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The secret sauce to your sales success? It’s what happens before the sale. It’s the planning, the strategy, the leadership. And it’s more than demo automation. It’s the thoughtful work that connects people, processes, and performance. If you want strong revenue, high retention, and shorter sales cycles, the pre-work—centered around the human—still makes the dream work. But you already know that.
The Unexpected Lever is your partner in growing revenue by doing what great sales leaders do best. Combining vision with execution. Brought to you by Vivun, this show highlights the people and peers behind the brands who understand what it takes to build and lead high-performing sales teams. You’re not just preparing for the sale—you’re unlocking potential.
Join us as we share stories of sales leaders who make a difference, their challenges, their wins, and the human connections that drive results, one solution at a time.
Jarod Greene (00:00):
Welcome back to The Unexpected Lever, the show where we sit down with some of the best B2B leaders in the world to unpack the levers that actually move the revenue needle. People, processes, platforms. This season, we're focused on one of the biggest shifts in all three, artificial intelligence and sales, not the hype, not the abstract theory, the cold hard reality, the real stuff, the practical lessons from the leaders on the front line who are living it, telling us what worked, what didn't, and what they would do differently if they were starting all over again. I'm your host Jarod Greene and today I'm joined by Nayman, my Washingtonian, my fellow Washingtonian Mr. Chad Sly. Chad's had a mix of sales leadership roles at companies I'm very fond of. I'll let him tell you a little bit about that. But wherever he's been, he's worked with sales leaders to improve win rates, drive revenue performance through a deep voice of customer win-loss analysis, insights, which have always been my jam.
(01:01):
I know throughout his career he's been at the intersection of sales leadership, sales process improvement and customer success with, again, a focus on helping teams level up. Chad, welcome to The Unexpected Lever.
Chad Sly (01:13):
Thanks, Jarod. It's great to be here.
Jarod Greene (01:15):
Great to have you, my man. So before we get started on your AI journey, I'd love to see where you are and start with the question I ask everybody today. So what's the most unexpected thing you use AI for personally or professionally?
Chad Sly (01:31):
Well, on a personal note, it's what am I going to have for dinner that night? I've learned that AI is pretty good. You get a list of things you've got in your house and it'll spin out a pretty good meal. Professionally, I think the most surprising thing or unexpected thing to me was AI as a thinking partner, especially doing deep account research and really getting into the cracks in an organization and finding out where you can really explore opportunities. Certainly the use cases of email writing and whatnot were expected, but I continue to be blown away by how valuable it is as just a thinking partner.
Jarod Greene (02:11):
Yeah, absolutely. We always ask guests too. Is there something you found it in the context of the deep research that was intentional? Did you push that boundary and say, "Hey, I wonder if it can go this far?" Or was it more it happened and you had your wake what moment I wasn't aware?
Chad Sly (02:26):
It's partly the speed of it all. I'm old enough to remember when we were all using Dun & Bradstreet and other types of manual data, we'll call it physical data sources and how difficult account research was at that point. And you had to play 20 questions with your prospects to find out just what the lay of the land was. For me, it was the ability to take all the available data on an organization that you're trying to get into and then have it spit out just the facts. And then as you start asking it questions and inviting it to help you interpret, that's where it really changed the game a little bit for me because now you're so much more well-informed when you show up to those calls.
Jarod Greene (03:13):
Totally, totally. I remember I've been through many sales methodologies, but I remember one and one class was focused on building your business case and why you would invest in a particular technology, solution or service. And I remember working with maybe some of the younger reps, and this wasn't too long ago. It was before I think AI really scaled to support sales. The entire class was, here's how you read 10Ks and 10Qs. So for reps, not just out of college, but for early in 10 years, zero to five years. Hey, I know you may not have learned in college how to read a 10K or a 10Q, but from a sales perspective, this thing's dripping with insights and information. And I just think now how that has completely changed, not only as a practice, but almost as an expectation.
Chad Sly (04:01):
I want to say five years ago, there was a slew of companies that formed providing that kind of training, teaching reps how to read financial reports and things like that. And this is when AI started to really come into play. Now you should know how to read those reports. You should still have that skill, but the way an AI can process it for you certainly is so much faster.
Jarod Greene (04:26):
Yeah, it is dramatically and demonstrably different. So let's talk a little bit more about your AI origin story, so to speak. So I found every team, every individual I talk to, every moment, there's a constraint, there's a bottleneck, there's a realization where you say, "We can't keep doing it this way, gang." So was there a specific trigger for you? Was there a business outcome you were trying to achieve? Was this just a thing you were trying to accomplish? What moved it from interesting to necessary?
Chad Sly (04:55):
For me, it was the realization this is way more than email writing, template creation, PowerPoint decks. This is a strategic partner. And then when we got into really the robust agents that are available now and the managers that you can create and build, that's where I started to see it and say, this is obviously a massive wave. I think that there are still challenges. I think we still face some challenges around adoption and incorporation of AI into just daily life. People don't quite know exactly how to make that a part of just their world. But I think that we're getting over that hump in a lot of ways. Totally. And so it's really the moment it clicked for me, I guess, was when I talked to a gentleman, he was in the mining industry his entire career for 30 years and on the IT side and built an AI tool using AI that could manage all of the compliance permits that mine operators have and how he had done that for his employer and then it expanded from there and other people wanted it.
(06:07):
Now he's got a business and it's just him. That was a moment where I was like, okay, I see the future. I see the vision. I see where this is going.
Jarod Greene (06:15):
It's different. It's different. So Chad, let's talk about the part I think most people skip on the journey. When you started with this, did you sequence it? Did you think about solving a people problem, a process problem, a platform problem? What's the mix and range that you initially explored AI to help you and the team with?
Chad Sly (06:33):
It was an efficiency play. What were the things that we can offload that we're spending time on? List building, a prep target identification. I mean, all the nitty-gritty just admin work that Salesforce have to do was the start of it. And it started with really sentiment analysis. Who were the hot targets? And then what would be the resonant message and getting started that way and then adding to it, adding things to it, learning how we could each become a builder, how we could build our own. And then from there really took off. And it wasn't like a unified effort. We had different members of the team that were further along in their journey and we started teaching each other, and then that's how we really started to embrace it.
Jarod Greene (07:19):
Any interesting learnings, any hurdles along the way, culture, data quality, adoption, trust? What barriers did you run into, if any?
Chad Sly (07:28):
Yeah, I think the biggest barrier that I see and that I continue to see is AI implementations will fail if we apply old world implementation thinking to AI rollouts or AI initiatives. And the reason is the velocity of the development of AI is so high that we don't think about them differently and we don't accelerate adoption or accelerate the implementations. By the time we get things settled, it'll be completely different. We're going to have to go through that cycle again. And that cycle carries a real human cost to it. Every time you roll out something new, there's a switching cost that you have to deal with. So being thoughtful before you pull the trigger, but once you pull the trigger, you've got to move quickly. You have to lead with how your people embrace it. And I think that might be the biggest component that's missing.
(08:22):
It's not a training problem. It's a human adoption problem. It's change management, change management 101, but you need to lead with how they themselves are going to incorporate it into their world and what that means to them. And then you roll out the technology and the play. I think right now what we're seeing in the market is it's being dumped on people and employees are scrambling to figure it out and be compliant, but they're treading water
Jarod Greene (08:49):
In the best cases right now and totally drowning in others.
(08:53):
Yeah. There's a lot of stuff out there. And we just find from our seats and from my point of view is I see this mix of everything you said. It's top down. It's the sales leader, the CRO, the enablement leader, the operation. There's a mandate that says, "Yeah, you got to use AI in sales. This thing's transformative. There's a board mandate to use it. You guys got to use it. " And it's on top of a world, Jed, you and I talk about this a lot. Sellers have 15, 20 tools already. And now each of those tools has its own AI workflow, AI widget, AI agent. And so you already have this conflict of, "My CRM agent said this, but my competitive agent said this, but my content agent said this, but my deal desk agent said this and they're fighting with each other. And so that's a whole mess to sort out.
(09:42):
" And then we also see this kind of bottoms up approach where it's just like Paul in the Midwest region found Tool Z on the weekend and he's using it for this. And then he told a friend, he told a friend and then he got bottoms up. And as much as we want to be compliant and productive, man, that is a disaster waiting to happen when you have 50, 60, seriously, AI things to help a rep do their job. So I'm curious to see how it all pans out, but it ain't slowing down. That's for dang sure.
Chad Sly (10:15):
No, and you look at, this is a similar to what happened in the sales tech space. We all bought 50 different tools. This is before AI was really a thing. We bought 50 different tools and each one of them performed a different function. And what happened, it all became shelfware. And that will happen to AI if we don't adjust and adapt. What's different about AI is in the earlier scenario, none of that sales tech really was human replacement technology. Whereas now AI is already replacing full cycle reps in some industries. And so that's the adaptation that has to come and it's a completely different way of thinking. This is not a tool that we're buying to make everyone's life better. This is a tool we're buying to perform an actual function within an organization.
Jarod Greene (11:06):
Yeah, it's different. It's different for sure. So let me ask you this though. So you've seen it, you've seen the journey evolve, you're on it yourself. Let's talk wins and losses. Is there something that you've used it for or set of use cases that you're extremely proud of? It made you better, made the team better, made something faster, made something more effective. What's a win you want to talk to AI?
Chad Sly (11:28):
It really started very simply as far as creating mini GPTs where you could plug in a set of parameters or data and it would spit out the account research and the messaging track and it would incorporate in the subject matter from the company. So it would deliver not just what's the current state at the organization, but what's your best lead in for your solution to that company? And it would do it. You just had to not even type a full prompt, but just a few of us. I think that was a game changer for us where I still am not ... You talk about things that were not wins. I'm still not sold on AI as a communication tool without my input. We all now receive 20, 30 or more AI written emails a day. And you can tell that they're AI written, they have a very distinct sort of flavor to them.
(12:24):
So I'm not there yet. As far as communication, it's probably, which is interesting because that was probably the first use case we all thought would be.
Jarod Greene (12:30):
Can't speak for me. Not yet. Yeah, don't do that. You confuse everybody and then get me in trouble because I didn't say that.
Chad Sly (12:38):
So
Jarod Greene (12:39):
That works. Just on the flip side then, any learning, I think your learning you just told me was that it's not ready to speak on your behalf, but something you do that didn't quite work as planned, taught you an important lesson?
Chad Sly (12:50):
Where we ran into trouble or where I've seen others run into trouble is that sentiment analysis piece. There's tools specific for that are built out there. And I think you're still better off using those dedicated tools than having an AI or trying to build whatever AI you're using, whether it's Claude or Gemini or ChatGPT and getting a real type sense of burning platforms in an account didn't work out as well for us. So we still rely very much on the other tools that are out there, which have their own AI baked in, which is part of the game. But for us, it just didn't pan out yet. I say yet because I'm confident it will-
Jarod Greene (13:31):
Optimistic. I'm with you. I'll join you on that journey. I'm optimistic if it works all well in the end. Again, big theme when we talk about practical advice. There are some people still on the sidelines or just skeptical. They're not as bullish as you and I are. And whether it's a go- to-market leader or an individual contributor who's still not ready to do it, what would you tell them? What advice would you give them about getting started? What should they do and should they avoid?
Chad Sly (13:56):
I mean, the hard truth is it's here and it's not going anywhere. So who moved my cheese? Our cheese got moved and it will continue to be moved. You have to embrace it. It doesn't mean you have to make your entire life about it. It just means you have to start trying new things. And I mean, that's just age old wisdom. You have to adapt. And then in the initial launches, there was so much fear because we led with, oh, look how many humans this could replace. And that immediately triggered a panic or fear response and people became resistant. We got to take the temperature down a bit on that because first of all, it is going to replace jobs, but it's not going to replace other things that we human beings for. So don't be scared. Get in there and fiddle around with it.
(14:45):
My journey with ChatGPT began, I was trying to translate Shakespeare. I was trying to understand lines of Shakespeare. So start as basic as that. Worst case scenario.
Jarod Greene (14:59):
Just get started. You announced, but I always feel inclined to share. Some of the things I started using it for in the beginning were fantasy football drafts set
Chad Sly (15:08):
Up.
Jarod Greene (15:09):
Stuff I just got to do. I coached my daughter's softball team for a while as an assistant coach and practice routines. I got into things that made my life easier. Don't tell my wife, but writing her birthday card, just getting some stuff done around the house in ways that ... It's me, it's my brain, it's my prompts, it's my intention, it's my sentiment. It's just not me sitting down with a blank sheet of paper or a blank screen to come up with something from scratch. And then most of the time, I like what you said about thinking about it as a thinking partner and almost a sounding board. One of the sneaky use cases, Chad, I got for folks is I find that whatever tool you use, a lot of it just affirms your core belief, your core position. So help me write this deck, help me write this point of view, help me write this memo, help me write this presentation.
(15:58):
And it's all positive. It came from you and it came from the AI. It's got to be amazing. Red Romit, reverse engineer. Tell me where I'm blind. Tell me where this has weak spots. I'm going to present this case to Chad tomorrow. Be Chad and rip it to shreds. Get me ready for the world where there's objection, there's doubt, there's uncertainty. And so the ability to do that, I think are some of the ways that I think will advance the calls. And again, you don't have to tie it to anything dramatic or deals on the line or you got a million dollar thing tomorrow. Maybe not, but I love the advice on start somewhere and get weird.
Chad Sly (16:37):
Yeah, I think a great use case. It is all sales reps have deals in their pipeline that have stalled. Ask it why your deal is full. Begin there. Open ChatGPT, Claude, whatever, and give it some basic facts about your deal and find out, just have a conversation with it. You'll be surprised. It'll spark your thinking and you'll have a path forward. Start there. If you haven't embraced that start there is my best advice.
Jarod Greene (17:03):
Great. Great practical advice. All right. Two more questions to get you out of here. When you think about the most impactful part of the sales process you'd look for AI to automate, what would it be?
Chad Sly (17:14):
I think that for me, some of the most valuable are just the admin steps, like taking a call transcript or the summary of the transcript and putting it to the CRM without ... I don't have to touch it. Those kind of things. I think where I would like to see is more around forecasting and pipeline hygiene is helping with that. I think every sales leader will appreciate that also like you did get seed vegetables to get sales reps to go clean up their pipeline and having an AI that could do that intelligently based on CallNotes email and just adjust close dates and deal stages and things like that. I think that is the future of forecasting. Amen.
Jarod Greene (17:58):
Take the guess where you just made a lot of sales leaders happy and perk up because who wants a shaky forecast? Not many sales leaders I know. Chad, is there a book, podcast resource that has influenced your thinking about AI, sales, go to market recently?
Chad Sly (18:12):
I kind of tend to read a variety of things. So I don't know if I can point to a specific one.
Jarod Greene (18:18):
You can point
Chad Sly (18:18):
To this
Jarod Greene (18:18):
Podcast if you want.
Chad Sly (18:19):
Yeah, this podcast. Yeah. I listen to you, Jarod.That's what gets me there. Nothing specific. I try to read most of what's out there and filter it through the lens of my experience and where I see things going. I like to listen to what smart people are saying. There's certainly hype and that's just the nature of new innovations that'll settle down at some point and we'll all get to the real meat of what it is in our lives. But I just gather information from as many sorts as I can. Sorry, I don't have a more specific.
Jarod Greene (18:50):
The transcript's going to say this and then everyone's going to ... Yeah, I'm going to pick up subscribers like nobody's business. Simple layup then. Where can folks connect with if they want to learn more, follow you, connect?
Chad Sly (19:01):
I'm available on LinkedIn and happy to connect and network and share experiences.
Jarod Greene (19:07):
Awesome. Appreciate you, Chad. That was fantastic. Thanks for sharing your perspective. The wins, the lessons learned, the thinking around how you're approaching AI and sales and how you advise other teams. For anyone listening, this is what we do here. We serve as practical, battle tested insights from leaders in the trenches, doing and living the transformation. I'm not just talking about if you enjoyed this episode and want to hear more, give us a follow, share with your team. Leave us a review if you feel so inclined. We'd love the feedback. I'm Jarod and I'll see you next time.
(19:37):
You've been listening to The Unexpected Lever. This stuff gets you fired up and you want to talk about it with other leaders. Join the Powerline Slack community. It's a modern open access community for go- to-market professionals and AI enthusiasts alike. We're all ready to turn buzz into business outcomes. Join by going to vivun.com/community. We hope to see you there.