Media Mavens: In Conversation with Shannon Mulligan

Shannon Mulligan is the definition of a multi-hyphenate with a penchant for comedy, expertise as a beer sommelier, and a passion for writing. She has successfully navigated a dynamic career path spanning over 15 years, many of those working in partnership with us at Cleo.

Shannon’s knack for humanizing brands and creating engaging, relatable content has set her apart in the industry, so we sat down with the dynamo to delve into her copywriting journey, the inception of the Freelance Squad, her insights on the intersection of AI and creativity, and more.

CLEO: Shannon! We’ve had the pleasure of knowing and working with you for quite some time, so we know you have a lot of hobbies and interests (comedy, beer sommelier-ing, writing). About that last part, how did you get into copywriting (that thing you’ve been doing for the past 15 years)? 

SM: Technically, my copywriting journey started with the birth of my enormous 11lb son… I was off on maternity leave and applied for the role of copywriter at Ritual. I’d always loved writing and it felt like a dream job to get to do it all day (author’s note: I was, at the time, unfamiliar with how doing something for a living does tend to suck some of the fun out of it). I took a chance on a cover letter that talked a lot about my dad and reality TV, and low and behold, it worked!

On the un-technically side though, I’ve been doing copy for ages… from writing joke-y out-of-offices to trying to craft the perfect message on a team birthday card, having fun with words has always been something I’ve loved. Life is short! Make it funny!

CLEO: You’re all about humanizing brands, which has always been apparent to us in everything you do. From your writing style to the imaginative design of the new Freelance Squad website. Why is this so important to you and the effectiveness of your work? 

SM: I’m such a big believer that we should suck as much joy from life as we can. Even for the biggest, most straight-forward B2B brands, we’re still talking to people at the end of the day, and that’s who I want to market to. 

I love working with brands that really understand that and are willing to take some risks in their copy, design, and marketing—it’s truly the best way to connect with people and stand out in a super competitive crowd. And aside from actually connecting with people, you’re also going to have team members who are happier, more imaginative, and more eager to complete the work and invest time in it, meaning a better end product. Sure, not every blog or web line needs to be funny or thought-provoking, but it still needs to connect on a deeper level.

CLEO: We can imagine how your experiences as a freelance writer led you to founding the amazing Freelance Squad, but we want to know the details. First, how did you come up with the idea? Second, for those who don’t know yet, what is FS exactly? 

SM: Ah, the ol’ elevator pitch! Well, luckily buildings are really tall these days, so hope you’ve got time. 

The Freelance Squad is a collective of talented, vetted freelancers who create whatever marketing need you’ve got. We’ve got copywriters, designers, web designers and builders, PR experts, SEO leads… you get the idea. All of our freelancers are so great at what they do, and I’m so privileged to work with them! Whether our clients have a single need—optimizing their paid ads—or a big ask with lots of parts—launching a new website—we’re there to pulse in and get the job done efficiently, with incredible results and stress-reducing process.

As for how I started things, it truly was almost an accident. I’d been a freelance copywriter for about two years, after being laid off April 2020 while six months pregnant with a toddler now at home full-time until the child care centers reopened (five months… five long, long months). I was exceptionally fortunate to have some former coworkers connect me with a few freelance opportunities, and I really loved it.

Of course, once you’re writing copy for the sausage-making factory though, you’re eventually gonna end up on a how-it’s-made-tour. And I did. I saw two main problems: one, clients inevitably needed more help for things I wasn’t qualified to do, and they hated the LinkedIn/UpWork search, and two, not every freelancer is great at getting new business. 

I’ve always found that last part to be inherently unfair: if you’re talented at what you do, it shouldn’t matter that you suck on a cold call or you hate posting on LinkedIn (spoiler: so does everyone else). And I knew firsthand that clients weren’t loving the search either. So the idea started floating around to merge these two problems and create a solution… in fact, Blair was probably the first non-lives-in-my-house person I mentioned this idea to, and I distinctly remember mentioning that I wasn’t going to start until both my young kids were in school. 

Today, the Freelance Squad is about two years old, and I’m so happy and grateful for our growth. 

My youngest starts JK in September. 

CLEO: Speaking of freelancers, AI is a topic of concern. Not only is it on everyone’s mind, but it seems to be a part of everyone’s business now for efficiency’s sake. As someone who manages a freelance collective and supports/promotes original content creation, what do business owners need to know about using AI?

SM: I wholeheartedly believe there’s a place for AI in creative work; it’s just about finding the right spot for it. It can be amazing when you’re stuck in a rut and need a new line of thinking.

What I really want to spend more time on though, both personally and professionally, is improving my skills on how to use AI. It’s so much more than just asking for rough drafts of blog content, and I think can really open the door for efficiencies in the right hands, as long as the intent isn’t to fully replace, because we’ve all seen those results, and they ain’t great.

CLEO: As someone building a company that supports other companies and creatives, how do you balance growing your own business with providing services to help others?

SM: On every single call with new freelancers, I talk about helping them navigate their own rates. I jokingly re-use the line that it’s because we all want to retire some day, but truly, I think that’s such a valid and fair line. 

I love what I do. I love helping other freelancers earn what they deserve. And I love helping the companies we work with grow and thrive and bring valuable services to their audience. But I also think that we should only be putting so much of our own personal time and energy into our jobs, because there’s so much more out there. That amount of energy is different for every person, and someone who spends a lot of evenings working after my kids go to bed, I don’t yet have the balance I want, so I’m not going here to critique anyone. And hey, some people genuinely like working all the time, and I’m not going to yuck that yum either. 

But I do believe that generally we’re all leaning a little too far into work and I would love to see that pendulum swing a little more towards finding joy and rest wherever we can. Unless you’re on a deadline for me, in which case I would love for you to find that rest perhaps after you send through that document okay? 

CLEO: On that note, how do you keep yourself organized and productive with so many moving parts in your business and everyday life? Do you have any tips, hacks, or tools you can share?

SM: Mostly through Deirdre, our director of operations.

While that’s a serious answer (she’s amazing and wonderful and you should hire her for all your project management needs), this answer is always changing for me. 

I’ll always recommend Notion as an almost-perfect tool that helps us keep our clients, projects, freelancers, and internal tasks streamlined. We’ve even created some templates that I would have absolutely loved as a new freelancer. One thing I find tricky as someone who loves organization but isn’t the best at it is that I’m often changing how I track tasks… one week it’s a checklist, the next it’s a database, the week before it was a pen and paper. Notion ultimately lets me adjust and change how I’m tracking my weekly tasks and still helps me keep on track, because I’m an A-type personality who hates missing deadlines. 

And yes. My inbox is also my to-do list and is out-of-control, but in like, a controlled way, you know?

CLEO: How have you used the online space to grow your own business?

SM: It’s funny, we’ve been around for two years yet it’s only been about eight months since we’ve even had an actual website. We’ve been so fortunate to have a lot of our business come through referrals and word-of-mouth, and that will always be my #1 choice because it truly means our clients are happy with the work they receive.

For the past three months we’ve been experimenting a little with our own SEO strategy though, partly for fun, partly to practice what we preach. What I’ve loved about it is that it’s another avenue for us to just write for fun… yes, we incorporate SEO best practices, but because we’re writing for ourselves, there’s a glorious freedom that comes with it that I think we all generally miss.

CLEO: And a fun one to finish off, what is your favourite way to take a break from work? 

SM: While I’m probably a bit of a workaholic, I also am a believer in carving out time for yourself… which I do every day for lunch as I read Celebitchy or fan fiction and eat bread and cheese. What can I say, it’s a really fast meal to prepare?