Past event

Bridging the Leadership Divide - A Leadership Roundtable

Our 2025 What Talent Wants survey revealed a critical insight: only 36% of underrepresented professionals feel their leaders effectively support career growth, signaling a major…

Virtual Free to attend
Bridging the Leadership Divide - A Leadership Roundtable

About this session

Our 2025 What Talent Wants survey revealed a critical insight: only 36% of underrepresented professionals feel their leaders effectively support career growth, signaling a major opportunity for improvement. Additionally, 75% of respondents want to see more diverse leadership in their organizations.

Join us for a Leadership Roundtable on Friday, February 21st at 1 PM ET, where we’ll dive into actionable strategies for fostering career growth, creating upskilling opportunities, and building a more inclusive leadership pipeline. We’ll kick things off with the latest data and trends—then we want to hear from you! How is your organization tackling leadership development and career support?

Key discussion topics:

  • Upskilling for Leadership: How to equip emerging leaders with the skills they need to succeed.
  • Building Inclusive Leadership Pipelines: Strategies for identifying and elevating top talent.
  • Mentorship & Sponsorship: The role of leaders in championing underrepresented professionals.
  • Measuring Progress: Tracking success and accountability in leadership development.

Don’t miss this opportunity to collaborate, share insights, and take meaningful steps toward closing the leadership gap!

Meet the speakers

Milena Berry

Milena Berry

Co-Founder, CEO and Board Director at PowerToFly

Milena is the Co-Founder, CEO, and Board Director of PowerToFly - the fastest growing global platform dedicated to fast-tracking economic equity by upskilling and connecting underrepresented talent to roles in highly visible sectors. Milena’s on a mission to partner with top 100 brands to bring them a slew of diversity solutions provided through the PowerToFly platform.

Milena was born in Bulgaria and moved to New York City a week before September 11th to pursue a Masters at ITP NYU. Prior to co-founding PowerToFly, Milena has contributed to numerous startups, and had a blast being the CTO of Avaaz.org where she oversaw the technology to support growth to over 30 million members.

Milena is a frequent commentator on how companies can diversify their teams, especially in tech. Her work for PowerToFly has been recognized in Business Insider and she was named Fast Company’s Most Creative People in Business in 2015. Her biggest accomplishments are her four children who constantly push her to rethink what work-life balance means.

Sienna Brown

Sienna Brown

Head of Growth at PowerToFly

Sienna J. Brown is a visionary Leadership Strategist and Global Speaker with over a decade of experience partnering with global leaders and institutions. As the Head of Growth at PowerToFly, a scaling Series-B start-up, Brown drives innovation and expansion.

Throughout her career, Brown has been instrumental in helping organizations gain investment while prioritizing diverse talent. Her expertise lies in developing strategic programming to enable, elevate, and re-energize leaders to guide organizational transformation. Brown's approach focuses on redefining work through inclusion, impact, influence, and integrity.

Previously, as Sr. Director of DEIB at PowerToFly, Brown built a department from the ground up, delivering strategic learning and development programs that increased employee engagement and advocacy in over 50+ global organizations.

Her work has gained recognition on platforms such as Forbes, TedX, Insider, CNN, and NPR. Brown collaborates with organizations to create transformative strategies that secure employee, consumer, and financial investment while staying true to their vision and values.

Rob Ribar

Rob Ribar

Director, Events & Marketing

Robert Ribar is a New York based professional with over fifteen years of experience in programming diverse content, community engagement, executing dynamic events and comprehensive marketing campaigns. He currently leads PowerToFly’s B2C and B2B events, including the Diversity Reboot virtual summit series, the biggest conference in DEIB. Rob also oversees the company’s dual marketplace marketing strategy as well as playing a key role in community growth and partnership programs. At PowerToFly, Rob has produced events for American Express, Meta, Morgan Stanley, Microsoft and Slack, just to name a few. Prior to joining PowerToFly, Rob served as Production Coordinator at DKC/Hangar4, working on events for Pixar, Jaguar LandRover, FanDuel, L’Oreal and producing the reopening of the Hudson Theatre on Broadway. He also worked as the Associate Producer for the Tony Award winning production company Triptyk Studios developing works for film, television and the stage with such artists as Stevie Wonder, Linda Perry and James Gandolfini. In his spare time, he co-hosts the Dear Watchers comic book podcast, writes scary stories and programs film screenings under the Sleepover Trading Company banner.

About PowerToFly

The bridge between professionals and the companies building what's next.

PowerToFly connects talent, community groups, and industry leaders in one platform. Meet hiring managers, recruiters, and peers from anywhere — and with our virtual events and exclusive career content, hone your skills and grow your network all in one place.

Community
1.1M+ Professionals across every industry, domain, and geography, ready to contribute wherever they're needed.
Events hosted
2,000+ In partnership with employers across every industry.
Verified experts
380K+ Specialists in healthcare, law, finance, and more, vetted and ready.
Countries
190 A truly global community, so you can connect and grow your network without borders.
Women & BIPOC
75%+ More perspectives across the network means better outcomes for everyone.
Years building
12+ Since 2014, building infrastructure for professionals to do meaningful work.

More Chat & Learns

See all events →
October 14, 2026
For employers

Beyond the Pilot: How to Lead an AI Transformation That Sticks

Most AI initiatives don’t fail because of the technology. They fail because companies underestimate how much the right people, in the right roles, with the right implementation support around them, actually matter. In this session, leaders from across industries will share what separates organizations that scale AI…

Hunter Lee Canning Eryn Peters Ken Sterling Kelly Blackmon
5 speakers
Watch recording →
October 14, 2026
For employers

The Hiring Gap: Why Most Companies Are Looking for AI Talent in All the Wrong Places

Finding great AI talent isn’t just about technical skills anymore, and the companies figuring that out are moving faster than everyone else. They’re looking for people who already understand their industry and can bring real-world context. Join us to learn what smarter sourcing looks like these days and why…

Meg Alexander Jennyn Herrera, MBA, SHRM-SCP Fran Griffin Katy Peichert
5 speakers
Watch recording →
October 14, 2026
For employers

From Data to Deployment: Why the Humans Behind Your Model Determine Its ROI

Your AI model is only as good as the people shaping it. That means bringing in experts with varied backgrounds, industries, and lived experiences, because that breadth is what produces outputs that reflect the world your customers actually live in. In this deep dive, we’ll talk about what it takes to train, evaluate,…

Rob Ribar Mara Gates Milena Berry Shawntay Skjoldager
5 speakers
Watch recording →