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One Year at Wheels Up Collective

It was just about a year ago that I lost my corporate position I’d held for exactly, to that day, 11 years. It was a big deal when I decided not to replace it. I’d been doing content marketing as a salaried employee in big tech for just shy of 17 years. And while I had no shortage of passion for content or the industry, I had developed a deep loathing for the way that we worked. So when Wheels Up Collective invited me to join them as Managing Editor, I was keen on their promise that working here would be different.

I’m happy to report a year in, that it is. Here are a few reflections from my time on the team about what it is we as a group have gotten right.

Image of a person holding a cupcake and a candle

Work doesn’t have to suck. Not to put too fine a point on it, but I was right. You see, long before the pandemic made remote work and virtual coordination a widespread reality, I was a passionate advocate for this particular way of working.

As a neurodivergent and chronically ill person, trying to contort myself to fit the 9-5 workday, chained to a desk in an environment that I had little ability to modify for my needs was not only a draining and inefficient use of my potential for contribution, it was also at times, deeply painful. Plus, the pretense of it just never made sense to me. Working in the Seattle metro area, it was normal to lose 2-3 hours a day commuting. At work, most of our time was spent alone in our offices anyway. And when I was trying to force productivity on a schedule that wasn’t aligned with natural ebbs and flows of mental, emotional, and physical energy, I consistently felt like I was faking my level of inspiration and enthusiasm at least part of the time I was there. It seemed like others were faking it at least part of the time too. No part of that arrangement made any sense to me.

The pandemic seems to have woken the more open minded companies up to my way of thinking. And it afforded those who were already aligned with the mindset to start something new, as was the case with Wheels Up. The results are clear even in just the year that I’ve been with the agency. Asynchronous schedules can be compatible. Dispersed workforces aren’t just functional, but are effective, innovative, and thriving. Culture is intentional and takes ongoing commitment and action to maintain. And employees who are comfortable, who are empowered, and who are enabled to integrate their work and their lives as needed produce better, higher quality work for their stakeholders. In the case of Wheels Up, we produce better content for our clients.

Establishing processes creates efficiency. I know, I know. “Process”, to many, is a dirty word. Especially when spoken by someone with a background like mine. In a (virtual) room full of creatives, everyone gets worried when the ex-Microsoftie with a long career history in big tech starts talking about process. They’re fearful, I’m sure, that their work will be stifled, hung up, overwhelmed by bureaucracy or mired down in red tape. I get it. I’ve been there too. But I’ve been on the other side, too, where great ideas fall apart without at least a little process to bring it together. And as a proud efficiency dork, I can tell you: The right amount of process makes a creative team flourish.

Some of the processes that I particularly like, and rely on completely at Wheels Up, include:

  1. The creation and use of templates - whether it’s for SOWs, creative briefs, client intake forms, or working documents for our writers, templates help. As we figure out the pertinent information needed for each type of file, we can add it to the saved template so we’re sure to capture it next time, and not burn client hours (or a creative’s brain cells) trying to track down the info they need.

  2. Good workflow management tools - the right workflow management tool is important for any organization, and is perhaps even more vital for a workforce that’s dispersed and asynchronous in nature. If we can’t physically tap each other on the shoulder when it’s time to pass the baton, we need a tool that’ll help us do it from afar.

  3. Best practices for using the tools that we have - tools these days are only as helpful as we make them. A workflow management system, for example, isn’t all that effective, if it’s not clear whether a task is yet actionable, or if clicking into the task, you don’t find the links or information you need. That’s why it’s important to pair the right solutions with the right habits, agreements, and rules. If a team is committed to a predefined level of collaboration, it’s then that each member can soar.

  4. Naming conventions and file structures that work - it’s so easy to create a document on your desktop and name it something like “April blog”, but if you’re working with a group, those are the habits that hold everyone up. Creating files in the cloud is a must for a virtual team - doing so in shared folders where the appropriate level of access is already granted helps too. Take it to the next step by naming files with information any file-seeker is hunting for: Client name, deliverable description, and stage the deliverable is in are my go-tos.

  5. Meeting hygiene that makes good use of everyone’s time - I can credit Microsoft for teaching me the importance of good meeting prep. After all, meetings are what we did about 70% of the day. While agency life (thankfully) keeps me on calls far less, it’s still an easy way to burn time (and $). We’d all be wise to learn from what big tech already knows: Meetings should only include participants who are directly relevant, an agenda should always be sent out ahead, notes should always be taken, and a meeting’s not complete until a recap is shared.

I have no interest in taking any content professionals I work with down a path of red tape with an exhaustive list of to-dos. But it’s true that organization is what keeps a creative team cranking. Finding that balance - the right commitment to order that enables inspiration to run free and creativity to flourish - that’ll be a forever passion for me.

Flexibility, responsiveness, and agility are paramount. This is probably true for all marketing agencies, but it’s especially pertinent for ours. At Wheels Up Collective, we specialize in serving clients with startup businesses in tech. Startups are energized, creative, and alive, but they’re also usually rife with instability as they pivot, learn, grow, and change. Being in the technology space means that the clients’ business itself isn’t the only rich source of change - so too is the landscape, the competition, and the opportunities their business is navigating. That’s why, at Wheels Up, we’ve built our team, our contracts, and our particular way of working to prioritize flexibility, responsiveness, and agile thinking our partners can truly rely upon.

There is always something to learn. Whether you’re slaying goals faster than ever expected, or struggling to make any progress at all, taking a moment to assess the data around you can make all the difference in changing - or maintaining - the status quo. At Wheels Up, that routine reflection is a practice, and when it comes to client outcomes it shows.

Relationships matter more than anything. From founder to newbie, project manager to peer, or agency rep to their client, the quality of connection dictates the outcome every time. Partners work better when they care about how one another is doing. We organize work more effectively when we understand one another's constraints. Content strategies are more attuned when hopes, dreams, and fears are made collectively familiar. And the whole list here takes practice with and commitment to authenticity. Vulnerability is best exchanged within safety, and that only happens when relationships are built consistently, and effectively over time. We take that to heart here at Wheels Up with each other, and with each of our clients too.

My first year at Wheels Up has been a rich one with so much practice, learning, and growth. I’ve worked with the coolest clients, learned about the most interesting products, and partnered with some of the best writers and designers I’ve ever met. The best part is, I know this is just the beginning. Here’s to year one, looking ahead to many more.


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