What Peloton’s #TogetherWeGoFar Taught Me About #Perspectives2020

Michelle Boockoff-Bajdek
4 min readMay 5, 2020


Next week marks two important milestones for Skillsoft and SumTotal — we embark upon our first 24-hour follow-the-sun digital experience, Perspectives 2020, and we unveil our new brand to the world. Either of these initiatives on its own would feel daunting, but together, they’re downright overwhelming.

To prepare for Perspectives 2020, my team has worked countless hours over the past eight weeks. We had to reimagine what a live, in-person event could become if we turned it on its head. We’ve crafted a truly immersive experience; rather than just deliver an old format via a new channel, we’ve taken full advantage of everything you can do in the virtual world. Because of this, we’re able to offer Perspectives 2020 not just for the select few, but for the many. It’s open to everyone and free to all. It’s also shaping up to be more dynamic than anything we’ve done onsite in the past.

Meanwhile, our new brand has been a major focus for me since day one. Seven months ago, I joined Skillsoft from IBM where I was the CMO of IBM Watson. It was a privilege and pleasure to serve as the steward of one of the company’s most iconic brands. As you can imagine, it taught me quite a bit about the power of a brand and the durability it can have in market — an opportunity Skillsoft was missing out on. And so, my mission was to craft a brand that reflected where we are as a company as well as where we’re headed. To build a meaningful brand in market, we had to connect with people both functionally and emotionally, creating stronger, more purposeful relationships with leaders and learners alike.

But this past weekend taught me something important — Perspectives 2020 and our brand initiative are not two discrete programs, but rather inextricably tied — the former serving as the manifestation and physical representation of our brand. And, this insight came from an unexpected source.

I learned it from Peloton.

Each May, Peloton holds its annual Homecoming, where traditionally thousands of people travel to New York City for the brand’s largest member event. Tens of thousands more participate from their homes — on their bikes, treads, and digital apps. For five years, Homecoming served as a symbol of community that brought people together physically and emotionally. Until this year.

With social distancing in place, it was clear that the sixth annual Homecoming event needed to be something different. But, it also became something very special, and something available to all. This weekend’s #TogetherWeGoFar experience did not disappoint. From “Live from Home” cycling, tread, yoga, and strength classes that drew thousands to Encore Favorites, Peloton delivered an experience that eclipsed the Homecomings of previous years, in my opinion. And in doing so, Peloton let their brand shine through.

I found parallels between what they did and what we hope to achieve. Here are a few of the key takeaways I’ve already shared with my team as we move into the home stretch for Perspectives 2020:

It’s not about us. It’s about the community. For us, that community comprises the leaders and learners who want to help people become the best versions of themselves — professionally and personally. In Peloton’s case, the community is strong because there is a place and a tribe for everyone; a way to connect, stay accountable, and celebrate milestones. It’s one of the reasons Peloton debuted their #tag feature, which allows people to build and acknowledge the affinity groups to which they belong (for me that includes: #togetherwegofar, #bensarmy, #powerzonepack, #PelotonBoston, and, of course, #skillsoft). And Peloton has long recognized that people want to have an intimate connection with their favorite instructors. There is something so powerful in a high five from an instructor; they become instant shareable moments.

It’s building ecumenical engagement. The Peloton platform is fantastic, but it’s not the only place to engage. Favorite instructors took to social media platforms like Instagram to promote upcoming weekend classes; participated in IG Live sessions with their fellow instructors, and storied their own class experiences. Social media is exceptionally powerful, particularly when your brand stands for inclusion and community.

And it’s gotta be real. Things happen, whether they be technical issues or sound challenges, but Peloton took them in stride, acknowledging minor snafus, but not dwelling on them. And perhaps the most beneficial lesson for me was how Peloton humanized their instructors. They removed the full production studio, offering “Live from Home” classes that gave us a glimpse into the personal lives of these people. One stand-out for me was the instructors’ IG Live sessions during Friday night’s Dance Cardio party. It made us all want to get up and shake it a bit. (Even Peloton superstar instructor Matt Wilpers.)

As I look back on the weekend in which I participated in a number of classes (and — I admit — cried like a baby when Jenn Sherman played “We’re Coming to America” from The Jazz Singer), I hope that I can take what I’ve learned and apply it to Perspectives 2020 next week. We all want to belong. We all want to engage. And, at this time more than ever, we all want to keep it real.

Finally, we want to ensure that our brand — one that believes that everyone deserves an opportunity to learn and grow — shines brightly.