Building High-Performance Global Teams with Patrick Mahaffey: From SEALs to Startups

**Brian:** [Music] Welcome to another edition of the Nearshore Cafe podcast, sponsored by Plugg Technologies, that’s Plugg (P.L.U.G.G.) dot Tech. I’m Brian Sampson, one of your co-hosts, an eight-year nearshoring veteran. Alongside me is Kent Cameron, our Australian LATAM digital nomad. Kent, it’s great to see you again. Tell us a little more about our guest today.

**Kent:** Yeah, sure, I’d love to take that. Today we have Alicia Kellstrom. So, she’s an expert in external talent resourcing, and yeah, so she’s here today to talk to us a little more. So, I’m curious, Alicia, to get your thoughts on the future of work. I know that you’ve got a lot of experience, like over eight years, I think, in the sort of gig economy world, and I’ve got some experience in that side too, but I’d love to get your thoughts on the future of work and start there, I guess.

**Alicia:** Yeah, I mean, it’s a huge opportunity for companies to become differentiated in their market by accessing external talent. And the future of work, obviously, being exponentially growing post-COVID, and everyone kind of understanding the landscape of how this works, and that it does work, and that you really can have access to incredible global talent. It’s just a really great time to be in this space and to be exploring the opportunities and to ultimately enable the talent that wouldn’t have access to incredible jobs and access to really cool companies otherwise. So, I’m excited to keep talking about it.

**Brian:** Yeah, absolutely. What’s booming? Where would you start if you were, say, really intrigued about getting started in the gig economy? Love to hear your thoughts. I mean, I’ve been thinking about that for eight years. Where would I get started if myself?

**Alicia:** What’s booming? What you can typically see in the trends are always emerging technologies. So anytime something new is coming out, external talent and folks in general just really have a strong appetite for becoming experts in that space so that they can own it, basically. So, I would say new technologies and then differentiating from incumbent solutions for other kind of established categories of work. But where you can really get better exposure for customer support type work, or design and creative is huge too. That’s a big trending category of work, and it’s huge. Where you get started, that’s a really good question. For me, it was always the low-hanging fruit and the easiest thing. So, I mean, when I got started just looking for talent, I was looking for camping sites in California because I missed the ‘you had a registration point’ and so all the campsites were completely booked. And I didn’t want to go through the research on a terrible website to figure out which campsite near me was going to be available for how many spots. So, I hired a freelancer to research campsites in California within like a two-hour driving distance, with a water feature, with available sites for like two sites. And within eight hours, I had a list of available campsites and I was able to book them. That just saved me so much time and effort. So, the low-hanging fruit of things that you wouldn’t necessarily think that you could use a freelancer for market research. When I’m talking to customers, just to get the feel for how to work with external talent, do something small so that you can just experience it first and then you can kind of grow from there. So, market research, anything design and creative, building a logo or designing a logo, SlideShare data and analysis type work. I did my own podcast, and I had someone from Ukraine create the intro music. You know, something like that.

**Brian:** Yeah, yeah. I would love to get a little more into your professional background. We’re really lucky to have you today, by the way. Upwork is where you spent seven years, and I remember from our earlier conversation, you talked about moving from an engagement role into sales. I’m sure there are some different perspectives, and what I think would be really interesting for me, and Kent, and our viewers is if you could talk about the types of clients who were serving, what they cared about, how they saw the global talent world, talent pockets. I think that’d be some really fun stuff for us to dig into.

**Alicia:** Sure, it’s a lot. Yeah, so, and I just want to caveat, I’m not a spokesperson for Upwork in any way. I’m just speaking based off of my experience and working at Upwork on the client side as an account manager. So, yeah, I did join as a customer engagement manager, and that comprised of everything from onboarding new customers to their customer support requests, to helping them post jobs and walking them through the onboarding and the interview process, ultimately getting them to contract with external talent. And it was from mid-market to large business. And then throughout my tenure there, I transitioned into the strategic sales role. So that was working with the Enterprise and the Fortune 500, across CPG, retail, manufacturing, technology, pharma, and healthcare. So, everyone’s coming from a different perspective. They’re all looking for different solutions. So, it really depended on who the buyer was, where they sat in the business, and then what they thought that they could do as the low-hanging fruit, essentially. Or they had a lot of experience working with freelancers, and they just wanted to leverage the technology platform to make it a much more seamless experience for them. So, facilitating the contracting and the payment to the workers as well was an important characteristic for them. That way, they could just focus on the work product and making sure that they were getting the deliverables that they were looking for. I think I answered some of your questions, and I might have missed a few.

**Brian:** Yeah, no, that was a great intro to it. What I think about when you’re in the service business, and Upwork especially, is kind of interesting because it’s a tech platform, but there’s a large service component. And maybe how some of those clients, because you were doing strategic selling to some big customers, and the world is big, right? And there’s a lot of nuances with Asia and Latin America and Africa, Eastern Europe, even nearshoring to Canada, right? I’d love to get your take on maybe some of the themes of those conversations. Like, when companies were trying to optimize for speed, how did you think about that from a delivery side and what you were selling versus quality versus other things that might have been factors?

**Alicia:** I think what talent platforms like Upwork and other talent marketplaces do is they give you a better view into the talent that you’re reviewing, essentially. And so, you can make a better informed decision on who you’d like to engage with based off of their professional background that you would not necessarily have that view into if you’re working with, you know, paper resumes and LinkedIn profiles, et cetera. So, platforms similar to Upwork, on Upwork, you’re allowed to upload your portfolio so people can actually see the work that you’ve delivered in the past that’s not covered under an NDA. So, you know that they can share more with external people. So, I think that that’s a really big component because it mitigates the risk. The biggest barrier is they don’t know these talents, and they don’t know them personally enough to, and they don’t want to stick their neck out because it’s their job on the line. They need to show proof of value with working with external talents. So, by having a view into the portfolios and the profiles, you kind of mitigate that risk a little bit, and it creates a better experience overall. Plus, there are oftentimes ratings, and so you can see how they’ve been rated in previous work as well. And so, that definitely was top of mind for our customers and for me too. I mean, when I’m looking and reviewing potential workers, it’s really helpful to be able to look at those profiles so that you can kind of see, ‘Is the design aesthetic I’m looking for?’ You know, categories like that.

**Brian:** Yeah. And then to piggyback on something Kent was saying about trends and where the world’s going, can you tell us a little more about the viewpoint on remote work and global talent? Maybe pre-COVID, and then how that has changed over the last couple years, especially from the bigger company perspective?

**Alicia:** Yeah, I mean, I would say anecdotally that pre-COVID, there were some companies that were already really thoughtful about working with external talent and enabling that environment within their tech stack. So, they were really interested in creating a safe environment that people could, I don’t know, code or provide work products, but that they could control. And then other companies were not as forward-thinking as that, and so they really had to pivot when COVID happened. And, for their own internal workforce, for their FTEs, so that they could work from home and people could still get work done. So, I would say COVID accelerated that in a major way for the large companies and allowed them to start thinking a little more strategically about it because they needed to keep up with their competition. So, it was really important that they were able to support that from an infrastructure standpoint. And yeah, I wouldn’t, I mean, folks that were opting into external talent pre-COVID were just kind of ahead of the ball, and then everyone had to kind of catch up when COVID happened. So, it was kind of inevitable that if COVID didn’t happen, maybe those companies would have fallen behind, but it kind of helped everybody catch up to the same point, and now we’re all moving forward from there.

**Brian:** Very interesting. Yeah. Was there anything that you were surprised by with that, or maybe your customers were surprised by with the quality or the scale, or anything with some of these talent markets that they might have overlooked prior?

**Alicia:** I think the biggest point, and the most surprising, is how quickly things can get done and how quickly external talent can be onboarded and already working. Some folks with traditional models expect a weeks-long process, an approval process, and a paperwork process. But these types of marketplaces really expedite that on your behalf. And then you could start working with someone if you’re really motivated and you have a strong interview process in place within 24 to 48 hours. And then you can start getting work product 24 hours after that. So, I think the speed is the most surprising factor. You need to make sure you know what you’re looking for, and you’re only going to get as good as you expected. You know what I mean? Like, you’re only going to get as good as you prepared for, basically. So, if you’re not super clear and defined on what you’re looking for, you’re not going to have a good experience. But if you are familiar with working with external talent, and you know the metrics that you need them to, and then you can build in a process where there’s QA along the way, then you’re going to have a really good experience. But you need to be thoughtful.

**Brian:** Okay, Kent, what do you think about that from the digital nomad perspective and doing TA as well?

**Kent:** It’s a good question. I was thinking about the speed and quality piece, or, you know, most customers want good quality fast, right? I think that’s one key thing that certain people are looking for. So, we’ve got this technology boom at the moment in the AI, and it’s certainly something I think is impacting speed and quality, right? So, I wanted to maybe ask, are you noticing any impact there, and in what areas, and how’s it changing the game?

**Alicia:** I mean, I’ve read the headlines. I haven’t read the full articles, but I kind of hear the noise that’s happening around AI and how it’s impacting certain categories of work that would previously have been done by a person, and potentially better. But if you’ve played around with like one of those technologies, you again only get as good as you give. So, you really need to know what prompts to use, and you have to inform the technology on the tone you’re looking for. So, you can either do that with the AI, or you can do that with a person. And I don’t know that you can build trust with an AI, right? So, trust is something that’s still going to be a major factor in relationships with working with external talents. So, for the quick and dirty stuff, or things that don’t impact the core business, sure, use that technology and play with it, or see what it can do for you. I mean, I found it to be incredibly powerful, but ultimately, you’re not going to be able to have that trust factor. So, having your team in place as a fail-safe is always going to be a good idea. But to be fair, I’m not in that field, and so I don’t know as much as I could possibly know there. Do you have a differing opinion, or are we in alignment?

**Kent:** I, honestly, I think there’s a lot of uncertainty because most people are thinking, ‘Hey, how do I use this thing? How does this work?’ And, ‘Do I know how to use it to its full capacity?’ I think there’s still a massive learning curve going on at the moment, and I think there’s lots of room for opportunity there on both sides. So, it’s a good question. I honestly, I’m no expert, but I think those are the things we should be thinking about, is like, ‘Okay, what are customers or clients expecting moving forward?’ Because, you know, we were talking around, I think Alicia was talking about lower-hanging fruits. That’s one piece of lower-hanging fruit, is just to work with something that costs $20 a month, versus pay a freelancer and invest a lot more. So, I think that’s a conversation we need to sort of embed and bake into the services we’re rendering. So, yeah, that’s my thought process anyway.

**Brian:** Alicia, I was hoping, without disclosing any names or anything that you’re not supposed to, if you had any anecdotes you could think of, maybe a sales process with one of your customers, and just how some of those conversations went and worked through, and like the light bulb moment they might have had about global talent versus thinking domestically?

**Alicia:** I think the one anecdote that really landed well is that it’s the concept of work that can be completed by ‘following the sun.’ So, you can enable teams globally. And one of the stories that I’ve done myself is I engaged with a freelancer by 5 PM. I said, ‘All right, I gotta catch a flight.’ By the time I landed, the video had been edited. So, it was like I didn’t have to be involved. I just had to list what needed to be done, ‘Here’s the content,’ and I can go about my life, and the work is being completed. And I think that’s kind of the unlock, is that this is not to replace work. So, folks get a little bit worried that this is going to take over my job, or I’m going to be replaceable. No, you’re going to work on the core work that is important to your skill set, and then you can enable more work to be done by delegating or handing off things that will help you in your work. And you look like a superstar because you’re able to do 2x amount of work, or whatever it is. Or something for me myself, it’s like I’m talking to customers, and I’m preparing materials, and then I can work with a freelancer who can make my slide decks look really polished. They just need to look at our brand guidelines, and they can do all the formatting for me. They’re going to do it way faster than I’m going to do it, and it’s also going to help them because it gives them work to do and economic opportunity while I can focus on the strategic relationships that I’m working on, right? So, I think it’s that ‘follow the sun’ kind of paradigm where you’re able to literally hand off work and then the next morning it’s done. Or something that you’re not super skilled in, maybe data and analysis, where you really need to understand some sort of trend. And so, you can enable someone who’s an expert in that to help you with that. So, I think that would be the kind of conversations that we would have with our customers about the exponential value that they would be able to receive.

**Brian:** Love it. Speaking of ‘follow the sun,’ and I know you’re no stranger to airplanes and flights and so forth, have you had a chance to travel anywhere interesting internationally for work or just for life? Either one, we love travel. You know, Kent and I have been around a little bit too. We’d love to hear about you.

**Alicia:** Yeah, so I’ve not traveled internationally for work, except for there was one trip that I didn’t get to go on because I was on maternity leave to Costa Rica that I was very upset about. So, my team went instead. But personally, I’ve traveled to Thailand and a few places in Europe: London, and most recently, Amsterdam and Berlin, two years ago, Paris, and then Mexico. But yeah, I definitely need to travel more. I wish I could.

**Brian:** Out of the cities you just mentioned—Berlin, Amsterdam, London—you know, we’re going very European here. Do you have a favorite out of those?

**Alicia:** I think Paris is my favorite city in general, but London is a lot of fun. Amsterdam was great. I wish that I had gotten out of Amsterdam a little bit and explored more of the Netherlands. But yeah, Paris is near and dear to my heart, and I very much enjoy Paris.

**Brian:** Yeah, tell us more about your time there. What did you do?

**Alicia:** Well, most recently, it was my second trip to Paris. And I went with my husband who had never been to Europe before, and he’s an artist, and so he was just loving all of the graffiti and street art. And then we went to the Louvre, and I was pregnant, and after like six hours, I was like, ‘Can we go because I’m tired?’ And he was not ready to leave. But we definitely also did a little bit of a food tour there. I tried the French onion soup in every single restaurant that we went to. And we did a lot of cheese and bread, and it was really wonderful.

**Brian:** Well, that’s awesome. One question we’d like to ask everybody is, if you think internationally, your best purchase under $50 in another country?

**Alicia:** Yeah, oh man. So, my first trip to Paris, I bought this beautiful velvet skirt, and it was just gorgeous. I can’t fit into it anymore, but that is probably my favorite. I want to reupholster it onto something because I just really love that. But I loved collecting art, or just street art from the cities that we visit. So, I think my first trip there, that painting at the top is from Paris. Yeah, so, those kind of like the memories that you can look at and say, ‘Oh yeah, I got that when I was in Paris.’ Nice, nice.

**Brian:** Yeah. Are you a coffee drinker, Alicia? What was your best cup of coffee abroad?

**Alicia:** Oh my gosh. So, abroad, I was, well, maybe no, Puerto Rico, well, she’s not really abroad either, I guess, anymore. But the Cuban coffee there is super strong, super amazing. Love it. And let’s see, the instant coffee, instant coffee anywhere is a different experience. It’s much more caffeinated, especially when you don’t know how many scoops to use. So, that was always a lot of fun when you’re kind of like, ‘Oh cool, instant coffee,’ and then you’re just really, really awake for the next couple hours. I love it. That’s great. Yeah, great.

**Brian:** And then I also wanted to ask you, going a little bit back to work, for companies, and especially I’m thinking maybe small to mid-sized companies, that are just starting to recognize this global talent world, what are your number one or number two tips to give to them as they’re just curious and want to get started but don’t even know what to do?

**Alicia:** Yeah, no, I would tell them, ‘Don’t take an FTE req, a full-time req, and copy-paste that into a project plan.’ That is not what you’re looking for. You need to break it down into components. You need to break it down into discrete deliverables of what you’re looking for. Unless you’re hiring customer support hourly for eight hours a day, and then you just need to be very clear on what it is that you need that person to be doing with KPIs. You can’t just say, ‘Do customer support,’ you need to have like, ‘How many tickets do they need to do?’ You really need to be thoughtful on how you structure your projects. And you need to make sure you’re speaking the same language about something. So, I had a customer that wanted to build a software site, and they were using a term like ‘dynamic.’ They wanted it to be dynamic, and they were not speaking the same language. ‘Dynamic’ for them was responsive and pop-ups and exciting features on the website. Whereas ‘dynamic’ within this particular tool was like, you could add modules or you could add components to the page. So, it wasn’t the same thing. So, you really need to make sure that when you say something of what you’re looking for, that you know what that means and that the person that you’re working with also knows what that means, and you’re on the same page. And then also that you have the contacts within your organization to then implement the thing that you built. So, if you’re not the tech person, then you need to partner with the tech person to talk to the freelancer or the external talent to make sure that they can implement it. You know, maybe they don’t have the same version of the software, stuff like that. So, just being really collaborative with all the cross-functional partners within your organization that are going to have any sort of footprint against this project. Make sure everybody’s on board, everybody’s on the same page, and they’re all speaking the same language, and be very, very thoughtful on the deliverable.

**Brian:** That’s a great anecdote just about the word ‘dynamic,’ and it makes me think about idioms and how things can get misunderstood. Well, thanks, Alicia. Thanks, Kent. Another great conversation here on the Nearshore Cafe, sponsored by Plugg Technologies, Plugg.Tech. And if you want to learn more about Alicia, we’ll drop her LinkedIn profile in the podcast notes. Thanks again, everybody, and we’ll see you soon. Thank you. [Music]