From IT leader to tech spinoff CEO: How to win a CIO-plus role

Early in his career, Andrew Brock was told by a mentor that, to reach the C-suite, you have to take assignments across the various drivers of a P&L: marketing, operations, information technology, and so on.   

At the time, Brock had held finance-related roles of increasing responsibility at household brands such as Kraft and PepsiCo at the time, and the advice piqued in Brock a curiosity that has since marked his career. It led him to accumulate cross-functional experiences that eventually landed him at Associa, which, serving 7.5 million homeowners globally, is the world’s largest residential property management company.

In rather short order, Brock was tapped to lead the launch of Associa’s first client shared-service center, and the success of that initiative propelled him to the perch of CIO, where he inherited corporate IT and the remnants of a forgotten software development group that came via a previous acquisition. Again, his curiosity was piqued. 

“I wondered if we could use the development group to start building our own products,” Brock explains. “We were paying a lot of third parties to provide digital services to our clients.”

Leaning into white space

As it turned out, they could, in fact, build their own products. Soon after repurposing the development group, Brock and that team launched the company’s first digital product: a solution through which residents could pay their HOA fees digitally. This solution, along with other early products the team developed, significantly reduced costs, inspiring Brock to consider whether these products might be commercially viable on the open market. 

The opportunity, as Brock explained, was that the market was fragmented. Associa, as large as it was, owned less than 10% of the residential property management market, even as the market leader. This intense fragmentation meant fewer barriers to entry for entities looking to introduce new solutions, so Brock and his team determined that “if we built a product that worked for us, it could also work for the open market.” And they were right. As these products built a client base and a sales team was mobilized, it became easier to cross-sell more digital services, and by doing so, they created for Associa not only a new organic revenue stream, but a platform by which they could scale their acquisition growth strategy — which, in the era of prop-tech, focused increasingly on digital services.

Once the operation was earning profits and boosting EBITDA, Associa’s leadership formalized what had started as a few experiments into a proper business unit, and to address the reality that their customers consisted mostly of their competitors, they spun off a new entity, called HOAM Ventures, tapping Brock as president and CEO, a title he would add to his existing one Associa’s CIO.

If you, too, are a CIO seeking expanded roles in the C-suite, you’re likely wondering: How can I emulate this strategy? Brock, who admits that luck and timing have been paramount in his career, modestly offers the following advice. 

Establish the right foundations

Brock says he never would have earned more responsibility had he not brought order to IT proper. “Our systems had to be up, stable, and secure, and if any of that went off the rails, I would not have had the time or confidence of my peers to pursue this path.”

He emphasizes the importance of hiring leaders that can “manage the operations as you are leaning into the white space,” and he rejects the notion that, by empowering such a team, you might render yourself redundant. “It can be scary letting go, but it’s a necessary step to allow the space required to determine your beachhead, and, ultimately, scale any business.”

Brock suggests that, if, as a CIO, you lack a cross-functional upbringing, you can build these aspects of your resume in myriad ways. For example, you could volunteer to lead a large acquisition integration, which Brock sees being especially relevant. “You’re analyzing a company, function by function, examining their merits, and figuring out how to put the pieces together to maximize value.” Moreover, the highly cross-functional nature and visibility of integrations can only help you gain relevant experience, he says.

If your company isn’t acquisitive, Brock advises joining the steering committee of another cross-functional transformation program, an opportunity available to most CIOs. When such a program is executed thoughtfully, it wins hearts and minds, adding stamps to your functional passport. 

State your intentions and carry yourself accordingly

Even with the right team and resumé, ascending to “CIO plus” requires some self-advocating. “Nobody is going to ask you to take on this role,” Brock explains. “There’s a lot on you to make your intentions known.” 

For Brock, this meant talking with CEO John Carona. Brock recalls expressing early on that, while he was grateful and honored to serve as CIO, he was open to more. “I shared that if the opportunity were to present itself, I was keen to explore a broader leadership role,” he says.

Additionally, as he was coming up, Brock carefully cultivated his brand, so that when he would in fact get the chance to expand his responsibility, his peers would support his candidacy. “Of course, I’m the technology specialist when it’s needed, but that’s not how I brand myself or operate within the organization,” he says. “I try to ask operational and budgetary questions that demonstrate my grasp of the business. If you aren’t intentional about this strategy, you could get pigeonholed.”

Seize the CIO mandate

Luckily, as CIO, you have a unique purview in the organization. “You’re the only person that can see holistically across the organization and how all of the systems, functions, and process work together,” Brock says.

By coupling this view with your responsibility to chart the company’s digital transformation, you discover new avenues to create areas of opportunity, he points out.

“There’s bound to be customer and business needs adjacent to technology that haven’t been explored: This is your chance to stake your claim. You have to discover it, want it, and raise your hand,” he says.