Management Blueprint | Steve Preda

298: Mine Gold in Your People with Andrew Jernigan


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Andrew Jernigan, CEO of Insured Nomads, is on a mission to redefine insurance for the globally distributed workforce. His Globally Distributed Company OS includes communication, documentation, education, and integration—core pillars that help companies effectively manage international remote teams.

We learn about Andrew’s journey from banking and global living to founding Insured Nomads—a company providing health, travel, and risk coverage for digital nomads, remote teams, and expats. Andrew shares how cultural nuance, asynchronous collaboration, and documentation help build trust and cohesion in a fully remote environment. We also explore how comprehensive global health insurance differs from standard travel insurance, what digital nomads often overlook, and why benefits like mental health access, cybersecurity, and global lounge access are becoming essential for the international workforce.

Mine Gold in Your People with Andrew Jernigan

Good day, dear listeners, Steve Preda here with the Management Blueprint Podcast, and my guest today is Andrew Jernigan, CEO of Insured Nomads, providing frictionless travel and health insurance for globally distributed teams, expatriates, digital nomads, remote workers, travelers, world schoolers for a successful international lifestyle. Andrew, welcome to the show.

Well, thank you, Steve. And hi, everyone. I’m glad you’re tuning in. This is going to be a fun episode.

Yeah, it is going to be fun. I’m super excited about what you have up your sleeves about how you built this business, because this really a post-COVID type remotely operated business that you have, and it’s a global business. You have like an interesting background. You lived in Amsterdam for several years. You’re married to a Brazilian woman.

I lived in Ghana, worked in England, Thailand, Emirates. Running a cross-border team is something I’ve been part of for a couple of decades now. So this is a valuable conversation for the way the world works today and the future of work as well.

Yeah, so basically you are the target market of your company, maybe, that you call the Insured Nomads. So tell me, what is your “Why,” your personal “Why,” that inspired you to start Insured Nomads in the first place?

I’ve lived the lifestyle, I’ve had the plans and then fast forward a few years, I brokered over 26 of the international companies in our space and realized, took me back to my banking days back out of university, where I was building online banking and a lot of the FinTech components many years ago. And I realized, wow, insurance needs that kind of change. Healthcare, financing of healthcare needs reform. And so brought together some leaders in the industry and said, let’s do it differently. Took off to build Insured Nomads for health insurance and short term travel insurance that meets today’s standards. And this was before the pandemic was declared. I was working from Rio de Janeiro, Brazil, Belo Horizonte and Rio de Janeiro. And my co-founders were oceans apart. And this was birthed and soon after pandemic was declared, and the trigger effect of that, of realizing, okay, flexible, hybrid, remote first, digital first, etc.

Work dynamics have affected the world.
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Yeah. So basically, you fell into this. So you had this international background, then suddenly the Zoom revolution came and it made it possible, or somehow people’s paradigm shifted and suddenly it was totally okay to meet on Zoom. If you can meet on Zoom, then you can meet with anyone in the world on Zoom, basically, and then suddenly the world becomes your oyster because you can hire people anywhere in the world. So how did that evolve and how do you put the blocks together? Was it hard to start to build a culture with more people?

Well, prior to this, we go back in time, we had ICQ, we had AOL Instant Messenger, Yahoo Instant Messenger, etc. and others in other cultures and regions of the world. Then all of a sudden, Skype was born and Skype was acquired by Microsoft and recently killed since they had Teams. The technology has shifted even though we’ve used forms of it over the last 15 to 25 years. So, companies have used BPOs, they’ve outsourced to other countries, and now that has migrated to outsourcing of task to people and spread around the world to say, okay, don’t just do task or project, be full-time as a contractor with us. Or be full-time as an employee, even though we don’t have an entity there, we’ll just send you money every month and then realize compliance is needed. So, let’s use an Employer of Record or a Professional Employment Organization (PEO) to pay payroll and local taxes. And then you have banking and payroll element, payment transfers that have to evolve cross border. And then you’ve got language issues, communication issues of, oh, I didn’t know when I said that it was interpreted as this. English of your region versus English of my region.

Interesting.

Then emotional intelligence of having bad bosses always compared to having to have a trust culture in a remote distributed format. You have an emotional educational opportunity to bring people into the type of behavior that’s expected, communication that’s expected through a distributed team rather than a local culture.

Okay, that’s very interesting. So let’s dissect this a little bit.

Yes.

You have developed kind of a framework around this, which you may call Globally Distributed Operating System (OS). So what does that look like? What are the elements of it to build an operating system that can make you effectively manage a global company with virtual employees?

There are some key components. As I go back on what I was saying a few minutes ago,

communication is one of the four foundational elements.
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That word is too generic because there’s nonverbal communication. You have your camera on, all of a sudden there’s visual communication, but does laughter mean the same thing in their culture as yours? Does seriousness versus a smile during a business meeting have the same expectation? So, communication is really learning behavioral interpretations. And so having a core of communication for a globally distributed operating system, you actually to have understanding and empathy and relationship, but yet, you’re not going out and sitting at a dinner table with that person. You’re not in person often.

So how do you do it?

It truly takes, I think, several elements of trust, empathy, listening, and then understanding.
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And a lot of that, I think, is learned and taught so that in each team and department, people actually see beyond the first layer. They hear beyond the first layer of what’s typed in Slack, in Teams, and emails. And that’s very gradual. That’s not an instant.

Do you have a training program around this so that you kick some people?

It’s under development. Yes, it’s a process. Because even though people have worked remotely before, often they’re working remotely or from home and commuting in every once a month or once a week, they may be working from an unhealthy environment. So still, with a globally distributed, cross-border international team, there’s that communication element, then documentation is key. Because if you don’t have processes and scope of work and just your culture written, it takes many times for us to hear something. And then if we’re hearing it through our own filters.

So where do you document all that? Is there like a central repository where you keep this thing?

Yes.

Have people read it?

There is. So online central repository, wiki area. And I think that’s key because onboarding, you can give people, you can send people documents, but something that’s constantly being updated that it’s like, okay, this was added, but the education of it, of going deeper than what’s in print, because words, whether spoken or printed or published, have many layers.

A picture paints a thousand words, but a thousand words have ten thousand meanings.
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That just, I don’t know if that’s exactly true, but I process as I speak through these things. And so we can have your vision and values written in 20 words, a list of four values and a vision of 16 words. But each one of those needs to be unfolded as the dominoes fall with all the layers of depth that are necessary. So education through every time there’s an all hands call, a community call, there’s reiteration of those, the mission, the vision, the values so that examples are given, that it becomes multi-dimensional. Then the fourth element here is integration. Because when it’s spoken and heard, when it’s read and processed a bit more, is through the illustrations of how these things are applied that people can then integrate. So you’ve got communication, documentation, education, and then integration, those four components.

Okay.

We can’t integrate them into our behavior unless we truly understand them.

Yeah, and the reinforcement and then the integration. In my mind, the integration piece is how you integrate your core values, your vision, your strategy into every fabric of the company. So every tactic, the office, you have an office, but you have a virtual office, perhaps you have maybe a metaverse office, I don’t know. Some people have that, the team name, how people dress, how the Zoom background they use, this can all be integrated into every element.

Yes, for example, if you’re trying to integrate the element of a sense of urgency into people’s behavior, we can say, okay, make sure and approach a new opportunity with a sense of urgency. But if we don’t document and say, that means replying within six to 24 hours, ideally within six hours max, have that documented and then educate of, okay, that’s what we mean by this. Not an email saying, hey, I got it, an auto responder, but a solution. And then the integration is seeing it happen, seeing it drop into the CRM with, and seeing that, okay, it’s actually, the behavior has been applied and correctly. When I think about these things in the distributed workforce,

the future of work, I'm part of the Future of Work Alliance, which is leaders around the world looking at how do these processes need to change. There's a lot for us all to learn, I believe, in this.
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So if you have people from different cultures, is there like a dominant culture? Is there a European or a US common? You use English as a language that kind of determines to some degree the culture. What is it onboarding like? So if you hire someone in Egypt, how are you going to inculcate the culture into that person?

It is gradual. And of course, we have to guard because we become like the people we’re with. So as you’re bringing in people from all over, everyone’s values intersect and things rub off on each other. So this is a very cautious thing you have to do, because if you’re in the Netherlands and you only hire people from that small town, it’s going to be a whole lot easier to control the culture if that’s what your ideal is. But if you’re a multinational entity and you’re hiring people from all around the world and you want to have that element, then it’s a whole lot easier to appeal to your customer, your client base, and have your internal conversations much more like your external because you’re dealing with people from all around the world as customers

it's actually nice to have people internally from all around the world so that you're learning from each other and you're ready for the client from the unknown culture whether they're Yemeni or a mixed company
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where the founders, ones from India, ones from’s from Sweden, one’s from Singapore, and one’s from Argentina. You can go to that company saying, I identify with you. That happened this morning, actually.

Yeah.

They looked at us and said, oh, you’re from Uruguay? I’m in Argentina. Oh, you’re from here? I’m from there. Ah, we like you. It’s a thing of camaraderie and rapport building. It’s like we get you. You’re not just talking about insurance. You operate a team like ours. You get it. You see the difficulties.

That’s fascinating. I’ve worked many times ago. I’ve worked with a Dutch bank, actually, ABN AMRO Bank. At that time, there was a pre-merger, pre-sale and then repurchase of the brand. And it was a highly international bank, big history, 250 years since the Dutch Antilles when it was founded as a Dutch India company. And it was a very international bank, but still it was at the core, it was a Dutch bank. The board of directors was full of Dutch men and they essentially exported their culture wherever they went, they exported the culture. However, in contrast, I had a friend who was a private equity fund manager and I was living in Hungary at the time. And basically, his office was in London.

I said, why did you make this office in London? Why did you do it in Budapest? It’s much, much easier. He said, what we do is we try to invest in different countries in Central Eastern Europe. And if I don’t go to London, I won’t have the access to the best talent from these countries that can help me invest there. So he went to London and then he hired people from all these different countries. And then he could show up as a local, but also with all the connections that the London presence would give him. Interesting. So what does your business look like? You have like a distributed leadership team as well? You have people from different cultures?

We do. So as I hear that, I think, okay, a Mauritian Brit who lives in Bangkok, a South Korean that lives in Atlanta, a Brazilian that leads our medical underwriting and all things global assistance, and an American myself who is not very American these days after living around the world for 20 plus years. I think it’s extremely valuable. This week had an opportunity from a Japanese company, a Japanese insurance company that wanted to collaborate with us to distribute our plans. They didn’t reach out to me. They reached out to our chief commercial officer who’s South Korean and they hit it off. Similar age and just cultures much more unique than someone who looks like, okay, I’ve only lived in the US my whole life, not going to reach out there.

I think people do see the values of different cultures as they do different ages as well.
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Now, how do you crack the code on the time zones? Because if you work around the world, it means you have to be awake around the clock, perhaps.

Or have team members around the world?

Yeah.

But that means there is sacrifice. There is sacrifice on rotation of, okay, we’re going to have an all hands call, a team call of different departments. That means at times some people may have to get up at five in the morning when it’s going to be five o’clock on the other side of the world and the next time on rotation. It may be nine o’clock there when it’s nine a.m. And it requires sacrifice for sure when you’re working with the different time zones and an extra attention to detail.

Yeah, it’s going to be exhausting. And then do you also travel to some of your countries of operation?

Yes. I got in last night from New York City, but Saturday night I got in from a business trip to Milan. And the week before that, I was back in New York City. The week before that, I was in London. The week before that in Philadelphia. It’s a flow where in real life visits in a global team require travel. A team member from Qatar met me in London and same thing on the most recent trip to New York, team member flew in there. So those are essential elements are that the offsites of everyone, team off sites and then key leadership off sites to where you meet up away from where you normally work in a centralized or a specified location, because communication is different when you’re in person The level that you can educate is different. So therefore, the integration becomes much more applicable.

So you then make an effort to do some meetings where the leadership team flies in and you’re all physically in the same location?

Oh yes, that’s a necessity.

Yeah, that’s awesome.

And there are good companies to even help organize those. There’s one called offsite.com that helps companies all around the world. And that’s one of our product areas to serve those companies that are gathering at one centralized location because the risk is there for injury, for travel interruptions. And so they come to us for the travel insurance, for their group, for going to conferences and gathering for regional meetings.

Yeah, that’s interesting. So what else is important for a digital nomad or someone who travels a lot, a world citizen, or someone like you who works around the world managing a global company? What kind of insurance elements are applicable that maybe are unique to this kind of lifestyle?

Having comprehensive health insurance and not relying on travel insurance is one of the first things I think that people should realize is critical.
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Travel insurance was built for a trip, a holiday, vacation, conference, a wedding overseas, etc. It’s being used mistakenly as medical insurance. And people who are living the long-term lifestyle as a solopreneur, a startup founder, a remote worker, a digital nomad, an expat, they need health insurance. It’s automatically renewed every year so that if a major diagnosis happens, they’re not going to say, go to your home country and use your health insurance for that. And you have to pause your whole lifestyle and return to your country’s healthcare system to a place where you may not have a home anymore.

You may not have that network because you’ve been on the road too long. And you don’t wanna go to your home country. That’s maybe possibly why you started this lifestyle. This way of working.

So comprehensive health insurance is essential. It's more costly, but it's more comprehensive. Getting one that is actually covering your needs.
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  You may not be planning on maternity with your benefits being needed by your partner, but those surprises happen. So make sure you’ve planned ahead with that, as well as does your plan cover you where you don’t need coverage?  Sometimes you can exclude a country, say exclude Singapore, and your price is gonna go down when all you are is you’re covering, you’re living in other Southeast Asian countries. And if you can remove Singapore, your rates could go down significantly. If you’re only going to be in Africa, often traveling among different Southern African countries possibly, maybe you reduce it so that’s the only region in your plan because cost of care is much lower there.

If it’s worldwide coverage because you need the US, then your prices are gonna be much higher. It’s getting a plan where there’s freedom of hospital, where you can go to the hospital of your choice is one of those key elements, because if they have a network, and they’re not the best hospitals in the city, that’s going to limit you. And people often don’t ask those questions. How much technology do they have? Are they relying on just on the legal contract that’s fine print that you have to search through read through? Or their native apps in the Apple, Google app stores, where you can file claims easily and you can use the services just like you would in a house service. Is it 24 hours a day? Is it multilingual? Do they speak your language?  Those are things that all are yeses with Insured Nomads, the examples I’m giving, but you’re probably healthy. You don’t anticipate using it. Like we insure our homes, and we get fire insurance in case it burns down, but the chances of it burning down are low. We still do it. With our body.

We never use it, yeah.

Right. So what extra benefits? We provide mental health therapy sessions. I think we all could use that a whole lot more, even if we just treat it like a life coach. We provide 24 hour a day spontaneous speak to a physician anytime within five minutes. You’re talking to a physician after the nurse finishes with you. We provide unlimited airport lounge access all around the world to you, your spouse, your children, anytime that 1600 lounges around the world, like four of them in Amsterdam, six of them at Heathrow. It’s a lot of lounges to get access to.

Yeah, it’s impressive.

No limitations because your lifestyle requires cybersecurity. We provide McAfee for 10 devices to protect against malware and against viruses, against hackers with VPN included. That’s the travel technology, the health tech, native apps, the customization of what benefits are there. Those are key things. And as you hear these things about running a global business

I think it's great to understand your health insurance. A group health plan can include local workers and those with a cross-border exposure when you're with Insured Nomads.
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That’s one of the biggest things the entrepreneur, the leader of HR or cross-border team can’t solve currently until the plans that Insured Nomads has brought is that you can include the local worker and the cross-border worker giving different levels of benefits all in one group plan.

So it’s completely customized. That’s fascinating. So if someone would like to learn more, they have this kind of business or they travel a lot or they have local employees in the Philippines that they want to insure while they have some team members who are traveling or maybe in the Middle East, where would they go to find out more and how can they connect with you?

Insurednomads.com and Insured Nomads on any of the platforms you’re using whether it’s Facebook, Instagram, X, LinkedIn, etc. Insured Nomads. We have easy to utilize contact and quote options and purchase options online. Or ask your broker, your benefits broker, tell them you want a plan proposal from Insured Nomads. We’re represented by leading brokers on every continent.

Fantastic. Well, that’s fascinating. I mean, the world is changing. It’s becoming more of a global village and you need to be insured wherever they go. I’m just thinking that I was in the Philippines last week with a client and I actually forgot to take out even travel insurance. And I got a couple of shots. I thought that I’m covered but then there was no travel insurance. So if something happened, it would have been a touch and go. So it’s a good thing to know. So, Andrew Jernigan, the CEO of Insured Nomads, a globally distributed and globally operating insurance company that can customize any kind of insurance, health insurance, travel insurance, cybersecurity for you and for your company, definitely check him out, insurednomads.com. Andrew, thanks for coming to the show and if you enjoyed that conversation, then make sure you subscribe to us on YouTube, you follow us, give us a review on iTunes and stay tuned because every week, I bring an exciting entrepreneur to the show who will share their framework, and we have the Globally Distributed Operating System today. So thank you, Andrew, for coming and thanks for listening.

Important Links:
  • Andrew’s LinkedIn
  • Insured Nomads LinkedIn
  • Insured Nomads website
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