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Rob Levin
Foreign.
John Jantz
Welcome to another episode of the duckdate marketing podcast. This is Jon Jantz. My guest today is Rob Levin. He's a serial entrepreneur and business growth expert with more than 30 years of experience helping small and mid sized businesses thrive by solving their most persistent talent challenges. He's the chairman and co founder of Work Better Now, a company that empowers US based SMBs to access highly skilled remote professionals, particularly from Latin America, to overcome hiring bottlenecks and build teams that drive growth and innovation. But today we are going to focus on his newest work, the new Talent Playbook. The ultimate guide for building your dream team. So Rob, welcome to the show.
Rob Levin
Thanks John. Great to see you.
John Jantz
So you were, before we even got started, you were talking about the speed of change. And that's really what's going to be my first question. I mean you've worked with, I've worked with small businesses for decades. In your view, what's changed the most about hiring in the last. I was going to say five years, but I could say five months, I guess. And what, what prompted you to write the new Talent Playbook?
Rob Levin
Yeah, and, and I'm gonna, if it's okay, John, I wanna go beyond hiring. I just wanna talk about talent in general and a ton has changed and in fact what the reason, the reason I wrote the book is. I still, I saw how the talent market changed and I'll, I can talk a little bit about that. But I also saw how business owners were still running the same talent playbooks, if you will, as if it was 2016 and a lot really changed in the pandemic. So let, let's talk about what's changed. There's, there's such a long list. I'll mention a few things. Number one, younger, let's, let's put it this way. And now it's arguable whether this happens every generation or so or, or not, but younger generations in the workforce, at least I'm hearing this from business owners like myself, Gen Xers, baby Boomers, the, the younger generations in the workforce work differently than, than the older ones do. And I think a lot of business owners are, are having trouble understanding, understanding that the biggest change perhaps out of, out of, out of all of them. And I have so many of them. But the one I think to focus in on is it's, and, and you wouldn't know this from reading the, the, the headlines, but it's, there's. I used to call it a talent crisis. In fact, in the book I call it a talent crisis. I'm not calling it a talent shift, where it's really hard for small and mid sized businesses to find the talent that they need. And this cascades to the point where it also means that they may be holding onto employees that are not the right people for them to grow going forward. And one way to think about how people's mindsets have not yet changed is you and I are old enough to remember when you used to hear bosses say something like, oh, they're lucky to have a job, right. You know, and there's still people with a similar type mentality. And that has totally changed the, a lot of the power, if you will. And I don't really like to look at it that way, but it's a way that people understand has shifted the employee side, particularly those top performers that we all want in our business.
John Jantz
You know, it's interesting you mentioned at the outset that you mentioned the idea that, you know, probably every generation thinks this and, and I, I suspect there's some truth to that, but it feels like the gap's bigger now, you know, because it's, it feels like a bigger shift. Again, I've only been through one generation, so to speak, but it feels like it is, you know, bigger. Talk to me a little bit about the fact that like, I'm talking to a lot of people, a lot of my peers, a lot of your peers, you know, have kids getting out of college and they're saying, you know, it's terrible out there. The job market's, you know, absolute disaster out there, you know, for the, for people coming out of college. And yet, you know, you just referenced the idea that the leverage is actually kind of with the, the job seeker. So how do you, how do you kind of balance that?
Rob Levin
That's a great, a great question. I, I have two kids in college and I'm worried about their job prospects. I'm actually telling them to start their own businesses. So if you look at the headlines, the headlines are mass layoffs, right? True. The headlines are AI is going to take jobs away, which I believe is true. And it may even start, it may start to be happening right now. That said, you know, in a business, when you're running your own business, you don't have an HR department, you don't have a training department, or most companies don't have a training department. What are you dealing with? You need people that have experience, that have an owner's mentality. You need that in a small business. You don't get that. It's, you know, somebody working in a large business. Rarely has that. You don't necessarily need that skill set. In fact, you probably don't want that skillset in a larger business. And you need somebody you, you, you meet, need somebody with at least some experience. Those people are hard to find. And the thing also thing to remember is like well you know, you might say well all of these layoffs are happening so these people are now available. The skill sets that you need to thrive in a large business are not necessarily the same skill sets that are needed in a small or mid sized business. And the data backs this up. You're probably familiar with nfib, National Federation of Mechanical. It's been around forever. They do, they do a survey or poll, I think it's every month and you'll, you'll routinely see, I think it's about a third of small and mid sized businesses cannot fill roles.
John Jantz
So one of the, one of the things you talk a lot about and, and you mentioned it a couple times, I wonder if you could kind of lay out this idea of the hidden talent crisis that you've really been speaking so much about.
Rob Levin
Yeah, it's, it's pretty much what we're, what we're talking about. It's, it's just really hard to find great talent at least, at least within the US and we could talk about, one of the chapters of book is about, you know, expanding your reach. Not only expanding it so that you can hire people remotely throughout the US or maybe throughout North America, but also Latin America, even, even Asia. So you have that and a lot of companies also where they're struggling is the other thing that's changing. Beyond talent is everything else in business. Right. So technology is driving so much change. AI is of course a great example. I don't have to tell you, marketing has changed how much in the past five years compared to the past 20 or 30 years. Right. And what, what does this mean for small and mid sized businesses? It means that they need new capabilities and their current employees if they hopefully there's an opportunity to upskill them, which is a big part that's, I think I dedicate about half of a chapter to upskilling your current employees to bring in those new capabilities in your company. But those, but if you, if your people are not upskillable, if you will, then you have, you have a serious problem on your hands. Especially if it's hard to hire the people that have those capabilities that you need to bring into your company.
John Jantz
Yeah. So there's a couple things to unpack there. I would suggest, you know, a Lot of people talking about all these jobs going away. In one hand, they are, but I think what they're doing is they're shifting to a new set of, you know, capabilities that somebody needs to have. So, yeah, some of the routine stuff that you just needed somebody that, you know, that could put in the hours to do the tasks, those are certainly are going to be things that AI does pretty well, and those jobs are going to go away. But by the same sense, this idea then of who's making decisions about what's good and what's bad, you know, what's the right decision, what's not, you know, what's, what's on brand, what's not. I mean, I think those people are going to remain, you know, humans, but they might either need to be different humans than you have today, or, as you said, upskill. So how do you, how do you take somebody that you hired essentially to do tasks? Because that's how you saw the role, who now, you know, really needs to do something that you didn't hire them for, they may be capable of doing, but you didn't hire them for that. I mean, how do you make that assessment? But then also how do you make that leap?
Rob Levin
Yeah, so let's, let's do this in a general sense and then we can drill down to AI because I think AI is a very specific situation. Although AI probably has a lot to do with the new capabilities that a lot of companies need. So the first thing to do is identify the new capability you need in your company. So, you know, I'm talking to Mr. Marketing here. So, you know, the marketing capabilities have, are, are changing. And the first thing you have to do is recognize, well, what is it that you need? And then the question is, is, you know, do I have somebody on the marketing team that is upskillable? Do they have the, do they have the desire to learn something new? Do they have that ability? Do they have the ability to not only learn it, but then bring that capability internal? And here's the good news about all of this, is that the training, you know, if it's a new capability, you're gonna have to look external for training, which is totally fine. In fact, companies should get really aggressive about this because there's so much good training out there. Much of it is low cost, if not free. You know, for example, on the marketing side, HubSpot, all of the major CRM and marketing platforms are all offering training, teaching you exactly what needs to be done. Because a lot of this, a lot of the changes in Marketing, of course, are technology based. So again, identifying what, you know, what is it that I need, and then finding the person in your company, giving them the time to do it, obviously paying for any fees that might be there and having an understanding with that person that, look, I, I'm going to invest in the training for you. This is good for you and your career. I do expect that you bring those capabilities in and then when they do that, be prepared to give them a promotion and the raise that they're probably looking for. Everybody, everybody wins. Now, talking about AI, AI in particular, my personal opinion on this, having done this myself, is that I think every business owner needs to go through a hands on AI course first. You need to really understand what the capabilities of AI are before you can start to look at people on your team. All right, I need you to, you know, think of this AI capability, let's say with marketing or with operations or et cetera. I think the owner needs to have some level of understanding. And it, in my opinion, is that you need to do some hands on AI training yourself first. I think everybody, everybody needs to do that.
John Jantz
Well, I think in a lot of ways what's holding some people back is it's going to require, I think, a total mindset shift. You know, there are definitely people who are looking at AI and just saying, oh, it can do that task that used to be done by this person faster, you know, as opposed to like restructuring how they even think about their organization. And so I think, I think in some cases, you know, instead of diving into how does this tool work, it's more how do I structure my entire organization, you know, for a new reality.
Rob Levin
Right. And that, that's why I think that the owner's AI training that they should go through has to be hands on because then you'll actually start to see what the, when you actually start to build something with AI, a light bulb will go, will probably go off in your head and you'll see what, what, what AI is capable of. And then we're using the term at work better now we're using the term AI first. We're now which, which, what that means is not to use AI to improve an existing workflow, but let's have, let's have that workflow totally redesign where AI is doing a lot of the heavy lifting. And of course that's gonna come with a lot of retraining of our team to go from doing the work to managing the AI agent or bot or whatever you wanna call it. That's gonna be doing Doing the work. But you know, there's a, there's another fundamental thing that really should happen be before all of this. And this, this is a big part of how the talent game has changed a lot over the past 10 years with an emphasis on the past few. So culture in your business has always been important. It is by far more important than ever. It is so important today. And why is that? Well, number one, I just give you a few data, not data points, but sound bites for this. Number one, the younger generations and there are, there's plenty of good workers in those younger generations. Culture matters a lot to them. Culture meaning, right. So that's one, that's. That that alone should wake everybody up and say, hey, this isn't something maybe I focused on in the past, but I'm going to start focusing on it now. And I dedicate a whole chapter in the, in the book on it. But also not only just having a healthy culture, but let's have a culture of accepting change and figuring out how to harness change as opposed to, ah, you know, kind of push it off to the side which a lot of people are still doing.
John Jantz
So there's a couple issues I was going to bring culture up so, so perfect segue. A couple things that I know are near and dear to you because it really impacts the business work better now structure. So when you mention culture, you know, a lot of organizations, small businesses today, you know, this used to just be, you know, a foreign thing, but today have fractional, just about everything. They, you know, bring in contractors to do certain jobs certainly work better. Now's, you know, entire business model is plac, you know, employees who are remote. So how do you manage culture? You know, it's obviously one way to do it in an organization where everybody's there, they're all in the seats, you have the company lunches. I mean you do a lot of the things that can build some of that. How do you manage that? When you have part time people, you have remote people, you have, you know, folks that are from different cultures. You know, for example, as work better now really supports. I'm, I'm curious if you ever get any pushback from that. You know, that very thing we, we
Rob Levin
used to get a little bit, it's going away rapidly. So in terms of our, our experience. But what I will also tell you is that the start, in my, in my opinion, and this has worked for us, it worked better. Now in my opinion, the starting point is defining your core values. Right? In other words, your core values are essentially like what do we want our culture to be? Right? So for example, some of ours is we put our talent first, we believe in excellence, you know, and so on and so forth. And we recognize on those we hire based on them. When we have to fire, we fire based on those. So there, there's a little bit of clarity there. Starting with those core values. Then the, the next thing you do in a remote environment. And by the way, it doesn't matter whether, whether somebody's in, you know, three states over or the next continent over remote's remote right? Is we over communicate. We over communicate. So we have a weekly staff meeting that we have. We have teams, we have updates on teams. We reiterate re. Reiterate anything that's important on email. It's really, really important to over communicate. Then I'll also add that KPIs in a remote environment, KPIs are important period. But KPIs for every job and several KPIs when possible, for every single role in the company is extremely important because at least now you have something you can measure people on. And then also this is one that I only talk a little bit about it in the book, but I've been, it's been coming up in conversations a lot more lately is something as simple as clarity. You know, I, I was talking with a business owner last week. I can't remember what the role was that they were discussing in their company. It was actually in my, in one of my CEO peer groups. And I said, you know, the way you're talking about this, I don't think you made it very clear. And this is a very polished business owner. I don't think you made it very clear what your expectations were. And then I don't think you had the proper check ins to make sure that this person was on track. So when people are in the same office, it's a little easier. Right there's the water cooler. You just kind of roll your, your chair back and say hey, you know, how are we doing this project? It's in remote, a remote environment. You need a little bit more structure. That's also where the communications come in.
John Jantz
You know, you mentioned that KPIs and I think a lot of people don't realize that those are a two way street as, as well, you know, I mean a lot of business owners are like I'm giving you these so that you know, I know if you're on track measuring you. But I've talked to a lot of employees, they're like, thank God you Gave me these. So I have. So I know what I, I'm supposed to do here. I know how to win. Because I think a lot of times it's just like, do the work and, you know, hope everybody's happy. And so I, I think that we sometimes probably underestimate those KPIs are as much for that employee as they are for us.
Rob Levin
I think they're actually more for the employee. And, and if anything, when I see a company that doesn't have KPIs, more often than not, what has happened is that the employer or the manager, who, whomever it is, who has the responsibility of, of, of overseeing somebody has not really figured it out themselves, what's important in this world. So how can you have clarity, you know, when, when you yourself don't know? And it's not okay to say, well, I know it when I see it, because it doesn't, it doesn't work when you're on the receiving end, you know.
John Jantz
And one of the beauties of AI, quite frankly, is that you can go to a ChatGPT or whatever tool, you know, even if it hasn't been trained that much, and you can ask it, what, here's our goal, you know, here's what we're trying to do. What should we be measuring? I mean, instead of trying to sit around and go, okay, I need to write all these job descriptions and KPIs or whatnot, you know, just, just have a conversation with these tools. And, and it, you know, it may not be tuned 100% to you because it's kind of doing the average of what the world does out there, but it may be a great way to start, rather than you just saying, I don't know where to start.
Rob Levin
Yeah, you know, I'm. I. What, what? One of the things that frustrates me, even pre AI, but certainly now in this AI world, is when somebody's like, well, I'm gonna do it this way, as opposed to actually trying to research the best practice which pre AI you can do based on an Internet search. Now, with AI, right, it's inexcusable to not have tapped into this wealth of
John Jantz
knowledge, benchmark your industry, no matter what the size your business is. Right? Yeah, exactly.
Rob Levin
And by the way, you know, yes, absolutely, you should be doing this and for every role, and that'll help you come up with the KPIs and projects and even qualitative ways to assess people and communicate what the role is all about. But let's also be clear, John, and you and I Know this, and I hope everybody's understanding this. You're only scratching the surface about what. With what AI can do for your company by using it as a thought partner, which is what we're talking about.
John Jantz
Yeah, yeah. I'm curious. What have you learned since you wrote the book and since you've been out there talking to people about the book? I asked that question specifically, or maybe because I've written books and I just always know that, like, I, I'll have conversations or I'll go on speaking and, and somebody will say something to me. I'll go, dang, I, I wish I would have put that in the book. That's great. You know, I'm curious if you had any of those AHAs.
Rob Levin
Well, I, it's slightly different. The biggest aha. I have is what we were just talking about. So the AI chapter of my book was written a little over a, a year ago. And, you know, now what's in there still applies. Which what I said a little over a year ago was experiment and encourage everybody to experiment. By now. Yeah, you have to do that. By the way, you should do that now. It's take a course and figure out what is what. What are some of the biggest challenges you have in your business and how can AI help you with those challenges, not only as a thought partner, but actually in doing the work. And then, and then you have to start to think about. And I, if I was writing the book today, this is what would be in it regarding AI is how do you get your team to go from doing the work to managing the AI, refining it, checking the results. Because, look, AI is not going to get it perfect all the time, but it's going to do a great job in a lot less time. And again, we're only scratching the surface on what the.
John Jantz
Well, it's interesting. I mean, you could, you could really point to that as maybe the major mind shift that companies need to have is to start encouraging employees to do just what you said. How can you get AI to do this work? Especially a lot of the routine kind of stuff. But I'm sure you're hearing from people that are the employees like, oh, yeah, work myself out of a job.
Rob Levin
Great.
John Jantz
So I do see that fear is that a lot of companies are just going into people and saying, figure out how to use AI to do your job. And I think the, the, the implied, you know, issue with that is like, then I won't have a job.
Rob Levin
Right. Which, which, you know, I guess it's on us employers to, to manage that and I can tell you what we're doing at work better now, which is we're telling everybody, look, this is the direction we're going in. We're going to provide the training, and then it's on the employee, really, to pick up the ball and to do it. And we told everybody we are not. We have no plans on. On any layoffs. We are expand. We're. We're growing. And with AI, we just hopefully are not going to have to add a lot of headcount. Right. And yet, you know, we'll. We should see improved outcomes. And I think this is an opportunity for all of our employees because we are going to work, I guess you can say kind of like pioneering, you know, company, our space and our size. And, you know, we. We're making it very clear, like, look, as long as you figure this out, again, we're providing the training. You know, your. Your job is safe. In fact, your job's going to be more important than ever. Yeah.
John Jantz
Yeah. Be more productive. Well, Rob, I appreciate you taking a moment to stop by the Duct Tape Marketing podcast anywhere you want to invite people to find out more, to connect with you, of course, but then also find out more about your working, find out more about your writing.
Rob Levin
Yeah, you can just. You can just search for new talent playbook. If you want to pick up a copy of the book or new talent playbook, substack or podcast, just Google that in and it'll pop right up. And of course, if you are looking for offshore talent, nearshore talent, in our case, that's workbetternow.com awesome.
John Jantz
Well, again, appreciate you stopping by, and hopefully you've dug out of that snowstorm in New York.
Rob Levin
Yeah, thanks, John. And great to see you. Thanks for having me on the show, Sam.
The Duct Tape Marketing Podcast: "Upskilling Your Team for What's Next"
Host: John Jantsch | Guest: Rob Levin
Release Date: February 26, 2026
This episode explores the rapidly evolving landscape of talent management and team building for small and mid-sized businesses. Host John Jantsch interviews Rob Levin, serial entrepreneur, business growth expert, and co-founder of Work Better Now, about his latest book, The New Talent Playbook: The Ultimate Guide for Building Your Dream Team. The discussion centers on how talent challenges have shifted in recent years, the impact of generational differences and emerging technologies like AI, and actionable strategies for upskilling teams to drive growth in an increasingly remote, technology-driven business environment.
Shift from Talent Crisis to Talent Shift:
Generational Changes in Workforce Expectations:
Mismatch Between Headline Trends and SMB Needs:
Remote and Global Talent Strategies:
Determining Upskill Potential:
Embracing Accessible Training:
AI Demands a Mindset Shift:
Leaders Need Hands-On Experience:
From “Doing” to “Managing” the Work:
Culture as a Defining Factor:
Managing Culture Remotely and Across Borders:
Clarity for Employees:
Navigating Employee Fears About AI:
Continuous Learning and Leadership Adaptability:
On the need for a new playbook:
On generational perceptions:
On upskilling and training:
On embracing AI:
On measuring success remotely:
On clarity and remote work:
On the opportunity and fear AI brings:
This episode is a valuable listen for leaders seeking to adapt their workforce strategies for the new realities of remote work, generational change, and AI. Levin offers both high-level perspective and practical tips for recruiting, upskilling, and empowering your team for business growth.