A new month means another Meet the Team feature! We sat down with Ritesh Chopra, our newest Content Specialist — a self-made content creator who turned freelancing into a full-time agency career. We're talking Winnipeg food finds, the sport that has his whole heart, and his journey into content creation.
How long have you been at the agency?
Just under 2 months.
So after about two months in, what's surprised you most about agency life so far?
One thing I've found interesting is how much overlap there is between agency and freelance work. I initially expected certain dynamics to fade at higher levels, but they're really just part of the craft at every stage. The communication style at an agency is more polished, but the core work is familiar — collaborating through rounds of feedback, paying close attention to the details that matter, and helping clients see the thinking and intention behind the work.
This is your first agency role — what drew you to Show and Tell?
To be honest, I was already in the field and always wanted to work for an agency. When I came across this position, I did some research on Show and Tell and was really surprised by their work. Looking at their website, I was impressed by the client work they had done for the University of Manitoba, University of Winnipeg, and other big organizations. I also came across the marketing for a bagel shop that had recently opened in Winnipeg, and I really liked it. When I found out Show and Tell was the agency behind it, that made me super excited about applying.
Tell us a bit about your role here at Show and Tell.
I'm a Content Specialist, so I help our clients with their content. My role includes video editing, copywriting, and content writing. I also work on our internal social channels, where I handle everything from writing and shooting content to video editing.
As a Content Specialist, you work across a range of areas — is there one you naturally gravitate toward?
Hmm... content writing and planning, I think! That's something that really attracts me. It’s above anything else for me.
Your bio describes you as analytical, creative, and people-focused — how do those actually show up in your work?
Analytically, you have to analyze the work inside and out whether it's a client project or an internal campaign you're working on. The more information you have about a project, the better the result. And then I'm really critical towards myself. I try to do everything with perfection. I'm not saying I'm a perfectionist, but I try to be! I keep working on something until I feel like it is exactly the way I want it. Sometimes that's hard because it takes a lot of time, but when you're happy with the results, I think that makes up for it.
In terms of creativity, when I shot content for our own socials, that was when I really got to put my creative skills to work. When it's for a client, you have to stay within the boundaries they've provided, and it can be hard to push those. So when I'm working on internal content for the agency, that's when I feel like I can really spread my thinking and creativity.
And being people-focused, even with your internal team, it’s very important to have clear communication and move together rather than working alone. If different experts work on the same project, the efficiency is so much better. You can't be good at everything, right? Especially with creativity, you need different minds on it. If you're the only one handling it, there will be a point where you get stuck and it starts going downhill. And in those moments when your creativity is struggling, it's very important to have people around you with amazing minds.
You studied Arts at the University of Manitoba rather than marketing — how did you build your content and social media skills?
I was always inclined towards marketing, so I ended up taking it as my minor. But that had nothing to do with my content writing or anything. I think that came naturally. I started writing scripts for a friend who was doing freelance work, and that sparked it. That’s when I started my own freelancing in Winnipeg, and day by day my confidence continued to grow.
Before Show and Tell you did freelance content work — what did that look like?
It's still going actually, I still do it on the side! I started by writing scripts for my friend in Vancouver, and then last year I started my own freelance work in Winnipeg. My first client was a dessert café, and through that work I got another restaurant. Then as I kept working, I started getting opportunities with more businesses and individuals.That's how I got started!
What would you say to someone who thinks they need a marketing degree to work in this industry?
That's not true at all! It's not necessary. Obviously it's helpful because they teach you the basics, but the industry is pretty different from what they teach in universities. For someone who wants to learn marketing, doing short-term courses in digital marketing or video editing really helps. But a full degree in marketing? I'm not sure if that helps as much.
What’s been an ad campaign or piece of content in recent years that really stood out to you, and why?
Hmm... honestly, the one I keep coming back to is the campaign for a bagel shop that opened in Winnipeg, run by Show and Tell! That was one of the highlights for me from last year. The way they spread their presence all over the city through socials, print ads, and billboards was amazing. And they are still selling out their bagels! I was really paying attention to their marketing when it was happening because I was working in the field. I remember thinking, I really like this work, I don't know who did this — and then when I found out it was Show and Tell, I was very impressed.
You're known for tracking down good food spots — what are your top Winnipeg recommendations?
Oh, that's hard! There are so many good restaurants in Winnipeg and I haven't even tried all of them. You think you've tried enough and then you look on Maps and there's still so many you haven't been to! But from what I've tried, I recently really loved Parcel Pizza — it's really close to our office. And then there's Naan Culture on Corydon. For dessert, I'd say Chaeban for ice cream. That was one of the first ice cream places I tried when I came to Canada and I was a fan right away.
What's been your best trip so far, and where are you hoping to go next?
My best trip so far was to BC with my friends. We travelled to Victoria and a place called Sooke, just near Victoria. We had an Airbnb and explored the area. Tofino was also one of the best places I've been! As for next, I really want to go to Europe. Czech Republic, Italy, and Switzerland. Those three places!
You're a big cricket fan — what would you tell someone who has never watched a match?
It's a huge sport where I come from, back in India. When you see the atmosphere at a high stakes cricket match, it's crazy. The crowd is crazy, the people watching from home are going crazy. I just love the atmosphere. When everyone sits together to watch a match, it's really fun!
Your bio says you're convinced you're a decent singer. Your friends have not confirmed this. If you had to audition for The Voice tomorrow, what would your song be?
*Terrified* Never! Never going to happen — it's only me who thinks of myself as a singer, so I'd like to keep it that way.
Follow up: What about a song you sing in private?
It's mostly Hindi or Punjabi songs. But recently I've been listening to Drake's new album, that was really cool. But nothing I can sing.
Editor’s Note: We may need to set up a team karaoke night to put this to the test.
What advice would you give to someone new at the agency?
I'm probably not the best person to ask since it's only been a couple of months! But I think you just get used to it. I'm still getting used to it myself. You have to give yourself time — you will get used to the environment and the working style.
Any last words?
I think you got pretty much everything from me! There's nothing to hide.
Editor's Note: For the readers — Ritesh recommends the TV mini-series The Spy for your next watch.
Now you know a little more about Ritesh! Stay tuned for the next Meet the Team.