Moving Up, Not Elsewhere

In her more than twenty-one years with a single company, Compuware, general counsel Kiley LePage has enjoyed a broad array of professional experiences

Kiley LePage

It was a perfect match from the start: In 1996, Kiley LePage, a fresh graduate from the University of Detroit’s Mercy School of Law, was looking for a job. Compuware, a locally based software company, was looking for an investor-relations manager. The company approached her, and she jumped at the opportunity. In the twenty-one years since, climbing to her current position as general counsel, she’s had a wealth of opportunities to develop her career in one place as business has boomed.

“I was lucky enough to be afforded opportunities for professional growth, including expanding responsibilities and continuing education, so I never felt stuck,” LePage says. “And that’s the goal, isn’t it? As you grow as a professional, you are—or should be—rewarded with additional responsibilities.”

Her company was already experiencing explosive growth when she first joined. “Compuware is more than a local legend here in Detroit,” LePage says. It expanded at a rapid rate throughout the late 1990s, after being publicly traded and rocketing up in stock value. After just a few years of acquisitions and staffing increases, its total number of employees had tripled. A year into LePage’s time there, it became clear that the legal department needed her help full time, so she transitioned to a role within it and, eventually, took over management of compliance and litigation.

Because the portfolios she managed touched every area of the company, the work was never dull. “There wasn’t a ton of repetition, I wasn’t reviewing the same contract day after day, and the work was always interesting” LePage says. She was also inspired by the company’s culture and philosophy during that period. “Compuware emphasizes collaboration always—and in all ways,” LePage says. “And that collaboration cuts out delays.”

She has continued to rely on this philosophy as the company has evolved. In 2014, it was acquired by equity firm Thoma Bravo, and as its lawyers were split between divested entities, LePage stayed with Compuware, ultimately moving into her role as general counsel. Working closely with a smaller team, she has since been involved in every type of legal issue company-wide.

Her rich, collaborative experience with the company was particularly vital in 2016 and 2017, when she helped Compuware close four acquisitions in a little more than four months. Working within that timetable, LePage says, was “an incredible achievement for the acquisition team and the company.”

Outside resources were doubtful about the viability of the schedule the company had laid out, but LePage knew the end result was never in question. “My biggest advantage is my institutional knowledge,” she says. Having worked at the company for so many years, she rarely has to dig through archives for a particular file or explanation because she’s experienced them firsthand.  If she can’t remember a specific detail from a matter, she likely knows someone who can.

Her long-lasting relationships have also been an asset, particularly the one she has built with Compuware’s chief financial officer, Joe Aho, who started at the same time as LePage and who continues to work with her on all deals and acquisitions. “We brainstorm, discuss, strategize, and share thoughts with each other throughout the day, every day, to make sure that the efforts of the finance and legal departments are aligned,” LePage says.

In recent years, Compuware has transitioned to become one of the few companies focused on mainframe technology, creating apps and tools that modernize and revitalize previously antiquated systems. The majority of its US employees are still located in one office in Detroit, and along with the CFO and other long-tenured colleagues, LePage habitually walks the floors to have direct and immediate conversations with the rest of the workforce. She says the shared mind-set of the longer-standing employees helps inspire the recently hired ones. And, now that she’s risen through the ranks herself, she says, “I can directly and positively affect the company’s future because I have a seat at the table, a voice in the conversation, and that has made all the difference.”

She mentions a recent experience with a colleague who came to her with a problem she wasn’t sure LePage could help her with. When LePage said, “Don’t be silly, there’s always something I can do,” both she and her colleague burst out laughing—because they both knew it was true. “I love solving problems, and I’m most professionally satisfied when I’ve had a positive impact, whether I’m negotiating a contract, a deal, or an acquisition or helping an individual employee,” LePage says. “I really enjoy—and do not take lightly—the ability to make a difference.”

As her company continues to lead the way in mainframe technology, LePage is excited, as always, to continue to evolve there as counsel. Her goal now? She puts it simply: “To retire one day—from Compuware.”