Bob Wolfley has worn many hats: Content creator. Social media manager. Brand manager. Senior director of campaign strategy. Director of social and partnerships. Unicorn.

His interest and talents in social emerged early. Wolfley points to the nostalgic days of internet angst for many: MySpace. Writing emo poetry on MySpace notes revealed a passion for creative writing. His passion led him to earning a degree in advertising and launching social media accounts for new chapters of his international fraternity, Phi Delta Theta.

In 2012 while working and traveling for Phi Delta Theta General Headquarters, he launched The Traveling Unicorn, an Instagram account documenting his journeys—but in a unicorn mask. His creative priorities shifted from managing The Traveling Unicorn account to his career when he joined MeUndies. But he’ll always be a unicorn at heart, whether he’s posting or not.

In 2014, Wolfley joined MeUndies as a customer experience specialist where he talked to strangers about their underwear, a catalyst to launching his formal social career. At MeUndies, Wolfley became the company’s first Social Lead, eventually becoming Brand Manager. He was also a director for Ubiquitous, an influencer marketing agency, and Canoo, an electric vehicle startup. He’s currently the Director of Social Media and Partnerships at Flock Freight.

But across all of these career milestones and titles, a common thread emerges when it comes to Wofley’s perspective: disruption as a path to professional and brand evolution.

I spoke with Wolfley to learn more about his career and the importance of disrupting industries to uncover innovative opportunities. We talked about his approach to marketing through award-winning content like the “Define Your Load” campaign with Steve Burns, which earned a Cannes Lion for B2B Creative in the Challenger Brand category in June 2023. Along with campaigns, we discussed making risks on social and his views on innovation, like artificial intelligence.

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What are some of your social media hot takes?

Every generation will have its own social media platform. For my generation, Millennials, the majority of us will be primarily on Instagram. My parents are on Facebook, Gen Z is on TikTok. What’s next? It will come.

What is your favorite Traveling Unicorn moment?

It was the first time I popped up on the Instagram Explore page, the old-school one, where it only showed nine posts. It was my first piece of video content too. The content was absurd and the engagement it started receiving was something I had never seen with anything I had produced before.

I was dumping a bunch of chips and Cheetos into my unicorn mouth and it was kind of like this voyeur-esque pan into the room from the hallway. It’s just this unicorn eating all of these chips and dumping them all over its face. Big mess, but obviously for the content. Shout out to my best friend for filming it and helping me clean up.

I think it was probably one of the first moments that gave me an early signal that I had figured something out and the account could grow.

Another favorite moment was being recognized by people at music festivals. I would have the unicorn head on a big totem at the Electric Daisy Carnival, Ultra Music Festival or other events, and when someone would come up and ask if I was the Traveling Unicorn, it was like, “Oh, wow, I made it. Am I famous?” Obviously not, but it was a cool feeling.

Why is disruption important to you and why is it so relevant today?

Disruption comes from innovation. If we don’t innovate, there’s complacency and stagnation. It’s important to me to find career opportunities with brands that align with my own personal mentality and attitude toward disruption.

I want to ensure those are connected or running parallel with each other because you always have to have a similar balance in social media. If we publish the same kind of content for three, to six, to 12 months, what performed the prior month or quarter might not perform the same today. You have to stay on your toes and continually consider what you can do differently. What are the trends? What are the different formats that we can use to engage community or produce content?

That daily disruption includes the things we can implement to keep getting better and connect more and more with our followers and community.

Your mantra of disruptive innovation is shown in Flock Freight’s recent ‘Define Your Load’ campaign, which features an unlikely nostalgic spokesperson. Why Steve from Blue’s Clues for the campaign?

One element of choosing talent was data on our target audiences. We have two primary segments: shippers and carriers who are ages 30-55. For this campaign we wanted to target the shipper segment and those individuals working in supply chain and logistics positions at brands. At first, we were thinking more of an investigative journalist from Dateline or 20/20.

We tried reaching out to those investigative journalists, but most were under contract with shows—many of which were a little more conservative and didn’t approve of the amount of cursing proposed in our campaign scripts.

But, we couldn’t cut the cursing out. Even with the bleeps, we had to roll with the creative concept because we believed in it so much. With our creative partners, we went back to the drawing board thinking through other investigative-type personalities out there, and Steve from Blue’s Clues was one of those options.

I wasn’t the person that came up with Steve, but when I heard the idea I knew it had legs because we could do so much more on social media. There was more reach and notoriety. And it definitely came through with the results of the campaign, the response and the overall sentiment.

A year prior to the ‘Define Your Load’ campaign, Steve Burns came back into the limelight out of nowhere. I think we all remember that moment. I was even one of those guys who thought Steve Burns died.

For folks who recognized Steve Burns, adding in the cursing element had shock value. There were some people that didn’t recognize him, but when they did, it was the perfect surprise and delight moment for viewers.

Flock Freight’s ‘Truck Stop Talks’ and ‘Humans of Trucking’ provide a glimpse into the lives of professional freight drivers and none of the interviews are scheduled. Can you elaborate on your approach to marketing in a unique way?

Think of Flock Freight like a marketplace. We’re bringing carriers and shippers together with our patented shared truckload technology that rideshares freight on empty truck trailer space. We work with some really cool brands, but we can only do so much in co-marketing with those companies that ship with us. When we go that route, we’re talking a lot about [Flock Freight]: the results the shippers experienced, the partnership and the benefits that our technology unlocks for those shippers.


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But let’s be honest, that’s a lot of ‘us’ talking about ‘us.’ Those case studies are very valuable for Flock Freight, but on social, talking about ourselves all the time doesn’t resonate. In order to differentiate and bring a fresh approach to our social strategy, we did an analysis of all the other players (peers and competitors) in the logistics and supply chain space. Some trucking companies recognize drivers in certain ways, but they don’t do deep storytelling. In this niche, there are online communities like Facebook Groups and sub Reddits where carriers and professional truck drivers talk to each other. While analyzing these, a few themes came out that gave us insight to go this way.

In these online communities, carriers and drivers exchange stories and experiences, good or bad banter and confide with each other about day-to-day challenges and the pros and cons of the profession. Additionally, we learned that for the average person who is not in logistics or transportation, their primary interactions with truck drivers are on the road and their perception is negative because it’s often related to a semi-truck that’s in their way or slowing them down.



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But there’s a human behind that wheel and in the cab of that semi truck. They have a story. They have a family. They have challenges, interests and hobbies most people don’t know about. The whole essence of ‘Truck Stop Talks’ and ‘Humans of Trucking’ is to humanize professional truck drivers, show appreciation for their hardships and experiences—the things they do to keep the entire supply chain moving. Anything and everything that’s in our houses or offices was on a truck at some point.

Those insights showed us we had an opportunity to tell these stories in a fun, yet meaningful way. There’s a mix of tones, which we love because there are opportunities for truck drivers to relate when they find and consume this content.

Even for folks outside of our industry, people can always relate to or find inspiration, education, and value from human stories.

Many B2B brands are concerned about proving the ROI of social. How can social teams and marketing leaders make a case for bigger risks?

There is no silver bullet to getting buy-in for risks—big or small.

It’s all about taking insights and if you lead with insights, you’re already headed in the right direction. Insights are the cornerstone to the foundation for social media strategy and content pillars. For new content or risks, track the early signals, like engagement, but qualitative signals are just as important, too. With a combination of both quantitative and qualitative positive signals, those can give you the permission for similar types of content or tactics.

I believe professionals working at B2B companies often get in their own way, overcomplicate how they market their product or service and think because they’re B2B, they have to be buttoned up and can only go to market a certain way. I saw this simple post from Jacob Shipley on LinkedIn and he captured my thinking perfectly: Social media isn’t B2B or B2C. It’s P2P. At the end of the day, we’re people talking to people. Don’t talk to businesses about a product. Talk to people about their problems.

Jacob Shipley's LinkedIn post that reads,"Social media isn't B2B or B2C. It's P2P. At the end of the day, we're people talking to people. Don't talk to businesses about a product. Talk to people about their problems."

I don’t know who needs to hear this but organic social’s primary role in the funnel is the top–awareness. Will ‘Trucks Stop Talks’ or ‘Humans of Trucking’ convert a new shipper or carrier to work with Flock? That would be awesome, but probably not. However, it allows us to step outside of the “conference room bore core” that most B2B companies get stuck in and instead, tap into emotional storytelling, which can be so powerful in terms of brand awareness and recall.

Going back to Jacob Shipley, it’s about people to people. No matter if they’re working in a business, looking for a new supplier or a vendor, if you’re able to market to them as a person, you’re already going to be well ahead of the competition. That’s included in the layer of risks that we’re taking, big or small.

The ultimate goal is to create social media content that provides value to the end viewer or consumer and using emotional storytelling—that’s what people connect with. Within social, you have to learn fast. You have to understand what early signals happen and how to leverage or weigh them.

I think back to growing the Traveling Unicorn into a pretty large account in the early days of Instagram, and I recognized those signals quickly. I tested and experimented a lot with the Traveling Unicorn, MeUndies, and Canoo. All the wins and learnings from those experiences have given me the insights and confidence to continue to take risks.

Can you speak to balancing quantitative and qualitative data when sharing insights with social teams?

Yes, metrics are great, but you need layers. I think follower growth, impressions and then the health of those impressions using engagement rate should always be considered, but don’t harp on them.

Sometimes you’ll have one of those posts where you’re like, “This is going to crush. We nailed the creative.” That post goes live and 24 hours later it’s way below performance expectations, but there might be a signal or two within it that gives you some idea to keep going.

There could be a comment that really touched somebody. Every time there’s a comment with that positive sentiment, there’s probably a handful (if not more) of people that thought the same, but they just didn’t comment.

You always have to have that balance between quantitative and qualitative data with any kind of social reporting. It’s really tough in any aspect of marketing to not fall into paralysis by analysis.

Don’t overcomplicate it. Go back to your gut belief. Give it more time, or do another test to see if you get similar results or make some tweaks for the next piece of similar content.

For the Steve Burns campaign, we had a lot of quantitative metrics we were tracking, but the validation and success of the campaign really came from the qualitative metrics, primarily the comments, shares and the sentiment within those comments and shares.

I’d be lying to you if I said prior to the campaign launching that we didn’t ask ourselves the questions, “Is this too much? Is this going to land with our audience?” But what gave us that boost of certainty we needed was sharing the creative with all of Flock’s teams to get feedback, and of course leadership was one of those teams. I wish I was in those executive leadership team meetings when our chief marketing officer was sharing the scripts and then ultimately the final videos. It would have been great content capturing those conversations and reactions.

What other advice would you have for marketing leaders when it comes to creating a social presence?

People who are in social media leadership positions have been in the game for a long time and they all started somewhere. They started on Instagram, Vine and Facebook for companies in the early days.

As you level up, you start to get more removed from the trenches. Social customer care, community management and social in general are changing every single day. Features, trends, how to leverage platforms—don’t remove yourself from those trenches, or else social media is going to leave you behind.

My advice for people in social media leadership positions would be to continue consuming social media, saving awesome campaigns, bubbling up trends and engaging with your community. Keep your ear to the ground on what’s happening.

Also, whether it’s on your personal account or a burner account of some sort, still be out there creating because that’s where you can test and learn the most. Then you can apply what you learned to your brand’s social media strategy.

In social, you can only control what you put out there. You can’t really control how it performs because of the algorithms, what’s in your followers’ feeds that day, etc. At the end of the day, put your best foot forward with the things you can control: strategy, creative production, etc.

If the content is based on insights, brings your followers value and it’s pushing your brand forward, then hit that “post” button.

What advice would you give to social media managers who are in the trenches managing these sophisticated social presences?

Do your sweeps, plan your content, experiment.

When I tell people I work in social media, people will say I’m on Instagram, TikTok and Twitter all day–which I am, and I learn something new every day. This space doesn’t slow down and it’s fun!

At times social media can be overwhelming and exhausting. I still have those days even with currently managing the smallest audience I’ve managed in my career so far. Take advantage of your notification settings, really leverage the features so you don’t go crazy and manage expectations with your manager for when you’re on and offline. It’s the very small, granular things that can give you longevity with a career in social media.

Create offline expectations with your manager or team, so you’re able to disconnect. It’s a grind and we all have experienced social media dopamine. Something performs really well, it’s the highest high. Two days later, something doesn’t perform, it’s the lowest low and it can take a toll on you—but that cycle is going to continue no matter what.

That’s why I keep saying don’t overly sweat metrics or else you’ll just drive yourself crazy and hate working in social media.

You’ve worn many hats. How have you navigated the different challenges in these various roles? How did you recognize your wins and areas of improvement?

Across all of these industries, I’ve always wanted to do things differently. When I came into these industries—underwear, automotive, freight and logistics—they were ripe for disruption.

In underwear, the only players at the time were Victoria’s Secret and Calvin Klein. MeUndies was doing something differently with their men’s underwear subscription. There was an opportunity to market differently. Instead of over-sexualized content and imagery, there was an opportunity to market by creating community and connection through body positivity and a new form of confidence. The electrification and digitalization of vehicles created the opportunity to be different in the automotive space as well.

That’s how I decide what brands I work for. If a brand wants to be in the sea of sameness, I’ll pass on riding that boat.

Something else I’ve learned throughout my career no matter the company or industry: you need to provide value on social media to your ideal or current followers. And that’s not by being like everyone else. That is how I’ve been able to navigate and find success.

I’ll admit, always wanting to try something different isn’t easy and creates challenges. There’s a learning curve for every industry and I love the challenge to learn the ins and outs as quickly as possible. When I’ve changed industries I ask myself: How quickly can I understand this space, the pain points, the benefits and the value my new company offers, etc?

Social already moves fast and with technologies like artificial intelligence (AI), things are changing even quicker. What is your advice for building a sustainable career in social?

Be ready for change and embrace it. There are tools out there that will help you be more efficient. AI is one of those, in a variety of capacities.

AI is like the dishwasher or washing machine in our homes. Think of all of the time you save not washing dishes or clothes by hand. Because of these tools, you can do more impactful things because those tools are able to do things a bit more quickly for you. That’s how I’m thinking about AI.

There’s all the conversation about AI taking jobs, but I think it’s also going to create a lot of jobs. I believe there will always be a human element to social media, but the industry will leverage AI like an assistant or tool. Social pros should be ready to test and embrace tools of innovation that make them more efficient so they can focus on the more impactful things.

For example, in the social sphere, think about managing social media without Sprout—scheduling posts, listening, all of that. Sprout is a tool that makes life so much easier for someone in social and I think AI is going to do the same.

To learn more about navigating your career journey, read our guide on what it takes to build a long-term career in social, based on advice from three social media executives.