Greg Caplan (left) was an advocate for remote work before it was cool – or an essential public health measure. In 2015, he co-founded Remote Year, a work-abroad program that fused the adventure of international travel with the professional community found often, but not exclusively, in an office. 

For years, he and the Remote Year team helped program participants negotiate out-of-office stints with their managers. They cultivated a culture of creativity and hard work within their programs; in fact, several Remote Year participants got promoted while abroad. 

Remote work is the future, Caplan told everyone who asked. Not everyone believed him. Offices were the norm.

Then the coronavirus pandemic hit. 

Abruptly, every company that could pivoted to remote work. At the same time, a complex mesh of global travel restrictions emerged, and Remote Year had to suspend operations. 

Caplan was vindicated. He also needed a job.

He landed at Chicago-based Cameo, where he’s been interim CMO since May. The platform — which allows fans to buy short, personalized video shout outs from celebrities — has been booming since the pandemic began. From March to May, Cameo bookings grew 1,000%, Inc. reported. 

Celebrities, including A-listers like Tiffany Haddish, swarmed the platform, seeking extra income in lockdown. Civilians, meanwhile, have bought Cameos to apologize to each other, break up with each other, or simply to give each other as gifts. 

That means Cameo, already a 2020 winner, is well-positioned to win the 2020 holiday season, too. 

We chatted with Caplan about Cameo’s holiday strategy, its “natural growth loops,” and the future of remote work. 

Greg Caplan on his Interim CMO role at Cameo

MARKETERHIRE: What drew you to Cameo’s interim CMO role? Do you see parallels between this role and your CEO role at Remote Year?

GREG CAPLAN: Well, I met the founder of Cameo, Steven [Galanis], because he wanted to come on Remote Year. I spent a long time trying to get him permission from his former employer. When they wouldn’t let him go, he quit and started Cameo. We built a relationship through that experience, and when Remote Year paused operations, I reached out to him. Cameo was just exploding through COVID, and I started helping out. That evolved into jumping in the interim seat to head up the marketing function.

Thinking about the growth and the marketing at Cameo is really neat. We have people who have a lot of influence and followers on the platform as the supply, and they frequently tell their fans to come and book them on Cameo, which is a huge growth loop for us. When people buy a Cameo, they're also buying it to share, so that's another great growth loop. These two embedded, natural growth loops help fuel the business, and I’m always trying to think about how we can optimize those two loops, and how we can add fuel on the fire through a more traditional paid marketing strategy.

Are there any marketing efforts you’ve led since you started at Cameo that you’re particularly proud of? 

We've learned a lot about what compels celebrities to share their Cameo profiles. Charity and giving back is one of the main ones. So we’ve created more opportunities for celebrities to donate their Cameo earnings, in partnership with different charities. That's been an incredible accelerant for us. We've raised millions of dollars in the last few months for different causes, like Rock the Vote and the NAACP. 

Financially speaking, the charities get a cut of the Cameo proceeds in some of our partnerships; in others, all the proceeds go to charity, but they're for more constrained periods of time. Those generate a lot of awareness and traffic, so even though we don't make money directly, it's still valuable.

I heard that in July, Cameo soft-launched promotional Cameos, which business owners can use in advertising efforts. This struck me as really innovative — can you tell me a bit about how it’s performing, and your vision for it? 

Yeah — it’s very cool to see businesses use Cameos creatively. We’ve seen B2B businesses use Cameos to support the lead process in enterprise sales. We’ve seen people booking Cameos for Facebook ads and TV commercials. On the supply side, an ever-increasing component of the celebrities on the platform have business pricing. It’s usually a little bit more expensive; celebrities usually set a consumer price, and a higher price for a business use case. 

Any buyer in particular have a ton of success with a promotional Cameo?

There’s one company, Help Scout, that actually uses Cameos as part of their win-back strategy for lapsed accounts. They have some fun messaging from certain celebrities that makes their email strategy more engaging.

Does Cameo ever buy promotional Cameos to promote… itself?

All the time. Of course. Drake’s Dad [Dennis Graham] is on Cameo, and we’re doing a campaign right now where we actually have him doing something for us, for an ad. We’re working on a huge holiday campaign right now, and we have tons of celebrities involved in it.

Cool! So promotional Cameos are part of your holiday strategy?

Definitely. We're using promotional Cameos. We’re also using existing Cameos, which we’re cutting and splicing in with permission from the talent on the platform. It's a little bit different for us than it is for other brands buying promotional Cameos. Celebrities benefit when we highlight their Cameo accounts. 

Greg Caplan on remote work

I’m guessing you’re working remotely right now — where are you in the world?

I'm in Chicago. I was actually living in Mexico City for the last couple of years, but during COVID, my wife and I moved back to Chicago. It's been a lot of fun. We actually just had a baby a couple months ago. 

Congratulations! Did starting your role at Cameo remotely teach you anything new about remote work?

One thing I will say is that Zoom fatigue is real. I've been working remotely for almost a decade now, and I have never been in so many Zoom calls as I have in the last few months, now that everyone's working remotely. It’s a lot. I'm sitting on these video calls all day and it's just taxing, mentally and emotionally. 

You do need to build rapport and trust over video sometimes, especially with new people. But I’ve been trying to move as many calls off Zoom as possible, and I’m taking them walking. I just try to be active, try to be outside, get my blood flowing, be mobile, and have a little bit of balance throughout my day.

I try not to wake up first thing in the morning, roll out of bed, get in front of the screen and sit there all day on video calls and then go to sleep. That’s not a way to live.

Speaking of remote work — as the founder of Remote Year, you were an advocate for remote work before the pandemic. Now, basically all non-essential workers work remotely. How do you think that’s changed the conversation? 

I think COVID accelerated existing trends, and I think it pretty meaningfully accelerated the adoption of remote work. We're seeing double digit year-over-year growth in remote work penetration in the marketplace. I think without COVID, it would have taken two or three years to see that kind of growth. 

But for almost a decade before this, I was shouting about how this was an inevitability. It’s just much better. It doesn't make sense to only talk to people who happen to be within a few miles of you. It doesn't make any sense professionally when you're trying to do something that’s actually impactful. Digital communication makes a whole lot more sense, and we're doing that already with texting and emailing and phone calls and video calls — I just think COVID forced all our interactions to be done that way. 

Are people going to go back into office? Absolutely. Will they be co-located with some people? Sure. But a diminishing number of the conversations people have will be with the people in the same building as them. The majority will continue to be with people outside that building. 

When you say remote work is just “much better” than office life — I’m not sure everyone would agree. Anecdotally, I’m hearing from a lot of people feeling burnt out and isolated. Any thoughts on why that might be?

Well, I don't think “remote work” means “work from home without an in-person education childcare system during a pandemic.” People are conflating remote work with a lot of other things that are currently happening that make life more difficult. Hopefully we get to a world where schools can open up again and then restaurants can open up again and coworking spaces can open up and people aren’t forced to stay in their houses all day forever. But I think  the idea that you don't need to be co-located with all the people you're interacting with on a professional level —  that’s here to stay. 

That makes sense. And I imagine once the pandemic ends — whenever that is — some people are going to want to stay remote permanently.  Any advice for people trying to get their managers on board with that? I know you were privy to a lot of these types of conversations at Remote Year.

It’s all about having a very clear business case for what you want, and an explanation as to why it will be beneficial to your company or your role, and mapping out the workflows and comms flows that touch your role. How will they work while you’re remote?

Everyone's just finishing up working remotely, so I don't think it will be so challenging for anyone to make that case for staying remote. It’s not novel anymore. I don't see any manager saying, “Everyone needs to be together all the time.” It'll be more about people being together at certain times for certain reasons. Maybe the team comes together for an intense week once a year. I don’t think many teams will be together every single day, no matter what, locked into their screens, not talking to each other — like we were before. 

But you can't get what you don't ask for.

In my experience, people often felt too intimidated to even start the conversation about going remote. They expected the worst. But when they brought it up, they generally found that their managers were receptive.

Let’s end on a fun question: Who’s the celebrity you’re most excited is on Cameo’s platform?

This is very personal to me, but my wife and I, our song is “Cheerleader” by OMI. When I proposed to her, a pianist was playing that — and then we had our band at our wedding play it. When I joined Cameo, I found out that OMI was on the platform, and right before my wife gave birth to our son Leon, I got a Cameo from OMI wishing her well in the delivery. That was very special to both of us. He sang “Cheerleader” to her, personally. 

This interview has been condensed and edited.