Turning the Page: Our Journey with Skyward

Five years ago Ben Roux and I started Skyward, or at least, stumbled into it, starting something that would define our lives for the past half decade. The story goes like this: I got an email from my good friend Trevor Waldorf passing along what he thought was a tiny design-only project for JJ Osbun and Julia Jackson at Grounded. Turns out that in the course of talking with them, that the project was much bigger than anybody thought. I immediately recognized the project as bigger than just design so I give Ben a call, and we end up working for the Grounded foundation for over a year.

Over time, the vision for what we wanted to create grew into something neither of us could have foreseen. We never wanted to be a massive behemoth, to become an agency relying on outsourcing arbitrage while we sat there and managed and collected a fat paycheck. No, we always wanted to be the ones getting our hands dirty, to be making a difference in the actual products we were working on. And we knew we had so much more to offer than just design and development. Our amazing clients recognized this and we quickly became their trusted source for strategy and feedback as they forged their companies. They trusted us to be real. To be brutally honest. And to hold them accountable. In a client-consultant relationship usually the consultant is a yes man, a pass through for the clients ideas (I’ll be writing more about this in another post). To challenge our clients to be better was to swim upstream and fight decades of established norms, to try to be better than the status quo.

The path wasn’t easy. There were times when we didn’t make payroll for months, but ultimately we turned Skyward into something that we could stand behind and be proud of. Our client retention was possibly some of the best in the entire industry — some clients we worked with for over two years. Our revenues grow in tandem, by the end we were generating close to 1Mil (ARR). But it was never about the money — to me the biggest joy was working on some amazing products and companies that were making a difference in peoples lives. 

As the sun sets on Skyward, I find it both challenging and necessary to share our journey’s culmination. Starting Skyward was more than a business venture; it was an experiment to see if we could innovate on the agency model, create a company that supported our lifestyles, and contribute to a building companies that made a difference. While today marks the end of this chapter, it also opens the door to reflection and gratitude.

The Journey & Acknowledgments:

I want to extend my deepest thanks to everyone who believed in us and all of our amazing clients. To Ben and Adim for their amazing work as Co-founders of Skyward. To our clients — from our humble beginings with Grounded and helping them with their work with the BBC, Hillary at Summerbell with her tireless work in creating the only solution for dyslexic readers to dramatically improve comprehension and speed, to working with Wes at Trace (Genealogist.com) helping people get access to their family history, Nere at Sanu helping to democratize access to precious metals in a country with unstable currency, to working with Sarah and Jenn at Studio BE and helping people be more mindful at work, Liia at Child Guidance Resource Centers helping the largest provider of childrens mental health in Philly, to Ben Peterson at Photofeeler, giving people real human feedback on their dating photos so they are more successful, among many others.

To the other people that truly helped along the way, including Trevor, the reason we existed in the first place, Hayley Fremuth and Harrison Wood for their excellent work with Skyward, Kaushik Chauvarti (SP!!) for pushing us, Jenny and Liia for always having our back, Dahlia Dill for her rock steadiness, Andy Stone, Julie Penner, Keith Gruen, Dan Holloran and Fletcher Richman for their mentorship, Adam Taylor and Amy Baglan for making me the designer I am.

Lessons Learned & Looking Ahead:

The decision to close Skyward was not made lightly, but I find that all-remote founding teams can grow cracks. If I learned one lesson it’s that spending quality time with the people who matter to you, whether it’s your life partner or a co-founder, is the best way to ensure smooth working relationships. So much is lost in virtual communication. Peppered in there are other lessons about strategic alignment and resilience. However the big thing is that you have to love what you’re doing as a founder. It becomes harder and harder to justify going on when your heart isn’t in it anymore.

While saying goodbye is always bittersweet, Skyward has built so much and made some incredible contributions, I’m really proud of how far we’ve come. I’m proud of my own personal growth, full of gratitude for the people we’ve worked with, and really excited for the future. I’ve created an agency model that is repeatable, unique, and nimble. I’ve grown incredibly as a product designer, as a founder, in business strategy and as a manager of people. I’ve successful managed the financials of a million dollar company. I built value in dozens of verticals. I’ve collaborated with some brilliant founders, helping to steer their visions. 

In the coming few weeks I’ll likely be talking about my next moves on here. I have a small project in the works that I’m hoping will return me to my roots in Healthcare tech. If you have connections for me, people who need high level UI/UX work send them my way, or perhaps you know somebody that just need me to step in and make something shiny. I look forward to staying connected and sharing my journey with you all. 

You can also follow along at alex-mark.com, or simply shoot me an email at alex@alex-mark.com

Thanks to all,
Alex