Ann Gillespie: Succeeding in Both Branches of Government

Not many people enter state government after a successful decades-long run in the private sector.

Even fewer end up serving in both the state Senate and the executive branch.

That’s the path of former Milbank Fellow Ann Gillespie, now serving as the acting insurance commissioner of Illinois. She’s added a whole new dimension to the term “adaptive leadership.” She has brought a collaborative nature to complex challenges like the nursing home workforce and regulating insurance markets, and has demonstrated a fluidity to enact and implement good policy in both branches of government.

It wasn’t part of her initial plan.

Seven years ago, Gillespie was mulling her next act after taking early retirement from a successful legal and management career in the health sector. She was in her late 50s, her kids were grown, and she had plenty of options. But at the time, neither politics nor public office were on her radar.

In January 2017, she decided to travel to Washington, DC, for the Women’s March. 

It was a galvanizing experience.

Back home in the northwest Chicago suburbs where she has spent most of her life, Gillespie connected with women who had been at the march and wanted to “keep on doing things.” The group that once fit in a living room now has about 1,200 members. A dozen or so now hold local or state office.

Gillespie is among them. 

After the march, she began working with advocates in her community pushing for an increase in the minimum wage. Local Democratic officials took note and encouraged her to run for the state Senate in 2018, even though she was in a traditionally Republican district. Gillespie won both a contested primary and the general election.

“I was not only the first woman to hold the seat,” she said. “I was the first Democrat.”

From Private to Public Sector Leadership

Drawing on the well-honed corporate leadership skills and health care expertise she had acquired in executive positions at places like CVS Caremark, Gillespie made her mark swiftly as a legislator. She was invited to join a bipartisan, bicameral Medicaid working group as well as other health-focused Senate panels.  

She had successes. She helped Illinois move to a state-run Affordable Care Act health insurance exchange to better tailor the program to the state’s population. She has worked to improve staffing ratios at nursing homes. She has had setbacks, too, like a stalled effort to revamp “community benefit” requirements for nonprofit health systems that don’t pay taxes.

But overall, she has relished this move to the public sector, this second act.

“It was great,” said Gillespie. “I felt like I could take all the things I’ve learned over the course of my career and be able to put them to use in a different environment.”

She’s had to adapt her corporate leadership skills not once but twice, first to her legislative position and now to her job in the state executive branch.

In those first years as a lawmaker, Gillespie earned the governor’s trust and respect. Last April Gov. J.B. Pritzker tapped her as insurance commissioner. (She’s “Acting” until the state Senate confirms her, likely when they reconvene this fall.)

Pritzker didn’t have to twist her arm. The post puts her in the unusual position of being an implementer for programs she helped bring about as a legislator.

“We do so much work in the General Assembly to pass laws,” she said. “And I wanted to be on the side of implementing some of the work we did.” She’s also been able to help people in the legislative branch better understand how state workers in the agencies do — and vice versa. And that deeper understanding breeds respect.

Collaborating and Adapting

In both the legislature and the executive branch, her guiding star has been the same.

In the corporate world, where she was a leader but not a CEO, she explains, “I could never do anything by fiat. You always had to collaborate.”

Top-down had never really been her leadership style anyway. Having received her Six Sigma Black Belt certification in creating and improving professional processes, she’s known for practicing what’s become known as “adaptive leadership.” This leadership style involves flexibility to allow for managing and adapting to a fluid environment, as well as a team-based approach.

That approach to leadership means “looking at, understanding, your audience, understanding what you might have to shift in order to move your goal forward,” she said. Listening is paramount. But she didn’t just lead. In the legislature, she says, sometimes you have to follow – or at least navigate before moving ahead.

“I had done some regulatory work when I was practicing law, but I didn’t have the political background. So, I had to learn how to navigate the political side of things. I had some great mentors in the General Assembly who I would go to, repeatedly, for advice and for counsel on how to navigate some of those waters,” she said.

She recalls asking “many questions.” But she quickly learned how to spot pathways, form alliances and get things done.

Legislative Accomplishments

In 2023 she carried legislation that will allow Illinois to run its own Affordable Care Act health insurance marketplace. In the photos of the bill signing ceremony, she is standing by Gov. Pritzker’s side.

The state-run exchange, to be fully implemented in 2026, gives Illinois more options to make insurance more cost-effective and patient-friendly than the federal exchange. One protection on the new state exchange that Gillespie cites as an improvement is barring health plans from conducting a utilization review that could result in less care during the first 72 hours of inpatient mental health stays “when it’s so important to stabilize the patient.” Insurers aren’t allowed to make retroactive denials about those critical days either.

“We’re converting to a state-based exchange on the marketplace so that we can have a little more control,” she said.

One of her other big achievements in the legislature was creating a more effective approach to nursing home staffing. Illinois since 2014 had been trying to boost staffing ratios via incentives in its payment system. But six years later, as the pandemic unfolded, not much had changed. In fact, Illinois’ staffing ratios were among the worst in the country.

It was time to try something different.

Gillespie and allies on both sides of the aisle worked with the state Medicaid agency, which wanted to flip what it had been doing. Instead of giving the nursing homes money to bulk up the staff – and then not having them follow through – the new law required the homes to make progress on staffing in order to get more money. The reforms also included bolstering the responsibilities and career path for certified nursing assistants (CNAs), with a longevity stipend for CNAs who stayed on the job that went directly into their paychecks, not to the nursing homes.

“We saw a remarkable improvement,’ Gillespie said. In about a year and a half, Illinois went from the bottom of the pack to the national average.

One of the unusual aspects of her career is that she has had three such different perches – private sector, legislative, and executive. Gillespie is leveraging that experience to trying to break down the skepticism and cynicism that people in one of those sectors can have about people working in the others.

“The process [of making state policy] can make you cynical,” she said. “Or you can try to bring an optimism to the process.” For Gillespie, the choice has been optimism.