Setting and communicating transparent goals with Sam Pessin of Remote Year

Maren Kate
Welcome to From 5 to 50, the podcast dedicated to helping startups and founders survive and thrive through the early stages. I'm your host, Maren Kate, and we're here with Sam Pessin from Remote Year. Welcome to the show, Sam.

Sam Pessin
Thanks, Maren. Thanks for having me.

Maren Kate
Absolutely. So when did Remote Year get founded?

Sam Pessin
We started Remote Year in late 2014. My co-founder, Greg, and I were living in Chicago at the time.

Maren Kate
And what was the why behind starting it?

Sam Pessin
Well, when we first put up the website it was actually Greg that put up the website and he, to be honest, wanted to just travel and work remotely himself. So when none of his friends, including myself, could do that with him he looked to the Internet and put up remoteyear.com to try to find some people that do it, and as I saw this all happening and unfolding in our apartment, in Gold Coast, and in Chicago I was pretty intrigued because I grew up all over the place with my family. My dad was a journalist and my family moved every four years to different countries all around the world when I was growing up and so all of those experiences were challenging at times. They were also really, really formative for me personally and when I think about what we're doing for other people who do our programs it's very similar to that. And I get a lot of excitement every day for helping other professionals have experiences like this and really connect with diverse cultures, diverse people and I think, ultimately, that leads to empathy and understanding and in the longer term peace, love, and prosperity.

Maren Kate
Absolutely. I mean, empathy is a huge one when you travel, and then even just from a kind of nuts and bolts business standpoint it opened your mind when you start traveling, if you're an entrepreneur or professional, to cultures, ideas, things you wouldn't think of before. And it also is nice, because it gets you out of the mindset of wherever your particular city is. So if you have the Silicon Valley mindset, when you start traveling and going all over the world and seeing the different ecosystems it makes a big difference in your thinking and kind of expand your mind.

Sam Pessin
Yeah, and I think that's important, not only personally, but also professionally, right? I mean, the professional ecosystem is continuously getting more and more global, and having the soft skills of a global experience like this and the ability to connect with different people from different cultures, speak different languages, and operate in different environments like that is extremely valuable in a professional context.

Maren Kate
Absolutely. All of the companies I've started since I was in college have been fully remote and I didn't even realize they were remote-first when I was making them, it was just that I was poor and I needed people to help fill skill gaps like building websites and helping with email marketing and so I went on to these old school boards where people put up what they were good at and you connected and hired them. And now it's amazing to see how the ability to work remotely not only has changed the professional landscape but is continuing to change it. I guess that leads me to the question, what did your co-founder do for work that he was able to work remotely?

Sam Pessin
So his background is in digital marketing so he had started an e-commerce business, sold it to Groupon, was working at Groupon for about a year and then when he started working remotely he basically picked up some freelance digital marketing gigs and was gonna travel the world but it was just looking for people to do it with.

Maren Kate
Had you ever worked remotely before?

Sam Pessin
I had not. I was in consulting for about three and a half years and then I worked at a small agency in Chicago for about a year before we started Remote Year. This was my first remote experience and, actually, when we hired our first four people to help us run the program and find the people to do the program all of us were in different cities around the United States. So the beginning of our roots, even in the very early days of Remote Year other than Greg and I living in the same apartment, was fully distributed and fully remote. We were actually using Skype at the time, we made a quick upgrade to Zoom which was a great one for us. That's been in our blood since the very early days of Remote Year and I think we've learned how to navigate both the positives and the challenges that come along with a remote environment.

Maren Kate
So just take a step back, what is the business model for Remote Year? I mean, in layman's terms how do you guys make money?

Sam Pessin
Yeah, so we offer four and twelve-month work and travel programs and those programs come at a fee that you pay to join them. So our 12-month programs are $29,000 spread across 12 months. So you pay a $5,000 downpayment and $2,000 a month and our four-month programs are $11,500. You pay an upfront downpayment of three and a half and then $2,000 a month. And what that includes is basically an end-to-end work and travel experience. So it includes all the travel between the destinations on your itinerary. You spend a month in each city regardless of the length of your program so the four-month programs go to four places, the 12-month programs go to 12 places. So it includes all the flights and first and last mile transportation, your accommodations in every single city, which is apartment-style accommodations, a workspace in each city as well that's 24/7 accessible, a bunch of local experiences and activities that are included in that experience, as well as some add on options, and then finally, and potentially most importantly, our amazing and full-time staff some of whom travel with you for the whole time during the experience and some of them are positioned locally as a local team to really make your experience special while you're in each place.

Maren Kate
Awesome. And correct me if I'm wrong but I feel like in watching Remote Year over the last few years the business model and the company has evolved a little bit. Is that right?

Sam Pessin
Actually not that much. I mean, the main evolution has been we started with only a twelve-month program and now we offer four-month and actually also six-month programs but other than that the business model has stayed somewhat consistent.

Maren Kate
And people are coming with their own jobs, right? You're not connecting them to employment.

Sam Pessin
That's right. So one of the prerequisites for joining Remote Year having a remote job but one of the services we actually do offer is what we call our Enterprise Solutions Service and basically what that means is if you need some help with your employer to help talk about Remote Year and the benefits of Remote Year to your company we actually do have a full-time team that helps our potential customers, potential remotes, pitch that to their employers and have that conversation and the right way to talk about the real company benefits.

Maren Kate
And do you sell the enterprise too?

Sam Pessin
We do a little bit. It hasn't been a huge focus for us the last couple of years but we do intend to focus a little bit more on that in the next year which is really positioning Remote Year of benefit for employers.

Maren Kate
Okay, cool. Yeah, that makes a ton of sense to me at least. So are you guys bootstrap, self-funded, did you take on institutional investment?

Sam Pessin
First two years we were basically Bootstrap. We raised a tiny bit of capital from family and friends right before we launched our first program which was really more of a rainy day fund and we operated as a bootstrapped company for about 18 months after that before we raised our Series A from VC funds. It was led by Highland Capital Partners in late 2016. So since then, we've taken on that and a little bit of additional institutional capital to fuel the business.

Maren Kate
Okay, so what's the total amount you've raised?

Sam Pessin
We've raised a little over 15 million now.

Maren Kate
Okay, and what's the current size in terms of the team?

Sam Pessin
Our team is just over 100. We just recently broke 100 which is exciting.

Maren Kate
Completely distributed, correct?

Sam Pessin
Completely distributed. Our local teams are fixed in their cities and we have some other folks as well that are just working from home and then some people are traveling with programs so it's a mix but we are fully distributed and all of our communications happen over Zoom.

Maren Kate
Are there any growth numbers you can share? Revenue, users, etc. just to give the audience kind of an understanding of how you've grown since inception, especially just how you've racked the need for that 100-person employees.

Sam Pessin
Yeah, so we measure that in what we call our Nation Community. So once you do a program you become what's called a citizen. While you're doing a program you're a remote and when you complete your program you become a citizen of what we call the Remote Nation. And as a member of that community, you have benefits of purchasing specific services and also being a part of our digital community on Slack. So we measure our ongoing growth through the size of our nation and we just crossed the 2,500 mark which we're really excited about. So that's the size of our entire staff and community of folks who are currently doing or have done Remote Year programs.

Maren Kate
Okay. So with the environment, you built a company and completely remote. What have been the biggest pros and the biggest cons? What's been the hardest part of scaling a team to 100 people distributed and what has been the best part?

Sam Pessin
I think the benefits are that we just have a great ability to recruit amazing talent in a remote environment. I think there are so many people that are prioritizing flexibility and remote work over most other attributes of a job and that's been hugely helpful for us. Obviously, we really start with the mission and people join Remote Year because they care about what we're doing and care about the impact that we're having. But it certainly helps to be flexible in that way and have that option for people along the way. And I also think the other huge benefit for us is it forces us to focus on results and outputs because in an environment where you're not sitting next to each other in an office you don't always see what people are doing all the time. So you have to believe that they're creating the outputs that they're being paid to create and that they're on the team to create and you need to find a way to measure that. So it really forces you to be disciplined about measuring outcomes and measuring results all the way down to an individual level.

Maren Kate
That's one of the things I love the most about running a distributed company is that it embodies the mantra of results over optics. And obviously, it's not easy to set up that incredibly granular to high-level results kind of dashboard but once you do get it set up it makes all the difference in the world. It's just like the point of truth.

Sam Pessin
Yeah, and I think even before the results dashboard, which is important, there's also the goal setting and the goal cascading process, right? Like we have 100 people on our team and for us to measure results it needs to be clear to each of those humans what they're being held accountable for. So we have a pretty organized cadence of annual and quarterly goal setting that happens at a leadership level and a board level and then eventually gets trickled down to the teams and eventually the individuals as well to set goals two times per year that we actually use to sort of measured results against and I think that ongoing annual process is a really important part of doing that effectively.

Maren Kate
What frameworks have you used, if any, to do that?

Sam Pessin
We don't use any specific sort of public framework that other folks use. I think we try every time we do this to think about the long term in the first part of that exercise and then sort of bubble that down to the short term. So where do we want to be in 15 years? Okay, great. Therefore, where do we need to be in five years? Okay, great. Therefore, where do we need to be in 12 months? And then that really starts to make sure that the things we're doing today are in line with the place we want to be in the long term. So that's sort of, at a high level, what we tried to do. Obviously, there's a bunch of different exercises and conversations we have to tease out that creative thinking and that work.

Maren Kate
Okay, so you're not using a specific framework like OKRs, Traction, or anything like that?

Sam Pessin
No.

Maren Kate
Okay. In terms of just getting real and talking about the pain points and scaling up, I'm sure you've been through multiple. As you've scaled what has been the hardest part around the sales process, and acquisition, revenue generation? What's been the biggest pain point there?

Sam Pessin
That's a good question. I mean in the very early days we, Greg and I, ourselves were the ones who are trying to get people to come on programs. So as we evolved from that we needed to find a good way to have other people communicate those same messages to the community of folks who wanted to do Remote Year. I think as we've continued to grow from there I do think that there are times where in-person touch points are really helpful. So we try to bring specifically for, we call them the Program Placement Team is sort of our sales team, they help you select a program, and for them, I do think some in-person touch points are really important. For all of our teams, in-person touch points are really important and so we've tried to create a budget and a program basically for people to be able to do that at least one time per year to meet their team in person and spend time connecting. Because I do think that distributed environments can be incredibly effective at ongoing goal measurement and operational cadences. But I also think that in-person touch points can be really, really powerful from a strategic and a cultural perspective.

Maren Kate
Yeah, I agree. In terms of when you think of the 100 people you have on the team right now, how does that kind of break down? If you look at it like a pie what pieces are sales versus marketing versus engineering?

Sam Pessin
Yep, so we have about 50 people total of that 100 that are on what we call our delivery team. So those are the people that run our programs and operate our cities every single day and really deliver what Remote Year is to our remotes and to our customers. So that's about half the team and then most of the other half of the team is sales and marketing and then we have a handful of finance, people operations, and other folks on the team.

Maren Kate
What's the most successful growth hack you ever tried as you've scaled up Remote Year?

Sam Pessin
Honestly, in the early days, our biggest growth hack was PR. We really just scrapped around ourselves to find some journalists that were excited about Remote Year and gave them a one-pager to basically just copy and paste or make their own edits on and we got a lot of buzz in the early days that enabled us to get it off the ground without spending any money on marketing channels. So that's one of the biggest reasons why we were able to bootstrap it at the beginning without additional capital invested in the business.

Maren Kate
Do you think that model still works today? If founders are going directly to journalists, obviously, they have to have a pretty engaging product that has a consumer focus.

Sam Pessin
Of course, absolutely. I think that is a really powerful way to get some press.

Maren Kate
Okay. Yeah because I think normally we imagine everything's so noisy at this point. There's so much content, there's so much everything, but sometimes forget the unscalable things and how powerful those are especially in a world of Mixpanel and all these automated email flows and everything. Sometimes when you just reach out to someone manually like, Hey, here's what I'm doing or I'd love to chat, it makes more of an impact now because the world is so noisy and automated.

Sam Pessin
Absolutely.

Maren Kate
So my last question that I'm going to just give, well, I guess it's not my last question that I'm going to give you. My final three. What do you consider your secret sauce as a leader? What's your unique genius have you noticed as you build this?

Sam Pessin
I feel like I'm the wrong person to ask that question to but I'll try to answer it. I think I'm pretty stable and even-keeled and can generally keep people calm in times of stress and also provide a stable environment for our team to work in and stable expectations for them on an ongoing basis. I really try to champion the whole goal setting, goal cascading, and board-wide sort of goal adherence process and try to make that data public to the team as well on an ongoing basis on our monthly all-hands calls and in our weekly emails that Greg sends out. So I think that's probably what I would say but might be better to ask the rest of our team that one.

Maren Kate
I think that's an undervalued skill set for growth stage and early stage founders is having a stable calming effect on a team. I think a lot of times what I've seen is founders tend to, and I'm probably the same way, be a little more erratic, a little more up and down, constantly changing directions and that really does wear on the team after a while. So that actually makes sense as a superpower.

Sam Pessin
Yeah, it's a tough balance, right, because you do want a little bit of that. You don't want to just be comfortable and stable. But I do think that trying to maintain some expectations over at least a quarter or a month depending on what team you're on I think is really important.

Maren Kate
Absolutely. Okay, last three questions. So what is your favorite book or podcast from the last year?

Sam Pessin
From the last year, my favorite podcast is The Wilderness, which is Jon Favreau’s podcast, and basically about the evolution of the Democratic Party in the US and it's just a really, really interesting listen.

Maren Kate
Interesting. I haven't heard of that one. I'll add it to my list. What business tool could you guys not live without at Remote Year?

Sam Pessin
I feel like by now you could probably guess my answer and it is Zoom.

Maren Kate
What are the second and third?

Sam Pessin
Well, I do think I actually just want to talk about Zoom for a second because I think it is so critical to how we do our work. When you're in an environment where most of your communications verbally are on this software platform it really needs to be well suited for your needs and I think that the way that Zoom has built their platform it's by a pretty good margin far superior to any other video communications platform out there. It's been just such a huge tool for us to grow our organization and also even our customer base. We use a lot of the other standards. We use Slack. We use all the Google services. And those are really the main ones that power Remote Year.

Maren Kate
Okay, cool, and last question for founders listening who are somewhere between the 5 and 50-person stage, what's the best piece of advice you've either received or can give when you were going through that stage at Remote Year?

Sam Pessin
I would just say always preserve your grit and your perseverance. It is the most important thing and there are always times that are going to seem like a doomsday scenario or just an insurmountable challenge or mountain that you have to climb and there's always a way to do it. There really is. I think that's one of the biggest lessons I've learned in the last four years is that there have been times where I just wasn't sure if that was the case or not and as long as you just stay focused and keep your head down and work with the amazing people around you there's always a way to not only get through something but to probably make it a huge win for your company and for your team. I think it's just a mindset thing that is often really hard and I'm not even perfect at always having it but I think it's a true statement. If you are nimble and smart and dedicated there's always a way out of anything.

Maren Kate
I like that and I think that actually ties to one of my favorite books that I've read in the last few years, which is Grit by Angela Duckworth. I've read that a few times and it's just a good reminder actually. Awesome. Sam, this has been so great. How can people find you and Remote Year online?

Sam Pessin
Yeah, so our website is just remoteyear.com and so that's the best way to learn more about Remote Year and if they want to reach out directly to me my email is just sam@remoteyear.com.

Maren Kate
Awesome, really appreciate it. This podcast has been brought to you by Avra Talent, a firm dedicated to helping startups grow their teams from 5 to 50 and beyond. To learn how Avra can help your company, schedule a free consultation at avratalent.com. That's A-V-R-A Talent dot com.