The True Leadership Podcast

In this episode, Jessy sits down with Erika Betancourt-Rivera, Chief Human Resources Officer, to explore what it truly means to lead in today’s evolving workplace. Erika shares how her philosophy of “take the good and leave the bad” shaped her leadership style, grounded in trust, teaching, and continuous self-work. She reflects on the challenges of leading across generations, adapting to new expec...

In this episode, Jessy sits down with Kurt Fischer, seasoned HR executive and advisor, to explore leadership through the lens of experience, self-awareness, and continuous learning. Kurt shares lessons from decades of leading global organizations, including the importance of clarity over assumptions, aligning with values-driven environments, and learning from mistakes without losing confidence. He...

In this episode, Jessy sits down with Meg Audette, international development executive, to explore leadership shaped by humanity, humility, and resilience. Drawing from her work in conflict zones and global organizations, Meg shares why true leadership begins with trust, not performance. She reflects on adapting leadership across cultures, building confidence without losing humility, and navigatin...

In this episode, Jessy sits down with Clayton Still, transformational leader and military veteran, to explore leadership shaped through adversity, action, and service. Clayton shares how his early life, military experience, and a defining moment running into a burning building reframed his understanding of leadership. He challenges the tendency to observe instead of act, emphasizing that true lead...

In this episode, Jessy sits down with Vanessa Parker-Lewis, transformational CHRO, to explore leadership through the lens of agency, introspection, and courage. Vanessa shares a defining lesson from her godmother that reshaped how she sees responsibility in every interaction, along with her journey from operations into HR. She speaks candidly about self-advocacy, investing in herself despite resis...

In this episode, Ty sits down with David Pearson, Chief Human Resources Officer and executive advisor, to explore the evolution of leadership from control to empowerment. David shares how early lessons in integrity, hard work, and humility shaped his journey, and how letting go of ego became a turning point in his leadership. He dives into servant leadership, building people over processes, and wh...

In this episode, Jessy sits down with Pat Porter, CHRO and enterprise people strategy leader, to explore the foundations of impactful leadership. Pat shares how mentors and early experiences shaped his approach, emphasizing communication, accountability, and the importance of being “verbal, visible, and not hesitating.” He reflects on adapting to change, navigating uncertainty in the age of AI, an...

In this episode, Jessy sits down with Davide Savenije, Senior Vice President of Editorial and a leader shaping the future of B2B journalism. Davide shares how personal challenges, including a pivotal life transition, reshaped his leadership from people-pleasing to clarity, honesty, and self-awareness. He explores the importance of mindset, the power of direct communication, and why true leadership...

In this episode, Jessy sits down with Eduardo Gonzalez, Emmy-winning art director and creative leader behind globally recognized worlds like League of Legends: Arcane. Eduardo shares his journey from execution-driven leadership to a more collaborative, team-centered approach. He reflects on the influence of early mentors, the pressure to push beyond mediocrity, and the importance of balancing inte...

In this episode, Jessy sits down with Michelle Carter, Executive Vice President at Mastercard, to explore what it takes to lead at scale without losing the human element. Michelle shares how self-awareness, diverse perspectives, and intentional reflection have shaped her leadership approach. She unpacks the tension between driving immediate results and building for long-term growth, and why motiva...

In this episode, Jessy sits down with Fabian Ekstrom-French, Senior Director of Partner Marketing at Esper, to explore the foundations of confident, high-impact leadership. Fabian shares how early lessons in encouragement shaped his leadership philosophy and why inspiring belief in others matters more than having all the answers. He reflects on the critical shift from control to delegation, and ho...

In this episode, Jessy sits down with Luke Mickelson, founder of Sleep in Heavenly Peace, to explore how leadership evolves from success to true significance. Luke shares the pivotal moment that shifted his focus from achievement to impact, and how small “tiny moments” can lead to life-changing purpose. He reflects on the challenges of founder identity, the importance of leading by example, and wh...

In this episode, Jessy sits down with Deboleena Bose, Chief Human Resource Officer and global transformation leader, to explore what truly sets great leaders apart today. Deboleena shares why leadership is rooted in care not as softness, but as a strategic advantage in times of uncertainty. From early lessons in inclusion to hard-earned growth through failure and global leadership, she reflects on...

In this episode, Ty sits down with Rob Gifford, VP and Managing Editor, to explore leadership in a world defined by constant change. Rob shares how early experiences in sports, community, and mentorship shaped his approach to leadership rooted in action, humility, and trust. The conversation dives into leading through uncertainty, from building digital news operations to navigating the chaos of th...

In this episode, Jessy sits down with Caroline Ang Wright, a seasoned revenue leader known for blending operational rigor with people-first leadership. Caroline shares a powerful early lesson that reshaped her perspective: make yourself bigger, not the company. From there, the conversation explores what it really means to lead—creating the conditions for others to thrive rather than having all the...

In this episode, Ty sits down with Colleen Brown, corporate director and former public company CEO, to explore leadership in the face of complexity, disruption, and uncertainty. Drawing from early life experiences shaped by absence and responsibility, Colleen shares how leaders develop the capacity to act without clear answers. The conversation challenges traditional views of governance, emphasizi...

In this episode, Jessy sits down with Dennis Czajkowski, a veteran operations leader, to unpack the unfiltered reality of leadership. With over 30 years of experience, Dennis shares hard-earned lessons on self-awareness, failure, and what it truly means to lead people, not just processes. He reflects on pivotal moments where leadership broke down, forcing him to step back and rebuild from the grou...

In this episode, Jessy sits down with Eugene Demaitre, Editorial Director at WTWH Media, to explore leadership in an era of constant change. Eugene shares how stepping off autopilot and embracing uncertainty shaped his career, from journalism to robotics and AI. He unpacks the balance between vision and adaptability, and why leaders must stay grounded while navigating rapid technological shifts. F...

In this episode, Jessy sits down with Diana Langston, founder of Kind But Tough, to explore the powerful balance between empathy and accountability in leadership. Drawing from her experience scaling high-growth SaaS organizations, Diana shares how leaders unlock bold thinking and high performance by building trust, not fear. The conversation dives into self-awareness, communication, and the import...

In this episode, Jessy sits down with Chris Kowal, Global VP of GTM and Partnerships, to explore leadership through the lens of authenticity, energy, and self-discovery. Chris shares pivotal moments that reshaped his approach, from learning to cut through noise early in his career to stepping back during burnout to reconnect with purpose. The conversation dives into vulnerability as a leadership s...

In this episode, Ty sits down with Shelly Mahon, Vice President of Marketing, to explore leadership through one of life’s most demanding seasons. From career reinvention to personal loss, Shelly shares how challenge became a catalyst for clarity, growth, and deeper alignment. The conversation unpacks what it means to lead with humility, curiosity, and humanity in high-stakes environments, while na...

In this episode of the True Leadership Podcast, Jessy James sits down with Chelsea Starley, a sales leader known for her human-centered approach to business and leadership. Chelsea shares how positivity, vulnerability, and authentic connection have shaped her journey across industries. She opens up about imposter syndrome, the challenge of setting boundaries, and the ongoing work of believing in h...

In this episode of the True Leadership Podcast, Jessy James sits down with Aaron Leeder, a business development leader known for building high-impact partnerships and thriving executive communities. Aaron shares how leadership is shaped through small, consistent decisions that form powerful patterns over time. He opens up about navigating ego, losing a seat at the leadership table, and redefining...

In this episode of the True Leadership Podcast, Jessy James sits down with Allison Rona, a product marketing leader known for scaling growth-stage companies through sharp strategy and strong execution. Allison shares how early leadership experiences shaped her people-first approach, emphasizing psychological safety and authentic connection. She opens up about finding her voice in high-stakes meeti...

In this episode of the True Leadership Podcast, Jessy James sits down with Nathan Ives, a veteran executive leader with decades of experience across consulting, technology, and operations. Nathan shares how early mentorship in the Navy shaped his belief in ownership, accountability, and high standards. He reflects on losing and reclaiming his leadership edge, the role of coaching in overcoming fea...