responsibly as a force multiplier. Rather than eliminating the critical thinking work around deal staging and qualification, AI should automate information capture and coaching, freeing reps to go deeper on customer pain mapping, internal champion strategy, and account-based selling. Reynolds also previews how CROs must evolve: from command-and-control closers to process and systems designers, measuring pipeline quality before chasing pipeline volume.
What we cover in this episode
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2:15
Why Most CRM Implementations Fail Companies ask reps for too much data, creating noise instead of signal, without foundational alignment on qualification criteria or process discipline.
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8:45
Deal Qualification as Competitive Advantage Ability to identify qualified versus unqualified deals early separates top performers from underperformers; poor qualification forces reps to chase bad deals instead of deeper engagement.
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15:30
Stakeholder Alignment and Deal Size Impact Engaging only junior stakeholders drives smaller deal sizes, longer cycles, and lower close rates; senior stakeholder access multiplies deal value and speed.
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22:50
Customer Journey Mapping Without Delay Organizations resist mapping buyer journey thinking it takes months; but a one-hour workshop with key leaders identifies critical customer moments and sales process gates.
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31:20
AI Automation Plus Strategic Thinking AI should automate data entry and call-to-CRM transcription, but reps must still manually assess deal stage and understand L1-L2-L3 customer pain to drive coaching.
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39:45
Pipeline Quality Before Pipeline Volume CROs often chase pipeline growth without first establishing clear qualification definitions; growing bad pipeline is unmeasurable and creates false confidence.
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47:10
Math and Metrics in Go-to-Market Attribution and sales metrics are imperfect; the trap is over-reporting messy data instead of first validating foundational processes and definitions are in place.
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54:30
Future of CROs: From Closers to Systems Architects CROs will bifurcate into process-driven data-driven leaders building AI-powered teams versus old-school gut-feel managers; the former will significantly outpace the latter.
The lines worth sharing
If a rep doesn't know what stage their deals are in, that's a real problem. Sales reps need to decide what stage a deal belongs in because time is the most precious asset.
Eddie Reynolds · 7:20
The best reps don't win every deal they pursue, but they win a lot because they know when to walk away. That's the number one differentiator between great reps and struggling reps.
Eddie Reynolds · 12:40
We can now use AI to automate the workload of updating CRM, giving reps more time to initiate and grow relationships. But if the rep never looks at the data, they're not thinking about the right questions.
Eddie Reynolds · 5:50
If you don't have clear qualification criteria documented, you don't need to run a pipeline report. You already know it's a mess without looking at it.
Eddie Reynolds · 41:15
Common questions from this episode
Should AI automate CRM data entry or should reps keep filling it out manually?
AI should automate routine data capture from calls and emails, freeing reps from admin work. But reps must still engage with deal staging and qualification decisions; if they never open Salesforce, they stop thinking strategically about deal health.
What is the biggest reason CRM implementations fail?
Companies ask reps for too much data (25-40 fields) without clear qualification criteria or accountability. This creates noise not signal. Best practice: three to four core fields per stage, enforced by managers during pipeline reviews.
How do you improve close rates and pipeline quality without just chasing more volume?
First define clear qualification criteria (like MEDIC or MEDDIC). Train reps to disqualify early, engage senior stakeholders, and understand customer decision-making and pain. Only then measure pipeline growth; bad deals disguise as volume.
How long does customer journey mapping actually take?
One to two hours with key leaders to identify critical customer moments, decision gates, and required outcomes. This baseline is enough to start testing and iterating; don't wait for perfect 90-day research.
What will sales look like in two years as AI matures?
CROs will split into two camps: process-driven, tech-savvy leaders building AI-powered teams versus old-school gut-feel closers. The former will scale reps through systems and engineering; the latter will plateau. Most will see fewer, more effective reps.
Why does senior stakeholder access matter so much for deal outcome?
Senior stakeholders control budget, decision timing, and implementation success. Engaging only junior contacts forces smaller deals, longer cycles, and higher churn post-sale. Top reps negotiate access to the economic buyer early.
SEO meta description
Eddie Reynolds on why CRM implementations fail before they start, how AI can automate data entry without killing strategic thinking, and why deal qualification separates top from struggling reps.
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Eddie Reynolds
Union Square Consulting
CRM data entry AI automation
sales deal qualification
RevOps
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Read the full transcript · 53 KB
EDDIE REYNOLDSHey there, and welcome to another episode of Selling AI. Today, we're diving into the world of RevOps, 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 the 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 go-to-market should run, and a strong thesis on how to leverage AI in the process. He came up with a finance background, and now he runs his consulting firms, and he brings a statistical data-driven lens to go-to-market that oftentimes is a lacking one. So, in today's episode, we debate whether processor behavior is a real driver of sales performance, talk about a little bit about what headless Salesforce 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 RevOps and AI. Welcome to the show. Thanks for having me, and what an awesome introduction. I'll just add one thing. I've also been carrying a bag
EDDIE REYNOLDSin selling since I was 16 years old, so hopefully that adds some color to our conversation for today.
WARREN KUCKERI love it. I have a different background, so that'll be a good contrast. I was just founder, read books until I figured it out, and now I'm a slightly below-average sales guy after a decade
EDDIE REYNOLDSof doing it. 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 in Salesforce, and now you're a go-to-market engineering expert. What pulled you in that direction? Give us a bit about your career arc there. Yeah, sure. I don't talk about selling cars very much. First of
EDDIE REYNOLDSall, it doesn't always have the most positive connotation, but it was a long time ago. 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. Everybody I talked to that ran their own business said, go learn to sell. Since I wanted to own a Ferrari dealership, it made sense to sell cars. 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 Porsche, which at the time was my dream job. I think the thing that I gravitated towards was always process. 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 over the summer when I was 18. I think he just had no idea that I was only 20 years old. Everybody else that I worked with was 35, and they were able to carry the conversation and have this gravitas with the type of people that were buying Porsches that I didn't have. 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. I always thought from an operational perspective, if I talk to X amount of people per day, and if my close rate is Y percentage, then I can hit my target. 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. It became my competitive advantage versus other people that had been in the
EDDIE REYNOLDSjob for 10 or 15 years where I was just starting. Awesome. Yeah, that's a really cool
WARREN KUCKERstory. And obviously, that type of selling is just 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
EDDIE REYNOLDSwork. 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 good deal health. You had a different approach. You think that there's something that companies get wrong when they're kind of driving this type of CRM and implementation and CRM usage. Dive in. Let's go. What's your thesis in that area? Well, I don't know that I would say that companies get it wrong, but I think you and I had a
EDDIE REYNOLDSdiscussion previously about not forcing reps to fill out med pick 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
EDDIE REYNOLDSthis. 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, I 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, you know, 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 and, 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. Yeah, that's a great call out, right? Because again, you cut the admin work out
WARREN KUCKERof filling out a CRM with which a decent amount of time is about updating the rest of the org about what the sale 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. You've got that work down, but you don't want to lose the
EDDIE REYNOLDSessence 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 paradigm? Or is it just any way to
WARREN KUCKERkind of get that in front of the rep and have them manage a deal appropriately?
EDDIE REYNOLDSYou 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. It 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 going to 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 going to 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 going to accept this calendar invite until you do that. Those, 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 of 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 miss quota and make it virtually impossible for management to forecast accurately. Yeah, that's a, that's a really good call out,
WARREN KUCKERright? 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
EDDIE REYNOLDSanyone. But in the same token, you don't want to 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 could 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 haven't 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? Well, I think the next layer of progression
EDDIE REYNOLDSfrom 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 Salesforce. I manage a
EDDIE REYNOLDShandful 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 misquoted 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 are 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 medic or med pick 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 KUCKERThat's really fascinating because I don't do a good enough job of this myself. How large of this particular
EDDIE REYNOLDSproblem 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 underqualified, right? So that's, 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. And there's like, it's what should be done. I don't necessarily see a lot of
WARREN KUCKERin practice, which might be, is probably my fault as a leader. To answer your question. Yes. I think the problem is so much deeper than even what I've described so
EDDIE REYNOLDSfar. 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 were engaging. So this is something I've seen firsthand in so many organizations. If we are engaging at a junior level, then we are going to have more transactional deals. We're going to have lower close rates. We're going to 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 concrete things that I've seen. You've got a rep that's constantly closing 50 and $100,000 deals in SMB 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. 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 of 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, you know, 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. I think this may be like because a question that tactically doesn't matter so
WARREN KUCKERmuch, 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
EDDIE REYNOLDShave, 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 like the knockout effective is when you're getting deeper and deeper into deals, you're also pulling your own internal stakeholders. Now you're CEOs, like let's say C-suite is talking about forecasting those deals and their worst deals. So there's like a, you're absolutely right. The time commitment snowballs for the whole organization. I guess the question would be like in the midst of-
EDDIE REYNOLDSI would 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,
EDDIE REYNOLDSfor 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, 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. Right, right. With all of, let's say with this efficiency kind of like
WARREN KUCKERparadigm, do you feel like it's like, great, we should go increase quotas across the board.
EDDIE REYNOLDSOr should you 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 juicing the numbers. And I know this is a hard, broad question to ask, but like, what are your thoughts on that in terms
SPEAKER_04of like, what should be the end result of the productivity gains?
EDDIE REYNOLDSWell, I mean, let's just look at what's happening in B2B SaaS or B2B tech right now. I mean, close rates are for many companies between 10 and 20%. Meanwhile, they're trying to get 3X pipeline
EDDIE REYNOLDScoverage. And so what is three 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. Um, and that I, I personally think just from a philosophical perspective, that's incredibly like demoralizing. My first job in, in banking, I was at 504% of my quota and it just was a fantastic feeling. Like 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, right? If you have 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 med pick. I mean, 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 we do, 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, you know, 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. Um, 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'll end up with a lot of very unhappy customers.
WARREN KUCKERUm, no, that's, 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 going to 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 French or 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, uh, 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. Um, I would say.
EDDIE REYNOLDSWell, if you don't mind me like kind of like, um, pushing us in a different direction for a moment, like let's talk about AI. Like, I think that there's incredible opportunity for AI to help both save time reps and make saved 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 pick 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. Um, 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. Um, I couldn't agree more, right? Like
WARREN KUCKERin theory, we should, the sales reps should be able to slow down and be more strategic. And let me give
EDDIE REYNOLDSyou 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 in to 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 you think we can create an environment for reps to get that information, to serve it up appropriate for them. So they're spending that time to strategically work through their deals. Now that
SPEAKER_04they should have a little business space and space and breath to do that. What's that? What's a good delivery system for that?
EDDIE REYNOLDSSure. So I saw exactly this when I worked at Salesforce. And so, um, for context, I sold into SMB mid market. When I was at Salesforce, I have cursory level knowledge of what they did with
EDDIE REYNOLDSenterprise, 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, um, 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 don't 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, 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. Um, when they're meeting about my piece of software, like what are they talking
WARREN KUCKERabout in the meeting and how do I drive that conversation? Got it. And so I don't remember
EDDIE REYNOLDSbecause this is over 10 years ago. So if you get my memory, I don't remember exactly what field that might've been, but I'm pretty sure there was something like, you know, 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, um, thing that, you know, you can imagine how complex it would get. Like 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. Right? 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, right? You have to have pipeline inspection. So 10 plus years ago, management would go in and they'd say like, 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. Right? So I go in and I see the biggest strategic deal across North America. I'm talking about my bosses, bosses, bosses, bosses, boss at the time, um, Tony Redoni, who we've had on the, uh, the podcast. Um, he would go in and look at these deals and he's like, okay, 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, 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 like, uh, revolted. Uh, 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. Um, because that's like, that's not going to work. Like no sales rep can actually sell when they're being held to that level of admin work. Right. 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, uh, even possibly other data sources. Uh, I forgot about like, you know, data enrichment tools like zoom info, clay, et cetera. And they can go and fill in all of this information for us. And then now also coach us and say like, here are the risk factors we're seeing in your deals. Like you were on this call two weeks ago when they said like the decision maker and decision making process is X, Y, Z, but, but, but, and 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. Yeah. I mean, that's, um, that's absolutely the case. Right. Um, I like that,
WARREN KUCKERthe split between keeping it simple, right? Like, so your bosses, bosses, bosses, boss, and Salesforce isn't going to look at 40 fields either to determine what's happening on his most important deal. He's going to look for the three things that he knows he's going to find to see if we 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 REYNOLDSI would say is the SE on a multimillion 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, is that we can now train the AI to say like, here's our, 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, you know, a lot of people don't like it anymore, but I've always thought it, 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 for, which is the true for many companies was no decision, right? 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. Right. So when you think about something like medic or MedPic, why is like, 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. Right. 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 transcripts and emails, look for these things.
WARREN KUCKERThat's a, that's a perfect segue into, I'd say a little bit more of the work you're doing now with UnionSquare Consulting. When you're approaching engagements now or people approach you now,
EDDIE REYNOLDSwhat are some of the common themes and like new problems that are rising? 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 are those engagements look like these days? Yeah. So it's such an
EDDIE REYNOLDSinteresting question because it's so informed by the marketing that we do. So we scream from the
EDDIE REYNOLDSrooftops that we can help solve certain problems. And then unsurprisingly, the people with those problems come to us, right? Yeah. So I'll just caveat it with that. But like 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. 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 going to 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 close date and, you know, 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 we're 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 okay, 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? Like I, does that mean we're going to close 33% of that? That's not what we've been doing historically. So how, like, 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 to 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 KUCKERYeah. So, um, qualification being big, um, and I would say I'm asking you to broad brush a lot of different engagements. Um, when you think about how you're managing like your deal health and your pipeline post-qualification, do you, do you often spend time to map the buyer's journey and try to
EDDIE REYNOLDSstage out the sales process in this, let's say more minimal way than most organization. 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, um, it can take time. Um, you're trying to do some guesswork if an organization isn't working well. Um, or is something you usually defer? It's like, let's say, 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
SPEAKER_04the question, the process and what questions you should be asking to exit what stage.
EDDIE REYNOLDSI think it's a difficult balance, right? I don't think anybody hires us or a full-time VP of rev ops or go to market strategy and operations, uh, 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, uh, and come back to me and tell me what our customer journey is. No one says that, right? But so I get a lot of resistance when I bring up the idea of a customer journey to a CRO, not always, but sometimes, but my pushback will be, look, like there are various levels of this, right? 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 a hundred 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 like, what does the customer actually want? And I'll give you a concrete example of this. I, 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 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, is that we needed to do, you know, if, 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 re-qualifying it. Then I need to do full discovery. Then I need to bring in the decision makers and re-qualify them and do full discovery. Then I bring my SE in and then they re-qualify it and 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. They 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 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 incredible, like 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 like 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, I 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 KUCKERYeah. 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. I'm lonely 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. These are, 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, again, like an 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? Well, I think it's really hard. And I think there's a lot
EDDIE REYNOLDSof 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 just, I'm not even talking about startups. I'm talking about companies that are 20, 30, 40, 50 million, sometimes even a hundred million dollars in revenue. They don't have any of these report, like this reporting in place. And the CRO is in every deal or almost every deal. And they kind of know, like 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, you know, 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 figured 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 are, 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, is that at the end of the day, go to market is a very imperfect science. I mean, let's take marketing attribution as an example and let's run that through the scientific method. Okay. 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. Um, 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. Uh, and then they, and then we like 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, you know, this is the percentage attribution for the podcast versus the cold call versus the newsletter. And this is what's driving revenue. Like it is just plain, like 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 and go to market strategy and ops and the people that are having to make the hard decisions in the CRO and CEO role. Um, uh, I won't piggyback on that marketing attribution thing
WARREN KUCKERbecause our listeners have heard me beat that drum at least five other episodes. I couldn't agree more. Um, uh, that marketing attribution is silly though. Whatever happens last is not where it should get attributed, um, along the way. All right, great. Well, last question. Uh, we'll try to do a little
EDDIE REYNOLDScrystal 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, like, but better, or it might look different when it comes to sales process? Man, like you're basically asking me to predict like where AI
EDDIE REYNOLDSis going to go in two years. So who knows? Right. Um, so I think like, if we just look at like historic technology adoption and we think about like the.com boom and bust, I think that we're going to go
EDDIE REYNOLDSthrough 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, and I do think that AI can help solve some of these problems, but like 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. We 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 ops 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. And this is how we're going to ensure security and reliability and how we're going to debug it, et cetera, et cetera, et cetera. And 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 role. 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, okay, like 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. And I think that the old-school CRO that just personally tries to help their reps close every single deal and forecasts manually with gut feel and makes these gut-level decisions across the board are going to be phased out.
WARREN KUCKERThat's a great mini forecast when things are moving really fast and we don't know where it's going. So I like that shift, I like that paradigm. I think with everything we talk about in this space, a lot of times it seems like AI is going to eliminate some layers of red tape and actually 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? And 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 REYNOLDSYeah. And I think the other question is, 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
EDDIE REYNOLDS10 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 I 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're 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, I would also say that hopefully this comes back and like 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.
SPEAKER_34I like that F1 comparison. I'm definitely going to use that because that's absolutely the way it
WARREN KUCKERshould 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 need to also help build the car, right? Like and figure out the process and
SPEAKER_13tell us what's wrong on a mechanical level. Awesome. Eddie, well, really informative, really illuminating.
EDDIE REYNOLDSUm, where can our listeners find you? UnionSquareConsulting.com. You can find me,
EDDIE REYNOLDSEddie Reynolds on LinkedIn. And if anybody wants to see our core frameworks, go to UnionSquareConsulting.com
EDDIE REYNOLDSbackslash 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. Awesome. Well, I'll drop that link in the show notes. It's been a pleasure having
EDDIE REYNOLDSyou and looking forward to seeing what you guys continue to drive and go-to-market over the next couple of years. Thanks for having me.
EDDIE REYNOLDSBye.
