Building the Room Where Women Rise: Rebecca Woods and Bluebird Leaders
In 2024, I was at a crossroads. I was trying to figure out my voice, not just professionally, but who I really was and what I wanted to stand for.
I leaned on a few trusted people during that season. A mentor pushed me forward, another introduced me to a community I had never experienced before, and I walked into my first SOAR conference not quite knowing what to expect.
What I found changed everything. Real friendships. Genuine support. A room full of women and allies actually showing up for each other.
It gave me the final push I needed to launch Tech She Secures.
That’s what Rebecca Woods built.
And I’ve been a proud Bluebird ever since.
So, when I say I’m honored to share this interview with you, I mean it personally. I’ve wanted to share Rebecca’s story with this community for a long time. I think you’ll understand why once you read it.
Opening + Origin Story
I was introduced to Bluebird Leaders through Sarah Richardson, and saying yes to attending SOAR and joining this community ended up being one of the best decisions I’ve made. Before Bluebird Leaders existed, what gap or need did you see that made you feel called to build this community?
Before I created Bluebird Leaders, there was a major gap in seeing women in healthcare IT, especially in healthcare IT leadership.
The idea really started when I went to my first CHIME conference. I went down to the first mixer, and everyone at the bar kept asking what I did for CHIME. When I turned my badge around, it actually said CIO. They didn’t even realize I was a CIO.
I know I was young at the time, I was 30, but when I looked around the room, there were barely any women there. And this was almost 15 years ago.
That moment stuck with me.
For those who may know your work but not your full story, how would you describe who you are beyond your titles and roles?
I'm a leader at heart, but also a motivator. I find that I'm often able to help people change their perspective and get to where they really want to go. I love helping people achieve the ideas and dreams they have in their heads.
My background stems from being a very competitive athlete, and I carry those leadership qualities forward not only when I build my teams, but also in how I’m raising my two small human beings, who both happen to be girls.
I want them to be strong and ready for the world.
Building Community with Intention
Bluebird Leaders feel different from many professional spaces. There’s a genuine sense of care, support, and “we actually want to help each other.” Was that intentional from the beginning, and how did you protect that culture as the community grew?
I think I’ve been able to set the tone for Bluebird Leaders from the beginning. People see that I’m open, loving, and truly want to help others excel. As Bluebird Leaders has grown, people carry that mindset forward.
I also have a different perspective when it comes to meetings and conferences. As someone who truly struggled in school growing up, I really don’t want these experiences to feel like school.
I believe we can mix friendship, family, and business together while still having a lot of fun. That’s why we have things like Pink Feather dinners and PJ parties at night for networking. We also recently added Color and Coffee during the day on the last Friday of the month.
Those moments allow us not only to support each other professionally, but also to actually get to know one another. In the long run, when you need advice, are trying to solve a problem, or even making a business decision, you’re going to call the friend you trust, not just some random individual.
What does real community mean to you, especially for women in healthcare and technology?
Community to me is exactly what Bluebird Leaders is becoming.
It’s a phone-a-friend network that helps you prepare for your next opportunity, something that often comes from conversations with people you trust. For years, men built those kinds of networks on the golf course or while playing poker.
We’re building that same kind of community for women, one where we circle around each other and help each other out, whether it’s navigating a new job, supporting someone through a loss, or celebrating a milestone.
It also creates a space where women don’t feel so lonely at the top in the C-level suite.
Leadership, Visibility, and Creating Space
You’ve created spaces where women feel seen, supported, and encouraged to show up fully. Why do you think creating safe but challenging spaces for women leaders matters so much?
For years, many women didn’t feel like they had a voice at the table or a place where they could openly talk about challenges.
Creating a safe space where women can share, support each other, and grow is something we truly pride ourselves on with Bluebird Leaders.
We also help mentor younger individuals and others earlier in their careers, giving them the motivation and power to believe they deserve a seat at the table and that their voice matters.
In your own leadership journey, were there moments where you didn’t feel like you belonged or had to create your own seat at the table?
Absolutely. I think there are always moments, even now, where you second-guess yourself about certain seats at the table.
For me, though, I’ve always had a clear direction about where I wanted to go. When I became CIO, I always knew I wanted that role. What I didn’t realize was how difficult it could be to be in the boardroom as the youngest person by far.
While everyone else was talking about grandkids, I was sitting there pregnant with my second child. I had to carefully choose my words, whether it was explaining the technology challenges the hospital was facing or making sure I wasn’t dismissed as just some young person with a “crazy idea.”
Sometimes you really do have to watch how you frame things.
There were also moments when I was laughed at, not believed, or when other leaders tried to intimidate me. I think that's where I learned to stay calm in all situations and not freak out, because in the end things usually work themselves out.
The Leap
You’ve had a long and successful leadership career, and at some point you chose to build your own company. What led you to take that leap of faith and create something of your own? What helped you find the courage to do it?
Oddly enough, what led me into entrepreneurship was being laid off.
At the time, I was at the height of my career as a VP of Provider Services at a hospital organization. Suddenly I found myself applying to what felt like thousands of jobs.
I decided to take the summer off and spend time with my kids at the beach. At the same time, I trained for my first marathon.
My husband eventually gave me the push I needed to start my own company and go out on my own. That was in 2018, when I launched Bluebird Tech Solutions.
For women who feel the pull to build something of their own, whether a company, a community, or a movement, what advice would you give them before they take that leap?
It's hard to take that jump, that leap of faith. But if you truly have passion for something and your gut is telling you it’s the right decision, sometimes you just need a phone-a-friend, someone like a Bluebird Leader who will encourage you and remind you that starting your own company isn’t as intimidating as it might seem.
It does take a lot of blood, sweat, and tears. But the payoff can be phenomenal if you’re willing to put in the hours.
Fuel for the Journey
Leadership can be isolating, especially at higher levels, and the work you do for both Bluebird Leaders and your own company, Propel Health Advisors, can be incredibly demanding. How do you personally take care of yourself, and are there any favorite self-care rituals that help you stay grounded?
One thing I’ve always stayed committed to is movement. As an athlete, I need to work out, lift weights, or train for some kind of race to keep my mind steady.
Running has always been that outlet for me. It’s often when I come up with my best ideas because I’m not sitting in front of a computer. My mind has space to wander and daydream.
Over the years I’ve completed a marathon, several half marathons, and even a Half Ironman, which includes a 1.2-mile swim, a 56-mile bike ride, and a half marathon run.
This year I’m even considering an open-water swim race in New Hampshire that’s about three miles long.
Industry Lens + Looking Ahead
With your vantage point across healthcare IT and leadership, what trends or shifts do you think leaders should be paying closer attention to right now?
I think leaders should be paying much closer attention to their employees and what their needs really are.
Many people are having a very difficult time with work-life balance right now. And while that’s hard, I also believe that when someone isn’t truly passionate about their role, work-life balance becomes even harder.
Leaders should be communicating with their teams and asking questions like, “What do you really want to be when you grow up?” Helping people grow into the roles they want is what true leaders should be doing.
As you look ahead, what excites you most about the future, both for Bluebird Leaders and for yourself personally?
I’m truly excited to see where Bluebird Leaders can go and how we keep growing.
I also truly value all the partnerships we’ve built with so many organizations. I see Bluebird as something that can plug into many larger organizations like CHIME, HIMSS, ViVE, and others.
That’s exactly why I set Bluebird Leaders up as a nonprofit. I wanted it to be something that could collaborate widely and show that true collaboration is possible, while also helping other phenomenal organizations grow women in IT and healthcare IT.
If you could leave the Tech She Secures community with one reminder or piece of advice, what would it be?
Reach out. Build your network. Make connections.
Those “phone-a-friend” relationships will last for life and will always be there for you.
I also encourage every woman to continue building her personal brand, especially on LinkedIn. Don’t be afraid to post things just because you’re worried about someone judging you.
There’s always someone out there quietly watching who may need to hear exactly what you’re about to share.
Signature Tech She Secures Question
Tell us about the “BADdest” challenge you’ve taken on in your career—the boldest, most authentic, and driven moment you’re most proud of—and how it shaped you.
I think the boldest thing I’ve done is establish Bluebird Leaders.
The first year I launched it in June, and then I took a huge leap and organized the very first conference that November. We had 80 people show up.
My gut hurt the whole time leading up to it. I didn’t think anyone was going to come. I wasn’t sure anyone felt the same way I did about the need for this kind of community.
But when those 80 people showed up, and especially when Ed Marx came with his wife as one of the speakers, that’s when I realized I might be onto something.
Year after year it has grown, and I’m still amazed. It’s become a community of people who circle around you and help you navigate the hardest challenges.
Closing Reflections
After sitting with Rebecca’s words, one thing stayed with me: “There’s always someone out there quietly watching who may need to hear exactly what you’re about to share.”
That reminder captures so much of what community really means.
It’s also why I started Tech She Secures. It’s why I said yes to Bluebird Leaders. And it’s exactly why I knew I wanted to bring Rebecca’s story to this platform.
If you’ve been sitting on something, an idea, a leap, a version of yourself you haven’t fully stepped into yet, I hope this conversation gave you a small nudge forward.
And if you’re not already part of Bluebird Leaders, go find them.
Rebecca, thank you for building a place where women don’t have to figure things out alone, and for reminding all of us that the community we need is often closer than we think.
Sometimes we just have to say yes.
Maliha
Disclaimer: The content on this blog and website reflects a combination of my personal experiences, perspectives, and insights, as well as interviews and contributions from other individuals. It does not represent the opinions, policies, or strategies of any organization I am currently affiliated with or have been affiliated with in the past. This platform serves as a personal space for sharing ideas, lessons learned, and meaningful reflections.
