Paul Rees

Cohort 2013, MCDM
Cash App, Creative & Content Strategy Lead

Please share a bit about your role and what a typical week looks like at your job?

 As the Creative and Content Strategy Lead, I set the direction for how our performance ads and website engage our target audience and drive business goals. I’m also heavily involved in the creative and content reporting process, feeding insights and learnings back to our production teams that we use to optimize performance.  

A typical week doesn’t really exist for me, but my top priorities this week include: finalizing a paid social creative brief that is targeting a new audience segment; presenting creative performance findings to a cross-functional team, and leading a discussion on what’s working—and what’s not; review and provide feedback on a new webpage promoting a new product; and dig into customer reviews and keyword data to plan next month’s editorial roadmap.

I love that my role allows me to zoom into the execution details one day, and then step back the next to think about how it all ladders up to our business goals the next.

When it comes to best practices and distributed teams, what are some standout behaviors you’ve seen succeed?

Asynchronous collaboration is definitely one of those buzzwords you hear a lot when working remotely, but it can be a huge factor in a team’s success when done right. It’s basically a team’s ability to work collaboratively (e.g. discuss, share, and respond to feedback, make decisions) without having to be in the same meeting. There are endless tools available to facilitate this style of working, but whether or not it is effective comes down to the rituals and structure your team puts into place.

We’ve started using Gemini for note-taking in almost every meeting, and it’s been a huge help. It documents the conversation clearly, which is great for people who couldn’t attend—and it’s just as useful when you need a refresher weeks later. We also rely heavily on comments to discuss work and keep context visible. This allows team members in different time zones to pick up work when one time zone signs off, and the open discussion means everyone can see the full context. I’ve personally learned a lot about why decisions were made by reading through comment threads from years ago.

What is something that most people get wrong about distributed teams? 

A lot of people assume remote work automatically means better work-life balance. While that can be true—my lack of commute means I have more time to get ready in the morning or can squeeze in a haircut on a weekday—the increased flexibility without structure can backfire. It’s easy to fall into the trap of always being “on,” especially when your laptop is just a room away. Setting and protecting your boundaries is essential.

Distributed teams often connect on computer-mediated platforms. What are some of your favorite hacks to personalize the screen? 

I keep my camera on for most meetings, whether it’s a 1:1 or a larger group. Some people are more comfortable with cameras off, which is fine—but I think the nonverbal cues and connection that video facilitates is important for people getting to know you.

Also, be intentional with your background. You don’t need the perfectly styled bookshelf, but something personal—a guitar, a piece of art you love—can spark real conversation and help build a connection with your coworkers between talking about work.

Finally, any last pieces of advice for people joining distributed teams for the first time? 

Onboarding remotely feels strange at first, especially if you’re used to onboarding in person. You’ll be excited, your desk will be set up, you’ll have a few intro calls… and then there will be long stretches where it’s just you, reading and absorbing context, wondering if you’re doing what you’re supposed to be doing. Or at least that’s how it was for me. I’d recommend using that quiet time to dig in and soak up as much context as you can from company wikis, old docs, Slack threads, etc. But also be open with your manager to make sure you both have the same expectations about those early days and weeks. If you feel like you’re not getting what you need, make sure to voice that.