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Challenge and believe in yourself

Jan Garrison

Engstrom addresses Culver students


January 28, 2022

Jamie Engstrom looks for opportunities to challenge herself. For 23 years, she has worked for Caterpillar Inc., the world’s leading manufacturer of construction and mining equipment, diesel and natural gas engines, industrial gas turbines, and diesel-electric locomotives. She has risen through the ranks to become the vice president with responsibility for the Global Information Services Division and the company’s chief information officer.

She leads a global team responsible for managing the hardware, software, and systems that keep the Fortune 100 company running 24 hours a day, seven days a week, 365 days a year. When there is a problem, she told The Rubin School for the Entrepreneur class, it is common for it to happen on a holiday or weekend. It is an always-on environment.

Engstrom visited Culver Academies on Wednesday, Jan. 19, to address members of Culver Girls Academy and students in The Rubin School. It is part of the continuing women in business series as part of CGA’s 50th anniversary. She covered the challenges of being a leader; being a woman C level executive at a company where 20 percent of the more than 100,000 employees are women, and managing the work/life balance.

Work/life balance has taken on a new level of importance over the past two years. Engstrom and her team have developed ways for employees to work through the COVID-19 pandemic. It continues to be a set of “challenging circumstances,” she said, as employees are now moving to a hybrid environment, as they continue to balance the needs of family and work.

For Engstrom, dealing with work/life balance is not unfamiliar territory. She spent three years living in the United Kingdom, leading the IT team supporting Caterpillar’s Electric Power Division. She quickly learned the pace is different and setting aside time for coffee or tea is an important part of developing professional relationships.  It was an opportunity for the staff to come together, talk, and enjoy each other’s company. “We need to adopt that work environment across the globe,” she added.

She was asked to take the overseas post, not because she was the most knowledgeable, but because of her soft skills for building teams, her adaptability, leveraging strengths of others and problem-solving. It was a major change, moving 4,000 miles from her family, and she admits, “I was scared to death.” But it was also the opportunity to challenge herself both personally and professionally.

She realized “the way you know is not necessarily the right way.” The experience taught Engstrom that regardless of your nationality and the cultural norms you’re accustomed to, it’s important to be open to new perspectives, because it helps create a more inclusive environment. The challenges and opportunities she faced have made her a better leader and person.

“It’s easy to be comfortable,” Engstrom explained, but “nobody wants to work for a weak leader. You have to challenge yourself, learn and get stronger.”


Engstrom meets with CGA students after her talk.


And, she explained, she understands that she oversees people “who are way smarter than I am.” It is her job to make them successful by removing roadblocks, advocating for them, and making sure they stay updated in their training “so they can do bigger and better things.” Their individual success makes the entire team successful.

Engstrom got involved with information systems while studying business management at Illinois State University. She had a counselor who said there were openings for application developers with Y2K (Year 2000) approaching. There was a growing concern that internal clocks in computers would not be able to make the transition from 1999 to 2000, so she had a double-major in business management and information systems. She joined Caterpillar in May 1999. The Y2K concerns were unfounded. The new century  rolled in without a glitch.

Since that time, Engstrom has held various positions within the company across the procurement and information technology divisions. Her background includes global leadership accountabilities in large-scale systems transformations, global data center management, worldwide network, servers and storage, database management, help desk operations and desktop management. Prior to becoming CIO, she oversaw the information systems for the Financial Products Division. She has lived in Peoria, the United Kingdom, and Nashville, Tennessee.

She credits her long tenure with Caterpillar to the steadfast vision and the culture built on strong core values. That includes leaders being willing to sit down with their employees to get to know and understand them better.

Everyone, and especially women, should seek out mentors and sponsors, Engstrom told the CGA students. It doesn’t have to be the same person. A mentor is someone who makes you feel you are in a safe zone, so you can be vulnerable and authentic. Also, a mentor will tell you the things you may not want to hear. A sponsor is someone in your company who will advocate for you and speak to your results.  A sponsor can and does provide coaching, but she acknowledged it is important to have a mentor you can lean into for transparent feedback for personal development.

Engstrom also stressed “learning agility,” which is the willingness to change your perception. When bringing people into a team, she is looks for those who are willing to “create the how” rather than saying “we can’t do that.” That is why it is important to know your people so you can leverage their strengths and skills together.

Her advice to the girls was to have confidence in their abilities and be willing to voice their opinions. Too often, women don’t trust their own judgment. One of her favorite sayings is “I made 99 mistakes today, but I got one thing right.” Accept that failure is an essential part of the learning.

And, remember, that “leadership can come without a title,” Engstrom said. Be authentic, approachable, and positive with others. For yourself, be willing to take risks and overcome that negative self-talk.

“Believe in you.”

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