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Upskilling Your Team for What’s Next

Upskilling Your Team for What’s Next written by John Jantsch read more at Duct Tape Marketing

Catch the Full Episode:

Overview

In this episode of the Duct Tape Marketing Podcast, John Jantsch interviews Rob Levin, serial
entrepreneur, chairman and co-founder of Work Better Now, and author of
The New Talent Playbook: The Ultimate Guide for Building Your Dream Team.

With over 30 years of experience helping small and mid-sized businesses solve persistent
talent challenges, Rob shares why the traditional hiring “playbook” no longer works. He
explains how the pandemic, generational shifts, remote work, and artificial intelligence
have fundamentally changed the talent landscape.

The conversation explores the hidden talent crisis facing SMBs, why culture is more critical
than ever, how to rethink KPIs in a remote-first world, and what it really means to become
an AI-first organization. If you’re still managing talent like it’s 2016, this episode offers
a roadmap for building a future-ready team.

Guest Bio: Rob Levin

Rob Levin is a serial entrepreneur and business growth expert with more than three decades
of experience helping small and mid-sized businesses thrive. He is the chairman and co-founder
of Work Better Now, a company that empowers U.S.-based SMBs to access highly skilled remote
professionals, particularly from Latin America, to overcome hiring bottlenecks and build
high-performing teams.

Rob is the author of The New Talent Playbook: The Ultimate Guide for Building Your Dream Team,
where he outlines a modern approach to talent strategy in an era defined by remote work,
rapid technological change, and AI disruption.

Key Takeaways

1. The Talent Crisis Is Really a Talent Shift

Despite headlines about layoffs, many small and mid-sized businesses still struggle to fill
critical roles. The skills needed to succeed in large enterprises often do not translate to
the owner-minded, adaptable talent required in SMBs.

2. The Old Hiring Playbook Is Obsolete

Many business owners are still operating as if it’s 2016. Power dynamics have shifted, top
performers have more leverage, and younger generations prioritize culture and meaning at work
more than previous generations.

3. Culture Is a Strategic Advantage

A clearly defined set of core values is the foundation of a strong culture—especially in remote
and hybrid environments. Companies should hire and fire based on core values and intentionally
build a culture that embraces change.

4. Remote Teams Require Structure and Over-Communication

In a remote environment, clarity and communication must be intentional. Weekly meetings,
consistent updates, and well-defined KPIs are essential to maintaining alignment and accountability.

5. KPIs Benefit Employees as Much as Employers

Well-designed KPIs are not just management tools—they give employees clarity on expectations and
what it means to “win” in their role. A lack of KPIs often signals unclear leadership rather than
poor employee performance.

6. Upskilling Is a Competitive Imperative

As technology and AI reshape roles, companies must identify the new capabilities they need and
aggressively invest in training. Affordable and high-quality education is widely available, and
businesses should leverage it.

7. Business Owners Must Lead the AI Shift

Before expecting teams to use AI effectively, business owners must gain hands-on experience
themselves. Understanding AI’s capabilities firsthand enables leaders to redesign workflows,
not just automate existing tasks.

8. Move from Doing the Work to Managing AI

The future of many roles will involve managing, refining, and validating AI output rather than
executing routine tasks. Organizations must help employees transition from task execution to AI
supervision and optimization.

9. Become AI-First, Not AI-Improved

Rather than using AI to enhance existing workflows, companies should rethink processes from the
ground up with AI doing much of the heavy lifting. This mindset shift can dramatically improve
productivity and scalability.

10. Global Talent Expands Your Competitive Edge

Expanding your hiring reach beyond local markets—across the U.S., Latin America, and beyond—opens
access to skilled professionals and helps solve persistent hiring bottlenecks.

Great Moments from the Episode

  • 00:03 – Introduction to Rob Levin and The New Talent Playbook
  • 01:14 – Why the talent market has fundamentally changed since the pandemic
  • 02:15 – From “They’re lucky to have a job” to employee leverage
  • 04:11 – Why layoffs don’t solve the SMB talent shortage
  • 06:02 – Understanding the hidden talent crisis
  • 08:27 – Identifying new capabilities and upskilling your team
  • 10:53 – Why business owners must take hands-on AI training
  • 11:56 – Becoming an AI-first organization
  • 13:20 – Why culture matters more than ever
  • 14:23 – Managing culture in remote and fractional teams
  • 16:41 – Why KPIs are more for employees than employers
  • 18:26 – Using AI as a thought partner for performance measurement
  • 19:45 – What Rob would update in the AI chapter today
  • 21:28 – Addressing employee fears about AI replacing jobs
  • 22:42 – Where to find The New Talent Playbook and connect with Rob

Quotes

“There’s such a long list of changes, but the biggest one is that the old talent playbook just doesn’t work anymore.”

“KPIs are actually more for the employee than the employer. They give clarity on what winning looks like.”

“Don’t just use AI to improve a workflow. Redesign the workflow so AI is doing the heavy lifting.”

“You’re only scratching the surface of what AI can do for your company if you’re not using it as a thought partner.”

Resources Mentioned

  • The New Talent Playbook: The Ultimate Guide for Building Your Dream Team by Rob Levin
  • Work Better Now – Nearshore talent solutions for SMBs
  • National Federation of Independent Business (NFIB) hiring trend surveys

Connect with Rob Levin

 

John Jantsch (00:03.266)

Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is John Jantsch. 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’re going to focus on his newest book, the new talent playbook, the ultimate guide for building your dream team. So Rob, welcome to the show.

Rob Levin (00:46.516)

Thanks, John. Great to see you.

John Jantsch (00:48.632)

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 I could say five months, I guess. And what, what prompted you to write the new talent, playbook?

Rob Levin (01:14.184)

Yeah, and I’m going to if it’s okay, John, I want to go beyond hiring. I just want to 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 can talk a little bit about that. But I also saw how business owners were still

John Jantsch (01:18.638)

See you soon.

Rob Levin (01:35.142)

running the same talent playbooks, if you will, as if it was 2016. And a lot really changed in the pandemic. So let’s talk about what’s changed. There’s such a long list. I’ll mention a few things. Number one, younger, let’s put it this way. And now it’s arguable whether this happens every generation or so or not. But younger generations in the workforce, at least I’m hearing this from business owners like myself, Gen Xers.

baby boomers, the younger generations of the workforce work differently than the older ones do. And I think a lot of business owners are having trouble understanding that. The biggest change perhaps 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 you wouldn’t know this from reading 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 on to employees that are not the right people for them to grow going going forward. And 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, they’re lucky to have a job, right? And there’s still people with a similar type mentality and that has totally changed. 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 Jantsch (03:07.862)

Right, right.

John Jantsch (03:20.32)

Mm-hmm.

John Jantsch (03:26.638)

You know, it’s interesting you met at the outset of that. You mentioned the idea that, you know, probably every generation thinks this and I, and I, I suspect there’s some truth to that, but it feels like the gap’s bigger now because it’s, it feels like a bigger shift. Again, I’ve only been through one generation, so to speak. Uh, but it feels like it is, um, you know, talk to me a little bit about the fact that I like, I’m talking to a lot of people, uh, uh, a lot of my peers, a lot of your peers, you know, have kids getting out of college. Um, and.

They’re saying, you know, it’s terrible out there. The job market’s, you know, absolute disaster out there, you know, for people coming out of college. And yet, you you just referenced the idea that the leverage is actually kind of with the job seeker. So how do you kind of balance that?

Rob Levin (04:11.624)

That’s a great, great question. 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,

John Jantsch (04:20.7)

I’m

Rob Levin (04:39.634)

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, 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 skill set in a larger business.

And you need somebody 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 and it’s been around forever. They do they do a survey or poll. I think it’s

John Jantsch (05:31.79)

Sure.

Rob Levin (05:36.682)

every month. And you’ll routinely see, I think it’s about a third of small and mid-sized businesses cannot fill roles.

John Jantsch (05:45.198)

Thanks

John Jantsch (05:48.504)

So one of the things you talk a lot about and you mentioned it a couple of 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 (06:02.418)

Yeah, it’s pretty much what we’re talking about. It’s just really hard to find great talent, 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 U.S. 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. A.I. is, of course, a great example. I don’t have to tell you marketing has changed how much in the past five years.

John Jantsch (06:34.638)

Yeah, yeah.

Rob Levin (06:43.408)

compared to the past 20 or 30 years, right? And what does this mean for small and mid-sized businesses? It means that they need new capabilities. And their current employees, if they…

John Jantsch (06:45.102)

Sure. Yep.

Rob Levin (06:54.79)

Hopefully there’s an opportunity to upskill them, which is a big part that I think I dedicate about half of a chapter to upskilling your current employees to bring in those new capabilities in your company. if your people are not upskillable, if you will, then 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 Jantsch (07:10.894)

Mm-hmm.

John Jantsch (07:20.558)

Yeah, so there’s a couple of 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, what’s the right decision, what’s not, what’s on brand, what’s not. I I think those people are going to remain humans, but they might either need to be different humans than you have today, or as you said, upskill. So how do you take somebody that you hired essentially to do tasks, because that’s how you saw the role, who now 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 (08:27.24)

Yeah, so let’s do this in a general sense and then we can drill down to AI because I think AI is 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 up skillable? 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 if it’s a new capability, you’re 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

John Jantsch (09:27.224)

Yes.

Rob Levin (09:46.146)

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’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 wins. 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, pick up this AI capability, let’s say with marketing or with operations or, etc. I think the owner needs to have some level of understanding

And in my opinion is that you need to do some hands-on AI training yourself first. I think everybody needs to do that.

John Jantsch (10:53.646)

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, we can do that task that used to be done by this person faster, you know, as opposed to like restructure 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 (11:23.698)

Right, and that’s why I think.

that the owners 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

John Jantsch (11:29.934)

Yeah.

John Jantsch (11:36.13)

Right.

John Jantsch (11:47.726)

Mm-hmm. Mm-hmm.

Rob Levin (11:56.304)

redesign where AI is doing a lot of the heavy lifting. And of course, that’s going to come with a lot of retraining of our team to go from doing the work to managing the AI agent or what bot or whatever you want to call it that’s going to be doing the work. you know, there’s another fundamental thing that really should happen.

before all of this. And 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 group that 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

John Jantsch (12:30.051)

Yes.

Rob Levin (12:47.082)

those younger generations. Culture matters a lot to them. Culture, meaning, right? So that alone should wake everybody up and say, hey, this isn’t something maybe I focused on in the past, but I’m gonna start focusing on it now. And I dedicate a whole chapter 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, you know, kind of push it off to the side, which a lot of people are still doing.

John Jantsch (13:20.366)

So there’s a couple issues I was going to bring culture up. So perfect segue. There’s a couple of things that I know are dear and dear, dear and dear to you because it really impacts the business work better now structure. So when you mentioned 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 bring in contractors to do certain jobs.

Certainly Work Better Now’s entire business model is placing employees who are remote. So how do you manage culture? 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 folks that are from different cultures, you know, for example, as Work Better Now really supports them. I’m curious if you ever get any pushback from that, you know, that very thing.

Rob Levin (14:23.604)

We used to get a little bit, it’s going away rapidly. So in terms of our experience, but what I will also tell you is that 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? So in other words, your core values are essentially like, what do want our culture to be?

John Jantsch (14:40.334)

All right.

Rob Levin (14:45.364)

So for example, some of ours is we put our talent first, we believe in excellence, 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’s a little bit of clarity there, starting with those core values. Then the next thing you do in a remote environment, and by the way, it doesn’t matter whether somebody’s in three states over or the next continent over, remote’s remote, is we over-communicate.

We over communicate. we have a weekly staff meeting that we have. We have teams. have updates on teams. We 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 it’s been coming up in conversations a lot more lately, is something as simple as clarity.

You know, I was talking with a business owner last week. 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 chair back and say, hey, how are we doing with this project? In a remote environment, you need a little bit more structure. That’s also where the communications come into play.

John Jantsch (16:41.72)

Yeah. You you mentioned that KPIs and I think a lot of people don’t realize that those are a two way street as well. You know, I mean, 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. I have, so I know what 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 think that,

Rob Levin (17:01.748)

That’s right.

John Jantsch (17:11.22)

we sometimes probably underestimate those KPIs are as much for that employee as they are for us.

Rob Levin (17:17.492)

think they’re actually more for the employee. 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, whomever it is who has the responsibility of overseeing somebody, has not really figured it out themselves what’s important in its role. So how can you have clarity?

John Jantsch (17:20.13)

More? agree.

John Jantsch (17:36.812)

Right? Right. Right. Yeah.

Rob Levin (17:41.172)

you know, when you yourself don’t know. And it’s not okay to say, I know it when I see it, because it doesn’t work when you’re on the receiving end.

John Jantsch (17:47.438)

Yeah. You know, and one of the beauties of AI quite frankly is that you can go to a chat GPT or whatever tool, you know, even if it hasn’t been trained that much and you can actually ask it what here’s our goal. You 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, don’t know where to start.

Rob Levin (18:26.514)

Yeah. You know, 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 going to 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, it’s inexcusable to not have tapped into this wealth of knowledge, right.

John Jantsch (18:42.914)

Sure.

John Jantsch (18:51.554)

Benchmark your industry no matter what the size your business is, right? Yeah, exactly.

Rob Levin (18:54.098)

Yeah. 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 Jantsch (19:21.966)

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’ll have conversations or I’ll go on speaking and somebody will say something to me. I’ll go, dang, I wish I would have put that in the book. That’s great. I’m curious if you had any of those a-ha’s.

Rob Levin (19:45.78)

Well, it’s slightly different. The biggest aha I have is what we were just talking about. the AI chapter of my book was written a little over a year ago. 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 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? then you have to start to think about…

And 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 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 capabilities are.

John Jantsch (20:52.152)

Well, it’s interesting. mean, you could, you could really point to that as maybe the major mind shift that the companies need to have is to start encouraging employees to, 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, you know, the employee is like, yeah, work myself out of a job. Great. So I do see that fear, you know, 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 implied issue with that is like, then I won’t have a job.

Rob Levin (21:28.884)

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 any layoffs. We are expanding, we’re growing. And with AI, we just hopefully are not going to have to add.

John Jantsch (21:35.939)

Yeah.

Rob Levin (21:58.46)

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 or space in 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 is going to be more important

John Jantsch (22:12.812)

Yes.

Rob Levin (22:28.374)

than ever.

John Jantsch (22:29.944)

Yes, be more productive. Well, Robert, I appreciate you taking the moment to stop by the Ductate 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 work and find out more about your writing.

Rob Levin (22:42.472)

Yeah, 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, near shore talent in our case, that’s WorkBetterNow.com.

John Jantsch (22:59.286)

Well again, appreciate you stopping by and hopefully you’ve dug out of that snowstorm in New York.

Rob Levin (23:04.936)

Yeah, thanks, John, and great to see you. Thanks for having me on show.

The Future of Remote Work: Navigating the Talent Crisis, Harnessing Diversity & AI Upskilling

The Future of Remote Work: Navigating the Talent Crisis, Harnessing Diversity & AI Upskilling written by John Jantsch read more at Duct Tape Marketing

The Duct Tape Marketing Podcast with John Jantsch

In this episode of the Duct Tape Marketing Podcast, I interviewed Rob Levin, a seasoned entrepreneur and co-founder of WorkBetterNow, a company specializing in providing talent from Latin America & The Caribbean for US-based businesses. Prior to that he started and built a media company serving small businesses in the New York area. Rob has served as a CEO and CFO of several fast growing businesses and began his career as a CPA.  Our conversation dives into the future of remote work, addressing the challenges of the talent crisis, the need to harness diversity, and the role of AI upskilling.

Key Takeaways

Embark on a transformative journey with Rob Levin as he talks about strategies for navigating the talent crisis, harnessing diversity, and implementing AI upskilling in remote work environments. Discover the importance of accessing a wider pool of talent, integrating remote team members into company culture, and investing in continuous learning initiatives. Whether you’re a business owner seeking to optimize your remote team or exploring opportunities in the remote work sphere, Rob’s insights will empower you to build a thriving business that stands the test of time.

 

Questions I ask Rob Levin:

[01:03] How was WorkBetterNow founded?

[02:48] What did you learn from the difference between your first and second assistant?

[04:33] Why the decision to focus on talent from Latin America?

[06:50] What have you observed trend-wise in the virtual assistant industry?

[12:21] What is Upskilling and how do you apply that as a value at WorkBetterNow?

[16:53] How important are documented processes in WorkBetterNow?

[20:02] How does AI come into play in the smooth running of your business and the efficiency of Virtual Assistants?

[21:25] Where can people connect with you?

 

More About Rob Levin:

 

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Connect with John Jantsch on LinkedIn

 

This episode of The Duct Tape Marketing Podcast is brought to you by Work Better Now

Visit WorkBetterNow.com mention the referral code DTM Podcast and get $150 off for your first 3 months.

 

John (00:08): Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is John Jantsch and my guest today is Rob Levin. He’s a co-founder and chairman of Work Better Now, which provides talent from Latin America for US based businesses. Prior to that, he started and built a media company and serving small businesses in the New York. Rob has served as the CEO and CFO of several fast growing businesses, McGann’s career as a CPA. He lives in New York City plays guitar, has seen over a thousand concerts and even promoted Big Rock Xmen in college. That’s new to your bio, but Rob, I didn’t know that about you, but welcome back to the show.

Rob (00:46): Thanks, John. It’s new to the bio, but it actually happened quite a long time ago,

John (00:50): So let’s just talk about music then.

Rob (00:52): Sure. Let’s do it

John (00:54): Actually. So I’m curious, going from your media business before then, starting a placement for all intent and purposes company, what’s the origin story of how you got work better now going?

Rob (01:06): Yeah, I hired my first assistant in 2013. First assistant didn’t work out. It was part-time, which I don’t recommend except it, except if it’s really necessary. The second assistant just changed my life, actually. The first assistant was pretty good, but the second assistant changed my life because I was now free from so many things. I can’t believe I didn’t think about this sooner. It was free from so many things that were keeping me from the things I like to do and the things that really added value not only to my business, but even to my personal life. And as time went, and as you know John, I know a lot of business owners like you do, and everybody was asking me, and this assistant was from El Salvador and everybody was asking me constantly, where’s your assistant from, et cetera. And I was referring them to another company. So what happened over the years is I just realized that the assistance that my friends were getting from this company just weren’t as good as my assistant.

(02:02): I said, you know what? I think I can do this. I was on the west coast on a business trip and a friend of mine from college joined me and I was saying, I’m going to start this business. And I was telling him every business owner should have an assistant. And he goes, I’m in. And I said, what do you mean you’re in? He goes, I’m doing this with you. And I said, okay, well, you’re going to do all the work and we’re going to split everything 50 50. That was 2018 actually about six years ago, February, 2018, and we started the business and we were providing assistance by the end of the year. And then I think as then, I’m not going to say we pivoted, we evolved into not only providing executive assistance for business owners, but providing over 40 different roles for small and mid-sized businesses.

John (02:47): I’m curious, did you learn anything, or maybe in hindsight you learned something like why the first assistant worked? Second one, I’m sorry, didn’t work out as well as the second one worked? I mean, was there some dynamic in either what you did or who they were or did you learn anything from that?

Rob (03:04): Yeah, I did. In this case, the first assistant I had was part-time and she ended up taking a full-time gig with the other client that she had. So there were two reasons why I decided that I don’t really like this part-time option for not only for me, but for anybody. Number one for that reason is that they’re going to have another client and they’re probably want the security of full-time work. And number two, well actually three reasons. Number two, what I also realized after two months is you think you only have 10 hours a week for an assistant, and then that gets blown out of the water very quickly, and before you know it, you’re well over 40. There’s plenty of work for them to do, and you even think about hiring another one. And then the last one is, and this one’s really important, I want somebody who’s dedicated to me. So when they’re working from nine to five or whatever it is, I want them just thinking about me and my business.

John (03:55): Yeah, that second point that you made I think is a really valuable one because I’ve talked to a lot of business owners and I’m telling ’em all that’s the first hire you should make is get yourself out of the grunt work so that you can focus on marketing or sales or client fulfillment. And a lot of ’em say, well, I just wouldn’t have that much for ’em to do. And I think you’re absolutely right. Once you actually started experiencing somebody taking some stuff off your plate, you start thinking, oh, well they can do this and this. I hadn’t even thought of. We’ve done the same thing. I mean, we’ve hired part-time folks, and fortunately some of ’em have worked out and grown to full-time roles because we realized that you have particularly focused on finding assistance in Latin America. I’m wonder if you could talk about is there something unique about folks that come from some of those parts of the world that make them such a great fit for us businesses?

Rob (04:47): I think there’s a few things. Let’s see where to start. So number one, there’s great talent in Latin America. They have great experience, they have incredible attitudes. People who just show up ready to work, they’re focused on your mission and just dedicated to helping you and with a smile on their face. Also, if you compare it to other parts of the world, the culture is a lot more similar in Latin America to the US as it is compared to other parts of the world. And then I think their English, there’s plenty of people with fantastic English. And then the last one, which a lot of people don’t talk about is time zone alignment. And that’s really important because in other parts of the world, either people are working when they should be sleeping or they’re working at a different time than you are. And our clients, they kind of embrace the talent that we provide to them, the professionals we provide to them as part of their team, they just integrate them in part of their team. And it’s hard to do it when either A, they should be sleeping or when they’re not working at the same time.

John (05:51): Yeah, I know over the years, many years ago I hired an assistant out of the Asia area and the only way to align, as you said, was that they were going to work overnight. It was like, that’s part of the culture, that’s what everybody does here. And I was like, I’m not sure I want to make somebody work overnight, like you said, when they should be sleeping. So I think the time zone alignment is huge, especially if you’re going to have them start doing things with clients and things like that. I mean obviously they’ve got all aligned that way. Before I go any farther, listeners should know that we actually employ to work better now full-time folks on our staff. And I think some of the things you mentioned are very true. We have fully integrated them into our meeting rhythm on Slack and our standup calls and our culture building type of activities. And I think that if you were to ask them, they feel like they are a part of the team as much as really anybody on our team. So it’s definitely very, very doable.

Rob (06:50): Happy to hear that. Let’s

John (06:51): Talk a little bit, yeah, let’s talk a little bit about the landscape in general remote work. I mean, there’s some pretty obvious things that have gone on, but is there anything that you’ve observed from a trend standpoint right now?

Rob (07:06): Yeah, so it starts first with what’s going on here in the United States, and this applies to Canada as far as we can tell as well. And we have been and we will continue to be in a talent crisis. What do I mean by that? I mean several things. Number one, productivity of the US workers actually dropped despite all of the technology that is out there. Number two, there are more job openings than there are people looking for work. So just the numbers are not in the favor of the smaller mid-size business. By the way, I don’t know if big companies are in a talent crisis. Quite frankly, I don’t care. My world is small and mid-size businesses, companies seem to be laying off people, and yet small businesses can’t seem to hire small and mid-size businesses seem to hire the salary expectations here in the states are way up. And the time it takes to hire somebody is according to LinkedIn is like six or seven weeks, which in the world of a small business is years. So there’s a challenge finding exceptional people. And as you know John, in a small and mid-sized business, you can’t get somebody who’s just good. You’ve got to get somebody who’s exceptional because every single role counts. So you have

John (08:16): That and they got to wear a lot of hats

Rob (08:19): And wearing a lot of hats and just somebody who says, Hey, whoever it is you need me to do, I’ll do it. And at the same time I, I do think having had talent from Latin America now for over 10 years, I can start to see an inflection point. So if you think about it, large companies were offshoring, I don’t know, 30, 40 years ago they started. And that trend has picked up small and mid-size businesses have started to do it. I would say maybe 10 years ago, slowly in different parts of the world, Asia was really big. But now we’re starting to see a trend of two trends. Number one, more small and mid-sized businesses being open to offshoring. And I think that all happened in the pandemic when they got comfortable with remote because after all, going offshore subject, a couple of things, going offshore is really no different than going remote. And those couple of things are if you hire directly and you have your own payroll, that can get a little complicated. But if you use a talent provider, companies like work better now. That’s no longer your problem. And then we’re now starting to see trends of more companies wanting to hire from Latin America. So it’s a combination of all of those things happening. And I’m really knocking on wood, happy to say that we got a little lucky with the timing starting this business in 2018

John (09:37): When everybody all of a sudden realized, hey, maybe this remote work thing might actually be something to it.

Rob (09:44): It’s really about access to a wider pool of talent. It’s about access to the wider pool of talent which businesses need today.

John (09:51): And I think most people, you’re absolutely right, have realized that if I can get somebody that can do X, Y, Z, it really doesn’t matter the world we live in where they are. Talk a little bit about some of the cultural diversity that it brings. Again, large organizations have HR departments that help create diversity in the organization, right? Small businesses, I mean, again, that may be a goal that may be part of something they believe in, but much harder to achieve as a small business. Have you felt that at all? Did bring some diversity actually to the organizations?

Rob (10:27): So it’s a really good question, John. I think when it comes to small and midsize businesses, as I mentioned earlier, every position counts. And I think what’s most important to business owners is how can I find somebody amazing for this role who’s going to help me deliver a better customer experience, who’s going to fit in with my culture and is going to help the company achieve its goals? That’s how I feel that we are helping people. Yes, they’re from Latin America. They speak in at least one other language, which is sometimes advantageous. But I really think that what business owners are trying to do, whether they’re working with us or in general and not working with us, I think that everybody really just knows how important it is to get the best talent they can at any given time.

John (11:15): And now a word from our sponsor, work better now. Work better now provides outstanding talent from Latin America, hand matched to your business with over 40 roles across various industries, including marketing. They’re a reliable partner for consistently finding the perfect fit for your business. Simply tell them what you need and they’ll handle the rest hassle free. We have two work better now, professionals on our team, a marketing assistant and a marketing coordinator, and we’ve been blown away by their abilities, responsiveness, and professionalism. They’ve really become an essential part of our growing team. And to top it off each dedicated and full-time work better now professional is 2350 per month and there are no contracts to schedule a 15 minute consultation with a work better now rep and see how they’ll support your business growth goals, visit workbetternow.com, mention the referral code DTM podcast and you’re going to get $150 off for your first three months. That’s workbetternow.com. And don’t forget that DTM podcast code, you mentioned the word offshoring or outsourcing, but I’ve also heard you talk about a term that I don’t hear too many people saying, and I think it has an implication of something bigger and broader and that’s the term upskilling. You want to talk a little bit about how you apply that idea?

Rob (12:40): Yeah, upskilling. So upskilling is a trend that I think over the next five years you’re going to start to see a lot more of, right upskilling. The way we look at upskilling is you are looking for somebody with certain types of experience, certain types of skills, and you might find somebody that has most, but maybe not all of them. And what the smart employers are doing, and a lot of our clients are doing this, is they’re saying, alright, I know I needed A, B, C, D and E. This person only is A, B, and C, but culturally they’ll fit within our company. We’ll hire them and then either we will train them or we’ll use some outsource training, whether it’s LinkedIn or any of these other training platforms to acquire some of those other skills that they need. That’s a much smarter approach rather than trying to find that right person, which might take six or 12 months, which will have a huge negative impact on your company.

(13:38): And there’s another part to this too, which is with the talent that you already have. So the pace of change in business keeps increasing when you’re running a smaller mid-size business. To get good, you have to be better at so many more things today than just five years ago. So where is that expertise going to come from? And if you follow the who not how principle of Dan Sullivan and Strategic Coach, it should’t all be on the business owner. So the idea is you have really good people, get them trained again, whether it’s internal training or external training, and then they can bring those new capabilities into your company. And by the way, when you do that, you’re accomplishing two other goals, which is today’s workforce wants advancement opportunities and they’re also looking to learn more on the job. And so it’s like a triple win. You’re getting the capabilities you need, you’re keeping your employees really happy because they’re advancing and they’re acquiring new skills.

John (14:43): So particularly somebody who’s listening to this and hasn’t hired maybe remote at all, but certainly hasn’t hired an assistant, what are some of the things where I could ask this the negative way or the positive way, but how do you get them started or obviously what are the things that you’ve seen that have really made it not work for people?

Rob (15:05): Well, okay, so let’s start with what works really well and then what doesn’t work well is actually pretty short list. What works really well is really good onboarding. So we assist with that. We have a whole onboarding program. Some clients need it more than others. Other clients, they probably onboard better than we do. So it starts with really good onboarding and then it starts with something I alluded to earlier, which is integrating your remote professionals, whether they’re in Latin America or anywhere else, integrating them within the company, they’re like any other team member. That’s definitely a best practice. What tends not to work well?

(15:49): Oh, let me just add to one other thing that works well, and this probably goes for anybody that you have working in your company, which is clarity on communications in terms of how we communicate in the company, clarity, how we work, what are some of the cultural norms in the company, and also clarity on what if you do your job well, this is what it looks like. A lot of people can skip that step. And of course, on the contrary, what doesn’t work well is not setting up your remote professional for success, not being clear on how we communicate, not integrating them into the company, not explaining to them what success looks like and not also empowering them with just enough training so they understand in this remote world where you don’t have somebody next to you, where do you find, who do you go to when you have a question? Because when you start, you’re going to have questions. So really what doesn’t work is just the opposite of what works,

John (16:51): Right? Right. How important are documented processes? I know a lot of companies are big on here’s our user manual or here’s all these documented process, but that also that can be a distraction, that can be maybe a lot of work that isn’t really that valuable. How important do you think that is for getting a remote person going?

Rob (17:14): Yeah, so I’ll start with, I think the first thing, the most important thing that a company needs to do is establish its core values. And I’m going to explain why. Because you’re thinking like process core values, what do they have to do with each other? The core values, which shouldn’t only be just a list that’s up on a wall, it should be things that are actually adhered to and appreciated throughout the company day in and day out. When you start with those, what good core values do is if somebody doesn’t know what to do and they don’t have somebody to ask at a time that they have to make a decision, they should be able to turn to those core values for the right answer. So that’s where you start. As far as processes go, we’re big on with our team of about 30 or so people, most of which by the way are in Latin America as well, almost all.

(18:01): And what we’re really big on is processes. In some cases they have to be very detailed in terms of how to use HubSpot, for example, the way we’ve set it up. But in general, what we do, we don’t want to over go crazy with the details on the processes. We want to just basically say, here’s a general idea of how you do it. That’s enough enough for somebody who understands the core values and has some talent and the experience that you want to follow that and then do what they need to do. But I’ll take it a step further too.

(18:37): We still provide executive assistance in addition to those 40 other roles to people. And a lot of business owners, when they’re getting their first assistant, they’re like, Hey, I have to try to, I don’t have a manual, right? Well, one of the things we always do is say, that’s great, and I know you don’t want to create one because you’re a business owner. Last thing you want to do is create a manual, have your new assistant do it, and they will just have them document as they go along. And that’s very handy. First of all, the first few times they can go back to the documentation where they’re doing a task, but if they’re out for a maternity or paternity leave, somebody else can then just pick up that process manual. Very important on the executive assistant side, yeah,

John (19:20): I’ve become pretty obsessed with using video tools like Loom and stuff to just go through it. And I’m doing it. I just recapture myself doing it, and it’s a lot easier to create a process out of that. The other term that I read one time that I thought really made a lot of sense, a lot of times we’ll give people, here’s what done looks like. This is the definition of this being done. And then a lot of times they can go, oh, okay, well how I get there probably doesn’t matter to some degree. And I think that’s a great guidance too. So looking ahead, crystal ball, right? What’s up for maybe something you’re actually working on or watching? Obviously every show, I think in the last two years I’ve said the words ai. I don’t know if that comes into play into your business, but what’s the future look like for work better now?

Rob (20:11): So I have two answers to that. The first one is we trying to become a talent partner for our clients, and many of our clients now see us as a talent partner. What that means is if they have a job that can be done remotely and it’s not too specialized, let’s say like a software developer, they just start us. And that’s exactly where we want to be and we’re constantly orienting ourselves to do that. But getting to your AI question, we just launched a pilot of what we’re calling the WBN Academy, and that’s going to be a continuous learning program for our professionals so that they can expand the capabilities of our clients. And AI is obviously one of the core elements of that academy. We should be rolling that out to, all right now we’re up to about 330 or so professionals working for our clients. We should be able to roll that out to them by the end of the year, and we’re really excited about it.

John (21:07): Yeah, that’s really, when you think about it, you look at resumes and they say, oh, I know how to use Word in Excel or whatever programs. I think today it’s going to be, I have a full understanding of AI prompts. That’s just going to be a pretty mandatory skill these days, I think. Is there anywhere we’ve mentioned work better now? Several times work better now.com, but is there anywhere else you’d invite people to connect with you

Rob (21:34): On LinkedIn? Rob Levin, Rob Levin, work better now. There are a few Rob Levins, but if you type in Rob Levin work better now. You’ll definitely find me and you can also reach out to me through the website work better now.com.

John (21:49): Awesome. Well, again, I appreciate you stopping by. I think if you actually mentioned, you heard this on the Duct Tape Marketing podcast, I think that Rob might even give you a special offer of some sort. I believe so. Keep that in mind.

Rob (22:03): Yeah, thanks for, I totally forgot about that. John just mentioned Duct Tape Marketing and you get $150 off for each of the first three months for each professional that you

John (22:13): Hire. Awesome. Well, again, it was great catching up with you and hopefully we will run into you soon, one of these days out there on the road.