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Episode #31: Sam Pessin- Co- Founder & President - Remote Year

March 11, 2022 Ursus Staffing & Services Season 2 Episode 31
Hiring University! Powered by Ursus, Inc.
Episode #31: Sam Pessin- Co- Founder & President - Remote Year
Show Notes Transcript

Sam Pessin, Co-Founder, and President of Remote Year joins Hiring University to discuss the state of remote work; how far we've come, where there is work left to do, and will some employers revert back to traditional and mandatory in office work models!

"If your company does not support remote work or hybrid work options you are losing out on a lot of talent. Especially top tech company talent. I have so many friends that work in technology and at this point will not entertain a conversation with a company that isn't remote."

     -Sam Pessin - Remote Year

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Sam Pessin

[00:00:00] Jon Beck: What's up everyone. It's John Beck, your host of hiring university.

[00:00:03] Welcome to another episode where today we welcome Sam Pessin co-founder and president of remote year. If you don't know remote year, it's such a cool platform that Sam's going to share with us, basically taking or giving people an option for remote work across different countries, whether they're from a week, a month, four months or a year over 40 destinations.

[00:00:25] Before starting remote year, Sam was a consultant at Bain consulting and important to note. He is also an undergrad and MBA grad of the university of Michigan. Go blue. Sam, how are you? Welcome to hiring 

[00:00:36] Sam Pessin: you blue. Thanks for having me.

[00:00:39] It's really, really nice to be here. So 

[00:00:42] Jon Beck: the topic today is of course remote work. And we're going to operate under the assumption that unless you were living in a cave for the last two years, you know that this is a movement it's happening. And as we come out of the pandemic, hopefully coming out of the pandemic, we're going to have to figure out where all the pieces fit.

[00:00:58] So we're going to delve into, what is now the new normal. But before we jump in, why don't you in your own words, tell our listeners about remote year and the offerings that you provide 

[00:01:06] Sam Pessin: Sure. So remote years, a leading platform for remote working and learning globally, we offer work and travel programs for remote working professionals who want to travel around the world with their remote job, with a community of other like-minded individuals.

[00:01:22] , we also more recently offer retreats to both, consumers, so a wellness type retreat, and also to businesses like a corporate offsite. And those are our products. 

[00:01:33] Jon Beck: You highlighted recently in a LinkedIn article by Roger trap, by Forbes, which was entitled, why managers hold the key to the office of the future and in the article, Roger referred to what is happening as a paradigm shift.

[00:01:45] Now, I think you and I would agree that paradigm shift is an overused, corporate speak term, but is that really what we're seeing happening in front of us right now? 

[00:01:54] Sam Pessin: I think that the shift was, The communications ecosystem first and foremost, that's usually the first thing that remote or distributed companies embrace to create a remote first.

[00:02:07] The ability or workflow, if you will. We even did that in our early days. So like in the very beginning of remote year, we were running around with a small group of people trying to organize this global work and travel program. And, we had a bunch of people sitting in a room and one person was remote.

[00:02:23] And we realized that we all had to be communicating digitally on our own computers, on zoom or Skype or whatever we were using at the time to make sure. Collaborative and equal for everybody. And so I think once companies start to embrace those digital mediums of communications, where most meetings are hosted on zoom, even if some of the people are in the office and some of the people are maybe working from home or in a different state or location.

[00:02:52] So I think that the first part of the paradigm shift is. Around digitizing your communications and your meeting formats. So that flexible hybrid or fully remote can all exist and work effectively. I think in terms of the actual footprint, we obviously saw a huge spike during the beginning phases of COVID.

[00:03:12] And I think it's slowly resumed, more companies are going back to the office, but I think the main changes. Most companies have resumed to hybrid rather than fully in office. , I think there are definitely been some companies that are now fully remote that weren't remote at all before. But the more common model is hybrid where it's either a few days in the office or some of the people in the office and some of the people not in the office, et cetera.

[00:03:38] There's a lot of different versions of hybrid. 

[00:03:41] Jon Beck: Sam and I sat on a panel together, a couple of months ago now. And, for our listeners to our, um, regular listeners to the show, we're a remote company had been for five years. I've learned a ton along the way. And I appreciate your comments around the communication aspect because that's constant.

[00:04:00] And I think the biggest challenge for a lot of companies, it's also a constant evolution. We're always looking for ways to keep it fresh and. And to give people more options. And ironically, as a remote company, we've opened two offices this year because we wanted to have a home base for people. I bring all that up because one size doesn't necessarily fit all 

[00:04:22] large enterprise is going to respond very differently than the startup than the mid market and hybrid, is again an easy term to say, but what does it actually mean? Can you give us some examples across that spectrum of things that are working really well or maybe things that are. 

[00:04:37] Sam Pessin: Yeah, I think, maybe I'll start with the things that aren't, , which in my mind, I think it's really difficult when you have some employees in an office and some employees promote, that's probably the hardest model to make effective, and anything can be made effective if you have the right things in place.

[00:04:52] But I think that's a tough one because you sort of have the haves and the have nots in that world. And it's very difficult to make it feel like an equal playing field for people. , I think the models where it's some time in the office and some time not in the office, all is one company. That makes a lot more sense because everybody's on an equal playing field and you're still sort of taking advantage of the remoteness and the, the ability for people to stay home some of the time and actually be more efficient with just getting their work done.

[00:05:24] But then you have meetings and certain kinds of conversations in-person in the office. I think that's a really interesting model. The model that, that we actually embraced, which I like the most is. We are fully remote, but we have what I call short period high intensity in person, off-sites or retreats.

[00:05:45] , we do them depending on the team. One to four times per year. So everybody at least has one a year where they can meet their coworkers in person. And our leadership team, for example, does closer to four of those per year, where we get the leadership team together for quarterly planning, annual planning, et cetera.

[00:06:05] And it's usually a workweek or, or part of a work week, three, four, maybe five days at the most. You get together, you spend a day or two. Big strategic thinking about the future. And then you, you sort of boil that down to, okay, what's the next step we need to take to, to reach that future.

[00:06:21] And I think doing that in person accomplishes two things. One is you set the strategy and you brainstorm and you ideate, which are definitely more difficult to do a resume in my opinion. And number two is you bond and you have fun and you have dinners and. Play games and whatever your, your team culture is.

[00:06:40] And I think those two things are the two things that are particularly challenging to do digitally. And we embrace these sort of off-sites as a team that are really helpful to build relationships, maintain relationships, and build the strategy for the. Yeah, we do something similar and 

[00:06:58] Jon Beck: I agree that the human interaction time and the bonding time and establishing those relationships is as important as anything with that time spent together.

[00:07:07] You can't do it on a Brady bunch box on a zoom or a teams meeting the tricky part with this hybrid model too, which I think a lot of companies are wrestling as maybe spending too much time thinking about it, but I'll bring it up because we didn't even realize it when we opened up these offices was.

[00:07:23] The traditional rules and framework for, accountability and where people are. And I'll give you a very specific example. What seems obvious, or maybe even silly cause it did to me, but we opened up the offices and then we had people attending meetings. Some of them scheduled sometimes impromptu.

[00:07:42] Sometimes they just wanted to break up their day or we can go into the office. And then the questions came up. Well, do I expense my mileage to the office, , I mean, we didn't even think about it or consider it. , and we put a policy in place, but by the same token, I said, let's not spend too much time on this because we want to get people at first, if we're embracing hybrid and remote, we wanna embrace it.

[00:08:02] It all works out in the end of the wash, but I think a lot of companies get hung up because of the old framework. It doesn't apply to what we're doing. Does that resonate? Does that, do you identify with any of that? 

[00:08:14] Sam Pessin: Yeah, I mean, I think more so on the goals and the FaceTime part of it.

[00:08:18] We don't really have like a comparable , to the gas mileage thing, because we don't have a physical space where people are going. But the, our version of that is, I think when you're in an office you're often judged by. How much time you spend there. And it's really easy to fall into that trap.

[00:08:36] And I think even the people that say they don't fall into that trap subconsciously they do. It's really hard not to honestly. , and I think what remote forces you to do is measure outputs. And everyone talks about that. That's not such a revolutionary concept, but how you do it can vary a lot. For example, Having really clear and accountable KPIs that everybody owns that can be measured in some frequency of time.

[00:09:03] And we actually used to do monthly for that, and we've shifted some of it to weekly because I want this a really long time. And it's hard to create some rhythm and energy with the months. So certain things like the sales funnel or. Other pieces of data that we can actually measure weekly and monitor weekly, we tried to set goals and trackers and it creates this organizational energy that, is really fun and really cool.

[00:09:27] And I think something that, that probably didn't exist as much in an in-person environment because it wasn't needed to maintain that, that. Energy and rhythm of the team. 

[00:09:40] Jon Beck: If you're not supporting remote work, are you putting yourself at a disadvantage when it comes to actual 

[00:09:47] Sam Pessin: a hundred percent?

[00:09:49] There's no question about that. Like, I think whether that disadvantage is it could be argued to be advantageous for other reasons. I sure. But you are losing out on a lot of talent. Especially top tech company talent. I have so many friends that are, that work in that space. And at this point will not entertain a conversation with a company that isn't remote.

[00:10:16] And so black and white. Yeah. You are definitely losing out on that talent. I think some people are okay with that and some people are okay with that sacrifice for having. Really strong in person, environment and culture. I used to be kind of like an extremist about remote work.

[00:10:35] Like I thought it was the only way to go and, and we didn't even do off-sites back then. We did that first, I think, two years with, without ever seeing each other, we really wanted to push the limits of remote work because it was so close to what we were building. And I think that there, there are advantages to both.

[00:10:53] Of course. But I think if what you're optimizing for is the best talent in the world, then remote is, is the right model to go. Do you see a 

[00:11:03] Jon Beck: trend? And maybe it's too early to tell, but I think a lot of companies have been saying the right things about support for hybrid and remote, and as time marches on they're going to gravitate back to what they.

[00:11:17] We're doing beforehand. Are you seeing any indications that we've seen a little bit of that? 

[00:11:22] Sam Pessin: There's definitely some of that. I just think that the remote component of roles for potential employees who are going through the recruitment process so important to their selection criteria now, I mean, a lot of people have moved out of the major cities, right.

[00:11:38] And they no longer are looking for jobs in New York or in San Francisco. And so it's a requirement to find a remote role. So I think the fact that is continuing to be a competitive advantage for so many companies. It's forcing the other companies who want to move back to the office to at least very seriously.

[00:12:04] Remote roles or fully remote because, I think they realize that those other companies that are fully remote are going to out-compete them for that talent. 

[00:12:14] Jon Beck: You can't talk about remote work without talking about the great resignation or the great reshuffle. They sort of go hand in hand. There's all sorts of theories as to why it's happening.

[00:12:27] Money is part of this. Corporate culture is part of it. Managers are part of it, the ability to work remotely as part of it. There's also some who struggle with the fact that remote work and the great resignation are also calling out the concept of work-life balance. And some managers we've heard from.

[00:12:49] I now losing control of my employees if I am trying to manage or coach, or even in some cases, reprimand, I'm deemed as not being supportive of the movement per se. And so there's this, like the pendulum is almost swung too far. Where, where are we in that? Assuming you agree 

[00:13:07] Sam Pessin: and just to clarify, you're saying like, where are we in terms of the, um, PE companies being worried about losing their talent due to the great resignation, because there's, and they're scared to even give them feedback. Is that, is that what you're getting at? 

[00:13:26] Jon Beck: There's some of that's happening now. We want to be so supportive and we're holding on maybe in some cases too tight to the talent, for fear of losing them, that we're not getting what we should be from a productivity standpoint.

[00:13:37] Sam Pessin: I think that companies should remember that it's a market out there and. Just as much as your employees can leave you to go be a freelancer, which let's just say, that's the main trend. You can go find those freelancers as well, and you can actually embrace that and explore that and see what it feels like to work with people like that.

[00:14:01] And I think that actually might feel better for you as well. So I think that's the first thing I would say is. The, the gig economy platforms, the fibers and Upworks and Cadillacs and, brain trust of the world. They have amazing talent and they have an incredible value proposition, not just to the talent, but also to the companies.

[00:14:21] Yes. And so I think it's worth as a company exploring and embracing that a little bit. And I think it's also more directly to answer your question. As a company versus those great resident resignation alternatives, you have to have a unique value proposition to the employee. And I think it's worth companies spending some time given these trends, figuring out what that is, and by the way, giving feedback and coach.

[00:14:54] It's actually a differentiating factor about a full-time employment situation and a manager. So rather than be scared to give the feedback, I think I would embrace the coaching element and long-term relationship building and development and, growth of an employee. Actually can come more naturally from a full-time relationship.

[00:15:17] I think it goes back to 

[00:15:18] Jon Beck: our exchange on communication too. I think a lot of managers before the pandemic were probably not very good communicators, mentors, coaches, it's harder. It's hard to do. Management is hard. It's even harder in a lot of cases doing it remotely, and I've written a blog about this.

[00:15:38] I talk about a lot. The challenge is to become a better manager and whether you're sitting three feet or 3000 miles away from your employee, it's all about communication and dialogue and interaction and establishing that rapport. I think that's a big part of it. And I think there's opportunities as well, too, that maybe are even easier remote than they are in person.

[00:15:59] Sam Pessin: Definitely. I think that as a manager, you're one of the most important things is to build a relationship with your direct reports and building relationships. Going back to the earlier part of the conversation. I think it's hard if it's just done this way. And so whether it's investing the time to meet up in person here and there, or just really getting creative around how you use the digital mediums.

[00:16:25] I think that's, it's just so critical as a manager to, to invest in that, more so than it used to be, because you used to just be able to grab someone and go out to lunch from the office 

[00:16:37] Jon Beck: and multiple modalities. There's different ways to communicate. There's slack messenger, there's email there's conferences.

[00:16:43] There's in-person and again, one size doesn't fit all. Sam, what about, diversity and inclusion? How does remote work help? Assuming it does. 

[00:16:52] Sam Pessin: That's probably the thing that winds on the most, because it really flattens the global playing field. In terms of who can apply for jobs, who's qualified for jobs where you can find talent.

[00:17:05] Our team is. So global, I mean, it's partially global because our programs are global, but it's also partially global because we also just hire people in all sorts of different places in countries and parts of countries that, have skills and, those skills are what we're looking for. And, um, there are prices that we're willing to pay.

[00:17:26] And I think that's a really amazing and unique thing about the current world is that you can find. These skills and pockets of talent in different parts of the world that are just amazing and better and more cost-effective than what you could find, down the street 

[00:17:46] Jon Beck: you started remote year, seven years 

[00:17:48] Sam Pessin: ago, seven years ago.

[00:17:51] Jon Beck: Lots of change. You were ahead of the curve. What does it look like seven years from 

[00:17:55] Sam Pessin: now? Um, hopefully bigger. Um, it's funny because going into the pandemic, we were capitalizing on two trends and we still are capitalizing on these two trends. Millennials and gen Z really want to have experiences and travel over, owning expensive products and items.

[00:18:22] And the second is that people are working remotely and that's enabling them to have these incredible flexible lifestyles and leading into the pandemic. Everyone wanted to do a program like remote year. It was really easy to find. Humans that wanted to do remote year. It was much harder to find people who could do remote year, who had full-time remote jobs.

[00:18:44] And in March, 2020, those two trends flipped. And all of a sudden everybody was working remotely and nobody was traveling. And so now, as the travel is coming back, and I would say remote work is coming down a little bit, but not nearly as much as it was before, or as fast as the travel demand is as has resumed.

[00:19:05] We're trying to just build the brand that we've always been trying to build in a much better environment to build it. Our work in travel programs are just doing really, really well right now, compared to what they were doing pre COVID and definitely during COVID. Our shorter form trips are one month trips and, the retreats have been really popular because it's just an easier way to get started, especially when people are either.

[00:19:29] Uncomfortable working remotely abroad for such a long period of time, four months or 12 months, or just trying to dip their toe in the travel water since COVID resumed. Um, and you know, that's been really great. We're exploring entering the U S market, which is really exciting. We actually, today don't have any programs in the U S.

[00:19:52] And, we're considering a more digital experience that, that really enhances the community feel of this global remote work and travel and movement. I'm assuming that you are 

[00:20:05] Jon Beck: a consumer of your own service. 

[00:20:09] And if so, when is the last time you personally.

[00:20:13] Worked remotely or took a retreat or an extended period of time 

[00:20:15] Sam Pessin: away. Yeah. Um, I was a huge consumer of our services for the first five or six years of our journey. And about a year and a half ago, my wife and I had a baby. And unfortunately at least today, remote years programs don't support small children.

[00:20:31] So, joining our programs has been a little more challenging for me for the last 18 months. But, as a family, we still. Take trips for about a week or so every couple of months, to different parts of the U S more recently. And, and, and also the world, um, work remotely from wherever we are. So we're still living the lifestyle.

[00:20:52] Just not as directly on our programs. 

[00:20:55] Jon Beck: So that takes a little more coordination with a, with a little one, for sure. Sam, I have good news for you. I've created a way back machine. I have a ticket for you and we're going to put you in it to the point when you first started your career. What one piece of advice do you share with young Sam based on the experience and what you know now?

[00:21:13] Sam Pessin: I think my piece of advice would be really, really deeply prioritize above everything else, your employees and the people who are working at your company, because everything flows out from that. And that's only becoming increasingly and increasingly true. I don't think we did a bad job at that, but I think you can always do better.

[00:21:35] And if there was one thing I could have doubled down on, it would be. Pay people well, treat people well, and motivate them to just think and create and build the company. Because ultimately as a leader, I believe that my main job is to motivate others. Because as your company gets bigger and bigger and bigger, your own personal inputs become increasingly less relevant.

[00:22:01] Um, and what you're, what you're doing is you're, you're motivating and inspiring a team. And so, that, that's probably the biggest thing that I learned. 

[00:22:10] Jon Beck: That's fantastic advice. I, as I think about that, if, if Sam, or if it was me telling my younger self, when I understand that at an earlier age, I might, I think this generation is far more aware and, appreciative of culture and.

[00:22:27] How would accompany represents, , and hopefully that trend continues. That's why we're starting to see change. So definitely fantastic advice, Sam, before we wrap up, tell our listeners where they can connect with you, or if they're interested in, 

[00:22:40] Sam Pessin: in remote your services. Yeah. So you can find remote year on our website@remoteyear.com and, my email is just Sam Evernote, your.com.

[00:22:49] So reach out to them. Awesome. 

[00:22:52] Jon Beck: Thank you for coming on the show, and for your insights and, let's plan to do it again, in a year or so, and see how far along we are on this journey or not. I'm sure it'll definitely look different, hopefully in a good way. And for our listeners as always keep the faith, keep grinding, keep safe, and we will see you next time on hiring university.

[00:23:10] Thank you again, Sam. 

[00:23:11] Sam Pessin: Thanks John.