Shentel CIO Elaine Cheng

The Art of Encouragement: Elaine Cheng on Navigating and Leading the Digital Frontier

March 23, 2026 at 2:11 PM EST

In the technology sector, we are often obsessed with hard infrastructure. But as we celebrate Women’s History Month, Shentel’s SVP and Chief Information Officer, Elaine Cheng, is focusing on the people who make this infrastructure work.

In a recent appearance on the JSA Women in Digital Infrastructure video series and an article for TechDay, Elaine shared her journey from an unintentional tech recruit to a C-suite leader, offering advice on how women — and their male allies — can build a more inclusive digital future.

The Career Start and the Bus to California

Elaine’s entry into the world of technology wasn't a calculated move. When she started, the word "digital" wasn't part of the professional lexicon. She transitioned into the field through project management, learning the ropes just as digital infrastructure was emerging.

Her advice to those starting today? Embrace the unpredictable. Elaine uses a vivid analogy for career growth: "You might be getting on a bus that’s going to drive to California. You might not know where you’re going to end up in California, but if you don’t get on that bus, you’re going to stay where you are."

The takeaway is simple: Take the opportunity first and figure out the destination later. In an industry she describes as dynamic, being stationary is the only real risk.

Beyond the Resume: Mastering "The Art of Encouragement"

While we’ve made strides in representation, Elaine points out that the true measure of success is how we encourage people at all levels to lead. In her TechDay article, she details a concept she calls "The Art of Encouragement," noting that while mentorship (giving advice) is valuable, the real silver bullet for women in tech is sponsorship. This is the intentional act of opening doors, validating contributions in high-profile meetings, and speaking her name in rooms she hasn't entered yet. True sponsorship is about moving from passive support to active advocacy.

Elaine’s TechDay article breaks down these specific strategies, including "The Power of the Invite" and combating the "Only Syndrome," offering a guide for leaders who want to build an environment that promotes and celebrates the advancement of women in the industry.

Lead From Wherever You Are

You don’t need a title to be a leader. Elaine encourages corporate volunteering, which is raising your hand for special projects or pitching ideas to your manager. Even if an idea isn’t implemented, the act of being proactive makes you visible.

"Encouragement is not a zero-sum game," Elaine notes.

By dismantling the myth of the token seat at the table, women can move from a culture of competition to one of community. At Shentel, this philosophy of building internal relationships is what fuels the ability to connect external communities.

Join the Conversation

Are you ready to master the art of encouragement or take your own bus to California?