From Sax Player to CTO – Meet Chad Fowler, General Manager of Developer Advocacy at Microsoft

“Help first, sell last.”

That’s how Chad Fowler describes his personal mantra for the work he is doing through Microsoft’s startups and developer advocacy programs. Fowler, currently serving as the General Manager of Developer Advocacy at Microsoft, followed a circuitous path into the tech industry. He started his career not as a developer, but rather as a saxophonist, playing on Beale Street in Memphis. His interest in technology didn’t start because of some grand career plan, but rather because of his love for a video game – Doom.

Fowler, who now sports a Doom tattoo on his arm, says that his interest in the game led him to want to understand it, and ultimately to learn how to program. So, in the early days of the internet, sitting at home between sessions of playing Doom he learned about programing following a self-guided path. He didn’t even apply for his first job in tech – rather a friend pushed his manager to recruit Fowler, who landed his first tech job, as he describes it, “without interviewing or having any qualifications.”

Fowler credits his background as a musician for his success as a programmer and developer. “I brought with me the naïve, crazy musician-like desire to be great,” he said. “Musicians don’t do what they do because they think they are going to get a good job. They do it because they think they can add something to the world. I brought that kind of passion into my software development and that’s just how I approached it.”

Man playing saxophone

Photo Credit: Marc Pagani

Years after his first tech job, Fowler landed the role of CTO at Wunderlist, a cloud-based task manager that was acquired by Microsoft in 2015, bringing him into the company.

“I spent most of my career deep in the bowels of the open source world. I spent a lot of time in the Ruby community and co-founded and organized the official Ruby on Rails conference for over a decade. So, looking back to the late 90s and early 2000s, I thought there was no way I would end up working for Microsoft, considering what we all know of that history. That’s what makes it really fun to be here now, knowing how different things are today. For instance, 40% of deployed VMs on Azure are Linux. There's Node, JVM languages like Scala and Java, and Python; it really fits my cultural backdrop perfectly.”

Fowler outlined the ways Microsoft can engage with the startup community and what the company can learn from these companies:

What challenges do startups face that Microsoft can help them overcome?

“Having been a startup CTO myself, we can always figure out technology. However, the biggest thing you get lost in is how you deal with sales and scaling the business. You can build a wonderful product, get product market fit, build something sticky for users. But how do you get tons of users using it? How do you build a sales force, position the business so you’re attractive to large customers?

“There are things like pricing models and all sorts of science that typical startup entrepreneurs don’t have experience in. Often, developers will build something simple, they start with an idea, get passionate about it, build up the idea, and then they reach a certain point where they realize there’s all this complexity in the journey that they didn’t expect.

“With Wunderlist, we hired someone to build a sales organization for us, we hired a business development lead, we hired a CMO, all after we raised Series A and into Series B, which is near the phase where Microsoft is now focusing on in terms of our role with startups.

“We made nothing but missteps there. So, I believe there are a ton of startups that are like we were. Where they had all these skills to create a remarkable product; an experience that users loved. That’s what they were great at, and then you hit this awkward growth phase and you don’t know what to do. A lot of startups really stumble there.”

What should Microsoft learn from the startup world?

“As a startup coming into Microsoft, I think there is a ton the company can learn from startups, not just the ones we acquire, but the one’s we interact with.

“A big one is agility in the face of customer empathy; really thinking about customers and what they need first, emphasizing users and customer experience. I talk a lot right now about managing the user experience of our startup program. I think of it as if we were polishing Wunderlist from a design perspective. You can take the same sort of techniques and philosophies and apply them to the experience of interacting with startups and helping them through their journey.

“Ultimately, it’s the same sort of thing: you lose people along the way if you’re not thinking of them first, if you’re not ruthlessly polishing every detail as you go. That’s our task right now in Microsoft with all of our engagements with startups and developers - to polish it to so it is as perfect and customer focused as it can be.”

How does your experience as a CTO inform your perspective on what Microsoft can accomplish for startups?

“Sometimes as a developer, or collectively as a startup, you hit a wall where you think ‘ok, now I have an entirely new type of mountain to climb, and no concept at of how to climb it.’ It always amazes me when I see young startups and founders that hit that phase - they’ve built a great product, people love it, but now they need to pivot themselves individually, to become real business leaders, and there are so few who can actually do that and do a great job of it.

“So, for us, and for me personally, being acquired by Microsoft, gave us an answer to that. What that showed me is Microsoft knows how to do this. It was sort of a feeling of comfort coming into the company. Ok, we can do compliance, and can finally start selling to government and large enterprises, and a number of other things.

“At Wunderlist, we used to talk to large enterprises that reached out to us. We had our fledgling sales team that would come to me as CTO and say, ‘well we can sign a 50,000 user subscription to a big enterprise, but they need us to do, x, y, and z,’ where that is all kinds of stuff around compliance, legal agreements, things we weren’t really prepared for.

“So we had to turn down what looked like an extremely promising proposition and say to them ‘we aren’t capable of doing this.’

“That’s why I’m attracted to what we’re doing with Microsoft for Startups, because we can take that same power as a company and apply it to startups that haven’t been acquired by Microsoft, and amplify them and help them get past that scary growth stage.”