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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 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, mention the referral code DTM podcast and you’re going to get $150 off for your first three months. That’s 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, 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

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.