Isaac Sacolick is Digital Transformation’s North Star

Isaac Sacolick examines what practical steps companies can take when approaching digital transformation strategies

Isaac Sacolick is an expert in agile practices, devops, and data science—all of which are critical to successful digital transformation programs. As the president of StarCIO and author of Driving Digital: The Leader’s Guide to Business Transformation Through Technology, Sacolick was the perfect candidate to guest edit our dive into digital transformation.

Isaac Sacolick, StarCIO

Sacolick selected three executives he sees as thought leaders in the space: the State of Oklahoma’s Matt Singleton, AIA’s Jeffrey Raymond, and Texas United Management Corporation’s Ross Tucker. Here, we unpack their innovative strategies and processes for digital transformation.

When speaking of digital transformation, you could point to Isaac Sacolick as a true thought leader.

Sacolick runs the consulting firm StarCIO, which helps organizations implement digital transformation programs and focuses on agile transformation, data science and integration, product development, portfolio management, sales and marketing technologies, outsource enablement, and other related services. But previous to starting his own company, he has seen digital transformation from almost every angle. As an entrepreneur, he was a CTO at startups in the media and travel industries. As a corporate tech leader, he was CIO at businesses in the media, construction, market research, and financial services industries, leading transformation, developing customer-facing products, and establishing data-driven organization. Over the past decade he’s seen it all.

Now, he shares his advice with others. He writes blog posts for,, and InfoWorld. Last year, he published Driving Digital: The Leader’s Guide to Business Transformation Through Technology, in which he shares best practices for leading digital transformation. Sacolick sat down with Sync to discuss where the digital revolution has been, where it’s going, and how to stay ahead of the curve.

How has working in a variety of different industries helped inform your approach to digital transformation?

Isaac Sacolick: I was lucky, in some respects, that I got involved in the media industry in the 1990s, specifically with newspapers. I got to see what the impact of digital was on the industry before there was even the term “digital transformation.” Media and publishing got hit early, and retail is in the midst of a transformation. It’s more like a rollercoaster ride in retail as competition intensifies and as new technology capabilities enable better customer experiences. You’re starting to see it in industries like financial services and manufacturing, and I think the next big wave will come in things like healthcare and transportation.

Different industries have different time lines, but some of the underlying mechanics that force existing companies to consider transformation are the same: How do you get closer to your customer? How do you improve their experience? How are you integrating your experience online and digitally with offline and physical experiences? Those are important themes across all industries. How do you get more competitive with analytics? You need to become more automated and efficient because the cost structures, once digital takes hold, tend to have a significant impact.

Then, it requires a complete change in the cultural mind-set: How do you move smarter and faster? How do you be more innovative? How do you get more of your workplace involved in adopting and using technologies and collaborative experimenting and iterating on new ideas?

How do you feel about the phrase “digital transformation,” and what does it mean to you?

Sacolick: Right now it’s a little bit diluted. People apply it to mean a lot of different things. For me, it means that businesses really have to reimagine what markets they want to be in and how they want to rebuild legacy products as digital and data-backed experiences. The competition in their own markets is going to get tougher. To have long-term impact, organizations need to be competitive with emerging technologies, whether it’s with AI, blockchain, or IoT.

What are the biggest challenges facing legacy companies?

Sacolick: The biggest challenge for legacy companie first starts with thinking about transformation. There are a couple surveys that have come out in the past few years that say that 60 percent of companies don’t have enterprise digital strategies. If that’s real, then it starts with thinking about strategy, which can be a major challenge for some companies.

Even when they have a strategy on paper, I find that legacy companies have a hard time going from that paper strategy to execution. What they don’t fully recognize is that to take a strategy and start executing on it, it requires a bottom-up cultural change. It’s a bottom-up execution, and that means that you really have to engage the staff on what their ideas are and how to collaborate with agile practices and mind-sets. You have to engage them on doing pilots and proofs of concept to see what experiments are yielding value. You have to learn a lot about what customers are telling you, what the ecosystem is telling you. In my recent post, the number one reason why digital transformations fail is because executives fail to embrace that it’s a bottom-up transformation that will require change across the organization

How important is it to involve other departments in your transformation strategies?

Sacolick: Transformation really doesn’t happen without cross-functional teams. You can get projects done by saying this project requires IT to do this, marketing to do that, and sales to do something else. But when something’s going to be transformational, working in silos like that means that you won’t see where the intersections provide new ideas and new value. It is critically important to put cross-functional teams together that adopt agile practices and mind-sets and align on what they’re trying to accomplish, who’s doing what, and how do they get there.

You’ve said tech leaders delegate too much. What do you mean by that?

Sacolick: What I mean is that you can’t lead or be a leader in a transformation program by sitting in an ivory tower and managing things by delegating to your staff and reading reports and setting strategies. Things are happening too fast, and the technologies are changing too much. The relationships that you build with people to get them on board requires spending a lot of time meeting people.

My advice to leaders in this area is, number one, get out of the office, go meet customers, get your own vantage point about how they’re leveraging your products and services, and gain perspective on competition . That’s no longer just a job for sales or marketing to do. There’s so much technology in place at different companies that having a CIO or CTO go into a customer’s office and see what’s going on is highly valuable.

I also mean that CIOs have to spend a lot more time understanding the technologies and platforms that will make their transformations successful. Picking the right technologies and getting value from them can make or break a transformation program. How will new technologies integrate? How will employees be smarter and more productive using them? How will the technologies enable new products and services?

How do you see the CTO and CIO roles changing in the future?

Sacolick: It’s a role that is constantly changing in mostly good ways. I do think CIOs and CTOs, in particular, have to be looking out because as technology and digital become more important, there are some organizations that are looking to put more function and responsibility under the CIO. Then there are others hiring chief digital officers and splintering off a lot of responsibility from the CIO.

CIOs are valued by the solutions that they provide to the business, particularly around customer-facing issues, and they’re measured by how much they actually impact the business. They have to be business partners with a wider range of functions in their organization. That’s coming from the fact that almost all organizations are building or buying technologies that are involved in the customer experience.

Why did you decide to write Driving Digital, and what do you think readers can take away from the book?

Sacolick: I wrote the book because I felt that leaders in transformation programs needed to understand how to manage and run these programs. A very important part of being a leader is sharing what you know and teaching others. When I did a couple of talks a couple of years ago around transformation, I decided that it was important for me to take my practices on the StarCIO blog and now in Driving Digital to see how I could help others.

I got the sense that this was really an inflection point—that it was happening across industries. Although it was happening on different time lines, a lot of the practices that I have put in place are universally applicable across industries. I call them driving digital practices, the DNA of organizations to be successful around transformation programs.

In the book, I share best practices in product development, how to leverage data in decision-making, how to institute agile transformation, and how to influence culture change across the organization.

Photos: Peter Garritano