Transportation infrastructure is about far more than roads, bridges, and toll systems—it connects communities, drives economic growth, and creates opportunities for millions of people every day.
In this episode of the Toll Talk Podcast, hosts Kalie Jakovics and Alex Fakeri welcomed an inspiring panel of transportation leaders for a special Juneteenth roundtable discussion exploring leadership, mentorship, representation, and the responsibility today’s industry leaders have in creating opportunities for future generations.
The conversation featured:
- Robin Bramwell-Stewart, Deputy Director– The Port Authority of New York & New Jersey
- Rosa Rountree, National Operations Director – AtkinsRéalis
- Ron Fagan, Vice President – LJA Engineering
- Cassaundra Rouse, Executive Director – Illinois Tollway
Together, the panel shared personal career journeys, reflected on the significance of Juneteenth, and discussed how intentional leadership can help create a stronger, more inclusive transportation industry.
Leadership Starts with Learning
One of the first themes to emerge during the conversation was that there is no single path into transportation.
Several guests began their careers in accounting, law, finance, military service, or public policy before finding opportunities in tolling and infrastructure. Their stories demonstrate something many young professionals may not realize: transportation is an incredibly diverse industry that benefits from expertise across business, technology, operations, engineering, communications, finance, and public service.
As the industry continues embracing intelligent transportation systems (ITS), connected infrastructure, AI, digital tolling, and advanced analytics, agencies increasingly need professionals with varied skill sets—not just traditional engineering backgrounds.
This demand is being accelerated by historic investments through the Infrastructure Investment and Jobs Act (IIJA), which is funding improvements to highways, bridges, transit systems, ports, and freight infrastructure across the United States. The legislation represents one of the largest federal investments in transportation infrastructure in decades and is helping agencies modernize mobility for future generations.
Learn more:
- U.S. Department of Transportation – Infrastructure Investment and Jobs Act:
https://www.transportation.gov/bipartisan-infrastructure-law
For anyone considering a career in transportation, the panel offered an encouraging reminder: curiosity, adaptability, and a willingness to learn can open doors to opportunities you may never have imagined.
Mentorship Builds Future Leaders
Perhaps the strongest theme throughout the episode was the importance of mentorship.
Cassaundra Rouse reflected on how early leaders at the Illinois Tollway encouraged her to learn every aspect of the organization—not just her own department—and intentionally included her in leadership discussions that expanded both her knowledge and confidence.
Robin Bramwell-Stewart shared a similar experience, explaining how one of her earliest mentors challenged her to become an expert by putting in the work, remaining curious, and never being afraid to learn something completely new.
Those experiences are supported by research.
According to Gallup, employees who have mentors are significantly more engaged at work, more likely to believe they have opportunities for growth, and more likely to recommend their organization as a great place to work. Strong mentoring relationships also improve leadership development and succession planning—something increasingly important as many experienced transportation professionals approach retirement.
Transportation is evolving rapidly, and developing the next generation of leaders requires experienced professionals to intentionally invest in those coming behind them.
Learn more:
- Gallup – Mentors and Sponsors: What’s the Difference?
https://www.gallup.com/workplace/473999/mentors-sponsors-difference.aspx
Representation Strengthens Transportation
Another powerful discussion centered around representation.
Rosa Rountree reflected on attending her first IBTTA conference years ago and seeing very few women—and even fewer people who looked like her. That experience reinforced why visibility matters.
Representation is not simply about diversity statistics.
It is about ensuring different perspectives help shape decisions that affect millions of travelers every day.
Whether planning a new toll facility, modernizing customer service, implementing all-electronic tolling, or investing in roadway improvements, transportation leaders make decisions that impact communities across every demographic.
Research continues to demonstrate the value of diverse leadership. McKinsey & Company’s Diversity Wins report found that organizations with more diverse executive teams are more likely to outperform financially while fostering greater innovation and stronger decision-making.
Transportation agencies face increasingly complex challenges—from emerging technologies to evolving customer expectations—and diverse leadership helps organizations approach those challenges from multiple perspectives.
Learn more:
- McKinsey & Company – Diversity Wins: How Inclusion Matters
https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/diversity-wins-how-inclusion-matters
Transportation Connects More Than Roads
One of the most impactful conversations focused on transportation’s broader responsibility.
Infrastructure isn’t simply about moving vehicles efficiently.
It influences where people can work, how businesses grow, whether families can access healthcare, and how communities stay connected.
Cassaundra Rouse discussed how agencies like the Illinois Tollway must consider the communities they serve whenever making infrastructure investments or policy decisions. Equity isn’t separate from infrastructure—it should be considered throughout planning, investment, and long-term decision-making.
Similarly, Robin Bramwell-Stewart emphasized remembering the historical impacts transportation projects have had on some communities while ensuring today’s investments create opportunities rather than barriers.
These conversations closely align with the U.S. Department of Transportation’s focus on improving accessibility, strengthening communities, and ensuring transportation investments benefit everyone.
Learn more:
- U.S. Department of Transportation – Equity Action Plan
https://www.transportation.gov/priorities/equity
Juneteenth Reminds Us That Progress Requires Action
As this special episode commemorated Juneteenth, the conversation naturally expanded beyond history.
Rosa Rountree shared one of the episode’s most memorable insights:
Just because something has been declared doesn’t mean it has yet been fully realized.
That perspective became the foundation for a broader discussion about leadership.
The panel agreed that organizations cannot simply state they value inclusion or opportunity—they must intentionally create environments where people are mentored, supported, and given meaningful opportunities to grow.
Ron Fagan built on that message by reminding listeners that today’s leaders have a responsibility to identify future leaders, encourage them, and help them see opportunities they may not yet recognize for themselves.
For transportation professionals at every career stage, that message serves as an important reminder: leadership isn’t simply about holding a title. It’s about helping others succeed.
The Future of Transportation Depends on People
Technology continues transforming transportation through connected infrastructure, digital tolling, artificial intelligence, predictive maintenance, and smarter mobility systems.
But as this episode demonstrates, people remain the industry’s greatest asset.
Innovation only succeeds when organizations develop strong leaders, encourage collaboration, invest in mentorship, and create opportunities for diverse voices to help shape the future.
The experiences shared by Robin Bramwell-Stewart, Rosa Rountree, Ron Fagan, and Cassaundra Rouse illustrate that transportation’s future depends just as much on leadership and relationships as it does on technology and infrastructure.
Listen to Episode 45
Episode 45 is more than a conversation about transportation—it’s a conversation about leadership, mentorship, service, and creating opportunities that strengthen both our industry and our communities.
Whether you’re an experienced transportation professional, just entering the industry, or simply interested in how infrastructure leaders are shaping the future, this episode offers valuable insights from four remarkable leaders whose experiences continue to inspire the next generation.
Watch and listen to Episode 45 of the Toll Talk Podcast:
https://tolltalkpodcast.com/
