The next big thing: joining ENow as CTO

It is a cliché to talk about an opportunity that’s too good to refuse (not to be confused with an offer you can’t refuse), but sometimes it doeshappen.

I am very excited to announce that, effective 26 October 2015, I will be taking the position of chief technology officer (CTO) for ENow Software. In that role, I will be driving the development of their next generation of products for both on-premises and Office 365 monitoring. It’s a big step forward for my career, moving me simultaneously back towards the development world and further into the cloud. (It’s also a little surreal to see one’s job change announced in a press release.)

Before I get into the nuts and bolts of what I’ll be doing, a personal note: I want to thank Scott Edwards, Ben Curry, and all my coworkers at Summit 7 Systems. What a talented and skilled group of people! I accidentally learned much more than I expected about SharePoint from them, and both Ben and managing consultant Matt Whitehorn were instrumental in helping me identify soft skills I need to work on— always a challenge. I have huge respect for what the Summit 7 team has accomplished and recommend them in the highest possible terms to anyone who needs Office 365, Azure, AWS, or SharePoint design, strategy, or migration help.

So, the new job. In the CTO role, I’ll be reporting directly to Jay Gundotra, the CEO. I’ll be responsible for technical product strategy and implementation, the customer success team, technical presales, and internal IT. (I am still working on a transition plan to establish an ENow corporate aviation department, but don’t tell Jay.) That’s quite a broad scope, which means I can bring to bear everything I’ve learned throughout my career as a developer, consultant, and administrator. Driving beneficial change across these disparate fields is going to be an exhilarating challenge! Luckily I will have a really powerful team on my side, including Michael Van Horenbeeck (noted hooligan/tequila drinker, Microsoft Certified Master, and Exchange MVP) and Tony Redmond, a member of ENow’s advisory board.

ENow is already very successful in their chosen markets, but the cloud poses a brand-new set of technical and business challenges, both for them and their customers. The #1 question I hear from IT pros and business decision makers is simple: how will the move to the cloud affect me and my business? It’s interesting that I don’t remember many people asking that during the years-long transition from mainframe- and mini-based solutions to the x86 world; people just naturally assumed their skills would transfer. That hasn’t been the case with the cloud. Figuring out how to effectively monitor and manage cloud services when you don’t control the underlying platform is a tough problem. Instrument flight is probably a good metaphor here. On a clear day, you can see the ground, so flying is easy. There’s a visible horizon and landmarks. In the clouds, everything changes– if you’ve ever been in an airplane on a cloudy day, you know that you can see where the clouds are but not what’s inside them. Flying inside clouds is like being inside a ping-pong ball, with no visual cues you can use for orientation. You have to use your instruments to keep the plane pointed in the right direction and right side up. Moving workloads such as Exchange email or SharePoint to the cloud doesn’t lessen your need to monitor what’s happening, it just changes the way in which you’ll do it, and figuring out that change is a key task in my new role.

Of course, Microsoft is releasing new services and capabilities in Office 365 at a rapid clip, so another key challenge will be figuring out how to keep up with them and how best to bring ENow’s experience in simplifying the complexities of enterprise application monitoring to a world where Microsoft seems intent on giving everyone Fisher-Price-style monitoring and reporting tools.

Despite the new job, some things won’t change: I’m still living in Huntsville, I’m still not a Cowboys fan (sorry, Jay), and I’ll still be blogging here, although I expect to be writing some more strategy-oriented posts for ENow’s blog. Where I can, I plan to share details of what I’m working on, so stay tuned!