Episode 363: AI as Team, Not Tools with Bobby Lehew
Bobby Lehew has introduced hundreds of skucast guests over the years. This week, the introduction is his. On April 16th, commonsku named Bobby its first Chief AI Officer, a role that didn't exist in the promo industry a month ago.
Bobby has been at commonsku for nearly a decade, most recently as Chief Content Officer. Before that, he spent 15 years as CEO of Oklahoma City-based Robyn Promotions, where he helped architect the industry's early e-commerce company-store model and earned three consecutive Inc. 5000 rankings. He hosts the skucast (now past 360 episodes) and curates The AI Promo Brief. At PPAI Expo 2026, his AI session was named a must-attend by PPAI editors and packed the room to capacity. The reason for the new role? An industry moment that feels less like a trend and more like a reset.
On today's show, commonsku's co-founder and President, Mark Graham, turns the mic around and asks Bobby what the new role actually is, what he took from his first week on the job (spent at the HumanX AI Conference in San Francisco), and why the real AI shift for distributors isn't about the tools at all.
The Four Pillars of the Role
The role sits on four pillars, each feeding the others.
First, intelligence: tracking what's happening across the AI landscape and filtering the signal from the noise.
Second, platform: translating those signals into commonsku's product roadmap and shipping features that actually matter to distributors.
Third, community: listening to customers through AI roundtables, one-on-ones, and conversations at CEO Summit.
And fourth, the industry at large, tracking what AI means for promo and serving as an editorial voice when it matters.
Bobby isn't running this alone. Mark walks through the commonsku bench: Eku (Director of AI Operations, running internal workshops and AI enablement), Dileshni (VP of Technology), and Charlie Moscoe (VP of Product Management). The four of them are threaded together through Slack channels and roadmap reviews.
"We want to adopt a 'no user left behind' attitude — lockstep with the people at the edge of this technology, but also listening to folks still learning to live and work with it."
— Bobby Lehew
AI as Team, Not AI as Tools
The biggest takeaway from HumanX, Bobby says, is a shift in how operators should think about AI. Most distributors today use it as a tool: a chat window they babysit between tasks. The real leap is treating AI as a team member, where workflows run with less supervision, handoffs happen between agents, and automations compound.
The other insight from HumanX: context is the missing piece. Generic prompts get generic output. The distributors getting real leverage from AI are the ones feeding it what it actually needs — their customer data, their supplier relationships, their history on an account.
"The missing piece of all of this is context. The more you understand your customer, the more you understand your customer's customer."
— Bobby Lehew
The Quiet Growth Unlock
Bobby keeps coming back to one piece of math. Historically, scaling a distributorship from $10M to $20M meant doubling or tripling payroll. The AI unlock changes the denominator. It's the same growth curve but at a fraction of the hiring.
Bobby is careful not to frame this as the Amazon-style threat that dominated conference stages a decade ago. Back then, the story was about distributors surviving disruption. This one is about distributors driving it.
"We want to see someone that's a $10 million distributorship get to $20 million. Typically they would have to double or triple their payroll. With the solutions arriving with AI, we're hoping they would only have to increase by 20%."
— Bobby Lehew
In this episode, we also discuss:
- Why the parallels to e-commerce, cloud, and social aren't nostalgia — they're the clearest map for what's coming
- How The AI Promo Brief filters the AI news cycle for promo leaders every two weeks
- First 90 days: reimagining distributor workflow from first principles, not layering AI on top
- The merge of creativity and technology, and why building a presentation with Claude Code is no longer unusual
- What Bobby is watching at the frontier: design, agents, and the leaps in automation arriving this year
New to commonsku? Book a demo
Show Notes: Key Timestamps & Topics
[00:01:45] The four pillars of the Chief AI Officer role
[00:06:36] Meet commonsku's AI leadership bench
[00:11:34] Why AI isn't another Amazon-style threat
[00:13:24] The $10M-to-$20M math
[00:14:46] Context: the missing piece from HumanX
[00:16:08] AI as team, not AI as tools
[00:22:39] Why this reset lands differently
🎙️ Read Full Episode Transcript +
[00:00:00] [Intro music]
[00:00:06] Bobby: It seems like every several years a technological shift forces the industry to reset itself. The internet was one, e-commerce was yet another, and the cloud was yet another. Each one reshuffled how distributors work, what end clients expect, and where growth comes from. Now, I don't even know how to introduce this, but in today's episode, we're flipping the script.
[00:00:29] I'm the one in the guest chair. A few weeks ago, I stepped into a new role as Chief AI Officer at commonsku, and Mark Graham, commonsku co-founder and president, turns the mic around to interview me. Now, my first week in my new role I spent at the HumanX AI Conference in San Francisco. So Mark and I talk about this new role, what it means for our customers, but also what I took away from HumanX. And why AI as team, not merely AI as tools, is the shift that matters for all of us today.
[00:00:49] This episode is brought to you courtesy of all of us at commonsku. Over 900 distributors powering $1.8 billion in network volume rely on commonsku's connected workflow. Process more orders, connect your team, and dramatically grow your sales. To learn how, visit commonsku.com.
[00:01:09] Now here's my chat with Mark. Oh, and by the way, I'm not going anywhere for the skucast. You can expect more interviews with more customers and more AI in the future. Here's Mark.
[00:01:22] Mark: Bobby, a huge congratulations on this new and exciting role. Can't wait to ask you some questions to dig a little bit deeper into this.
[00:01:28] Bobby: You bet. Thank you, man.
[00:01:30] Mark: Alright, so commonsku just created its first Chief AI Officer role. Can you tell us what this role is all about, and how you would explain to a customer what you do and how you'll be able to help them?
[00:01:45] Bobby: Sure. For me it's like four pillars or four core keys to this role. First, there's AI intelligence. There's so much happening with AI — just deciphering what's going on and finding the signal from the noise is a big part of the job. I mean, these big models are releasing news all the time, and what Anthropic has done year to date is just insane. Gemini and Google too. So listening — like we started with the AI Promo Brief. That was a big part of our listening journey, just to tune into what was going on in the market, and now the proliferation is crazy. So the market landscape, what's happening with AI.
[00:02:21] There's a second part, which is the platform. Just sort of digging into and looking at workflows. Like this morning, it's kind of funny, but a snapshot of what my role looks like is me doing some deep work that Les and I were talking about, trying to figure out ways — I can't exactly say what it is at the moment — figuring out ways to get intelligence out of our own data. Working with AI products to do that. AI for the platform. So servicing opportunities with AI, because we're listening for one thing — we're tuning into what's going on in AI, and having a few of us on the team that are really critical for that. Like me and Eku, for example, are constantly listening for that, listening to customers. That's a huge part of this — training and enabling customers and feeding the roadmap.
[00:03:11] The third part — I mentioned the customers, but this is really about community. Mark, you and I have been around when these big moments, these step-change moments, have happened in the industry. These seismic changes. E-commerce was one. The internet, the cloud — we've been around for these massive changes. A big part of that was paying attention to what's going on at the frontier of technology, but also listening to our customers.
[00:03:31] So the way I see that — already when the news announcement went out to our customers Friday, there's a signup for roundtables, because I'll be hosting roundtables with people who want to dig in more and learn how to operationalize with AI. We'll be having one-on-ones with customers, whether they are customers from our Advanced tier or whether Enterprise, just listening to what they're doing. We want to adopt a "no user left behind" kind of attitude with them — meaning we want to be lockstep beside the people who are at the very edge of playing with this new technology, but we also want to listen to folks that are sort of learning how to adopt it and learning how to live and work with it.
[00:04:20] And then the fourth pillar is really just AI for the industry. You and I have always felt this way about the industry. We're tried and true. We're proud that commonsku's been built by promo, for promo, and so we wear our industry hat all the time. What is the impact of AI on the industry? How does that look in the landscape going forward? And sort of being eyes and ears and an editorial voice every now and then about what's happening when these new models drop.
[00:04:50] A great example right now is what's happening in the world of design. Friday, you know, Claude dropped this new Claude Design package. What does that mean for Figma, Canva, presentations inside commonsku? So things like that are happening in the landscape. And you can see it's where these four pillars just sort of feed each other as we walk through it.
[00:05:08] Mark: Yeah, that's amazing. And it's an interesting point you made about the AI sophistication of our customer base and the broader promotional products industry — that you certainly have some people who are at the very beginning stages of their journey. They're just learning about it, they may be a little bit nervous about it. And then you've got other folks that are power users that are using multiple LLMs to query multiple different databases and to help them run their business in interesting ways. And I think that you're such a unique set of experiences to be able to help people at both ends of that spectrum. So yeah, exciting to have you jump in.
[00:05:41] Mark: So why did the leadership team at commonsku feel like this was the right time to create this role? And how do you feel about this role personally?
[00:05:55] Bobby: As I gather, I think the timing is righteous because of the proliferation of development happening in this area, the speed at which development is happening, and the fact that we need to marshal the attention required to pay attention to advancements going on in AI. It's not just a role. For example, in our team, I represent one part of our AI leadership. Eku, and Dileshni and Charlie — they're all like — our Slack channels, what's going on with product development and intelligence and AI.
[00:06:36] Mark: Well, you mentioned a couple of names. So you've got Eku Malcolm, who is our Director of AI Operations and is effectively sort of your role, but internal to commonsku. So he's running internal workshops and making sure that every employee at commonsku is able to use all that AI has to offer in order to make them more productive and efficient and creative.
[00:06:58] Bobby: One more note on Eku's role. Like, we have CEO Summit coming up, and Eku is leading how he's been able to operationalize AI with our own team, with other distributors, so they can sort of learn how to do that.
[00:07:13] Mark: And that was a really interesting hire for us the better part of about a year ago, where we just knew that there was so much happening in AI and we could handle it off the side of our desk, but we just really wanted to have someone whose only job was that. There's been a huge, huge impact internally.
[00:07:35] Dileshni — she's our VP of Technology and is responsible for the management and the vision of our technical product. So she's working at the frontier of AI with all these cutting-edge new features as it relates to how it is that we can stay right at the frontier. And then also managing our very complicated infrastructure and making sure, as commonsku's user base grows, that we have a rock-solid application that can scale with our use.
[00:08:00] And then of course, many people may have met Charlie. Charlie has been with us for several years now. He is our VP of Product Management, and he's working very closely with Dileshni on the execution of our features and making sure that we can spec features that are on point with our customers. All of them touch AI in the work that you're doing.
[00:08:24] Mark: Bobby, how do you feel about this? You're part of the leadership team.
[00:08:28] Bobby: At the end of the day, Bobby, a lot of this also had to do with our relationship. I mean, we've worked together for almost 10 years, which is unbelievable to think about. And you and I had been collaborators for many years prior to that, speaking about technology and social media and creativity. How the industry was gonna defend itself from Amazon — remember those days, right?
[00:09:19] Mark: And bias aside, there is literally no one better in this industry, no one more experienced than you, to be able to tell those stories. You've done that for the last 10 years. And what a wonderful way to pivot and build upon that storytelling industry expertise. How many customer interviews and stories have you done? Hundreds and hundreds and hundreds. And there is no one that we thought would be better than you.
[00:10:15] Bobby: Thank you, Mark. You asked how I feel about this role, and I feel about this role and feel about where we're at just in technology in general like you and I felt in the days of e-commerce and the days of cloud computing, where we saw this tremendous opportunity. But you can magnify that times 10 with what's going on with AI.
[00:10:40] One of the things that happened in my own career as a distributor was that when e-commerce came along, we went through the dot-com boom and bust, e-commerce came along, and suddenly this strange thing called e-commerce was something you could view as friend or foe. You could view it as a threat, or you could be confused by it, or you could say, "You know what, this is interesting. This is a new frontier." And I was a part of that first wave of distributors. Brand Fuel was one of them that adopted e-commerce, and you were like, "We can utilize this technology."
[00:11:22] But fast forward in my work, interviewing distributors for the past several years, watching how commonsku has 10x'd their growth, their output, their workflow, and then seeing what AI can do with that on top of it — the gains we've made, no other platform has made. And now what we can do with AI is just kind of mind-boggling, really.
[00:11:34] Mark: Yeah, it is exciting. And I love that throwback to the e-commerce days. And there's no question, there were lots of people that were nervous about the impact of e-commerce. Remember the presentations that you and I, and certainly Danny Rosin, were in them — around how to survive in an Amazon world, as though Amazon coming in was going to completely disrupt the promotional products industry. Everything was gonna be done online. Everything was gonna be transactional, and the distributor, unless they adopted, were gonna be put out of business.
[00:12:21] I wonder whether there are parallels to that in AI, and whether in the next 10 years are we going to see no promotional products industry because it has been wiped out, or are we going to see a version where distributors that have adopted AI and have embraced this new technology are now going to come up with a different business model and a new way to grow their businesses.
[00:12:55] Bobby: I think you still see this big wave coming like we did with e-commerce. The thing with AI, what's different about this, is that this is an unlock for growth for distributors.
[00:13:24] What we want to see at commonsku — we want to see someone that's a $10 million distributorship get to $20 million. And in order for them to get to that jump, typically they would have to double or triple their payroll just to get there. With the solutions that are arriving with AI, we're hoping they would have to only increase by 20% or something. It's a very oversimplification of what's going on, but I see this completely as an opportunity.
[00:14:00] You and I have been to these tech conferences. I just got back — my first week in this role was going to HumanX in San Francisco. And you're listening to the founder of Cursor and Claude, folks from OpenAI, the folks who are at the front end of developing a lot of this. And you've been to these tech conferences too recently, and there's been a different kind of energy than there have been probably in the past 5, 6, 7 years. You're beginning to feel that buzz and that energy around the cool things that we can do and adopt and grow.
[00:14:46] One of the big takeaways I took from HumanX Conference that fits with this role is that they said the missing piece of all of this is context. The more you understand your customer, the more you understand your customer's customer. That's why this role is important for me. I'm like, I know our customer. You know our customer. You and I know this business, and we know our customer's customer fairly well, and we know that there's a lot more magic we can create from that knowledge.
[00:15:36] Mark: Well, and you think about context, and you think about — just one straightforward example, but you think about marrying AI and the power of an LLM with context, as you say. Yeah. All of the data that a distributor has about all their end clients, all the data that's in commonsku for their particular instance, and being able to marry that with an LLM to be able to query all sorts of exciting insights that allows them to see their customers and unearth different opportunities in a way they haven't been able to do before.
[00:16:08] Bobby: One of the key takeaways from HumanX was: AI as team, not AI as tools. We can use them as tools — we're all using them as tools all the time — but that step further is how do we advance this with AI as team.
[00:16:30] Mark: Bobby, what does the first 90 days look like for you in this role? What are you most excited about?
[00:16:34] Bobby: First 90 days for me is reimagining workflow. So working with my colleagues to think through, okay, so commonsku has 10x'd workflow production over the past several years. How do we do that again? So it's really reimagining where distributors are at now — looking at even just the org charts, the workflows that are going on between those employees and colleagues within a distributorship, and seeing how we can maximize that.
[00:16:58] I remember someone at the HumanX conference mentioned this: there was a system that was looking at improving the loan process. What they needed to do was break it apart entirely and just reimagine it with the tools that we have today. That's part of it, is just breaking it apart and reimagining it.
[00:17:25] And then with customers, just listening, hearing what they're doing with AI. Because one thing that you and I are very passionate about is the distributors look the same on the outside, but they're very different on the inside. They serve different verticals. They serve different markets. They might be a distributor who is focused on the tech community. They might be a distributor who is focused on the collegiate market. And the way they operate internally shifts a little bit.
[00:18:00] Mark: One of the pillars that you mentioned is AI intelligence. Can you talk to me about what the biggest takeaway was as it relates to AI intelligence, and how does it apply to the role?
[00:18:17] Bobby: It goes back to understanding the context. And you've seen this with folks that are trying to use AI — there's a little bit of a frustrating workflow you go through working with AI, and that is that you're educating it all the time. Context is a big part of it. Without getting too nerdy about it, but understanding your customer's details — data's very important. You can only really do so much with generic data in an LLM, and with AI you really need context.
[00:19:00] Mark: Let's talk about another pillar that's important: customers and community. What do you mean by that, and what do you have planned?
[00:19:07] Bobby: Again, just listening, hearing customers, hearing what they're adapting to, what they're learning, what they are doing. Because here's the most interesting thing about this technology, Mark: in almost any other case, technology required this huge educational component for you to just even begin to learn how to use the technology. AI now can train you to use its own technology. So what we're finding is distributors that are doubling down on it are becoming very advanced. They're wanting to do some pretty sophisticated things.
[00:19:45] Mark: And then the fourth priority and pillar is AI for the industry. What's your focus there?
[00:19:50] Bobby: It would just be sharing the things that are going on. This is a great time for us to talk about the AI Promo Brief if you're not a subscriber. So we publish the AI Promo Brief twice a month. There's lots of AI newsletters out there; this is the only AI newsletter that says, okay, here's the news that has happened in the past two weeks, but here's what's important for promo. And Mark, you and I know that with our promo glasses on, we can see through that lens. We can see that design news is important. We can see that working with clients, verticals — we just process all that AI news and say, okay, what's important if you're a promotional products distributor, leader, manager, salesperson?
[00:20:38] That whole muscle reflex that we developed is so important going forward for the industry, because we've been seen as this voice in the industry that looks forward on behalf of our customers.
[00:21:27] Mark: Maybe I just wanted to say, in closing — this is something I've been thinking about during the course of this interview — is that you've been in this industry for 30 years. I've been in it for about 25 years, around the same time. And you would've thought that people like you and I might be bored of this industry by now, right? What's fascinating about it — and I think that technology has a big part to do with it — is that the industry almost resets itself, and there's a whole set of new opportunities I feel every handful of years.
[00:22:00] As you mentioned: mobile, social, cloud, e-commerce, the list goes on and on. My observation is that this is a very dynamic industry. I think that we as an industry do a pretty good job of embracing new technology, or at least being curious about it. And I love the fact that the role that you're in right now continues that tradition that you started as Chief Content Officer, and the fact that you're here to help translate some of this for our customer base and for the industry at large — that's something to be really proud of.
[00:22:39] Bobby: Yeah, I'm glad we're closing on this note, because that is so important, what you just said. This is a reset. And so if you're a distributor owner, CEO — if you don't feel this already, you'll be feeling this soon. But most people probably do feel this, that this is one of those moments. This is one of those moments where I reimagine my business, where I reimagine how we work, where I reimagine what's possible, because this year alone, what we're gonna see is we're gonna see these leap-forwards in terms of automation with AI. We're gonna leave just the babysitting the chat windows, and we're gonna see far more advancement in automating tasks.
[00:22:50] But the other thing we're gonna see — and it's already happened only in the past, I don't know, three to four weeks — the leaps forward in creativity are gonna be phenomenal. We can see that the platforms are already doing an incredible job in creativity. I think, Mark — you know this — I build all my presentations typing in a prompt window with Claude and HTML. It's crazy. I use Claude Code to build presentations. And you're talking about a non-technical person that's using Claude Code to build presentations. That's the kind of leap forward that we're seeing in creativity, and this really interesting meld between technology and creativity and how they're becoming a much tighter organic structure than they used to be in the past.
[00:23:55] Mark: Yep. Absolutely. Well, Bobby, I wanted to thank you for your time. It's hard to get some time in your calendar — you're so busy now with this new role. But a heartfelt congratulations. It's been incredible to be colleagues with you over the last 10 years, and can't wait to see what this new role brings. And I know that the community and customers and certainly partners in the industry are really excited for you. So congrats.
[00:24:15] Bobby: Thank you, my friend.
Frequently Asked Questions
Who is commonsku's Chief AI Officer?+
Bobby Lehew is commonsku's Chief AI Officer, a role he stepped into in April 2026. He is the first person to hold the position, which commonsku created to lead the company's AI strategy — making commonsku the first platform in the promotional products industry to invest at the leadership level in AI. Bobby previously served as commonsku's Chief Content Officer for nearly a decade and spent 15 years as CEO of Robyn Promotions before joining commonsku.
What does "AI as team, not tools" mean?+
"AI as team, not tools" is the phrase Bobby Lehew brought back from the HumanX AI Conference in April 2026. It describes the shift from using AI as a chat window someone supervises between tasks (tools) to building AI into workflows as a team member — handling handoffs, running with less supervision, and compounding automations across a distributor's business.
How will AI change the promotional products industry?+
AI represents a reset moment for the promotional products industry comparable to past shifts like the internet, e-commerce, and cloud computing. According to commonsku's Chief AI Officer Bobby Lehew, AI functions as a growth unlock for distributors rather than a competitive threat, enabling reimagined workflow, faster client presentations, and meaningful scale without the disruption narrative that dominated the Amazon era a decade ago.
How can distributors use AI to scale without doubling headcount?+
AI enables distributors to scale output without proportional hiring. commonsku Chief AI Officer Bobby Lehew notes that a $10 million distributor historically needed to double or triple payroll to reach $20 million. With AI handling workflow, order entry, presentations, and customer intelligence, that hiring requirement can drop to roughly 20% additional headcount — changing the economics of how distributorships are scaled.
Who is on commonsku's AI leadership team?+
ommonsku's AI leadership includes Chief AI Officer Bobby Lehew (AI strategy, customer intelligence, and industry voice), Director of AI Operations Eku Malcolm (internal AI enablement and workshops), VP of Technology Dileshni (platform infrastructure and frontier AI features), and VP of Product Management Charlie Moscoe (AI feature roadmap and product strategy). The four collaborate across Slack channels and roadmap reviews.
What is The AI Promo Brief?+
The AI Promo Brief is a bi-weekly newsletter from commonsku that filters AI developments through the lens of the promotional products industry. Curated by Chief AI Officer Bobby Lehew, it covers model launches, workflow tools, creative applications, and strategic shifts with practical takeaways for distributors, sales leaders, and operations teams.
What is HumanX and why does it matter for the promo industry?+
HumanX is a premier AI conference that took place April 6–9, 2026, at Moscone Center South in San Francisco, bringing together 6,500+ AI leaders, founders, and investors. commonsku's Chief AI Officer Bobby Lehew attended during his first week in the role and surfaced two takeaways shaping how promo distributors should approach AI: context is the missing piece of most AI deployments, and AI should be treated as a team member, not a tool.