“My biggest hope for the future of women in leadership is that it’s no longer remarkable—it’s simply the norm,” said Rebecca Bennett, Vice President, Strategic Partnerships, Oshi Health. Rebecca is a partnership, strategy, and growth executive with 15+ years of leadership across start-ups, Fortune 50 companies, and the U.S. military. She led health system partnerships at Midi Health and Noom and held diverse roles at Johnson & Johnson. A former Navy helicopter and experimental test pilot, she continues to serve in the Pennsylvania Air National Guard.

In an exclusive interview with HR.com, Rebecca shares her insights on the critical skills for women leaders in 2025, the impact of upskilling, and her vision for a future where gender is not a barrier to leadership.

Excerpts from the interview:

Q. In 2025, what are the most critical skills women need to develop to thrive in leadership positions, and how can upskilling programs address these needs?

Rebecca: In 2025, women in leadership must develop critical skills to navigate an evolving business landscape. Strategic decision-making, executive presence, and developing confidence in one’s abilities are essential for driving growth and influencing key stakeholders. Additionally, resilience and adaptability enable leaders to manage uncertainty and foster innovation. Mastering negotiation and influence ensures they can advocate effectively for resources and opportunities.

As AI and digital transformation reshape industries, digital literacy is increasingly crucial, along with inclusive leadership skills to build diverse, high-performing teams.

Upskilling programs can address these needs through executive coaching, leadership development courses, and AI-focused workshops. Scenario-based training enhances decision-making and crisis management, while peer networks and sponsorship programs provide support and advocacy.

Combining formal education with experiential learning ensures women gain practical, high-impact skills. By integrating mentorship, hands-on training, and access to leadership networks, these programs can empower women to thrive in executive roles and drive meaningful change in their industries.

Q. What are the most persistent challenges you've faced as a woman leader, and how have you navigated them?

Rebecca: Early in my career, I learned that competence alone wasn’t enough—I needed to pair it with confidence and strategic self-advocacy to ensure my contributions were recognized.

Navigating these challenges required a combination of resilience, preparation, and leveraging strong networks. I made it a priority to excel in my technical skills, ensuring there was no doubt about my expertise. At the same time, I sought out mentors and sponsors, both men and women, who could provide guidance and advocate for me in key decision-making rooms.

Over time, I learned to own my leadership presence, speak up with authority, and push back when necessary. I also make it a point to support other women, helping to build pathways where they don’t have to fight the same battles alone. These experiences have shaped my leadership style, making me a more empathetic and determined advocate for equity and inclusion.

Q. Can you share a personal story of a time when upskilling made a significant difference in your career trajectory?

Rebecca: Pursuing my MBA at Wharton was a pivotal step in transitioning from the military to healthcare. As a Naval Aviator and test pilot, I had strong leadership and operational skills, but I needed business acumen to navigate a new industry. Wharton provided the financial, strategic, and healthcare expertise—along with a powerful network—that enabled me to make the leap. That upskilling not only gave me confidence but also set me up to lead and scale healthcare partnerships effectively.

Q. How do you balance the demands of leadership with the ongoing need for personal and professional development?

Rebecca: Taking care of yourself—whether through rest, continuous learning, or setting boundaries—not only sustains your effectiveness but also sets an example for your team. I prioritize personal well-being and professional growth, knowing that strong leadership comes from a place of resilience and adaptability.

As a lifelong learner, I make it a point to seek out new knowledge and perspectives, whether through executive education, mentorship, or staying informed on industry trends. Growth doesn’t stop once you reach a leadership role—it’s an ongoing process. By embedding learning into my routine and encouraging my team to do the same, I ensure that we’re all evolving together, staying ahead of challenges, and leading with fresh insights.

Q. What are your biggest hopes and aspirations for the future of women in leadership?

Rebecca: My biggest hope for the future of women in leadership is that it’s no longer remarkable—it’s simply the norm. Women shouldn’t have to prove their qualifications repeatedly or be the “first” or “only” in the room. Leadership should reflect the diversity of talent, perspectives, and lived experiences that drive better decision-making and stronger organizations.

Diverse backgrounds, thoughts, and experiences lead to more innovative, resilient teams and better business outcomes. I aspire to see more women in executive roles, boardrooms, and historically underrepresented industries—not because of quotas, but because systemic barriers no longer exist. True progress means women can lead authentically, without conforming to outdated expectations or constantly fighting for a seat at the table. My goal is to help create a world where leadership is defined by capability and vision—not gender.


 
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