Welcome back, Trailblazers! Today, Tiffany Benitez sits down with someone who is shaping the future of technology in a big way. Meet Stephanie Cheney, a product leader who has built her career by bridging the worlds of business and AI.

Stephanie’s story begins with a teenage love for coding and takes us through a winding path that includes entrepreneurship, a leap into software engineering, and ultimately leads to innovative AI projects. Her journey is proof that you do not need a perfect plan to succeed. “You don’t have to be an engineer in the age of AI,” she says. “Just start.”

We also get real about the challenges women face in tech. Stephanie shares how she has navigated rooms where she was often the only woman present and how important it is not to let those moments silence your voice. Instead of trying to blend in, she has learned to bring her own perspective to every conversation.

When it comes to AI, Stephanie offers a fresh take on why women are uniquely equipped to thrive. The skills that make great leaders, like giving context, building connections, and thinking strategically, are the same skills needed to guide AI forward. This is not just about learning new tools; it is about shaping what comes next.

Here are the key takeaways:

(3:13) Embracing who you are in the age of AI

(3:50) Why fitting into boxes holds women back

(6:14) Upskilling without starting over

(8:35) The risks women must start taking

(10:13) The real challenge of being the only woman in the room

(12:42) Why women are natural AI leaders

(14:28) The AI roles women should claim right now

(16:57) The future belongs to cross-functional skills

(19:31) The need for community and connection in tech

(22:40) Stop overthinking and just start

Stick around until the end because Stephanie’s advice on building community and staying ahead of rapid change is something every listener needs to hear. Subscribe, share this episode, and think about the bold step you can take today to prepare for tomorrow.

About Stephanie Cheney

Stephanie Cheney is the Product Director at Dualboot Partners, where she works with companies to integrate AI into product development and strategy. With over 20 years of experience across startups, venture studios, and consulting, she has led teams and built tools that streamline product delivery. She is also the co-founder of Flourished, an AI-driven insights platform for creatives. Stephanie focuses on helping businesses and individuals adapt and grow in the changing world of technology.

Connect with Stephanie:

LinkedIn

About Tiffany Benitez

Tiffany Benitez leads Data Governance at Compass Group USA, ensuring data quality, integrity, and compliance across all business units. She is passionate about driving data excellence and advancing women in tech and STEM.

Connect with Host:

Tiffany’s LinkedIn

Disclaimer

This podcast is for informational purposes only. The content should be taken as something other than professional advice. Listeners are encouraged to consult with professionals regarding specific situations or concerns.

Hey Trailblazers! Get ready for a conversation that hits different. Tiffany Benitez sits down with Saima Khan, Senior Vice President of Healthcare Digital at Compass Digital, to talk about what authenticity and inclusion actually look like when you are living it out in tech.

Saima takes us back to the dot-com era and walks us through her journey to leading large-scale healthcare technology today. Along the way, she unpacks the questions so many of us wrestle with. How do you keep your confidence when you are the only woman in the room? What happens when you stop waiting to feel ready and step forward anyway?

Representation also takes center stage in this episode. Saima shares how one female CEO changed the trajectory of her career. “There’s just so much power in seeing someone that looks like you and talks like you.” Her story proves why visibility is not optional; it is essential.

The conversation gets practical, too. Inclusion here is not a slogan; it is action. Saima talks about the real moves leaders can make, from amplifying overlooked voices to building women in tech groups that keep people engaged and growing. If you want to see allyship in action, this episode lays it out.

Here are the key takeaways:

(2:48) The power of authenticity and inclusion

(7:12) Starting out in tech during the dot-com boom

(13:17) Why representation changes everything

(14:31) The impact of seeing women in leadership

(16:57) What real inclusion looks like at the table

(18:21) Creating space and building diverse teams

(22:14) Mentorship that actually works

(26:32) Final advice: don’t be afraid to be yourself

By the end, you will find yourself thinking about the spaces you sit in and the voices you invite in.

Tune in to hear Saima’s take on authenticity, mentorship, and legacy, and discover how to lead in a way that truly changes the room.

About Saima Khan

Saima Khan is the Senior Vice President of Healthcare Digital at Compass Digital, where she oversees digital transformation across the healthcare sector. She has more than 20 years of experience in healthcare technology, including her role as Chief Technology Officer of Clinical Solutions at Premier Inc. Saima also serves as the executive sponsor of Compass Digital’s Women in Tech initiative, supporting mentorship, leadership development, and community programs across North America. Outside of work, she is a yoga instructor and an advocate for wellness, balance, and community.

Connect with Saima:

LinkedIn

About Tiffany Benitez

Tiffany Benitez leads Data Governance at Compass Group USA, ensuring data quality, integrity, and compliance across all business units. She is passionate about driving data excellence and advancing women in tech and STEM.

Connect with Host:

Tiffany’s LinkedIn

Disclaimer

This podcast is for informational purposes only. The content should be taken as something other than professional advice. Listeners are encouraged to consult with professionals regarding specific situations or concerns.

“I might just keep feeling invisible if I don’t speak.” That thought ran through Amanda Di Dio’s mind in a pivotal meeting, and she decided to speak.

On Women in Tech Trailblazers, Tiffany Benitez talks with the co-founder of Optimistic Design about the real work of finding your voice and using it. Our guest has led high-performing teams, partnered with big names like the Gates Foundation, and built a reputation for translating complex challenges into clear, actionable strategies.

Amanda shares how empathy and curiosity guide her leadership, and why she believes creating safe, human-centered spaces should be as valued as any technical milestone.

She reflects on breaking into tech at a time when everything was moving fast, from the first wave of mobile apps to new ways of delivering software. Along the way came lessons in navigating personalities, building trust, and knowing when to step forward.

Amanda also opens up about the quiet expectation for women to carry extra emotional labor and the impact of hearing, “You don’t need to take that on.” That one sentence, she says, was a turning point.

Here are the key takeaways:

(2:21) Breaking “move fast” mindset

(7:16) The value of speaking both business and tech

(15:50) The meeting that changed everything

(19:49) The ripple effect of using your voice

(21:55) The power of reaching out to strangers

(24:09) Why most jobs are filled through relationships

(25:22) One small moment can change someone’s value

If you have ever felt like your ideas were overlooked or your voice was not being heard, this conversation will give you the push to speak up. Press play, take the leap, and pass it along to someone who needs the reminder.

About Amanda Di Dio

Amanda Di Dio is the co-founder of Optimistic Design with over 12 years of experience in education, healthcare, technology, and social impact. She works at the intersection of product strategy, design research, and implementation, turning complex challenges into clear plans. Amanda has partnered with organizations such as the Gates Foundation and Renaissance Learning to create solutions grounded in real-world needs, fostering collaboration and keeping people at the center of the work.

Connect with Amanda:

LinkedIn

About Tiffany Benitez

Tiffany Benitez leads Data Governance at Compass Group USA, ensuring data quality, integrity, and compliance across all business units. She is passionate about driving data excellence and advancing women in tech and STEM.

Connect with Host:

Tiffany’s LinkedIn

Disclaimer

This podcast is for informational purposes only. The content should be taken as something other than professional advice. Listeners are encouraged to consult with professionals regarding specific situations or concerns.