To succeed in the world of venture capital, it’s important to master the art of calculated risks. That’s something Craig Cimini, head of The Cigna Group Ventures and vice president of strategy and business development at The Cigna Group, knows well.

Case in point: His position as the head of The Cigna Group Ventures is a far cry from his initial plans to be a chief hospital administrator, and Cimini uses his experience as a model for up-and-coming health care professionals.

“I always counsel people who are in the early part of their careers to not get too prescriptive about what their career path is going to be,” he said. “There are always going to be twists and turns along the way, and each one can be a valuable experience that will ultimately help them learn and grow.”

Cimini grew up in the Berkshires region of western Massachusetts, where he spent a lot of time outdoors. “I was a very independent kid, always going off hiking and exploring on my own,” he said. When he wasn’t trekking through the forest, Cimini was playing Little League baseball. He continued to play the sport in high school and college, and while his childhood aspiration to join the Major Leagues was not meant to be, his baseball experience instilled important principles in his life.

“I learned a lot about teamwork and achieving goals, important skills that certainly translate to how I operate today,” he said. He noted that close collaboration and the drive toward successful outcomes are key tenets of The Cigna Group Ventures, which continually seeks partnerships with early stage innovators to find new ways to improve individual health and to help make the health care system work better for everyone.

The path to leadership has twists and turns 

Cimini felt the desire to lead from early in his health care career, inspired by his work as an orthotist at the Orthotic and Prosthetics Clinic at Boston Children’s Hospital, where he crafted braces to restore mobility to kids with severe physical disabilities. “It was really fulfilling work that had a profound impact on the children as well as myself,” Cimini said. “But I felt I could make an even bigger impact if I could actually run a hospital like that one.”

He returned to school, earning a master’s degree in health administration at Cornell University. In order to gain the full purview of the health care industry, he needed to explore the “other side of the aisle,” he said, namely managed care. So he applied for and landed an internship at Cigna Healthcare under its HealthService Leadership program.

“I had a great experience and really valued the mission orientation of both the company and the leadership team,” Cimini said. “So I decided to work at Cigna full time after graduate school.”

The choice to join Cigna Healthcare was itself a calculated risk.

“It’s very important to me to know the people I would be working with, as well as who I would be working for,” he said. “I had no idea who my boss or my teammates would be when I accepted the Cigna opportunity. However, the Cigna people I did work with [during the internship] had a high degree of integrity. They worked hard and were very bright. My experience with those people convinced me that this company was the right place to be.”

Cimini started at Cigna Healthcare in 2008 in client informatics, then moved to strategy and business development, where he established and structured joint venture alliances between Cigna and health care delivery systems. “These health systems were looking to provide their own health plans in addition to being care providers,” Cimini said.

Cimini later became part of the launch of The Cigna Group Ventures in 2018, which focused on investments that drive health care innovation.

“There are a lot of really good ideas out there in the health care space that just need a bit of funding, as well as a strong corporate partner, to take them to the scale where they can do a lot of good and solve a lot of problems,” Cimini said. “We not only look for strong investments, but strong relationship opportunities that can maximize value for both partners.”

Cimini pointed to the investment partnership and eventual acquisition of virtual health provider MDLIVE as an example, but notes there also is value in deep partnerships with innovative businesses that want to stay independent. “Even with companies that we don't invest in, we offer to bring them to our businesses to see how we can work with them to accelerate their strategies and bring them to life,” he said.

Success begins with stopping to listen

Cimini shares that his “secret” to being successful in venture capital investing, as well as in any endeavor in work or in life, is taking the time to listen.

“It’s really important to listen to our stakeholders, business partners, and experts both inside and outside our organization to truly understand what problems they are trying to solve,” he said. “This is vital to determining how an external start-up company can potentially help to form a solution. Taking the time to listen, really listen, is one of the biggest lessons I learned early in my career that is as effective then as it is today.”

He stressed that being an active listener is a key to learning. “We all need to lean on our colleagues and industry experts and learn from the diversity of their perspectives and experiences,” he said, noting that he considers himself a lifelong learner. “I'm always trying to improve my leadership skills so I can help build and lift my team in order to accomplish our goals.”

The Cigna Group Ventures has accomplished a number of successful endeavors, both strategically and financially, in the last few years — and was awarded an additional capital commitment for $450 million by The Cigna Group in 2022. However, Cimini feels his greatest success is with his own team.

“Developing talent is what I'm most proud of,” he said. “The Cigna Group Ventures is composed of many apprentice-type roles, and I certainly wouldn't be successful without my team.”

Leading the way forward

Cimini is proud of what he and his team at The Cigna Group Ventures have accomplished, and he aims to continue exploring new solutions and swinging for the fences.

“We seek to be the premier strategic venture capital partner of choice in the health care industry,” he said.  “We aim to accelerate the business strategies of not just ourselves but of the companies we invest in — so we can bring more innovative personalized solutions to the market faster, driving both positive outcomes and the advancement of health care.”