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Becoming an IT Leader: An Insider’s Guide to Digital Transformation

What’s the best way for a company to take on digital transformation? If you had asked me that two years ago, I would have said something completely different than what I’m about to tell you now.

 

Two years ago, most of my career experience was at the big consulting firm, PwC, working on transformation projects for enterprises such as Google, Paypal, Apple, and LinkedIn.

 

Now, having gone in-house and focused the past year and a half on digital transformation at Coupa, I’ve been humbled.

 

To be successful with digital transformation in a high-growth company—or in any organization that’s rapidly changing—you need to shorten your time horizons dramatically, narrow your scope, and ruthlessly prioritize your efforts.

 

I learned those lessons through experience, and I’d like to pass them onto you. So here’s what you need to know.

 

Getting organized isn’t the sexiest thing to do, but it’s necessary
When I first came into Coupa as the veteran of dozens and dozens of transformations, I looked around and thought, “Yeah, I got this. I’ve seen it all before.”

 

And the first thing I did was look at the data.

 

Coupa had accumulated 10 years' worth of valuable data. But it was dispersed across multiple systems within marketing, sales, finance, operations, and the product organization.

 

We didn’t have a way to aggregate it so that we could identify opportunities for process efficiency.

 

That’s pretty common. If that’s your situation, and your company is looking to use analytics and artificial intelligence to drive growth and control costs—like nearly every company today—getting your data in order should be priority number one.

 

As we got into it though, I realized even that was too ambitious.

 

This wasn’t just about aggregating data in one place, but about the foundational, yet completely non-sexy work of data cleansing and modeling, and there was a lot of data.

 

As a consultant, to solve the problem, we simply would have thrown more resources at the project. This was clearly not an option nor was it right for Coupa.

 

Being a consultant is a lot like being a doctor who’s brought in to do a procedure in a clean hospital room with a full staff and a wide array of tools and instruments. On the other hand, working from inside a company, especially a rapidly changing one, is like being asked to MacGyver open-heart surgery in a warzone—you’ve got to make do with what you’ve got and scrape it together.

 

So, instead of tackling all the data in the organization, my team and I decided to prioritize the data we believed would deliver better, more timely information to an initial key group of stakeholders: Sales, marketing, and finance.

 

Aim small, win big—find the projects that make the biggest impact in the shortest amount of time
Once we had their data in order, we were able to start identifying the places where it made sense to automate.

 

We came up with two possible projects.

 

The first was: We had sales orders consisting of a lot of fields that had to be manually keyed in, in several different places. It definitely would make sense to automate that to free up people’s time.

 

The second project had to do with sales orders: It was taking too long for them to be approved. This was really slowing the organization down. A bunch of people needed to sign off on each quote, and it was all being sent and tracked by email, sequentially.

 

How would you choose which project to work on?

 

The first would’ve been rewarding, but when we looked at the resources on our team, we saw the time it would take—about six months.

 

Regarding the second project, there were complaints about the sales quotes issue coming in from several groups, and by solving it, the impact would be pretty big, so it wouldn’t be hard to get buy-in, which meant a lot less time, and a lot smoother effort.

 

We chose the second. And I’m glad we did. Because what I didn't realize was how much was going to change—fast.

 

Anticipate changes, and let that guide your decision making
Imagine trying to plant a flag while the ground is always moving beneath you. Coupa, like any successful startup, was growing by leaps and bounds.

 

In just one year, the number of employees grew 76%, to 1000 people. Ticket volume doubled.

 

There were four acquisitions, requiring a lot of integration work. And three new C-suite executives joined: A CMO, a CRO, and a chief customer officer, each bringing new ideas.

 

Had I chosen the first project, and put our team on it for six months, it would have been irrelevant by the time we finished. Things move fast at a startup, and priorities and needs move with them. When you’re running an IT organization, the demands on your team’s time will always exceed your supply, so you need to pick your battles.

 

Though I found digital transformation dramatically different in-house at a small company than as a consultant to large enterprises, I do think there are a couple of truths that cut across all organizations:

 

Don’t start with the technology, start with people and processes first.

 

That might sound crazy coming from a technologist, but after having 20 years of experience seeing every type of technology come and go, I’ve realized that if you get the right people in place, who are smart, agile, and flexible, and get the right processes down—you’ll have the gumption to make things work.

 

If you start by buying technology, thinking that it will automatically solve all your problems, you’re just going to own some expensive technology that no one's going to use.

 

The other thing to keep in mind is that digital transformation is a never-ending journey. Expect a lot of learning opportunities (a.k.a. mistakes) along the way. I certainly had my share.

 

That’s why, now, when I see a six-month IT project, it immediately strikes me as too long—there’s so much that can change even in that short window. So definitely throw out those five-year IT roadmaps! I made a one-year plan, and it was good for about one month.

 

The secret to success is to deliver the most value in the shortest time frame, evaluate your new position, and then do it again. Finally, have fun with it!