Portrait: Stephanie Bailey, Senior Director of Marketing at AgileCraft

The more women you see in STEM, the less intimidating it is for others to join

Gabriela Motroc
Hands of woman image via Shutterstock

Women are underrepresented in the tech sector —myth or reality? In addition to the Women in Tech survey, we also launched a diversity series aimed at bringing the most inspirational and powerful women in the tech scene to your attention. Today, we’d like you to meet Stephanie Bailey, Senior Director of Marketing at AgileCraft.

Is tech a boys-only club? So it seems. But the light of smart and powerful women is finally shining bright. We root for excellence and justice and, above all, we want meritocracy to win. This is our way of giving women in tech a shout-out.

A research study by The National Center for Women & Information Technology showed that “gender diversity has specific benefits in technology settings,” which could explain why tech companies have started to invest in initiatives that aim to boost the number of female applicants, recruit them in a more effective way, retain them for longer, and give them the opportunity to advance. But is it enough?

Women in Tech — The Survey

We would like to get to the bottom of why gender diversity remains a challenge for the tech scene. Therefore, we invite you all to fill out our diversity survey. Share your experiences with us!

Your input will help us identify the diversity-related issues that prevent us from achieving gender equality in technology workplaces.

Without further ado, we would like to introduce Stephanie Bailey, Senior Director of Marketing at AgileCraft.

Stephanie Bailey, Senior Director of Marketing at AgileCraft

Stephanie is the Senior Director of Marketing at AgileCraft, a company which helps hundreds of organizations to scale Agile to the enterprise. Although her parents did their best to cultivate her love for math and science by sending her to Science camp, special programs and more, as Stephanie matured throughout school and into high school, the focus and guidance weren’t there.

As the social and peer pressure grew so did the negative stereotypes.

My father was a CFO of Fortune 500 companies for most of my life and he wanted me to follow in his footsteps. He even bet me a substantial amount of $ that I would become a CPA after college. For those that know me, that thought is laughable (no offense to all the accountants out there) and lucky for everyone, I won the bet. My entire career has been spent in the tech space. Right out of college I was able to get my first job with a company that supported technology companies. Ironically, I started out as a financial analyst.

I enjoyed working with numbers and playing with real money. I was promoted within a year but I quickly learned that it wasn’t for me. So, as I saw an opportunity to move out of finance I jumped on it. My leadership team was willing to take a chance on me since they saw my potential and lucky for both of us, it paid off.

The shift really came with the birth of my first child. I made the choice to get into the workforce right out of college and put my MBA on hold. It came to a point that I had decided it was time to go back and applied at William & Mary EMBA program. I was accepted and couldn’t have been happier and then found out I was pregnant with our first child. So, as you can imagine, I had to decline the acceptance. I returned to work after the birth of my son but the environment had changed. Expectations were different. I still was on a good career path but the pace dramatically slowed.

The importance of having a role model

My role model is Beth Comstock, Vice Chairman of GE. She inspires me on many levels. Although I never met her, I admire and follow her for not only her role as a female executive but the career path she has taken to at GE. Her progression from CMO to Vice Chair is impressive.

It’s important for women in high visibility leadership roles to speak up and drive change and Beth does that. She makes a mission to leverage her power and influence to make a positive impact. Similar to Beth, I was an introvert growing up and I had to outlearn it. One of the challenges women face is not having the confidence to speak up. Being an introvert adds another layer to that challenge. She believes diversity drives innovation and I couldn’t agree with her more! I’m an avid reader (or should say listener to Audible) and her book recommendations are great!

She taught me her biggest success was my success and she meant it.

It wasn’t a smooth ride to the top

A Senior Vice President I worked for early in my career tried to stop me from learning and advancing. Everyone knew he favored men. He was condescending, would treat most women like “objects” but he was good at his job and consistently exceeding plan so it was overlooked. He “pit” the women against each other and it created a tough environment. Even though he talked about my career path through the years, when the promotion cycle came he always found an excuse not to make it happen.

It came a point that I wanted more – both to learn more and try a new role where I felt I not only I could make a positive impact but would help my career path. Another team had asked me to fill a role within their org and I was all in but to get there I had to get this executives approval first. Let’s just say he was less than supportive. Told me it was a dumb move, didn’t get the role, spoke poorly of the other team, and more. He basically looked at me as a traitor for leaving his organization vs supporting my career path and my decision. I politely told him thank you for his advice and moved on. In the end, the pain was worth it. This transition landed me with one of the best female bosses I have ever worked for. Her approach to leadership was night and day to what I had left. She was a servant leader. She taught me her biggest success was my success and she meant it.

A day in Stephanie Bailey’s life

I head up marketing for a male dominated, global, high tech start up. My team is responsible for the brand, demand generation, digital, product marketing, partner marketing, PR and more. Very cliché, but there isn’t a typical day here and as you can imagine, it’s very busy.

I work from home full time so right when I get up I am ready to go. Each day I get up around 6 so I have time before the kids and my husband get up. First thing I do is check email to see if anything important came in from the team in APAC while I was sleeping. Then I look at my to-do list created the night before. I get a thrill every time I cross something off that list. From there, I either focus on writing (I write best in the morning) or get started with the news. I read about our space, analyst reports and get all my social posts set for the day. The kids are now up and ready to go and I always take my daughter to preschool. It’s the fun part of the morning for me. We sing in the car together. This week’s favorite is “Chained to the Rhythm” by Katy Perry. It’s a quick drop off and them I am back to my desk. Many people stare and laugh at us signing so loud but as I tell my daughter, don’t let it bother you, keep going! I am building the confidence from an early age. So much for that introvert in me.

Next up is tackling some of the emails and deciding which hat in my role I will be wearing that day. An hour later I make it a goal to go and workout. When my husband is working from home, we go and run together. Gives us a time to chat and catch up, albeit while I am out of breath. Two days a week I head to Orange Theory for a class. If I can master one of those classes then I can do anything.

Then it’s back to the grind of the day. Between meetings and quick conversations and updates – I somehow fit in driving the marketing strategy, measuring the performance of the tactical plan, deciding on whether we pivot or stay on course. I always joke that my goal in marketing is to make sure all the sales guys are driving really expensive cars. I believe marketing and sales should work hand in hand so I have checkpoints with our sales team daily. How are leads flowing, are we driving the right pipeline, what else can we do to support you to move leads future into the sales cycle and more. I work for one of the most amazing CEOs. Our relationship really creates an environment to excel. He also loves marketing (and is good at it) so he and I touch base at least once a day.

Each night I try and stop by 6 pm to have dinner with the family. I’d say I have a 50/50 success rate here especially due to some of the later calls we have scheduled due to our global workforce. But as soon as I am able, I take a break. Most nights I drive some sort of carpool for sports so that gives me a great opportunity to not only spend some time with my son but on the way home to listen to my latest book on Audible. Almost complete with Beth’s recommendation of GRIT, highly recommend.

Once the youngest is asleep I am back online working for a few hours. Allows me to cross some more key things off the to do list and get ready to start all over the next day.

As you get deeper in technology, women shy away

As you get deeper in technology, specifically high tech and startups, women shy away because we are more risk adverse. We need more trailblazers. Women to stand up and be comfortable being the only female in the room. It can be intimidating. But you need to be willing to take the risk. That’s what I love about startups!


  • The pressure you put on yourself to conform – be you, be great, don’t conform
  • “Manspeak” – How many times you’ve been in a meeting where a male feels he has to “translate” what you said?
  • Sole survivor – being the only woman in the room or on a team. Don’t let the intimidation get to you
  • Pay gap – don’t be afraid to ask for what you want
  • Frat house – many peers of mine share the constant challenge they face: how men will act in meetings or when you travel with them. Don’t be afraid to speak up and share your opinion. It’s work, not college.

Equal pay or better pay for women translates into more money funneling into our economy since women are the decision maker for most household purchases.

The mission of Women In Technology highlights that when one woman helps another, amazing things can happen. As Beth Comstock says, diversity drives innovation. More women = more diversity = more innovation. Innovation helps drive our country forward. Innovation helps find cures for cancer, accelerates space travel, creates new products that protect us and make a safer world. We need these to continue to be the best country in the world.

Studies also show a positive impact in higher valuations and profits for companies when women executives exist. The more women you see in STEM, the less intimidating it is for others to join as well. Equal pay or better pay for women translates into more money funneling into our economy since women are the decision maker for most household purchases.

If anything, things have gotten worse. Over one million people came to the Women’s March in DC alone and it’s unfortunate how many people asked “Why did we feel the need to march? What exactly do we feel was being taken away?”

Change is not going to happen in the short term and it’s going to take a lot to see results from the current debate. The key is to continue to push forward. Large corporations need to step up and it can’t be one and done. Take Audi as an example, for the Super bowl they created an ad about equality. It was great, dad and his young daughter, great message overall but the backlash it received was shocking. Just looking at the hateful comments on the YouTube page provided a reality shot into how some people feel about the topic and our current state.

Point is, Audi shouldn’t stop. They and others can lead the way and continue to promote equality, diversity and more. At the same time, women need to continue to support women. We play a role in this pivotal change. If and when we do this, amazing things can happen and I am willing to play a part to pave the way for my daughter and her future.

Once a month I mentor as part of the Women in Technology program. Each time we are paired with a new “protégée” and each time the discussion changes but always ends back on the same core key areas. Within the program, participants are at various stages of their career, some are starting out, some have hit a plateau and some are just getting back into the workplace. At AgileCraft, our #1 thing we look for in a teammate is if they are hungry, humble and smart. I believe in that and carry that message to others.

Regardless of their stage, I always share the following:

  1. Create your personal brand
  2. Don’t be afraid to speak up
  3. Find a mentor
  4. Create a network and nurture it
  5. Always be learning, every day
  6. Celebrate and promote your successes and those around you
  7. Find something you love
  8. Surround yourself with people you like
  9. Support your female peers
  10. Make sure to connect with me on LinkedIn, always happy to meet

I don’t sugarcoat what it’s like to be a woman in tech. It’s tough but as you build your confidence in yourself and your career, it’s easy to work your way through the jungle.


Gabriela Motroc
Gabriela Motroc was editor of and JAX Magazine. Before working at Software & Support Media Group, she studied International Communication Management at the Hague University of Applied Sciences.

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