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Podcast EP 59 Rewind: The Truth about Voice AI – and Our Work to Perfect It

In this episode of Harder Than It Looks, host Brian Wolff welcomes back James Paden, Chief Product Officer at Parker Technology. Brian and James celebrate two years since James joined the company, and they unpack the AI products James and his team launched. Brian and James dig into the actual mechanics of a voice AI call, the five different AI models a single call runs through in about a second, and why building AI for parking is a challenge. James walks through Parker Technology’s newly launched AI agent, Ambassador, which comes in two powerful solutions. Ambassador Live provides AI-powered assistance, with human back-up always available. Ambassador Assist tackles a market Parker has never been able to serve at scale before - the everyday phone calls that flood parking offices. The conversations get into the guardrails behind the technology: the quality that Tammy Baker, COO, and her team had already established for Parker’s CSRs, and how that became the standard AI had to meet before it could go live.

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Podcast EP 47 Rewind: Collaboration Is Not Optional: What 30 Years in Parking Taught Maggie Vercoe

February 25th, 2026 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff sits down with Maggie Vercoe, COO of TEZ Technology and a 30-year veteran of the parking industry.

From starting in a parking booth at the University of Wisconsin-Milwaukee to helping build T2 Systems during its high-growth years – and now leading professional services, support, account management, and marketing at TEZ – Maggie shares the leadership lessons that shaped her journey.

This conversation dives deep into adaptive leadership, managing complex implementations, staying calm in conflict, and why collaboration isn’t just a buzzword – it’s a survival skill in parking.

Podcast EP 46 Rewind: The Night Everything Changed – Susan Cole’s Story of Grit & Reinvention

February 25th, 2026 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff sits down with Susan Cole, Founder & CEO of Cole Ticket Solutions (CTS) – a woman-owned business reshaping consumables, automation, and supply chain efficiency across the parking industry.

Susan created her own opportunities despite the many obstacles that came with starting a business during the pandemic. She shares how she entered parking more than 20 years ago, what she learned from growing markets across North and South America, and how those experiences shaped her decision to start CTS in the middle of the pandemic. Finally, Cole discusses her innovative Cole Cube supply model that has been debuted in San Francisco and Los Angeles.

The discussion centers around resilience, confidence in oneself, and a special connection Susan has to Harder Than It Looks. Tune in to hear a story of resilience, grit, and success in our industry.

Podcast EP 45 Rewind: Is There Such Thing as Too Much Parking? Urban Revitalizer Jeff Siegler Weighs In

November 26th, 2025 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff is joined by Jeff Siegler – author, urbanist, and founder of Revitalize or Die.

Jeff brings a unique perspective – challenging the idea that “more parking” equals “more progress”. He shares lessons from two decades helping towns revitalize, the emotional roots of civic decline, and why action is the antidote to apathy.

The discussion touches on leadership, walkability, car culture, and how the health of a community directly impacts the health of its people. Whether you agree or disagree, this episode will make you rethink what really makes a city thrive.

Podcast EP 44 Rewind: AI with a Human Touch: How PCI is “Breezing” Towards Innovation

October 22nd, 2025 | Blake Richmond

In this episode of Harder Than It Looks: Parking Uncovered, host Brian Wolff is joined by Dave Mueller, President of Parking Concepts Inc. (PCI), and Rafael (Raf) Abanilla, Senior Vice President of Operations and Innovation at PCI. Dave and Raf share their beginnings in the parking industry and the journey that led them to PCI. Dave and Raf share insights on their leadership traits, how they work to build a cohesive culture at PCI, and PCI’s “Breeze” technology suite that expands on their “AI Plus Human Touch” philosophy.

Podcast EP 43 Rewind: Hire for Heart, Train for Skill: Dean Ahmad’s Recipe for Leadership

October 15th, 2025 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff is joined by Dean Ahmad, Vice President of Parking and Transportation at Dallas-Fort Worth Airport (DFW). Dean shares his remarkable journey from entrepreneurial beginnings to leading a team of over 300 employees at one of the busiest airports in the world. Dean offers insights on building organizational culture, driving innovation, and developing employees. His people-first leadership approach has resulted in the highest engagement scores at DFW, fostering an environment of collaboration and achievement.

Podcast EP 42 Rewind: Big Ten School = Big Parking: How Gabe Mendez is Rewriting the Playbook

September 26th, 2025 | Blake Richmond

In this episode of Harder Than It Looks, host Brian Wolff sits down with Gabe Mendez, PTMP – Director of Transportation Operations at the University of Wisconsin Madison. Gabe brings over two decades of experience in the industry, and shares insights from his time in commercial parking operations to leading transportation services at one of America’s largest universities.

Podcast EP 41 Rewind: Disruption Ahead! Bob Murray & James Paden on Parking’s Next Big Shift

August 21st, 2025 | Katelyn Perman

In this episode of Harder Than It Looks Parking Uncovered, host Brian Wolff sits down with Bob Murray, CTO at CampusParc, and James Paden, Chief Product Officer at Parker Technology. These tech veterans share their experiences transitioning into the parking industry and offer insights on how outside expertise is driving innovation in parking operations.

Podcast EP 40 Rewind: Service, Struggle, and Strength – The Making of Amano’s CEO, Greg Brewer

August 14th, 2025 | Katelyn Perman

In this episode of Harder Than It Looks Parking Uncovered, Brian Wolf sits down with Greg Brewer, the newly appointed President and CEO of Amano McGann, Inc. Greg shares his inspiring journey from humble beginnings to leading one of the parking industry’s top technology providers. He offers insights on authentic leadership, company culture transformation, and balancing technological innovation with essential human interaction in parking operations.

Podcast EP 39 Rewind: Humans Still Win – The AI-Augmented Future of Parking

August 7th, 2025 | Katelyn Perman

In this episode of Harder Than It Looks, Brian Wolff is joined by James Paden, Chief Product Officer at Parker Technology. With 25 years of software experience, James shares his insights on the rapidly evolving world of AI in the parking industry. From the challenges of implementing voice AI to the future of customer service, this conversation explores how parking is both leading and adapting to technological change.

Podcast EP 38 Rewind: Live from IPMI – 9 Parking Experts on Tech Trends, Customer Pain Points & Parking’s Future

July 17th, 2025 | Katelyn Perman

In this special episode, recorded live on the expo hall floor at IPMI 2025, Brian Wolff, Heidi Barber, Tina Gray, and Courtney Cooper talk to 9 parking leaders about what’s working, what’s not, and what they’d change with a magic wand. From drones and data to broken gates and customer confusion – it’s a rapid-fire tour of the industry’s most pressing challenges.

All Episodes

Most Recent Episode

Podcast EP 59 Rewind: The Truth about Voice AI – and Our Work to Perfect It

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