2327 - Elevate Your Business Performance through Nearshoring and AI with WorkBetterNow's Rob Levin

23 Nov 2025 · 18 min

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Podcast Summary: The Thoughtful Entrepreneur - Episode 2327 Episode Title: Elevate Your Business Performance through Nearshoring and AI with WorkBetterNow's Rob Levin Host: Josh Elledge Featured Guest: Rob Levin, Chairman and Co-Founder of WorkBetterNow

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Episode Overview In this episode, Josh Elledge converses with Rob Levin about the transformative potential of nearshore talent for small and mid-sized U.S. businesses. Rob shares insights into how nearshoring can solve workforce challenges, reduce costs, and optimize business operations by leveraging skilled professionals from Latin America.

Key Themes

  • The implications of talent shortages in the U.S.
  • Advantages of nearshoring for small and mid-sized businesses
  • The integration of AI in business processes and talent development

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Key Concepts

Why Nearshore Talent is Beneficial

  • Talent Shortages: U.S. businesses face persistent difficulties in finding skilled labor, leading to high competition and rising salaries.
  • Access to Skilled Workforce: Nearshoring allows access to a pool of English-proficient, culturally aligned professionals from Latin America.
  • Operational Efficiency: Delegating tasks to nearshore workers enables business leaders to concentrate on strategic planning and revenue generation.

Roles Impacted by Nearshoring

  • Executive Assistants: Most sought-after role, allowing business owners to delegate operational tasks.
  • Marketing, Sales, Finance, and Customer Service: Key roles where nearshore professionals can enhance organizational capacity and performance.

AI's Role in Enhancing Productivity

  • WorkBetterNow trains its talent in AI to improve operational efficiency, accuracy, and innovation.
  • AI competency is viewed as essential for all roles, with a focus on maintaining human oversight in workflows.

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Simplifying HR Challenges

  • WorkBetterNow manages payroll, compliance, and legal responsibilities for businesses, reducing administrative burdens for employers.
  • Successful companies treat nearshore professionals as integral team members, ensuring cultural integration and clear communication.

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Rob Levin

Background

  • Position: Chairman and Co-Founder of WorkBetterNow, and host of the podcast "Great Talent Great Business."
  • Expertise: Focuses on hiring strategies, talent management, and helping small businesses grow through effective team building.

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WorkBetterNow's Mission

  • To provide dedicated, high-performing nearshore professionals to U.S. companies, enhancing their operational capabilities while ensuring cultural alignment and compliance.

Precision Match Process

  • A consultative approach to understand client needs and cultural fit, followed by a tailored selection of candidates for interview.

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Key Takeaways

  • Growing Trend: Nearshoring is increasingly common as businesses seek to overcome domestic hiring challenges.
  • Cultural Fit: Integrating remote workers into the company culture is crucial for maximizing productivity and satisfaction.
  • Continuous Learning: WorkBetterNow emphasizes ongoing training, particularly in AI, to keep their workforce competitive and innovative.

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Conclusion Rob Levin’s insights underline the significant role nearshoring and AI play in modern business strategy. With the right processes and partners, leaders can effectively build high-performing teams, unlocking their potential for growth and success.

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Links Mentioned

  • [Rob Levin’s LinkedIn Profile](https://www.linkedin.com/in/robertslevin/)
  • [WorkBetterNow Website](https://www.workbetternow.com/)

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Final Thoughts For business leaders facing a talent crisis, embracing nearshoring and integrating AI can provide a competitive edge. The episode closes with a reminder that successful business strategies hinge on effective talent management and cultural integration.

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Transcript

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0:04Well, hey, Thoughtful Leader. Welcome to the Thoughtful Entrepreneur. On this show, I interview purpose-driven founders, experts, and change makers who are making a real impact in the world. Want to be a guest? Simple. Go to upmyinfluence.com and click podcast. I'd love to promote your story to our audience of over 100 ,000 and across over 2 ,300 daily episodes and counting. Want to get booked on other great shows like this? Simple. Go to podverified.com and get your free guest authority score. Thousands of hosts are looking for high quality guests and Podverified connects you the right way. Now let's dive into today's episode.

0:58With us right now, it is Rob Levin. Rob, you are the chairman and co-founder of Work Better Now, and you are the host of the Great Talent, Great Business podcast. Your website is workbetternow.com. Rob, it's great to have you. Yeah, thanks for having me, Josh. Great to be here. Before we get going into the magic of what you do with Work Better Now, you always love just kind of finding out what our guests are passionate about or into or hobbies, interests, what they've been geeking out on lately. So I guess, what say you? Yeah, so as you can tell, I'm a bit of a music guy. I've been to over a thousand concerts and was just at one last weekend.

1:40Saw the Black Crows this weekend. I go to New Orleans Jazz Fest every year. I go to local shows here. So I've just always been a music guy. And in college, which was a long time ago, I promoted concerts like Elvis Costello and the Red Hot Chili Peppers and Meatloaf. And yeah, really cool. Oh my gosh, man. Yeah. And, and for those watching via video, you've got a album covers all over your wall. And, and, and when, as soon as you came on, I started kind of, I started trying to name the album covers. You got some great ones. Yeah. We were talking beforehand, Black Crows. I saw them open for ZZ Top in 1991 in Indianapolis.

2:22You live in New York city. So you get all of the best concerts. Yeah. Yeah. Although for the Crows this past weekend, I went upstate. But yeah, we get everybody's coming through here. Just about everybody's coming through here. Yeah. The big bands, the smaller bands, all that. Yeah. For someone who may not understand your passion of live music, what is it that you, like if you were to try to explain what you really get out of that experience, what is it for you? That's a great, great question. I feel like we could spend, you know, the entire podcast talking about it. There's, if it's music that I'm into, and you can get a sense, you know, I'm a rock and roll guy, but I like some other stuff too.

3:06There's just something, there's just a way it makes me feel being at a live show. And by the way, sometimes I feel that way just listening to music in the car. I'm just one of those people that's really moved by music. And I play guitar as well. I just love that feeling. Yeah. I think my favorite is for me, I think especially right now, it's important is I feel so much unity. You know, when I'm there and we are all there to celebrate this great music or this great artist, like I just, I feel like everything's right in the world, you know? So that's kind of one of my things. I love fist pumping people at shows.

3:46Absolutely. Yeah. I'm with you. Well, very cool. Well, Robert, talk about what is Work Better Now? So we provide high-performing talent from Latin America for U.S.-based, small and mid-sized businesses. And we do that in about 40 different roles in the sales category, marketing, finance, admin, including executive assistants, because every business owner should have an assistant, and then customer service. Okay. Well, go through maybe some of the reasons why nearshoring. if you want to maybe just talk about like the top three advantages of like who should be working with nearshoring what are those kind of those inherent baked in advantages and then if you want to like touch base on like who this is especially valuable for I'd love to hear it yeah so you know a year ago if you would have asked me that question a year ago the answer would be a little different where we are today as we sit here you know mid to late 2025 five, small and mid-sized businesses hiring offshore is no longer the weird thing.

4:50It's becoming more and more common. The question then is, is why is that? Well, we have a talent crisis in this country. You may not know that if you're just looking at the headlines because you're reading about layoffs and this and that, but small and mid-sized businesses need a unique, unique skill set and unique attitude set, right? Because you need people that are very entrepreneurial, that have an owner's mindset. And really what you're reading about in terms of playoffs and all of that, it really is, that's a big company thing. The business owners I know, and I know hundreds of them probably like you, they're struggling to find good talent.

5:25There's just not enough people in the workforce in this country. And then it's hard to find those people that fit in with the culture that you have in the company and are gonna go that extra mile that a small and mid-sized business needs to go in order to thrive. And at the same time, there's a great workforce in Latin America. They have great experience, fantastic English skills, and fantastic attitudes. They'll go through a brick wall for you. So when you combine all of that, it's the reason why our business is doing well, and there's other companies that do what we do as well. we're all doing very well.

6:05And the projections for the space is really strong. Again, because small mid-sized businesses just need that top talent. And it's getting harder and harder to find that talent in the States. Add on top of all of that, salaries keep going up here in the States, which is not a bad thing. But when you're hiring from Latin America, you're paying a fraction. You're not only getting great talent, but you're paying a fraction of what it costs to hire talent here in the States. Yeah, and regarding roles, what are some of the most popular roles that you end up helping to fill? Yeah, great question, Josh.

6:45So the number one role still to this day is an assistant, an executive assistant for the business owner, because more and more business owners realize that they have to focus on their unique ability, where they make the biggest impact in the company and get everything else off their plate. When you do that, you're really empowering yourself to grow. I know for me, it changed my life to the point where I started this company. Because when we started, all we did was provide assistance, and then we evolved to providing all of these other roles. So that's pretty much the big role. The biggest role is executive assistance.

7:18And then we're seeing a lot of companies, particularly ones that are growing, that they're now hiring assistants to serve a department. So I'll give you an example. a friend of mine has a pretty big commercial construction company here in New York, and we serve companies all throughout the country. And his estimating department is, they were stretched thin and estimators are very expensive. They're very hard to find. It's a six figure position. These are the people that come up with the bids and the, you know, the proposals and the bids for work. And it's a really important job because you have tight margins in the construction business.

7:51You bid too high, you're not getting the work. You bid too low, you're not making any profit. So he hired an assistant for the estimating department. Now, all of a sudden, they can handle 25 % more bids and their win rates going up. It's a no brainer. So we're seeing that as a big trend, but we put people into inside sales roles, a lot of people to support the marketing department, customer service, stuff like that. How has AI impacted many of these roles? And I guess the question that I would have for us, you know, AI competency is it's mandatory here. We're just not going to do things old fashioned if there are tools that can help produce better outcomes, you know, kind of speed up the work and also, you know, keep costs down while we maintain human oversight.

8:48And I'd love to hear how, you know, not overseas, but, you know, again, near shore solution providers or, you know, talent are using those same tools. Yeah, I can only speak about, you know, the Work Better Now and then the people that work for our companies, we call them Work Better Now, certified professionals. I can only speak about them. And I will tell you that it's for us, it starts with us, with Work Better Now, with our team itself. We have about 50 people on the team, not the 500 plus people that work for our clients. And we are aggressively leveraging AI everywhere we can in the company.

9:24And that starts with me and my partner. I'm taking AI courses every week where we're doing hands-on stuff because it starts at the top. And then our department heads are all leveraging AI where we can. So it's a big initiative for us. And then we have the WBN Academy, which is our continuous learning platform, where we're offering AI courses. and we're looking over the next 12 months, we're going to revamp the curriculum so that it's a lot more AI forward. Because funny enough, some of our clients, they're moving along nicely with AI. Some of them, they haven't touched it yet. So one of the things we're doing is if a company is already moving in that direction, well, our people at the very least can keep up.

10:05And for companies that aren't there yet, and they're going to have to be, otherwise it's going to be really hard to be competitive. you know, some of our certified professionals will actually be introducing AI into our clients. Because again, at the end of the day, there's no question AI is transforming the way that we work. Yeah, without question. The trends, other trends aside from AI, I don't know if there's anything kind of in your world. I know that there's been, well, some, depending on your industry, There's been a lot of policy changes, legal things. There's been a lot of movement this year, depending on your industry.

10:47I don't know if there's any that impact when you're working with nearshore employees or anything that you've experienced. Nothing on the policy side other than what some of our clients are telling us is, hey, I'm in a place like New York, where you have HR related laws at the federal level, the state level and the city level. And, you know, there it's a really big it's a it's a cost. It's a lot of time. And a lot of our clients are saying, look, I'm I was coming to you for these roles, but now I'm coming to you for a few more roles that these are people that we had here in New York or in another place like L.A.

11:27where, again, there's just a lot of regulation. And I'm not replacing them with people locally here. First of all, it's very hard to find. And yes, they're very expensive. But on top of that, like the HR hoops and hurdles we have to go through and the potential exposure on the HR side is just too great. That's another benefit of working with offshores. You don't really have those issues. Got it. And then if I wanted to be an employer or a contractor that was coming into the relationship in a very, very just primed for success kind of way, and I'm sure you've dealt with clients all over the map in terms of like how easy they are to work with or, you know, how much they get it.

12:12What are the traits of really great companies and leaders who work well with near-shore employees? It makes me smile when I get a question like that because it's a fantastic question. I thought you'd like that one. Yeah, yeah. So number one, our first core value, literally the day that my partner and I started the company, our first core value was we're going to put our talent first. Now, as an employer, you might say, wait a second, I'm the client. I should come first. Well, not really. And the reason for that is, is that if we put our talent first and we really care about them, and there's a lot of examples that I can share with you, then they're going to take care of our clients, right?

12:53But if we don't treat our talent well, that doesn't work well for anybody. And I learned that from personal experience. My old assistant, who's now the general manager of the company, she was my assistant. I hired her through another company and they did not treat her well. And I took note of that. So we're looking for companies that are going to appreciate that core value in addition to our other ones, but also companies that are going to integrate their offshore, their nearshore, their offshore people into their team. You don't keep them off in a silo. And those are the companies that are getting the best results.

13:28Our people are very happy, of course, and that means that they're working harder. So those are two attributes of what we would love to see in a company. It's a company that understands the importance of talent, the importance of putting our talent first, and then again, integrates the Work Better Now certified professionals that they have on their team with everybody else in the company. Yeah. All right. So to our friend that's listening and maybe they've hired people through Upwork, maybe they've hired, you know, true overseas contractors throughout the years. What's their next step? And what do they, like, if it's a conversation, like what usually happens there?

14:12Yeah. So, well, you mentioned Upwork, which is a great platform for project work. It's a very different experience, right? Because you're getting somebody to do a project. When you're hiring somebody from a company like Work Better Now, you're really bringing on another employee. They may not be an employee on payroll, right? You're paying them through us. We take care of all that stuff. But you're really getting another employee. And the way our process works is we have a, we call it a consult. It's anywhere from from 15 to 30 minutes where we want to get an understanding of what's the role that you're trying to fill.

14:44Of course, if you have any questions about how we work and all that, we'll answer that. But what's the role? Do you have a job description? Do we need to help put one together? Let's make sure we really understand the essence of this role. And then we go another step further, which is tell us a little bit about the culture. What's going to make a good cultural fit into the company? Because that cultural fit is something that either people have it or they don't. Right. Skills we can you can match up the skills that you need with somebody who has those skills. But at the end of the day, remember, also skills can be taught.

15:14Attitudes cannot be taught. So when we're when we're on that consult with a prospective client, we got to get a very good understanding of the soft skills and the cultural fit that that's that the winning candidates going to have in addition to the hard skills. And then we send it over to recruiting and we got our we got our precision match process. We match up three candidates. Our client will interview three candidates that are selected just for them. And then usually they hire at least one after that process. And they're working for them five days later. I also want to point out, Rob, your podcast, Great Talent, Great Business, which our friend can search in their podcast app right now and hit subscribe and listen.

15:56What do you talk about on that show? Yeah. So actually, we're going to be renaming that soon. It currently is still the Great Talent, Great Business podcast. but I have a book coming out in October called The New Talent Playbook, The Ultimate Guide to Building Your Dream Team. So I think we're going to rename the podcast to The New Talent Playbook, but I'm sure you'll be able to search for great talent, great business. And what that is, that's a discussion bringing in subject matter experts and more so even business owners that are doing a great job with talent. We might be talking about how they've built a successful culture or how they're using offshore talent or what do they do different when they're hiring?

16:31Because Because it's interesting, the biggest key to success of a business is talent. Yet nobody teaches us how to hire well, how to retain, how to build a culture. And we talk about all of those things. It's not just me sharing things from the book, but it's also people who are doing it either as a really top rated consultant to small and mid-sized businesses or a business owner themselves that just does a great job with culture and hiring and retention and all of that stuff. Rob Levin, chairman, co-founder of Work Better Now, the host of Great Talent, Great Business, soon to be titled something different, likely, in conjunction with your book coming out this fall.

17:14So congratulations on that. But again, your website, workbetternow.com. Rob, thank you so much for joining us. Thanks for having me, Josh. Really enjoyed the conversation.

17:27If you've enjoyed this conversation, I'd love to invite you to share your message with the world at podverified.com, where thousands of podcast hosts and thoughtful guests are connecting the right way. Podverified helps match you with the right stages for your level of authority. No more wasting time on brand new shows that just aren't a fit. Your guest authority score is free. And so are your first two podcast matches. Come hang out with me there. I'd love to learn more about your business, support your mission, and help promote you far and wide. Just head to www.podverified.com to get started.

18:10And of course, if you'd like to be a guest right here on The Thoughtful Entrepreneur, just go to upmyinfluence.com and click on podcast. Thanks for being a part of this movement. We rise by lifting others.

From the publisher
Unlocking the Power of Nearshore Talent: Insights from Rob Levin of WorkBetterNow

In this episode, host Josh Elledge talks with Rob Levin, Chairman and Co-Founder of WorkBetterNow, about how nearshore talent is transforming the way small and mid-sized businesses scale and strengthen their teams. Rob—also the host of the Great Talent Great Business podcast and author of the forthcoming New Talent Playbook—explains why nearshoring offers a competitive advantage and how companies can use it to build high-performing, culture-aligned teams.

Why Nearshore Talent Is Transforming the Modern Workforce

Rob explains that U.S. companies continue to battle a persistent talent shortage, rising salaries, and intense competition for high-performing professionals. Nearshoring solves these challenges by giving leaders access to highly skilled, English-proficient team members across Latin America who work in real time, align culturally, and bring strong loyalty and work ethic.

He shares examples of how roles such as executive assistants, estimating support, inside sales, marketing, finance, and customer service can dramatically increase organizational capacity. When leaders delegate operational tasks to nearshore professionals, they free themselves to focus on strategy, revenue, and growth. WorkBetterNow further strengthens this advantage by training all talent in AI, boosting efficiency, accuracy, and innovation.

Rob also highlights how nearshoring simplifies HR for business owners. WorkBetterNow handles payroll, compliance, and all employment-related responsibilities, eliminating legal risk and administrative burden. Companies see the best results when they treat nearshore professionals as integrated team members—with clear expectations, cultural inclusion, and strong communication rhythms.


About Rob Levin

Rob Levin is the Chairman and Co-Founder of WorkBetterNow and a respected authority on hiring, talent strategy, and small business growth. As host of the Great Talent Great Business podcast and author of The New Talent Playbook, Rob helps leaders build effective, scalable teams with clarity and confidence. Connect with Rob on LinkedIn.


About WorkBetterNow

WorkBetterNow provides full-time, dedicated nearshore professionals from Latin America to U.S.-based companies. Through its Precision Match Process and rapid onboarding, WorkBetterNow delivers culturally aligned, highly skilled talent while managing all HR, payroll, and compliance. Their mission is to help small and mid-sized businesses scale smarter by integrating exceptional nearshore team members.


Links Mentioned in This Episode


Key Episode Highlights

  • Why nearshoring is becoming essential for SMB growth
  • The top roles where nearshore professionals deliver the most impact
  • How WorkBetterNow trains its talent in AI for increased productivity
  • The importance of cultural fit and team integration in remote teams
  • How nearshoring reduces hiring risk, compliance pressure, and administrative load
  • A breakdown of WorkBetterNow’s Precision Match Process

Conclusion

Rob’s insights reveal the growing importance of nearshoring as a long-term workforce strategy. With the right partner and processes in place, leaders can build deeply committed,...

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2327 - Elevate Your Business Performance through Nearshoring and AI with WorkBetterNow's Rob LevinThe Thoughtful Entrepreneur · 18 min
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