The Remote Show

Show Notes:

Jordan's links:


Remote For Life book





Tyler Sellhorn (00:02):
In 2022, every business is a global business, but how do you onboard and pay team members in multiple countries? Remote handles payroll, benefits, taxes, stock options, and compliance, to help companies of all sizes pay and manage employees and contractors around the world. No hidden fees, just best in class global employment for a low, flat rate. Learn more at remote.com/partners/weworkremotely.
Hello everyone. My name is Tyler Sellhorn and welcome to another episode of The Remote Show, where we discuss everything to do with remote work with the people who know it best. Thanks so much for listening.
The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire.
Today, we are blessed to be learning out loud with Jordan Carroll. Jordan is the remote job coach. Jordan helps high performers land legit remote jobs to gain freedom and flexibility in their lives, and also helps remote first companies get connected to top candidates.
Tell us, Jordan, what is a remote job coach?

Jordan Carroll (01:07):
Tyler, that is the question of the century. First of all, thank you so much for having me, man. I really, really appreciate it.

Tyler Sellhorn (01:13):
You're welcome.

Jordan Carroll (01:13):
It's great to meet people from LinkedIn, from the internet, even though they may be complete strangers and then you see them the first time or talk to them for the first time, and you could just jump right in.

Tyler Sellhorn (01:23):

Jordan Carroll (01:24):
So I don't know how many [inaudible 00:01:25] you have like that, but that's like the normal for me now. Is that not just another normal?

Tyler Sellhorn (01:28):
Exactly. Yes. It's very common.

Jordan Carroll (01:30):
It's so funny how the world works. So what is a remote job coach, I consider myself just a career coach that focuses on remote work. There's this huge, huge gap, Tyler, in understanding how to be a unique applicant for jobs. That is something that we've never learned in school. That is something that has been neglected in our educational system.
So the way that I've seen it is not only is there a gap in figuring out how to be a unique applicant for jobs in general, once remote is added into the mix, then there's a whole nother layer of types of skills, of types of jobs, of types of companies, remote work models that you have to consider.
So my job as a remote job coach in the way that I see it is to help on the job seeker's side, especially for those high performers, those people that have really, really good potential to be awesome remote workers, to be good at what they're good at, and find a company that actually respects them and will allow them to live their ideal remote lifestyle.
On the company side, it's where are those remote first companies that are really evangelizing what's going on in this world with remote work and how can I amplify their voice? How can I put an air horn, like you'd say, to their voice? Because all of this is just about pushing remote work forward as a concept, as a movement, because when all of us are demanding that this is a standard, that this is a default, the whole world gets better in my opinion.

Tyler Sellhorn (03:01):
Well, plus one to growing the default into something that is much, much more desirable and beneficial to the Earth. I'm going to zoom in on something you said. You mentioned that you are a career coach focusing on remote job seekers. It almost felt like you were going to draw a distinction between career coaching broadly and specifically what you're doing when you're saying that you're the remote job coach. What do you see as fundamental differences for someone who is seeking a career with remote first companies versus a company that is RTOing it back to the commute?

Jordan Carroll (03:41):
That's a great question. Tyler, have you ever worked in an office?

Tyler Sellhorn (03:44):
I have.

Jordan Carroll (03:45):
Okay. So where would you draw some distinctions between working in an office and working in a fully remote environment?

Tyler Sellhorn (03:51):
Well, the big thing for me is when you default from a co-located environment, there is a geographic limitation to the places you can apply to jobs and whom you can hire. People have to either live there already or they need to be willing to move to that location.

Jordan Carroll (04:10):
Absolutely. And then, what about the experience of being in an office as an employee, versus being an employee in a distributed environment?

Tyler Sellhorn (04:18):
Well, I think it would come back to the geography yet again, because we're going to have to move our geography daily. On the days that we're working, we need to take ourselves to the place of work rather than the work coming to wherever we happen to be.

Jordan Carroll (04:29):
Absolutely. So it's almost like I don't even need to answer, I could just have Tyler do all my answers.

Tyler Sellhorn (04:34):
Hey, hey-

Jordan Carroll (04:35):
No, no, no. I will give you some me-

Tyler Sellhorn (04:38):
I'm here for y'all. I'm happy to be here biweekly, telling you how it is.

Jordan Carroll (04:44):
There you go.

Tyler Sellhorn (04:45):
But we're very excited to be learning from you as well. So tell us what you think.

Jordan Carroll (04:48):
Okay. So distinctions here, when you're in a remote environment, it takes a different set of skills. There is a learning curve. There was a time in my life where I remember going from not working remotely to working one day a week remotely. Even that shift for me was huge because what I would do is I would work from my bed and I would fall asleep on teleconference calls and I would do the bare minimum those days. I treated them like I had them off. So there's a mindset piece to this that starts with, "Oh, how is it that I create an environment for success in my home office?" for instance.
If you're someone who wants to go travel the world and work remotely, there's a whole nother mindset that comes with that. As far as bringing the things with you. Tyler, I know you're not seeing my setup right now, but I live in Mexico right now. It's not my home country, but I have residency here and I'm in an Airbnb, and I have a tri-screen monitor that I take with me everywhere, that's portable. I put it on the back of my computer and now I have three screens, which is pretty cool.
So it can go down to the logistics of how you set up your environment as a remote worker to become more successful, all the way to how does the communication change between someone who's in an office environment and their boss is sitting in the cubicle next to them, versus, "Oh, my boss is on a dramatically different time zone and I'm now relying on asynchronous communication and giving someone enough to be able to move a task forward or to give them an update of where I'm at."
Again, these are skills that are not taught. So people have to learn them the hard way. And what I try to do is create ways in which I can work with individuals or give them the information that fast tracks that learning curve from the remote skill side and then also from how do you stand out to a remote first company. With less geographical restriction on where they're hiring, there is a ton more competition. So now you're not just competing against people in the local talent pool, you may be competing with people all over the world.
So what are the things that you need to do to really stand out, to show, not just tell them, but show them how you can be a unique applicant and you are absolutely competent in the particular role that they're hiring for.

Tyler Sellhorn (07:04):
Okay. Coach us up, Jordan. You've ended your statement here talking about that idea. How do we become that unique applicant? How do we show the remote first companies that are hiring the jobs that we want? How do we demonstrate that? How do we not just build a remote first profile, but also tell those people about it? What are the things that we need to say? What is the things that are going to indicate to someone that's looking at us as a candidate, "Ooh, more of that, please?"

Jordan Carroll (07:33):
You stop applying to jobs. This is going to sound so counterintuitive, but almost everybody out there who is looking for jobs are just going on job boards and applying. And here's the thing, I know we work remotely as part of this, and it's a fantastic remote job site. I have my own job board as well. I have nothing against job boards. I have nothing against actually applying for jobs. The issue is that people have a reactive mindset when they're job searching. And what they end up doing is they just spend all of their time reactive, looking at boards, applying.
However, that is not a true, great way to job search, because you're basically going to these boards and saying, "What do you have for me today?" with your hands out and hoping for the best. What I like to think about when becoming a unique applicant is actually looking at your value from your past experience, getting super clear.
First and foremost, what are the roles that you can do and you can compete well in. Then two, getting super, super targeted in what type of company you want to work for. Is this a mid-sized organization that's 150 people to 500 people? Is this a large organization? Is this a small organization? Get really clear on the lifestyle you want to live. Because if you're looking at jobs just on a job board and you haven't properly filtered it, for instance, and you have this dream or ambition to travel to Europe and then travel to Africa and travel to Mexico, but you're just looking at jobs and you haven't pre-qualified these companies, you don't know if they're going to be a company that's capable of giving you that ideal remote lifestyle.
So start with targeting your role. Start with targeting your ideal lifestyle. Start with targeting the type of company and the industry. If you can get all those things down first, then what you do is actually go find a list of those companies out there that can hire you and give you that ability to live your remote lifestyle. If you want to live in rural Arkansas and just stay home with your dog, and that's your idea of remote work, that's a very different job search strategy than someone who lives in and is a citizen of Indonesia, but wants to travel the world. So we just need to understand that depending on where you're at and what your ideal lifestyle is and the companies that you target, all of this is going to be very different.

Tyler Sellhorn (09:53):
Well, shout out to the folks that are dialing in from the Ozarks and shout out to the folks that are just now stepping their toes into the digital nomad lifestyle. And I think that's super interesting to hear you invite us to stop applying to jobs and to start filtering our list based on some things that we might be able to identify by looking at a job description or a job advert.
And so, when you say, "Hey, let's filter this list," you mentioned a couple there, but can you underscore those things that might be the dimensions of a job search for a job seeker that's looking for that, as you describe, legit remote first job?

Jordan Carroll (10:37):
Yeah. So again, the criteria I think starts with your own personal skills and the jobs that you're actually qualified and capable of doing. Start with where you're at and then look a little bit into the future. So you always want to be going for what seems maybe a little bit out of reach as far as where you're at right now, and framing yourself as that next version of you.
And then, in the background, you're constantly trying to learn skills and trying to get some type of experience with those things. But then, as you're filtering these companies, I would really look at what type of culture do you want to be in, what type of mission. I have a whole blog article on this, by the way, on my LinkedIn.

Tyler Sellhorn (11:15):
I will get that from Jordan and put it in the show links for everybody. So don't go Googling for it. It'll be right there in your podcast player.

Jordan Carroll (11:23):
So the industry is super important too, because depending on the industry, that's going to really help us do maybe a broad Google search, where you could do best blank industry, remote companies. And just by coming up with those round up article lists, you could start to create 25, 50 count list of companies that now you're going to go qualify yourself. You're going to go actually look on their website. You're going to actually take a view at their homepage, their about, the type of people that work for them, where the people are located.
And again, you're starting with this mindset of, "I'm going to find the right types of companies for me first, that can give me the ideal lifestyle."
I talk to a lot of job seekers who do it the opposite way and then get into an interview process. And then, in the second or third interview, now they're discussing how remote the job actually is. That makes no sense to me. You're wasting their time. You're wasting your time. So do the more upfront work.
If you're going to cut down a tree, spend most of the time upfront sharpening the ax. Don't just dive in without any strategy. And that's what this application mindset is, is just throw out as many resumes as I can to as many remote jobs as I can, and see what happens. But you're going to spend more time and you're likely not going to have as good of a result. And I actually have my own examples too, anecdotally, that I can talk about, that I've actually done this before. So-

Tyler Sellhorn (12:40):
Please do. Let's expound on those examples.

Jordan Carroll (12:42):
Cool. So have you ever heard of Remote Year, Tyler?

Tyler Sellhorn (12:46):
I have heard of Remote Year. Shout out to all the folks that have been, I call it the digital nomads, the astronauts of remote work. They were the ones that helped us reach escape velocity pre-2019. So thank you very much for that, for you and others that are living abroad and finding ways to be productive when they're not near their hometown.

Jordan Carroll (13:08):
So Remote Year is this awesome company that if you don't know about it, it's almost like turnkey digital nomadism. You pay a monthly fee and then you go to a different country every month. You can do that over the course of a four month program, a 12 month program. They now even have just one month programs.
And basically, you travel with this community of people. You have an apartment in every location. You have a coworking space set up for you. You have events set up for you. You're just paying them that monthly fee and you're bringing your own remote job with you. So they don't take care of giving you a remote job. It's for people that already can work remotely, but just want that ease of use. "I'm going to pay your monthly fee and everything is set up for me on this itinerary."
So back in 2018, I got really excited about traveling the world. And I was like, "I need to get the hell out of Portland." I had this existential crisis. I broke up with my ex. I moved out of my apartment. And I ended up basically moving back to California in the span of like two months. And all this happened and I was preparing to basically go on this Remote Year trip. I found out about Remote Year. They did a great job with targeted advertising.
And I talked to my program consultant. So he's the sales guy. And the first call, he's in Argentina or something. He's got a surfboard at the background. He's at this little coworking space. It's kind of loud. But I'm looking at him like, "Dude, I want your life." I was like, "I don't know what you're doing to get this job, but I want it."
I also wanted to go on a remote year program. So I put the two and two together and I said, "Okay, I actually want this guy's job. I want to do exactly what he's doing, but I also want to go on a Remote Year trip. So why don't I go on a four month trip? And during that trip, why don't I get really close in proximity to the employees of this company? Why don't I know this product and service in and out, so that if there ever were a job open, I would be the first candidate that they would select?"
So I actually went on a Remote Year trip as a customer. During that trip, I became very, very involved. I would do presentations. I would reach out to employees and meet them along the journey and meet them in every single month. I would make it very clear, I wanted a job at Remote Year. And by the end of those four months, I did not have to submit a resume. Two people from their team submitted a resume for me because they could also get a nice referral bonus.
So my action of going and actually being a customer of the product, getting to really understand it, being very clear on what I wanted, and knowing that my background was really well suited for the program consultant role that I was going for, at that point, the interviews were pretty much a formality.

Tyler Sellhorn (15:48):
Shout out to finding out the life that you want and then taking the actions with which to get it.

Jordan Carroll (15:56):

Tyler Sellhorn (15:57):
Really, really cool to hear that story of your having joined Remote Year. Let's change some names to protect the innocent, but do you have any recent examples here that are post-pandemic, RTO type era of remote work job seekers?

Jordan Carroll (16:12):
Yep. Absolutely.

Tyler Sellhorn (16:13):
Tell us some other success stories.

Jordan Carroll (16:15):
I had one woman that I was working with that was changing from the advertising industry. And actually, you can go and see, these are all on my testimonial page. So I've got a bunch of people that talk about their specific experience. And the cool one about this was that she also didn't apply, but we were preparing an application for a global video conferencing company, which you may or may not know. And what we were trying to do was figure out how do we get into this company. And she was going from being in advertising to wanting to be in tech. She was about 10 years in her career and had been there the whole time. It was radio advertising too. It's a very different industry selling a very different product.
What happened was, there was a job listing up that she was really excited for. I told her to wait. And what I did was I connected to her to one of my friends at the company. And then, she also knew someone who knew someone at the company. So she reached out to that person. They got her connected and she had two informational interview calls with people at the organization prior to ever applying, prior to ever reaching out or anything. From those informational interview calls, she was able to figure out who the hiring manager was. She was able to get insight to what the culture was like. She was able to ask her full questions and really get to just paint this picture of what it would actually be like to work at that company.
From there, since we had determined who the hiring manager was, she reached out to him directly through email, and she was preparing all these assets. We also created a video introduction using the exact platform of this company. So she recorded it on their platform and she created a virtual background with their logo and their slogan. And she introduced herself directly to this hiring manager.
We get ready to send it. The day of, the job is unlisted. It's been taken down. Someone has been hired. She is freaking out. She's hitting me up. She's like, "We waited too long. I have all these assets now and I don't even know what to do." And I was just like, "Deep breath. Everything's okay. This is actually a great opportunity, because now you can build this relationship without the pressure of this job." So I said, "Redo the video, just explain what happened, explain that you had had all this ready and you were going to send it today. You saw that the job listing was down, but you were still really interested." She emails this hiring manager directly with the video, a great email. Within 24 hours, she had an interview scheduled. There was another job that was opening up within the week that hadn't yet been listed and she was a perfect fit for it. About a month later, she got the job.

Tyler Sellhorn (18:48):
Well, thank you for sharing those success stories. I know that lots of us out here are thinking about how can we be the one, because on the remote job seeker side, we just need the one. We don't need seven jobs. You know Kevin Jones, "I got six jobs, two phones," the whole bit. No, we just want the one job. And I guess, maybe let's flip it around, Jordan. I know that you're also coaching folks that are trying to attract... Those top tier talented folks that are ready to join a remote first company. How do we make sure as hiring managers that we're going to be demonstrating to folks, "This is the one that you want?"

Jordan Carroll (19:28):
Define what remote work means to you. It's so crazy. Oh, my God, this is a sore subject for me at this point, because I come from it much more so from the remote job seeker side, and the frustration that they see getting to an interview or getting to a place with a company. And then realizing that they're going back to the office, or realizing that their version of remote is actually hybrid, or realizing that way down in the job listing, in the fine print, it's actually not remote at all. This happens almost every day.
There's a broader issue here, that there's not standardization. I would love if the GitLab all-remote handbook was standardized throughout the industry. And then everybody just used the same words. But the issue is we have all these companies that are remote by accident, who during the pandemic have basically moved an office environment to virtual. They haven't changed their policies. They haven't really changed their communication protocols. They haven't changed the way that they interact with each other. They just kind of expect that they're just going to have Zoom meetings all day, basically. But that's not true remote work.
So the issue that I'm seeing mostly with companies is their inability to articulate what remote work means to them and being very, very clear to potential people that are coming in as candidates, "Here is our stance on remote work."
There's a new feature on LinkedIn. I don't know when it came out, but it's more so recent, and you can check the company Time Doctor, and I actually posted this about a week ago. There's this new little box on the LinkedIn company profile that says... It's like workplace type or workplace description, and you can put your level of remote and what remote means to you.
And Time Doctor is a really good example of this. If you go look at their company profile, they are super clear, and they say it in broad letters, and it's highlighted, and it's huge.
So I think for companies, have this information at the forefront of your communication, on your homepage, on your about page, on your LinkedIn company page. And just be really clear with all of your recruitment team. This is the crazy thing, even recruiters from certain companies, they don't even know. You have employees sharing jobs that are not in the recruitment or HR, and they don't even understand what type of remote it is.
Because I have people that send me jobs almost every day, and I have to actually scrub them and go through them and be like, "Okay, this is not actually remote. Can you check with your HR folks? Can I get connected with them? Because this doesn't make sense." And the listing is written incorrectly. And this is just more of a norm than it is not, which is really, really disappointing.

Tyler Sellhorn (22:01):
Well, let's all become remote on purpose. As you mentioned, like the GitLab folks. Let's ditch being remote on accident. Let's do as Jordan is encouraging us. Let's be super clear. Let's put it at the forefront. Let's make sure our recruiters actually know what it is that we're actually going to do with our return to-

Jordan Carroll (22:21):
The whole company, right?

Tyler Sellhorn (22:22):
Yeah. But I think it's one of those things that is the number one question during a recruiting process right now. And it will continue to be because there is no standardized, as you mentioned, format for how are we going to define this.
We recently talked to Kaleem Clarkson here on the podcast, and that is one of the things that he does in his work, is to advise companies, as you are, saying, "Hey, we need to be very explicit about how this is going to work, what does this look like."
You've mentioned the bit on LinkedIn, but what are the words, what are the phrases that we can put on our job descriptions or make up as a part of our recruiting profiles and those sorts of things? When we write up a job advertisement, what are the things that we need to say to be able to demonstrate, "Hey, we really do have a remote job" or, "Hey, wait a second. We don't have remote work yet?" How can we know?

Jordan Carroll (23:20):
That's a great question. I think the context changes depending on the platform in which you're sharing your job, because if you're posting on LinkedIn, for instance, a job, or you're posting your own site and you have an ATS system and you're working with that, or if you're posting on We Work Remotely... We Work Remotely is a great example of a company that gives people a lot more options as far as how I'm going to classify my remote. But LinkedIn is not to that level, because it's not a remote job board. So I think that they're a little bit behind and their availability of what you choose as the level of remote is not always clear.
So on LinkedIn, for instance, if you could do it in the first line, specify exactly what it means. Specify the exact things because flex jobs... There was a stat on flex jobs. This was maybe a year or two ago, but 95% of remote jobs have a geo restriction. It's crazy. So those geo restrictions should be said upfront, just so that nobody is wasting any of their time at all.
So work with what you have. If you're posting on your own website, I would love to see if you can hire anybody from anywhere, work from anywhere. Because even if you say a 100% remote, that doesn't necessarily mean a 100% remote work from anywhere. 100% remote just means that you're not going into an office, but there still might be a geo restriction. So adding in the geo restrictions right at the top, and in very clear. You can even do it in the title of the listing. I've seen a lot of companies do that on LinkedIn, who are not able to configure that little filter to their specification. They'll put, "Work from anywhere," in the actual title of the job listing.

Tyler Sellhorn (25:03):
You're using a phrase that I'm not sure that everyone is there yet on. You're talking about geographic restrictions on a work from anywhere job. Talk to me like I'm five here, because I want us to be able to figure it out with you.

Jordan Carroll (25:17):
Sure. Yeah. Okay. So remote jobs are not equal. Different remote jobs need to be done in different time zones, in different states, in different countries. And actually, the majority of them have some type of restriction. That is our fundamental understanding of remote jobs. Let's start with that.
Within the umbrella of remote jobs, there are some that actually don't have any geographical restrictions. They can hire anybody from anywhere. So it's just being very clear, depending on your company's needs, which often stem from tax purposes, different regulations, different legal things that get in the way of them being able to hire in certain countries. But if you take all those away, there are some companies that can hire anybody anywhere. And those types of jobs, where they can hire anybody anywhere, I call those work from anywhere. And that is an industry term that I've seen in a lot of different places. And I like that term because to me it's very clear; work from anywhere. Doesn't matter where you're from.
The difficulty with 100% remote for instance, is that can mean that the job is just 100% remote. As in, you don't have to go to an office, but you still might have a restriction of where you need to live, in a certain time zone, in a certain state, in a certain country.

Tyler Sellhorn (26:37):
Okay. Thanks for getting into the weeds with us here, Jordan. I think it's really important for us to start thinking as hiring managers, to be putting it in the title of the job if there isn't a field on the job board. We've got to be able to say, "Hey, you need to be within this many time zones of this place," or, "You need to not be in these locations because we can't sponsor your employment there." There are geographic restrictions, even in a "remote job environment". And we need to be learning from the experiences of those OG remote companies and following their example.
I just want to say thank you very much for teaching us today, Jordan. Appreciate you being, as you're describing in your upcoming book, you are remote for life. Just really appreciate you out here in these internet streets, representing the digital nomad lifestyle and helping others find the life that they want. You saw that person in Argentina with their surfboard on the wall. I pray that each of us will find it in our own lives. Have a vision for what it is, the life that they want to live, and then for us to go and get it for ourselves out here. For using remote work as a lever to make that happen. Thank you very much.

Jordan Carroll (27:57):
Well said, Tyler. Remote work is just a tool. It's not for everybody, but it can be the tool that can help you, just like it helped me, just like it helped your story, in giving us that ideal lifestyle. So I really appreciate you having me on here and getting the opportunity to talk about these things.

Tyler Sellhorn (28:13):
Thanks, Jordan. Thanks so much again for listening to the show and be sure to check out weworkremotely.com for the latest remote jobs.
And if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so.
As always, if you have someone we should talk to, any advice you have, or if you'd like to advertise on the podcast, please reach out to us at [email protected]. That's [email protected]. Thanks so much for listening and we'll talk to you next time.

← Back