Her Story
About Margaret
Margaret Grayson serves as interim CTO for a startup company in deep tech defense and security, a role she has held since March 2026 while under NDA. With more than 21 years of experience spanning startups, mid-size, and large organizations across multiple states, she most recently held the position of VP of Architecture at Expedia until January of this year. Grayson earned her bachelor's degree in structural engineering before pursuing graduate studies, completing a master's in computer science at St. Joe's in May 2002 and a second master's in international marketing at the same institution in May 2004. She furthered her expertise with a 2024 certification from MIT in machine learning from data to decisions. In addition to her professional roles, she contributes as a board member for How to Be Social (HTBS), based in Dallas. Grayson attributes her success to early mentors and the support of her husband, and she emphasizes values such as integrity, honesty, and situational leadership in her work.
Her Interview
Ten minutes with Margaret
01What do you attribute your success to?
I believe I had excellent mentors early on in my career, so mentorship has been key for the way my career has shaped up on a professional front. On a personal front, my husband has been very supportive of my career journey. So that is something that I definitely attribute to a supportive spouse.
02What’s the best career advice you’ve ever received?
I believe the best career advice I've received is, you can't please everybody in this world. 100% buy-in is not possible. So continue pushing forward with high bias to action, knowing fully well that not everybody will be pleased all the time with the decisions that I make. Because as a leader, sometimes we have to make tough decisions in favor of the company. I strongly believe in situational leadership, because every situation is different.
03What advice would you give to young women entering your industry?
Truth fearlessly. Choose fearlessly, back up your decisions by data, but at the same time understand fully well that you cannot please everybody with your decisions. Stand firm on those decisions as long as you make a decision backed by data and you are making the decision in favor of the company. Don't get guilt-tripped. When presenting to a wider audience, acknowledge and give credit without coming across as showing favorites.
04What are the biggest challenges or opportunities in your field right now?
The biggest challenge that I face in the field of work I would say primarily when I started off I had to prove myself. From a technology perspective right now for any organization and for me personally also is primarily to make sure that we go with honest transparency with our teams with the expectations that are there and tying those expectations to business outcomes. AI transformations are nothing like the digital transformations of the past. There are a lot of unknowns.
05What values are most important to you in your work and personal life?
Integrity. I strongly believe in keeping the commitments. Do right by the organization. Choose fearlessly and be honest in your functioning, because people value that. Even if it is bad news that you have to give, don't beat around the bush, be direct. As long as you show honesty and integrity, people will respect you for that.
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