Hey, I’m Matt. I’m a design leader with over twenty years’ experience building SaaS products, which means I started at a time when “SaaS” was competing with terms like “Rich Internet Applications,” and Salesforce set the world on fire with their “No Software” campaign.

Back then the browser was becoming a distribution platform for software, and “desktop class experience” was the north star. The web was weird and wild; to achieve our desired designs we needed things like IE specific stylesheets and spacer gifs. We watched the open web go to war with Macromedia’s Flash (before Adobe bought it and inherited the fight). jQuery and its cousins joined the push toward our desktop class desires, only then to see the iPhone’s release force the entire industry to reckon with something called “responsive.” The landscape of the web and software has never stopped changing, and now AI is here to do it all again, just faster and with higher stakes.

Where I’ve Been

Over that time I’ve had the privilege of working with some incredibly talented and passionate people.

I started at a shop in Cincinnati called Global Cloud, designing sites that ran on our own custom CMS. I learned more about the mechanics of the web there than any class could have taught me.

From there I joined Openfield Creative, a young agency in town doing some of the highest craft brand and web work I’d seen. In two years they taught me more about design discipline than I’d picked up in my life to that point. I’m still deeply thankful for that stretch.

Even with all that going well, I missed building software and felt the pull to lead a team, so I went back to Global Cloud. That’s where a group of us built DonorDrive from the ground up, a peer-to-peer fundraising platform for nonprofits. We had so much fun building it that we eventually just started calling the whole company DonorDrive. I spent the next 13 years there, building a cross functional team and growing that product alongside people I’d go to the mat for.

New Challenges and Fun

A few years in, InvoiceCloud acquired DonorDrive. A few years after that, DonorDrive found a new home, and my path stayed with InvoiceCloud. Today I’m VP of Design there, building a team and growing a product from scratch for the second time in my career. I’m proud of what we’ve built and where we’re headed next.

Why a Blog, and Why Now

I’ve wanted to start a blog for my entire career and never felt like I had enough to say. I worried I’d repeat things that had already been said better, or worse, that I’d be wrong, or say something that landed badly.

But design leadership is a genuinely hard role, and a lonely one at times. There aren’t many peers to compare notes with day to day. So I’m going to try writing some of it down, in the hope that it’s useful to someone else navigating the same terrain, or at least a little comforting to know someone else is in it too.

At the very least, we’ll have some fun.