I'm a Cloud Strategist and This Is How I Work Part One

30 November 2017

Hi, I’m Rich. You might recognize me from the SharePoint ecosystem, an occasional byline on CMSWire, my longtime work in the Microsoft Partner space, or roaming the sideline around various Milwaukee-area youth and high school football fields with my kids. I’ve had a rich (pun intended) and varied twenty years in what we’re now calling the “Digital” space. Most recently, I’m loving what I do as a Cloud Strategist at Rightpoint, and I’d like to tell you a little bit about how I work in my first of three posts in this series.

My job is a great job, and a fairly rare one. It lines up nicely with my interests, enthusiasms, and experience—but also has forever begged the question, “So what do you do, exactly?” I see this post as a bit like pulling back the proverbial curtain on how and why I do what I do around here.

No doubt, to be successful in this role you must have some level of abiding interest in, if not a love for, technology—or at the very least, the things it can do. For me, it was a synthesis of that interest in new and cool tech, a cultivated tendency toward order (information architecture) and a natural creativity (visual design, written expression), and finally a perfectionist’s delight in solving problems. This job doesn’t just let me solve problems, it actively insists that I do so—utilizing creativity, cloud platforms and the strength of an amazing team to make that happen. 

So What is a Cloud Strategist, Anyway?

I’ve seen the role of Cloud Strategist pop up in numerous places across LinkedIn, so I think it’s important to set some context for what this job means here at Rightpoint. You see, as a digital experience agency with technology at our core, our take on things isn’t always the take of the average bear. The cloud is literally the “technology at our core”, because it provides the platform underlying every experience we build.

At Rightpoint we have various teams and practices built around different elements of delivering those digital experiences—technology teams covering core capabilities like CMS, Productivity, Enterprise Applications and Cloud Infrastructure, and Experience teams covering Strategy, Design, and Change Management, just to name a few. Each one of our technology practices has a Solution Strategist mapped to them, and the Strategist focused on Cloud and Enterprise Applications happens to be yours truly.

Ultimately, everything I do is focused on our clients. Don’t get me wrong—I enjoy researching, analyzing, writing and deep thinking as much as the next guy (who on this team might happen to be Brandon Rozelle), but the reason I’m in this business is to share the output of all of that with my clients, and use it help them solve problems. This is very much a client-focused role, make no mistake. We’re called on a regular basis to meet with, listen to, and speak to the needs of corporate leaders in both the technology and marketing arenas. There’s no room for wallflowers in this bunch.

How I Do What I Do

It sounds like a sugar-sweet manufactured pop song from a ‘60s hit factory, and “how I do what I do” does have a similar balance of art and science to it. Like classic songwriting—which relies equally on certain common elements people find pleasing to the ear, and the alchemy of successfully combining those elements in a way that sounds fresh and unique every time—solution strategy rewards a consistent approach combined with a regular infusion of new and exciting ideas. It’s essential to stay on top of the latest news, trends and thinking around one’s area of expertise. In my case, that’s cloud platforms.

Part 1: Research

Microsoft Azure is obviously a major focus in that regard, but I also need to stay abreast of what’s going on with other cloud players like AWS and Google, as well as third-party hosting and managed services providers like Rackspace. In general, IaaS (Infrastructure as a Service) and all of its subsets are about scalability and security, while PaaS (Platform as a Service) and its various modern mutations are about capabilities and efficiencies.

Microsoft, Google, and Amazon are literally investing billions into these platforms every year, and staying on top of the ways they differentiate themselves from one another could be a full-time job all its own. Thankfully, there are people at places like Gartner, McKinsey and elsewhere, who do indeed have that exact full-time job, so I make a point of following them and reading their research and analysis on a semi-regular basis. Curiously, informal content sharing makes up over half of what I read—largely because it’s more topical and timely. I’m blessed with a fairly large LinkedIn network and as that company gets better and better with its algorithm, essential reading tends to bubble up in my newsfeed in a fairly regular cadence.

Finally, conversations with highly intelligent and experienced people are something I place incredible value on. It’s the old, first-hand account so beloved of journalists, and for good reason. Real-life stories and first-person opinions driven by direct experience are invaluable in forming a strong position on the topics that matter to my clients. If I haven’t worked with something directly, I find it’s essential to spend serious time picking the brain of someone who has. This is one of the reasons I enjoy working at Rightpoint. They say a rising tide lifts all boats—and when you’re surrounded by other top players, you have to raise your own game.

Part 2: Thinking, Writing, Creating

I spend another decent chunk of time creating—for clients, for public consumption, or for my own team. This could mean writing up position papers based on the research I’ve been digging into above, architecting a strategic technology roadmap for a client, working with technical experts to create an estimate for a services project, or even composing a post like this one for our Rightpoint blog or CMSWire. Beyond writing, I spend time presenting the things I create. That can mean getting up and walking through my work with a small group over a web meeting, a room full of clients or peers, or even a crowded expo hall at a major conference.

It’s hard to believe in this day and age of four-year programs and master’s degrees in “marketing technology” and “human-computer interaction”, but when I broke into this business twenty years ago it happened because I was good at writing copy. Along the way I was taught HTML, CSS, JavaScript and Photoshop through informal hands-on training, picked up Information Architecture and core usability skills as a matter of interest, moved into Enterprise Architecture from the top (i.e., the UI) down—an odd thing back in in 2004—and ultimately became a SharePoint consultant in high demand. Ten years after that, I found myself here—writing again. It’s nice to come full circle, but saying that doesn’t even begin to describe the journey or the full experience of this role.


In order to be successful in solution strategy in general—and cloud strategy in particular—you need to be well-versed in your own realm but free of ego at the same time, because you’re always part of a team. There are experts in other solutions who know their realms better than you do. There’s deep technical professionals whose hands-on experience in what’s now—never mind what’s new—is incredibly valuable. You’ll have clients who know their business better than you ever will. Understanding your role in that equation, and having the experience and self-awareness to see not just your own contribution, but those of others and the connective tissue that brings them all together? That’s the most important talent anyone can bring to the table in a role like this one.

Up Next: Influences 

Teammates and clients are a major influence—and a desire to work with tech and solve problems got me started. But beyond the basics, what gets me up in the morning and gets me going? What personal and professional elements go into the mix of doing what I do? There's quite a few inputs, many of them completely unrelated to the outputs, on the surface—and some of them will almost surely surprise you. That's a topic for a whole new post...check back next week for Part Two!

Rich Wood is the Senior Director of Cloud & Enterprise Apps at Rightpoint. Follow Rich on Twitter and LinkedIn

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