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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 talk with the best B2B leaders about the levers that actually move revenue, the people, processes, and the platforms. This season, we're going deep into one of the biggest topics and shifts happening across all three. The usage of artificial intelligence for go-to-market execution, not the hype, not the theory, but real practical insights from the leaders building go-to-market out here in the real world. I'm your host, Jarod. And today I'm joined by someone who's spent decades helping B2B SaaS companies scale through smart go-to-market strategy and execution. Mr. Jamie Walsh. Jamie's a seasoned go-to-market strategist and product market expert and the founder of Go-To-Market Factories, where he helps companies build and align the GTM engines for predictable growth. Jamie, welcome to The Unexpected Lever. Great to have you here.
Jamie Walsh (00:54):
Thanks for having me, Jarod. Appreciate it.
Jarod Greene (00:56):
Appreciate you. Now, before we dive into AI and strategy, let's start with you and your work. For listeners who may not be familiar, what are you focused on right now with your go-to-market practice?
Jamie Walsh (01:08):
Yeah, so a lot of companies need help with sales-led motions, how to speed things up. They're incumbents themselves and they're trying to ward off newer, faster, more nimble competitors. And they have to move a bit faster from the development side, but it also means that their go-to-market process has to move just as quick. It means a lot of things. A lot of times it is helping them collaborate better organizationally, re-organizing structures. Sometimes it's adjusting the process. And certainly now with all the tools available, it's finding unique ways to bring tools into the game and help support that process.
Jarod Greene (01:52):
Absolutely. And again, if there's a shameless plug time, where do people find you and how do they work with you?
Jamie Walsh (01:57):
Yeah, so I've focused most of my time on LinkedIn. I have a go-to-market happy hour podcast that I'm about to launch season two, so you can find that on YouTube and Spotify for season one. I hang out a lot of in- person events here in Pittsburgh. So if you're here, hit me up.
Jarod Greene (02:14):
There you go. Hey, this is the stage perfectly because again, we want to understand the business challenges at hand that make this AI conversation so fluid and useful, not just interesting. So told you I'd start with the unexpected and the odd. This is always fun for me. Jamie, what's the most unexpected thing you use AI for personally or professionally?
Jamie Walsh (02:37):
I tend to fluctuate my weight throughout the year. In the wintertime, I'm heavier. And in the summertime, I usually get into a good routine. So I've been using it, Claude in particular, to help me set up some goals and give me some daily things that I can work on. I use it already for my daily work tasks and I thought, well, maybe use it to help fill in the personal stuff and the health stuff that I need to work on, relationships and just my mind and my body. So they've all been very helpful in finding unique ways to keep me motivated, keep me doing things every so often.
Jarod Greene (03:17):
It's funny, at Martin Gomez yesterday, he said the same thing, same exact use case. He's a marathon runner. He says he uses Claude/GPT to track macros and what he can and can't eat and what he does drive the results he wants. And so this is an emerging use case. And then same thing. Mine is typically assigned to either different workout movement routines or softball routines for my daughter, just guidance on what she can do better. It's strangely good. It's a fun one. So thanks for sharing that, man. We always appreciate it. And so speaking of transformation, speaking of intentional implementation, is there anything you would see in the AI world where you wish you would do more personal or professional? Is there anything you look around the corner and want a little bit more from what you can do?
Jamie Walsh (04:13):
Yeah, I mean, there's always the desire to do more, but I think I temper that with just staying on top of what it can do today, really trying to utilize that to the best of its abilities, and then also trying to balance the amount of time that you dive down rabbit holes, trying to keep up with everything and what's new and all the tools. I talk about it regularly with the community. We have an AI enthusiast community here in Pittsburgh. It's like you can spend weeks going off on different paths on every new product and every fourth day you'd be switching to another product. And I try to say, let's root something that we can stick with, a platform, a framework, a tech stack we can stick with for a quarter or two, utilize the heck out of that. And then keep an eye on what's coming around and experiment a little bit, but don't get too caught up in switching tools all the time.
(05:10):
I just switched over from ChatGPT. I was three years using it from the day that it came out in November 2023 or 2022 to today. And six months ago, I moved over to Claude and I didn't realize the lift that it was going to take to get over to a different platform, doing much the same thing. I'm very happy with what I am, but that's a big lift.
Jarod Greene (05:33):
Yeah, for sure. Great, great insights. So every leader we talk to has that moment where, again, for you, it goes from, I'm curious, and this is something that's interesting into now something you lean on. Was there a particular moment or a trigger for you where you saw it go from, "Here's this novelty and here's this thing that's interesting into, oh my goodness, this is really something that's transformative."
Jamie Walsh (06:00):
I was a hybrid product manager, product marketer. I had a company called SAI 360. They do governance, risk and compliance, a Dutch company originally, and then it got acquired by American company. In 2018, our CTO announced this vision for Cognitive GRC, and it inspired something that had been hidden in me for a while. I was pretty enthusiastic about AI back in my MBA days, even so far back as my undergrad days, but it was more academic and there was a whole lot of tools available out there yet. So I got really excited about it, got to one of our meetings the next day and I was talking to him about it. He said, "Yeah, it was a five-year vision." He's like, "There's none of the tools that are out there ready to do this right away. We don't have the money to build this stuff." So he goes, "I know that the tools are going to be there in that five-year timeframe.
(06:56):
We just need to build towards that. " During the pandemic, I got really dove into a lot of podcasts around artificial intelligence and machine learning, clicking about GANs and LLMs and voice and virtual assistants and stuff like that. And it was really something that I was looking forward to and started to be using some tools like Jasper and Grammarly back in 2021 to just do things like build out my PRDs. I had to do blog content as a hybrid. So I'm building out SDR scripts and sales demo scripts and enablement materials and stuff like that.
Jarod Greene (07:32):
Similar journey, man. It wasn't an AI one, but it was 2018, it was a mid-year sales kickoff for me. I was a product marketer at Aptio and the mission for mid-year was I'm six months into the new role and CMO gets us all together and says, "Hey, what's the roadmap look like for 2025?" It's one of those exercises of write the press release for the thing you want to do in 2025. And it's like, it's a long time away, but okay, let's play. Kind of had this vision. I was just living in Seattle. I was watching Westworld a lot, the show Westworld on HBO, and it was doing always the Androids and the AI. And you kind of saw a future where, hey, if a human in a robot are indistinguishable and there's all obviously AI and everything else powering it, what's the world look like if our salespeople are host or our salespeople are Dolores, our sales engineers are Dolores.
(08:33):
It was that kind of conversation of where in those product market scars, Jamie, of I give you guys the messaging, give you guys the deck, I give you guys the content. I just want you to execute it. So the idea of what would the rep of the future look like if you could program them like a host. And that started this whole vision path and workshop and exercise about product marketing, marketing team. We'd write the script, we'd write the code, we'd write the runbook, we'd write what they would actually need to go execute. So it changed my thinking then, but there was no foresight then of what the technology would allow us to do. And fast forward here, 2026, man, we're really close, aren't we? I mean, we have avatars who act as BDRs, sales reps, SEs, the CSMs. There's a whole kind of go-to-market function where you see agents, and this is the worst they'll ever be.
(09:27):
There'll be a time when I think they'll be indistinguishable. No,
Jamie Walsh (09:30):
I was just going to say, if you don't think like that, you're going to be left behind for sure. Quickly catch up to you.
Jarod Greene (09:37):
You think about the journey, you think about the part that people skip when they talk about AI. When you started folding AI, even your early use cases into what you do from a go-to-market advisory practice or just your own execution, what were some of the, again, early use cases you thought about? What were some of the problems you were looking to tackle? What were some of the processes you had to redesign? Talk to us a little about that moment where you're getting scaled leverage. What changes for you? What changes in the world for you, your colleagues, your peers, your customers? What's different as you start to get traction?
Jamie Walsh (10:14):
Yeah, I mean, the pressure was different. I mean, we had to move faster than we were. We were doing 12, 15-month launch cycles. I was like, "That's not going to cut it. We got to get it down to 90 days." And so the first six months I was at Archer, we just spent building out these always on systems around competitive intelligence, analyst relations, customer insights, and also the content strategy and planning and even some of the execution of building some of that content all had to get automated in some ways, or at least systems built so that we could do things on a regular basis at scale and at speed. And when we did that, we were like, "Okay, great. Now we got to put in practice. Now we have to do this launch in 90 days. The SKO is in February. There's no moving that.
(11:07):
That's going to be the launch period." And we just got to work and we were surprised at how much the system had helped us have everything at the ready. We didn't have to do competitive intelligence. It was already there. We didn't have to go out and reach out to our analysts. We already had regular touchpoints and things that we were working on with them on a regular basis. Customer insights, being able to digest transcripts of phone calls and interviews, turning that into content, repurposing that content, all of that became much, much, much easier. And we were like, surprised. But then in the midst of that 90-day cycle, we acquired two companies. And by the way, they have to launch at the same time. One was two months out, one was a month beforehand. So no pressure, but we got it done and we went to SKO and killed it.
(12:05):
And the sales team went out and started using what we had built. And within a month or two, we started seeing actual sales turnaround from one of the two acquisitions. So it was a great time.
Jarod Greene (12:19):
That's awesome, Jamie. When you think about some of the challenges you face through that, what were those? The great wins, right? Great. Great victories, but there's some bumps along the way. What were some of the lessons learned and challenges you faced that you'll share?
Jamie Walsh (12:35):
Yeah. I mean, the biggest thing was I had to give the people that were working for me at the time, Grace, just to say, listen, it's all an experiment. And I know that it's going to be a challenge for us to work with in this way going forward. And as long as you realize that you're still at the end of the day responsible for the message and the content that goes out there, it's just giving you a headstart on it and accelerating you forward, be willing to try new things, bring new ideas to me and new tools to me. Keep it up with the tools and see what you could plug into your process was a big, big, big challenge for us. In 2023, the tools weren't nearly what they were today. Like you had Will Smith videos and we couldn't do Will Smith video generation for some of the stuff we did back then.
(13:30):
And we learned to adapt and review things and learn back then what prompt engineering was and all that stuff. But I think the team's better for it. One of the people that was on the team is now leading that team after I left. So I look at that as a success.
Jarod Greene (13:48):
Absolutely. So what practical advice Jamie would you provide folks? And again, I say it all the time, there are people who just have not gotten started yet. There are people who haven't gone down the journey. So what advice would you give them as they start to think about this?
Jamie Walsh (14:04):
Yeah, I mean, it's never too late. Don't get overwhelmed. Start with day one. Sign up for Claude, get a free account, get a free ChatGPT account, Gemini account, whatever floats your boat, but just start using it, start reading it. I mean, I did a weekend project installing and tuning Claude Code using Claude and just taking screenshots, "I got this error, blah, blah, blah." And it helped me build it out. I come from a technical background, so there's some things that non-technical people are going to struggle with, but you'd be surprised at how well the tools now help you do the things you're trying to do, even in a Meta moment. It's helping me build itself or configure the next generation of Claude and Claude for Work and Claude code.
Jarod Greene (14:57):
Well, that's a great use case. Sorry, lightning around really quick. If you could instantly automate one part of go to market for you, your customers, the folks you work with, you could have AI be a magic wand and just remove something or accelerate something, what would it be?
Jamie Walsh (15:13):
As it turns out, I'm trying to build all that framework into Claude cowork as we speak. I have a framework for the way that I do all this stuff. And like I was mentioning before, I don't try to get out over my skis in my production process, but I do experiment with things. I'm waiting to test out Ava, to be quite honest, that's an area I've done sales demonstrations for a decade or so. I've led teams, I've helped them structure and the discovery call that leads into the demo elaborate proofs of concept. I'm probably sure maybe a bridge too far for AI at the moment, but being able to do the thing that sells the most, which is listen to that discovery, figure out what the top challenge is and only show the parts of the product that solve those challenges. This isn't a training on how blah, blah, blah works top down, left, right.
(16:10):
This is, I have these top three problems. If you can show me how your product solves those things, take my money. To me, I felt like that's an art, not a science. Maybe I'll be wrong. No. It's now and become a science. I'm with you.
(16:25):
That's the one part that I think is still lagging.
Jarod Greene (16:29):
Gotcha. Gotcha. We got you covered there. Just stay tuned. Just I got you picking up what you're putting down. What book, podcast, resources has most recently influenced the way you think about AI and going to market?
Jamie Walsh (16:43):
So podcast wise, I watch Greg Eisenberg's Startup Ideas podcast two or three times a week. There's new stuff coming out there, new tools or new ways to use the tools to do something incredible. That's a great resource for people that just want to get the creative juices flowing and see what's possible out there. Book-wise, you're catching me in a place where I don't like to admit I don't read a ton of books. I listen to them because I'm always multitasking and doing stuff. Yeah. The last book I think I listened to was on pricing, big on podcasts, listening to about 60 to 70.
Jarod Greene (17:22):
Do you do 2X feed or you do the normal?
Jamie Walsh (17:24):
I do 1.8. 2X. I miss a lot of stuff, but 1.8 usually.
Jarod Greene (17:30):
Yeah. I tell people, I grew up on hip-hop music. I grew up listening to Das EFX and the Fu-Schnickens. I can understand the fast. So sometimes I'm two and a half. Not a flex. I just sometimes I can ... Right. Yeah. Gong calls too. Gong recordings too. We said it before, but where can folks find you connect if they want to follow you and learn more?
Jamie Walsh (17:51):
Yeah. So my website, GTMFactories.com as well as LinkedIn. I spend a lot of time putting content out there and engaging with a lot of other folks.
Jarod Greene (18:00):
Yeah, you do. And you do a great job at it. We certainly appreciate you. I know the community appreciates you. So thank you for all you do to help us all level up. This is a fantastic conversation. Thanks for your perspective. Thank you for your experience and thank you for sharing your lessons learned.
Jamie Walsh (18:16):
Thanks a lot, Jarod. Appreciate it.
Jarod Greene (18:19):
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.com/community. We hope to see you there.