"You're Inspiring People to Mute Your Logo" — A RevOps Leader on AI Outbound.

00:10 Warren Kucker: Hey there, and welcome to another episode of Selling AI. Today we're diving into RevOps from the seat of someone who's actually running it. we want to talk about what's working, what's broking, what's the future of go to market in the space, and how tech is just accelerating everything. I have Jimmy Downey on the show today. Jimmy is the VP of Revenue Operations at NextClass, runs a full stack, Salesforce, Gong, Clay, I imagine some other technologies since we just spoke in our pre-call just a couple weeks ago. in today's episode, we talk about How he kind of flipped his position on AI maybe about a year ago. How he kind of manages go-to-market data and the influx of technology to make sure that the go-to market operations just seamless at next class. and if you're pitching him a piece of technology, what might actually get his attention? so great, let's dive in. Jimmy, thank you so much for being on the show today.

01:01 Jimmy Downing: Awesome. Yeah, thanks for having me. Real excited to be here. you know, some people like to go out on the weekends. I like to stay home and build cool stuff for our RevOps function. so really excited, been looking forward to talking about it with you today.

01:13 Warren Kucker: Awesome, cool. Well let's let's get into it. give us a little bit of your background. how did you get into revenue operations? How did you get into the role and now? give us your journey into where you're currently doing at next class.

01:25 Jimmy Downing: Yeah, I think that this was probably relatable for a lot of people. I would consider myself an accidental admin of Salesforce back in the day. actually worked in a finance team. started my career actually collecting money. so working in accounting, we quickly started to transition over to Salesforce as our main CRM at the small HVAC company I worked at. and there was no one to really own the tool. So when I started working in the system, I started to fall in love with it and realized that a CRM like Salesforce is not only powerful, but it's about to take over the world. so I wanted to do more of it. I moved into consulting specifically for Salesforce. and then wondered what was next from there and moved to RevOps consulting. So I've been doing revenue operations consulting since then. until I've moved into my recent role here at NextClass, where obviously an in house resource. So That journey I think a lot of people it will resonate with. A lot of people have become an accidental admin because nobody was there to own the tool and they've kind of grown into it. Maybe they hated it, maybe they loved it. I was lucky to love it. so once I realized that there was more beyond Salesforce, that's what took me to revenue operations and I started to understand and lock into the tools that not only integrated with Salesforce, but worked alongside it to really superpower give the teams the superpowers that they need. you know, to run their marketing teams or sales teams or customer success teams at a high level. So, I love what I do. it's a hard job but it's very rewarding. So I'd have it no other way.

02:59 Warren Kucker: Awesome man. Well let's d dive into how things have changed over the past year, two, three years. let's talk about the tech in particular. From your perspective, what's like the baseline new technology, let's say LLM based or not, but new tech that everyone should have, should be using. what's the stuff that they could be using and what's maybe the end of the spectrum where maybe we're overpromising and under delivering when it comes to that go-to-market engine?

03:24 Jimmy Downing: Yeah, that's a really good question. It's a loaded question, right? Because over the past year so much has changed. In fact, you could look back to the beginning of this year, right, in January, and just look how different some of these AI tools are, right? Even the common ones that everybody hears every day, like a cloud or a chat GPT, that typically power some of the tools that you would buy for your team. there's been so much change, there's been so much improvement, and that's only going to continue, right? Like, one of the sayings that I hear over and over again is that This is the worst that AI will ever be, right? It's only going to get better. so where I'm seeing companies win right now, is in the simplicity of it all, right? Because it's so complex. There's so many layers to it. But the teams that can find the AI tools, or even models that just take a lot of those smaller wins off their plate, like whether or not it's just simple admin tasks, like cleaning up your inbox. maybe drafting emails at scale, maybe even updating your CRM records for you or enriching them, you're you're taking out of those like low level tasks that might take up more time than they should. and you're able to refocus that time and energy on things that are a little bit more of a high value. So I think that's really easy to get caught up in some of the hype that these tools can deliver. but historically if you look at the product and the tools that win that work well for companies, they're the ones that do one thing really well. Right. They're the ones that are focused on solving one specific pain point the best way possible. so companies that are finding success with either AI tools or some of these tools that are being developed by AI tools are the ones that are solving their exact pain points in their simplest form and freeing up that time to do more complex things that need a human touch.

05:17 Warren Kucker: That's great. is there anywhere right now that you're finding again it's a technology is overpromising or that like from like a revenue operations perspective in sales, CS or or marketing, it's not quite there yet and maybe needs to be left alone.

05:34 Jimmy Downing: Yeah, this is probably not the last time this will come up on this call. I am very much against using AI for an outbound motion. I think that this is a market that is doing more harm than good to your brand name, right? That kind of spray and pray mentality of let's just have AI draft as many LinkedIn DMs we can and send it out. How many emails can we draft and send it out? what you're doing is you're actually inspiring these people that you're targeting to mute your logo. Right, because it is annoying. It is frustrating to get that many cold DMs or maybe cold emails that are just missing the mark, that are either clearly generated by AI, or just not on topic or just completely wrong. and especially if you're selling an AI outbound tool and your tool is the one doing the outreach, somebody in my role is not gonna want to buy your tool because I know how it's going to come off to my potential buyers. Right. So very much against using AI SDRs to drive business. Now, on the flip side, using AI to manage inbound, great move, right? so I I think that you have to be really careful with where you're plugging in AI and just kind of like letting it off the leash.

06:49 Warren Kucker: Totally agree. is there anywhere, let's say I mean, outbound side that where's the dividing line for you? and like what can be done by AI, should be done by AI and shouldn't be?

07:00 Jimmy Downing: Yeah, I think that from the outbound standpoint, AI is really good at compiling lists for you to target. Right. it's really good at getting detailed about finding customers that are in your, I guess you'd call it ideal customer profile, ideal client profile, whatever you want to call it. Try to stay away from the the jargon speak of like your ICP. it it does a really good job of maybe visiting websites for you and kind of telling you more about. customers that you could be targeting yourself or you know, handing off to a team of BDRs that's going to do that outreach for you, right? AI thrives in doing a lot of that busy work, like I said earlier. you know, I I I've spoken to a few people about how they think about AI. and a lot of times the feedback is, you know, AI can do the the can be just as productive as a thousand people, a hundred people if you position it the right way. And When it comes to outbound, if you can point AI at the right spots, like maybe generating a list of people to target, that's much better than saying, Go target anybody that fits this criteria and send them a message, right? Because now you can take over as a human.

08:13 Warren Kucker: No, I think there's I think in the just in sales and go to market in general, I think the ideal RevOps function in the next few years is stripping away all the admin, all the back end side for their frontline sellers that they can and leaving them just what needs to happen from the human to human relationship, the touch there. So I think there's some really obvious dividing lines. We shouldn't have AI called calling. let's not do that. but should we have reps doing research as to what's happening in an account and gathering that research and scraping websites and look reading articles? Probably not. So let's like service up the research. So but let's go into the in between to see if we can find gray area in that line. Let's talk about cold emailing. what are your so you have spray and pray. How do you feel about automating cold emailing for let's say enterprise mid market account executives and they're sending out to fifty, seventy people a week a sequence of emails. Do you feel what side of the line do you think that falls on?

09:09 Jimmy Downing: Yeah, that's a good question there too. I think you're you're still treading the line of like I call it like just a noisy channel, right? there are you're gonna find more often than not your buyers aren't even opening emails that are clearly sent out using AI.

09:25 Warren Kucker: Mm-hmm.

09:26 Jimmy Downing: that they have not if they've had no previous interaction with you. they're just gonna mark those emails in bulk and send them off to their, you know, recycle bin, or they're gonna even worse, mark you as spam. so the the technique there needs to be a little bit softer I think and maybe try to find places that aren't as noisy, right? Your inbox is a very noisy place to show up. Same thing with LinkedIn DMs also. Very noisy place to show up. could you use AI to maybe send some mail to somebody's address to get their attention? Sure. Yeah. Could you spend some time on LinkedIn maybe interacting with the you know, the person you're targeting interacting with their posts or kind of taking an easier approach before you're sending one of those emails. yeah, you definitely could, right? Like I think that there's a strategy in showing up. whether or not you're showing up in somebody's comment section on LinkedIn or maybe in a group that you're part of on Slack. If people start to recognize your name, they're more likely to open up your cold email that you send them. So, That's what I mean when I say like I think that there's some value in that softer approach.

10:40 Warren Kucker: Yeah, so I couldn't agree more. I think I've I mean I've done it all at this point. and I've swung back towards I don't do any LinkedIn automation anymore. One I think LinkedIn does a good job of squashing anything that looks like automation, good for them. so but what I've done per personally is I use a piece of software to surface up when my people in my TAM or ICP have posted something on LinkedIn and I spent a lot of time commenting, asking questions, liking posts. so they're seeing my face, my name. and then after a series of comments, some connections, maybe some emails, maybe some cold calls, bolted on. so they're still a part of it. Now on the emailing side, I s I don't think that we're necessarily being rewarded by handwriting emails out because I actually don't think reps are very good at that part either. so like I I don't think most people can tell the line. I think the to me, but I love your perspective is the line is they should be like moderately reviewed by your reps to make sure that you're not sending out something that is blatantly obviously not like off the mark, right? if it looks like a rep might have sent this email, I think we're fine because just another piece of the puzzle there. so because what you don't want to do is interact a bunch on LinkedIn and then like burn that by sending an email that's completely not relevant or off base altogether. So, how do you feel about like that like middle ground and the battlefield there? what are your thoughts on that approach?

12:01 Jimmy Downing: Yeah. Agreed. I mean you're look, there there have been times where I have had a a lot of interaction with somebody outside of email and they do send me an AI generated email. My first instinct is to call them out on it, right? People love

12:16 Warren Kucker: Yeah.

12:16 Jimmy Downing: calling out somebody when they used an AI tool to write their email that they send you, right? It's like everybody's favorite pastime now. People are actually reading emails just to see like do I think AI wrote this? Right. There are ways to avoid that. And I like what you said about having an AE personalize it and give it a once over before something goes out the door. Absolutely. In fact, if I'm building a tool that's doing outbound now, one of the features I'm building in is to make sure that this tool can adopt that person's voice and their style of writing, right? Maybe even throwing in some spelling errors, right? maybe even throwing in some grammatical errors. It doesn't need to be perfect. Avoid the dashes, right? There should be a set of rules of How do emails get written? How do I communicate in different scenarios, whether or not it's email or LinkedIn DM or in Slack? There should be different styles that your tool can adopt to and help you automate, right? Cause that'll get you a lot further of the way there. so I think if you're going to be doing that cold outreach and having AI write your emails, go the extra mile and have it adopt maybe a voice profile of yours to fit how you speak and how you communicate.

13:26 Warren Kucker: we could talk about this until the cows come home, so we'll have to pivot a little bit. So, let's say six months to a year ago you had an ethos that you shouldn't layer on let's say new tools onto bad data. So if your data wasn't clean and you're let's say CRM or anywhere else, if you're gonna start adding some AI tools, accelerate some some sales motions or marketing motions or C S motions, bad data was gonna create big problems. You've shifted somewhat on this approach, or maybe you've shifted back. Give us your thoughts. How have you kind of evolved your thinking as to like when's the right time to implement these tools? Is data ever clean? what are your thoughts there?

14:07 Jimmy Downing: Yeah, this is a great debate still. because originally my take on this was if you're going to implement AI powered tools on top of messy data, you're just going to make it worse, right? And I think that that casted too wide of a net. I think that that was an unfair comment because I think that you should need to be smart about where you layer in AI tools and you need to focus on areas where your data is clean, where it's always clean, right? I think we can all agree that. you know, your top of funnel stuff, you know, your leads, your prospects, that's gonna be messy data. You might be dealing with duplicates, incomplete data. That might not be the best place to point an AI tool or layer in an AI tool. But if you look at your pipeline that's open, your team of AEs, for the most part, they're keeping a pretty clean open pipeline, right? They're working their opportunities, you're reviewing them weekly with them, maybe even daily. That's a pretty clean place to point an AI tool or layer in an AI tool. Same thing with current customers. Like you have a pretty good feel for who your current customers are. That's always accurate, right? that's a great place to have a tool powered by AI to be working. That's some clean data right there. So I think what you need to be do as a company is be self aware in a way and say, Okay, where is our clean data? Let's layer in some AI tools there. Because if you do the opposite and you don't quite think through that and you're starting to adopt tools that stacks on top of dirty data, well You know, the output's only as good as the input.

15:39 Warren Kucker: yeah, it's a good way to look at it, right? Like where could creating tools that accelerate a process create problems based on the data set it's on top? if you are just letting AI loose, creating outbound sequences on your CRM that has forty seven thousand accounts in it that have gathered over the past seven years, you're gonna struggle. right? So in the same token it doesn't seem like you maybe aspire to the ethos that like we need to make sure that that data is completely clean before we get started. How do you coordinate the right data? How do you use AI to clean up the data? but like being smart, targeted, and not creating chaos within your process with by putting bad money after bad. Seems like a really good ethos along the way. Let's go a little future forward. I I have a mindset that I think we're at finally at a point where revenue operations could live up to its new nomenclature, go to market engineering and they could actually engineer the process from awareness, your marketing, to interest to purchase on sales and post purchase and upsell on CS. I think that We have the ability to strip away all of the admin work on the frontline sellers and get them just doing the human part. do you think that's where we're going from a revenue operations standpoint? Do you think that's a bit of a pipe dream still? and what do you think the lever is, if it is possible?

17:12 Jimmy Downing: Yeah, I think that's where we're going. I mean, I think like I said earlier, I think the smartest companies are automating the small tasks and they're finding the quick wins and they're taking that admin type work off of people's plates. So I do think that's the direction that we are heading. and I think that there's like different ways you can bucket it, right? Like I think that everybody should sit down, you know, at their desk one day and spend thirty minutes going through an exercise of what can AI completely handle for me? What can AI handle but I still need to work on a a little bit? Maybe maybe AI gets me 80% of the way there, 85% of the way there. And then that third bucket being, what can AI not help me with that only I can do? Right. And that third bucket tends to be people's soft skills, the way they communicate, the way that they work, the way that they make people feel on a call if you're selling, right? Like I think that that's something really important in the sales world, even in the marketing world, right? So sure, I think that we're definitely heading in a direction where AI is going to take over a lot of those smaller administrative type tasks, but I don't think AI can ever really fully replace the skills that make people very valuable. I mean, unless you're talking about Excel skills, right? So sometimes people may be in a position because they're so good at Excel, right? Everybody knows that one person that if you ever put them in a Microsoft Excel competition, they would impress everybody in the room. with AI now, there's a lot of people in that bucket. Right. So

18:38 Warren Kucker: Mm-hmm.

18:38 Jimmy Downing: I think that's why it's important for people to kind of go through that exercise and maybe find out what sits in each category for me and what makes me unique. Because although AI is going to automate a lot of that simple stuff, a lot of that admin work, there's still going what it's gonna happen is you there's gonna be more and more importance put on that second and third bucket.

18:57 Warren Kucker: Yeah, interesting. How do you think that might evolve like the seller's kind of skill set over the next couple of years? Do you think that's gonna shift what makes a good salesperson versus what's made a good salesperson over the past five to ten years?

19:13 Jimmy Downing: Think it already has. I think that now the the best salespeople are the ones that can stay and should stay completely present during a call, right? Because if you think about two years ago, even three years ago, like it was almost offensive to have a call recorder in a Zoom call. Now it's so normal, people don't even flinch, right? Like if you told somebody that you were recording a call at the beginning, they're like, Yeah, obviously, right? Whereas two or three years ago, if you were like, Hey, just so you know I'm recording this call, are you okay with that? It might be a ten minute conversation. Well, what are you gonna use it for? You know, how how's it gonna be shared, right? So I think the best reps now are able to be present because they don't have to be taking notes. The everything is recorded, everything is already summarized for them after a call. So where do those reps add value? their personality. The the way that they do write those follow-up emails, right? Like are you writing a follow-up email that's, you know, so long that nobody reads it, or are you just Writing a couple sentences of just, hey, let me know when you want meet next, or hey, I know we're meeting Friday. You know, I'm not sending you a pitch deck, but here's a video for you to watch, a t one minute video, right? So the best reps are gonna be the ones that are saving that time with their notes being present on calls and then staying unique in the way that they stay engaged with people. so I think it's already happening. and the people that aren't adopting that, they're they're they're gonna start getting left behind.

20:35 Warren Kucker: Yeah, I think it's gonna be a challenge. I think We went through a small cycle of sales generalists having their day, being good at sales process, understanding how to run a good discovery call, how to run a buyer's journey. agnostic of industry has been really valuable. And it's how I as a founder thought we should hire sales folks over the past ten years. in to the point where in an interview someone told me they were like a big relationship seller and didn't understand any sort of like sales methodologies, that that wasn't the right person for how I wanted to run. Sales process, they could be wonderfully successful elsewhere, but I didn't think it was the right approach. I've done a a flip on this where I actually think it's tougher for salespeople. You almost have to pick an industry and stick with it for a while. And switching industries is gonna be increasingly harder. I think there's two ethos that are gonna play from a company and sales rep standpoint. The company needs just be extremely present in their industry. So like they need to know. lack of brand awareness is going to be a problem. You thought there'd be a lot of disruption from small players, but actually it's gonna go the other way because Gong could build any tech. Gong's brand name matters, right? So like being present in the market they're in matters. And then the same thing on the rep standpoint. I'd have a real hard time switching from an industry that I knew well and I knew the players, I'd switch within the industry so I could have those conversations and be well represented. regarded there. Do you feel like the the day like kinda like that sales generalist sales process, like heavy on the the tech technique of sales is gonna go by the wayside a little bit and the relationship settler will have their day? Or do you think there's space for both?

22:14 Jimmy Downing: Ooh. I think there is space for both, but it's way easier now for somebody to get up to speed in an industry that maybe they've never sold in before because now there are tools that can get your new reps up to speed based on your top performers habits, right? any of those sales enablement tools, like a gong that you just brought up, is going to have a very specific playbook to not just your product that you sell, but the industry that you work in. And it's really easy to hand that off to somebody now. Whereas back in the day, what did you do? Hand off a Google Sheet? now you hand off automated workflows in a tool like Gong or Salesforce that really all a rep has to do is be on top of stuff, hand it off to the tool, let the tool sequence this, let them bring the tasks to you on day one, day three, day five, day ten. Here's what's next. That's a lot easier than it ever was. So I think there is room for both. I tend to side on the relationship side because that's what I've seen work really well is not that pushy side or not that follow the playbook side, but instead build that relationship, understand what their pain points are, make sure you're providing value in those different areas. I've seen that work really well recently because the technology is handling the playbook. The technology is handling the next steps and it's almost holding your hand through the whole sales process based on how your sales leadership has defined it.

23:39 Warren Kucker: No, I I couldn't agree more. I think it's If it's gonna be harder for an organization and a seller to come into an industry they're not known very well and say, Hey, I think you have this problem, let me be the one to help you solve it. I think what's gonna happen much more is that people will understand what problems they have. they'll understand generally when they wanna solve them. The geman generation is gonna kinda slip. and then they'll go to the people that are trusted to solve it. and it's gonna be people they've seen at conferences, it's gonna be people they've met in real life, it's gonna be people that just had those good interactions in the past. and it'll be a little bit harder to crack in. So, from both a brand and seller brand perspective, along the way.

24:20 Jimmy Downing: Yeah. I I also think that this is a generational shift too, right? Because millennials as they move into these buying positions, they don't they typically don't like to be sold to. They'd rather be educated and make their decision, right? So that changes the selling process too.

24:40 Warren Kucker: Yeah. I had someone who wasn't in sales tell me something pretty pretty drastic that I hadn't really thought about. And he's like, Well, you're selling to CROs, you're selling to directors of sales, and you're selling to account executives, generalizing it. That's three markedly different generations and If you think about it, like they've grown up in three different environments. Your CRO may love to have a round of golf with their vendors, right? my my ethos when I was in a buying position a lot was I didn't really care to hang out with my vendors. Like have a meeting, tell me what works, tell me what doesn't work, and if and just fix my problems, we'll move on. And then if you look at, let's say, a millennial or like whatever the next generation, two generations below me would be, they've consumed a lot of their information on the internet in a way that we haven't before on short form video, right? So perhaps that's the way. What best way to walk someone through a buyer's journey who's 27 with decision-making process or power along the way. So it'll be an interesting approach. I think it'll really allow for, and that in perspective, you're right, like sales skill and understanding how your buyers wanna buy could be the human-to-human relationship that really AI is not gonna solve for. that'll kind of like be the new generalist. Generalist, but understanding how people wanna consume information will be interesting.

25:52 Jimmy Downing: Yeah. Yeah. If there's something

25:53 Warren Kucker: A salute.

25:54 Jimmy Downing: now that I would double down on in my career if I'm right out of college, it would be my soft skills. That's the one thing that AI will never be able to replace. That's the one thing that you'll always have an advantage over somebody else if you're good at it. Your people's skills are probably the most important they've ever been.

26:11 Warren Kucker: Yeah. So how do you think from a sales leadership standpoint and revenue leadership standpoint, we need to enable that? I think personally I think we need to stop having forecast calls. I'm gonna tell you what the forecast is. It's data. you have a decision date or you don't. I heard it on the call on the transcript, it doesn't matter. But what I wanna work on is how do you and understand when to ask the right question, if you're a vendor of choice and if you have a decision date on your software or not? Like how how do you see sales leadership kind of helping accelerate that shift into soft skills or more of the priority and processes, less so?

26:43 Jimmy Downing: Yeah, I tend to make a lot of sports references just because that's where my mind always goes here. I think that coaching is so important. I think that the type of coach you are, as a sales leader should should change based on who you're coaching to, right? Or how you're finding success selling, right? there's more and more on that now where Maybe you are going into a cold call sparring match with your BDRs instead of having a one-on-one talking about their future goals, right? maybe you are spending time with an AE practicing, you know, objection handling or how to close a deal, right? that coaching changes and and I agree, maybe you do have to spend less time forecasting because the data's already there, but now you spend more time on your people and develop their soft skills. Now you're developing how they approach calls. And you're explaining how calls are always going to be different, right? There's not gonna be one that's the same. There's not gonna be a sale that's the same. And if you're not able to think on your feet and pivot and have those good people skills to kind of avoid that awkwardness and kind of roll with the punches, I think that's gonna be the key.

27:54 Warren Kucker: Yeah, I think the to be really explicit too, I think we get away from saying, Do you have a champion on this deal and tell me why? And using that as the teaching tool. because we know if you have a champion or not. So like let's not worry about that, right? Hey, you don't have a champion and this is why. And these are the soft skills. They're like these are the questions that you could ask. This is the questions you're not asking, this is why they're not a champion and who you need to go find out. Like I think that soft skill coaching is really gonna escalate, which is also interesting because these are They're not like point in time skills you can just coach. They're mindsets and behaviors that need to evolve over time. It's just everything is gonna take longer now. Like these sales cycles are gonna lengthen, sales skills need to be developed over the course of years, and we need to get out of this rut where we churn sales reps every eighteen months and just like keep them for much, much longer in a way that makes sense.

28:43 Jimmy Downing: Yeah. I mean, you're also now you're talking to buyers where, you know, they're they're they're working with the AE, but that also is a window into how they'll be treated when they become a customer. Right. So if the AE is somebody that's listening and problem solving and, you know, making sure that they're focusing on your pain points, that's a window into how you're going to be treated when you become a customer and six months down the line you submit a ticket, right? Whereas on the flip side of that, you start to think like, well, if I sign up, like If I start using this product six months from now, is this how I'm going to be treated from a support standpoint too? Right. So I think there's that importance of like selling, but also there needs to be that continuity between like how does the company want to work with potential customers and their current customers?

29:27 Warren Kucker: Yeah. yeah, I have this it's a big ethos of mine, right? Like the sales team is the professionalism doorstep to how you're gonna be interacting with that company going forward. If you're if you're extremely professional and helping them make a decision from a buyer, that should be like this is how my C S team will be taking care of you along the way. If you're really thorough on follow-ups, right? Like you're really fast to respond, you solve problems for them, you're vendor agnostic, and you're showing that you're really just solutions focused, that's a really good sign. for what is like the sales relationship could be 90 days and the CS relationship could only be nine years, right? So like set the stage in a way that makes sense. You're absolutely right. I hadn't thought about those two. The aut automating away some of the admin work so they could focus on the relationship should help with that as well. Cool.

30:12 Jimmy Downing: Absolutely. Absolutely.

30:14 Warren Kucker: Let me I got two more questions for ya. I like to flip this on its head. I think oftentimes we forget as sellers that we're also also buyers. So for example, there's this ethos that our buyers are doing tons of research on their software before they're ever talking to an account executive. It's everyone saying it. and what I've kind of like countered with a couple of times is I'm a different type of buyer because it's just like someone prov presents something to me, it solves a problem, I get to make a decision, I buy right away. So I don't have to convince anyone to do anything. On the flip, I don't do that much research, right? So like it solves the problem, it seems like you're the ones that could solve the problems. I'm not getting to a huge commitment. I don't spend hours trying to figure out my which data set is better when I'm trying to enrich cell phone numbers. It's just I try it, I use it, it didn't work, I move on, right? from your perspective, as like a buyer of software, one, what's like a big pain point that you either solve for recently or or are trying to solve for now. and then two, what's an example of like a good buyer's journey that you've experienced recently, maybe with AI, an AI focus, or a bad one that seemed like overly engineered from an AI perspective?

31:16 Jimmy Downing: Yeah, I I I think I want to start with the second question there. I I think a great approach is getting people into like a free trial or a free proof of concept. even a paid proof of concept, I think, can go a long way as long as you're breaking even. Like if you have a product that's difficult to stand up and it's going to take your team some effort to stand it up for somebody that's a potential client, sure. Charge for that POC. If you have confidence in your product and you know it's going to perform well. I would get everybody into a trial into a POC that I possibly could because you know they're going to convert. And that is your time to also show them the white glove service that they'll get when they become a customer. So like I love that approach. personally that's worked really well for me as a buyer. I've loved being able to get my hands on a product because sometimes it's not about just what the product can do for a sales team. It's how's your revenue operations team going to be able to manage it? Can the finance team get the data out of it and the answers that they need? Right. And that all can be discovered during a trial or proof of concept. And a lot of times, those are the people that are your decision makers. if you can get a CFO on board, high likely chance that that's gonna close. Same thing with like if you get a CEO on board, high likely chance that that's going to close. So I really like that approach for getting people into your tool just so they can experience it and get their hands on it. Cause you get you you Essentially multi thread without having to do it.

32:43 Warren Kucker: Yeah, it's a way good way to look at it too, 'cause I think, both in the prospecting process and I'm gonna say that initial decision making process, you have to find value so quickly. You can't like dawdle around and perceive value for a while. I think the focus, I've gone away from like lack of momentum kills deals to like you lose your buyer's attention, right? So like when you lose that buyer's attention it's so hard to get it back. And so you're absolutely right, like during the prospecting process or let's say that POC process, how do you get them to instant value? They're in your platform. It's not complex to use. You use the word simple early on and they're getting value almost immediately from that process. Then later on, any complexity that comes along the way, I think that's a really good way to look at a a valuable buyer buyer's journey.

33:27 Jimmy Downing: Yeah, I've and I've seen it work. I've experienced it, right? There's there's a lot of times where it's hard to commit to a tool that you may not know enough about, right? Because I'm in a similar boat as you is I might not do as much research as I should do before I'm taking a demo call on a product. I expect to learn more about it on that demo call, right? What brings me to that demo call sometimes is just knowing that that product is replacing the product that I currently have or trying to for half the cost or better features or maybe they're not consumption based when I'm on a consumption based tool because a consumption based model scares me as somebody leading a RevOps team, right? So there's a lot of reasons that you take that first demo. And I'm with you. I don't necessarily have that hour or two hours to do good research and come completely prepared with a list of questions for that first demo. I'm there to get introduced to your tool, answer some questions that you might have for me so you understand what I'm looking for and what I'm trying to solve. And then go from there. I think the real value comes from that second and third call, when you really start to get into the weeds there. So, I think that answers your two part question there of of sort of how I work through that as as a buyer.

34:39 Warren Kucker: Interesting. That's fantastic. All right, cool. Well, maybe last question. Do you have an unpopular opinion as to where AI might take us in marketing, sales, C S?

34:49 Jimmy Downing: Yeah. okay, so I I love the whole vibe coding world. I love what's happening with the amount of speed that it takes to develop new features or new products that complement a product that somebody is selling. but I guess that my un unpopular opinion is that's what scares me. are these tools built in a scalable way? are they do they have efficient code behind them supporting them? Are they a house of cards? You know, there's w we're we're rapidly shifting from a world where you had a team of like engineers and developers that meticulously built a product, pressure tested it, did user acceptance training, did testing, did everything, to now a world where we're pumping out features in a week. one person's working on it. not as many eyes are on it, not as many hands are touching it. So, sure, it's really cool what people are coming out with. Like even free document generation tools, right? Like That's starting to exist in this world. That's not gonna be the end of it either. but that scares me at the same time. What happens to these free tools six months down the line, two years down the line? that may have been built too quickly. So, although I love it, I love the speed that we're going at, because now we're facing different bottlenecks. Usually it would be like development and engineering that's the bottleneck. Now it's probably that go-to-market function that's the bottleneck, but it does. I guess my unpopular opinion would be that is that there's a lot of unknown because I've seen things get overbuilt. if you if you think about it in terms of just like being a Salesforce administrator, Claude can build a lot of stuff in Salesforce now, right? It can build you a flow, it can write Apex, it can do stuff that usually would set the best people apart. but does it do it the most efficient way? Does it overbuild it? Absolutely it overbuilds it. does it do it the most efficient way? No, no, it does not. so if you do that for a year or two, your t you think your tech debt is bad now? Wait, wait after you vibe code everything in Salesforce for two years, then look at your tech debt.

36:59 Warren Kucker: Yeah. that's awesome man. That's a great take. Jimmy, where can people find you? You go to conferences, you post on LinkedIn, people wanted to follow your ethos, how can they get ya?

37:10 Jimmy Downing: Yeah, I'll be at the Revenue Operations Revenue Operations Alliance event in October in Boston. I'll be speaking there, so come there. we'll hang out, we'll chop it up. You can always find me on LinkedIn. I love a little bit of back and forth in the DMs. I love hot takes. I try to post a tip each week that either helps people or directly attacks something that you do that I don't agree with. but it's all in good fun. So if you want some entertaining and entertainment in your life on LinkedIn. find me there.

37:41 Warren Kucker: That's great. And that's how we met as well. So Jimmy, it was great having you on the show. Really looking forward to following you as you kind of go on this journey and figure out where the end state is.

37:50 Jimmy Downing: Awesome. Thanks, Warren. It's a pleasure. It's a blast.