Being COVID-Unemployed with Rich Surprise

Rich Surprise, now Director of Global Sales Development at Cloudbeds, shares his experience navigating the sales landscape in the era of Covid and layoffs.
Listen on Apple Podcasts
Listen on Google Podcasts
Listen on Spotify

or add our feed URL to your podcast app of choice!

Show notes

One of Rich Surprise’s earlier memories is standing in line, at the height of Communism, hoping there would be a loaf of bread waiting for him when his family got to the front.

After living in places like Senegal and Moscow thanks to a father who worked for the US State Department, he attended Virginia Tech, found a passion for cooking and hospitality, then pursued sales, and eventually landed a few other positions at some big-name companies.

And then COVID happened. Layoffs happened. Perspectives changed.

Rich, now the Director of Global Sales Development at Cloudbeds shares his journey, as well as changes he’s seen in sales since then, with RevOps Therapist and founder and CEO of Greaser Consulting, Jordan Greaser.

Jordan  00:00

Hi, everyone, this is Jordan, the owner and CEO of Greaser Consulting. On today’s episode, we have Rich. I’ve known him for a few years now. And he’s one of those guys, who was, as he put it, COVID-unemployed for the better part of a year. And so on this episode, you’re gonna hear, you know, just… and some of you might be to relate to this, like, really talented guy with a fantastic resume, has done great work in the past, just was on the wrong side of a layoff. And so, what went into that? What was his mindspace on that? How did he work through it? And how has that affected the way that he manages and works with people today? You know, I’ve enjoyed all the podcasts that I’ve been doing. I’ve enjoyed all the conversations. This is one of those ones, though, that I’m definitely going to remember and encourage you to lean in and enjoy.

Intro Jingle

Say you want some clarity in sales and marketing and SEP? Well, we have just the remedy: our podcast, RevOps Therapy. Yeah.

Jordan  01:14

Hi, everyone, this is Jordan. I’ve got Rich with me today. Rich, why don’t you go ahead and introduce yourself?

Rich  01:20

Hey, everybody, this is Rich Surprise. I am Sales Development Director here at Cloudbeds.

Jordan  01:31

So let’s talk about Cloudbeds. Rich. You know, I first met you, you know, years ago, and you were at Thomson… Thomson Reuters. They’re a massive company, like you’re, you’re slinging Outreach; you’re working for the marketing department. And then you know, I haven’t been in contact with you for a few years; I get a hold of you. And I’m not saying Cloudbeds isn’t the big time; it obviously is, but it’s clearly a very different company with a very different size. So you know, talk to me a little bit about how you got to where you got to.

Rich  02:06

Yeah, okay, so, so how and why am I here at Cloudbeds? Boy, where to start there? Well, I typically tell this story, because I get this question a lot through the recruiting process with candidates, and I think it resonates with them, at least they tell me it resonates with them. I always explain back… early life, right father was State Department. So we had the benefit of you know, traveling abroad when I was young, which isn’t necessarily, I guess, the norm, at least here in the States, right? It’s a pretty unique opportunity. So born overseas, started, I lived in Senegal; lived in Moscow, started school in Moscow and got to experience these different cultures and ways of life that it just really struck me especially when we moved eventually to the States, you know, standing in line during communism, trying to get fresh bread and fresh meat and not necessarily knowing if you’re going to get these items when you get to the end of this extremely long line. And we had it pretty well with, within the State Department. But those experiences sort of stuck with me, especially when you come to the States; you don’t necessarily have to wait in any significant lines, at least many don’t to kind of just get The Essentials. So that kind of stuck with me just the traveling and cultures from abroad, eventually got, started school in Virginia, went to Virginia Tech, didn’t want to go into the consulting world which a lot of my friends were doing at the time: Deloitte, PWC, that sort of thing. So got into cooking, studying to be a chef for like three years, helped two buddies open up restaurants…

Jordan  03:51

So far, this is nice and linear. This is a really linear story so far.

Rich  03:56

Pivoting around, yeah. I got into, like, hospitality, dealing with entrepreneurs and building businesses, which really kind of, kind of fed my soul in a way but then realized I didn’t want to be doing cooking for you know, nine bucks an hour in New York City just couldn’t, couldn’t survive like that and decided to pivot into sales. So got into sales, eventually, recruiting for four and a half years, got into Oracle doing sales development, which was an incredible, almost eight years as a sales development rep, moved into first-line leadership about 12 months after that, second-line leader, third-line leader, all within sales organization, eventually pivoted over to Thomson Reuters where it was the same role of director of sales development, but within marketing, which was an intentional decision because Oracle was very sales-driven at the time and Thomson Reuters being a very marketing-heavy organization at least with where sales development was; it was a great opportunity to sort of expand my knowledge. I then made an intentional decision to go to a company called Naviga, which was a software sales for newspapers, magazines, even like financial services, great opportunity, great boss, great culture, but it was terrible timing because of the pandemic. And we were just absolutely slaughtered by the pandemic. And the entire go-to-market team essentially was let go very out of the blue. So COVID-unemployed for about a year. And then a good friend, former colleague at Oracle referred me over to Cloudbeds. And it was probably the greatest professional, maybe even personal decision I’ve made in my, my life; it’s been an incredible experience. Because I wanted to make sure one, I believed and trusted the leaders that I was working for, especially my direct boss, wanted to make sure the product was something that, you know, there was growth. I could, I could see the success of this in one, two, five years and further, believed in the product. And then it also helped that it sort of touched on things that were important to me, which I touched on earlier: the travel aspects, not many people hate travel, but it was it was fun to be a part of; hospitality, something I’m passionate about helping small businesses. And then the cultural aspect. Cloudbeds has been a virtual job since, since day one, you know, when it was formed in 2012. So going virtual was, was new for me, but it wasn’t new for Cloudbeds. And seeing what they’ve been able to build in those, in those, what, almost 10 years now. It’s truly amazing. And being able to have managers and sales development reps and colleagues around the world and being able to see their, their lives and their, their holidays and their… the foods they’re eating and where they’re traveling is something I never really got to experience at any other job before. So very long-winded answer. I don’t know if that necessarily touched on your question. But that’s my story.

Jordan  07:24

Well, there’s, there’s so much to unpack there. And it’s not I mean, it’s not every day that I can talk to somebody that can say, “Hey, I stood in the food line seeing if they even had, you know, did you have bread today?” Right? You know, did the state-directed economics adequately say how many loaves of bread should or should not be baked today, right? That, that is not something I expected to hear. What, you said your dad worked for the State Department, what did he do?

Rich  07:55

He was in communications. So what exactly does that mean? I don’t know. I know he was going around setting up various US embassies with their phone systems and just communications within… 

Jordan  08:09

Tapping a couple of phone lines and, you know, just…

Rich  08:13

Probably some spy work going in there too, but he’s still alive… something Jane Fonda-esque.

Jordan  08:20

So he made it. Okay. This is the thing that I think a lot of people can probably resonate right now with, like, having lived through the pandemic. There’s quite a few folks that as you said, were COVID-unemployed. And listen, you’ve got a unique story, right? Like you, you went to New York City; you, you were cooking; you, you’ve been at Oracle for years. I mean, you’ve led teams. I mean, obviously very talented, skilled individual, and yet you know, you’re, you’re in the bread line and you find out there’s no bread, right? Like you spent a year, as you said, COVID-unemployed; how’s that, how’d that… like, did that mess with you at all? Are you, like you were good with like, I don’t know if I want to say good with it? But I mean, what goes through your mind there in that year?

Rich  09:13

Such a wide range of emotions, but it was definitely, out of the gate, a negative experience, right? Anytime you hear your boss call and, you know, break the news to you, which he was definitely heartbroken by the decision. It’s tough, right? And that sort of not quite depression, but it just brings you down and you sort of question yourself, even though it wasn’t anything directly related to your efforts, right? It was completely unintentional. So the first probably month was like, “What am I gonna do, right?” Yeah, I guess the first week was like, okay, you know, go golf and try and enjoy like the time off, and then then it turned into “Okay, what am I going to actually do? How am I going to pay bills?” It’s a tough one. And then you get kind of bored, or at least I was getting bored with like, going golfing is great, but I can’t do that seven days a week; it gets kind of expensive. And I have these bills to pay. So I was thinking, “What can I do to kind of just keep my mind fresh?” And like many in the world, I turned to day-trading, just to learn a new hobby; before it was just like managing 401k and just how to move towards retirement. But in day-trading, I was learning a new skill, more than a hobby, and setting yourself up for success, reading books, talking to a lot of new, new individuals, learning finances, learning the stock market, how, how all that works, and it was eye-opening. Especially… we could go down a whole rabbit hole with like the meme stock craze with Gamestop and everything. But there’s plenty of documentaries on…

Jordan  10:59

Were you one of the Redditers? Is that what you’re trying to tell me?

Rich  11:04

Followed it. Didn’t trade on it. I couldn’t do it. My risk tolerance is… I couldn’t deal with that now, but it was, it was wild to see.

Jordan  11:14

Is there anything from that experience with day-trading that like, like, are you still day-trading on the side? Is that something you’ve carried with you? Or was… it was like a pandemic thing that came and went?

Rich  11:27

Yeah, I mean, I would do… in the future, maybe look into it a little bit more. But it truly is a full-time career. I guess you could theoretically, you know, start trading at the open and, you know, pray, hope for the best. But you got to be locked, locked into these charts. And things can change in a millisecond. And what you felt was a good trade and a good position, all of a sudden flips on you. And if you’re in an hour meeting or 10-minute meeting, you can go from positive to negative very quickly.

Jordan  12:04

So when you were talking about spending a year in this unemployment, were you also like floating resumes the whole time? Or did you just hit, like hit a groove… and I’m really focusing on as well, and like the last little bit of this, like, were you trying but failing? Or like, you got into a groove, and then you got a referral into somebody? And then that was it; that seasonal life was over?

Rich  12:30

Yeah, so for the first probably two months, I was sending resumes around very actively. And it was the same sort of story, then it turned into kind of a networking game. Which, I gotta admit, I mean, I’m astounded by the number of, number of executives in the sales development, sales and C-suite beyond that are willing to talk to you because of the circumstances because they care; they’re concerned, and they’re willing to coach and give guidance. And I guess it’s sad to say, I’m shocked by how many are willing, were willing to talk. But they all said the same thing. It’s just like, there’s nothing available now. Like they all painted a pretty bleak picture about not necessarily me getting a job, but just me getting a job in the next six months. So it was until January of last year, when there was a little bit more access to vaccines, that’s when conversations really started happening, which is kind of crazy in itself, but started getting some more conversations where I would actually have to have relocated, which would have been tough because I’ve got two kids here, and they wouldn’t have been able to bring them along. So ideally, I was looking for a virtual job. And then one day just got a call from my old buddy at Oracle who had mentioned like “hey, you may want to check this company out.” One thing leads to another, seven interviews later, was able to, to land the gig but yeah, it was definitely more of like a… it started out as a “What am I going to do? Okay, I’m just going to apply apply apply.” Six months of just sort of like “Alright, when is this gonna… When’s this pandemic actually going to end?” And then finally, light… light appeared. I couldn’t have been happier. The experience was awful, but it was also a blessing in disguise.

Jordan  14:35

Could you… do you got like one or two ways through the course of that thing that you can say “wow, this is how it changed me for the good”?

Rich  14:45

Yeah. Honestly, I guess I was able to really look at what I wanted in life. It allowed me to prioritize those, those things. So at one point in time, I’d probably say, money was up there as a direct influencer on how I lived my, picked my jobs, right? And don’t get me wrong, it’s still very important, but I don’t make decisions based on…

Jordan  15:18

It’s good to be able to buy bread, right?

Rich  15:22

Yeah, exactly. And then just being able to prioritize my, my kids, my family; you know, I wanted to be able to take my son to soccer and take my daughter to riding and volleyball and not have to, like, run to an office and be able to have to prioritize a trip over their, their lives, which sad to say, for many years was not a choice. It was just sort of like, you, you had to do it if you wanted to put bread on the table. So I was able to put what I feel are the right priorities in order, by… in my terms not being forced to make that decision.

Jordan  16:06

So this isn’t really like a… this next question isn’t really a commentary on like, Cloudbeds because it sounds like it’s fantastic. And I’ll ask you a couple questions there. But like having lived through a scenario where, you know, your go-to-market team, I think you said was Naviga that has all the talent in the world or high-quality people… in the one day you’re working, and the next day, it’s just gone. Poof. Like, yeah, is there? Is there any part of that, it still kind of lives in the back of your brain? Like even though you love where you’re at? Like it’s, is there any fear that still exists? Or like that was a season of life, it’s over, you don’t think about it?

Rich  16:44

No, it absolutely exists. And even through my interview process, when I got the offer that my boss sort of referenced that, like that you could tell something in, within me, in a previous job, previous life kind of formed me to who I am today and how I’m approaching this job. It absolutely has; it’s sort of, it’s always there, right? It’s not necessarily changing, like my decisions, but it’s always like, “oh, man, I’ve been out of a job. I know how it feels, and I never want to be there again.” So in a way, I’m always doing my very best to just bust my ass and get the job done and impress those around me. And it does sort of eat away when you fall short on a report or a quarter or a week’s progress, right? It’s something that always eats away at you, but you want to use it to motivate and propel you versus sort of dwell on experiences like that.

Jordan  17:56

The thing that’s just, I think, interesting about either the last couple of years, as I’m sure you’ve heard this term, people talk about a shared experience. Like, we all lived through this together so we have this common bond. But at least in the conversations I’ve had, when it’s come to, you know, the whole COVID thing and together, like, man, it has not been a shared experience. And what I mean by this is like, could you imagine if you’re a Zoom AE during the pandemic, like, like, you’d have been maxing out that comp plan, you know what I’m saying, like, like, well, “I just got my yacht; I’m ready to roll.” And, you know, I don’t know how that how that all actually worked out. I’m just sort of projecting, right? And then, you know, there’s another individual and like, man, you’re doing great work, but the industry that you’re in like, like, you know, talk about the airlines, like, “you’re not flying; I’m sorry, you’re not going to fly.” Like… it’s not like your business model’s broken. It’s not like you have a product, but the situation has changed, and you can’t do anything about it. You’re not, you’re not any better or worse than that Zoom rep so to speak, but you’re making tons of money, and the other one’s not making anything. So I just, I think it’s hard right now, when you like, when you talk to people about this quote-unquote shared experience, because like, I’m telling you, your experience is not mine. Right? It’s just, it’s different, right?

Rich  19:21

Yeah, you can’t make any assumptions about whether it’s a pandemic or any event in life. You can’t make assumptions about what somebody is going through. And that’s another thing in just managing it today, right? Where mental health like three years ago was maybe a thing, but it wasn’t managed and there weren’t tools necessarily available to you as readily as they are today and many, many organizations, Cloudbeds included, offers some amazing tools to manage that. And as a manager, you need to have… I’ve found my coaching conversations are very different today than, than previous, previous years. Literally people, like, are, if they’re having a tough week, a tough month, a tough quarter making phone calls. And they just can’t get there because some blocker, some blocker, maybe it’s related to stress from, from the pandemic, that has come up more frequently now than I’ve ever experienced before. And those, those moments can be positive and negative, whether you’re planning for a wedding, a positive, and the stressors that come along with that, or you’re, you’re struggling and you’re maybe on a PIP and you don’t know how to get to that, how to get to success, because you’ve had this incredible life experience with stress from the pandemic. And now you got this stress and trying to perform. Everybody is, man, it’s affected everybody differently. And you have to, or I found that I need to acknowledge that and talk through those moments in, with a different type of gloves. I don’t know if that necessarily makes sense or not. But…

Jordan  21:14

So let’s let’s dive into that specific piece, though. Because I think there’s awareness now that like people were… I think people knew that before that folks are struggling. But now that, like, the whole world was shook, you can’t deny it. Okay. Yeah. But as a manager, this is one of the things as I talk with people, like they’re struggling trying to find that line of, like, when do you support and when do you push? And let me explain what I mean; at the end of the day, like traumatic events are going to happen in people’s lives, like maybe it’s a divorce, okay, maybe it’s, maybe it’s an illness, right? Like not just COVID. But there’s illness, maybe, maybe there’s something that’s out of your control, but it’s like coming against you. The point is, like, life is happening to everybody all around us. But on the other side, like there’s a business that has to run; there’s targets we need to hit. And so like, how do you navigate that line now, as a leader who’s like, you know, you’ve talked about coming from Oracle and sales focus and whatever, like you’ve been in environments where like, the line is the line; hit it or get out, right? And now like, even you’ve lived through an environment of like, for a year, is this my fault? Probably not. But like, I can’t get a job. And but like, life’s happening to me; the stress is real. Where’s that line at now, as you talk to people, and they’re bringing to you like, “I have anxiety”? Is it like, “Okay, you still need to get, you know, still need to hit your number,” right? Like, “I have anxiety right now.” “Well go on a vacation, like, see if you can?” And I’m not trying to oversimplify, but I’m simply saying, how do you, how do you navigate that with some of the awareness that you have today?

Rich  22:52

Yeah, I mean, for myself, when I’m having direct conversations, my managers are having conversations, I’m coaching them, it’s, it’s, you have to unpack every, every… not problem, but every issue in its, on its own. One person is going to be completely different than the next person. And at the end of the day, you have to explain what, what we’re here to do. And that is, yes, we’re here to reach goals, over-achieve goals. But, again, if somebody’s going through a divorce, it’s super important to me, having gone through one and knowing those emotions that you need to talk to them, care for them, and make sure that you’re supporting them both in their professional, and as much as you can, personal, personal endeavors, I guess. But you got to unpack it as much as you can, in order to, as a team one-on-one, find out what that right solution is. Is it a day off? Is it an hour away from the office? Is it the ability to go for a drive over the lunch hour? Like what does it take for you to get over these mental blockers or these not mental blockers, but actual, like real barriers? What do we need to do to try to move these or remove them entirely so that we can all get to our goals, because at the end of the day, they’re not happy. They’re not hitting goals, and then you throw on top of the personal things that are also bringing them down. If you can help with one of those, might not be working through a divorce, but it might be “okay, let’s work on getting you to today’s goals. How many dials did you make? How many demos that you set up? How many conversations did you have? And then let’s set a goal for the week.” So it’s not exactly mind-blowing stuff, but it’s actually just showing that you care and being able to… generally, people appreciate that and appreciate the, the willingness for you as a human to try and help them, and once they, they understand that generally, they reciprocate and flip their sort of mental state on its head and they usually are able to perform.

Jordan  25:17

I’m just listening to you sort of like work through this. And I just think there’s so much that’s happened over the last few years that, previously, if things aren’t going well, I’m not saying managers didn’t care. I don’t, I don’t think that’s, like, the right standpoint. But there’s, it’s like, this whole experience has been a forcing function, though, that like conversations that maybe you wanted to have, but you’re like, “well, this is work; let’s not cross that line.” And maybe this is even a result of all the virtual that, like, I can see into your home; you can see into my home, right? That there’s something there. It’s like, you’re allowed to talk about more all of a sudden; it’s even expected. You know, if I’m a rep, and I’m sure, I’m sure this isn’t always the case, but it seems like reps, in general, will feel more comfortable now to come up and say, “Listen, like, I know at work, I’m not quite missing it, hitting it. And I’m not trying to make an excuse, but I’m struggling even personally right now. Like, can you help me?” It, it doesn’t seem like it has the same sort of faux pas if that’s the right phrase to use, right? Yeah. What a time to be alive. Right?

Rich  26:36

Yeah, it’s wild. And just having gone through… I mean, I think everybody experienced the pandemic in the same, maybe not the same way. But they, they all had some sort of reaction to it, most negative. And I think that has allowed us to have those conversations about well-being, mental state, in a much more fluid manner than, than we’ve ever, ever had to before we even had that connector. And now in a very weird way, we’ve got that connection, and it’s allowed for conversations that may not have happened in the past or just been ignored. Right or wrong.

Jordan  27:22

So Rich, we’ll ask you one, one Cloudbeds question. I know we’re coming up on time. But yeah. Hey, now you’re in Cloudbeds. Are you? Are you like, are you? You were reporting to sales? Then you reported the marketing? Are you an SDR leader, right? Is that the case? Like that’s your vein? Are you in sales? Are you in marketing?

Rich  27:43

I’m in sales.

Jordan  27:45

Tell me the truth. What’s better: sales development in sales? Or sales development in marketing? Which side of the house does it live on?

Rich  27:51

Sales. I would go sales; it’s great to understand if you are able to connect with a company where it rolls under marketing to understand that, and by no means do I, am I an expert, but it was great to live and breathe that for a couple years. But having lived in both, I would have to say it falls more, more so in sales.

Jordan  28:13

Tell me… Give me one or two reasons.

Rich  28:19

Honestly, I’ve had better… the ability to convert at a higher rate by having the direct relationship with the sales reps. And being able to connect, partner with marketing versus the other way around. Where the relationship with marketing, when it was rolling into marketing, was there, was strong, but it was almost like sales didn’t trust the SDR or the sales development team. Because there’s still that inner workings of like, I don’t trust you, marketing. I don’t trust you, sales. But you’re trying to break down those barriers. I’ve found that it was more… what’s the right way to put it? I had more success breaking down those barriers under the sales umbrella and partnering with marketing versus the flip side.

Jordan  29:09

So what I’m hearing you saying is that the tribe, so to speak, of sales is more accepting of their own and marketing is more accepting of others. That’s the… right there. Yeah, okay. Hey, Rich, I appreciate you, you coming by. And I know we talked about some personal things in your life. So thanks for being willing to share it. And for the listeners today, thanks for tuning in and hearing a little bit about Rich and you know, we’d always be interested to hear what’s going on in your world. So feel free to reach out I think to either one of us. We’d be happy to chat but… Rich, thanks for stopping by.

Rich  29:46

Anytime Jordan. All the best.

Jordan  29:47

Alright, see ya.


Hot dog. That was a great episode. Thanks for listening. If you want to learn more about Greaser Consulting or any information you heard on today’s episode, visit us online at Be sure to click the Follow button and the bell icon to be notified on the latest here at RevOps Therapy. Thanks and see you real soon.

Share with your network