Harder Than It Looks: Parking Uncovered

About Harder Than It Looks: Parking Uncovered

We as parking professionals know that parking is hard. However, we make it look easy to those from the outside looking in. The myriad technologies, processes and people that a parking operator has to wrangle on any given day is mind-numbing, and every parking facility is unique. While certain verticals share similar pain points, we know better than many how nuanced every operation can be. We created this podcast to facilitate connections and illuminate solutions to common problems within the parking and mobility industry. We aim to do so by highlighting the voices of experts in the space, discussing trends and forward-looking technological innovations, and providing professional food for thought. All in an effort to help one another get better at what we know is harder than it looks…parking a car.

Publisher

Parker Technology

Category

business · technology

Language

en

Explicit

No

First episode

16 Aug 2023

Latest episode

2 Sept 2026

Latest episodes

74 episodes in the feed.

1. 

   2 Sept 2026

   EP 59: 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. Key Takeaways 1. AI is built to augment humans, not replace them.  AI can handle the fast, repetitive questions so human agents can focus on the complex, high-empathy situations that require more thought. 2. Building Voice AI in parking is a harder problem than most voice AI. Outdoor speakers, background noise, and real-time facility data (broken equipment, special event pricing) make the acoustic challenges far tougher than a cell phone call. 3. Ambassador’s guardrails were built by the Parker Standard. Tammy Baker, COO of Parker Technology, and her team have set existing quality standards for CSR’s. Ambassador was built with the same high standards, with a hard rule that any uncertainty routes straight to a human. 4. AI opens markets Parker couldn’t serve before. Ambassador Assist is built for high-volume, unpredictable call environments that were too complex to staff profitably in the past. Episode Highlights [01:00] James reflects on two years at Parker and how his outside perspective sharpened once he started paying attention to parking as a technology problem. [06:00] Why James and Brian believe capital and attention are flowing into the parking industry. [10:00] How Ambassador Assist opens a market Parker hasn’t been able to serve at scale – starting with university parking offices. [14:00] James walks through what happens during a Voice AI call: audio cleanup, voice activity detection, speech-to-text, the language model, and text-to-speech, all in about a second. [18:00] The hardest parts of building voice AI for parking: the noisy outdoor acoustic environment and the deep facility-specific knowledge required to answer correctly. [21:00] How every AI interaction gets tested, graded by other AI systems, and run through the same quality assurance process as human agents. [23:00] Why Parker is investing in AI even with two strong call centers already in place: speed multilingual support, and staffing flexibility. [29:00] The philosophy behind Ambassador: making it easy to reach a human and treating AI as expansion. [35:00] How Tammy Baker’s existing quality standard became the bar Ambassador had to meet, including the rule that any uncertainty transfers straight to a human. [44:00] Parker’s pricing approach for Ambassador Live and Ambassador Assist, and why alignment drives both models. [54:00] James previews his NPA Las Vegas session on the four levels of AI for building a parking roadmap, and where to find the Parker team at Booth 400. Notable Quotes “AI’s not there to replace. It’s there to augment, to expand, to make the environment faster.” – James Paden “Ambassador Assist meets our customers in an area where we haven’t been able to meet them before.” – James Paden “When I joined Parker, there was already an established bar that the AI had to meet.”  – James Paden About the Guest James Paden is the Chief Product Officer at Parker Technology, where, for the past two years, he leads the product and engineering teams behind the company’s parking support platform, including its new AI agent, Ambassador. James brings more than 25 years of software and product development experience, including leading SaaS strategy at small companies, working at a startup later acquired by Oracle, and founding and successfully selling his own company. James will be presenting “Operational AI Maturity: 4 Levels of AI to Build Your Parking Roadmap” on Wednesday, September 16th at 11:00 AM. Additionally, the Parker Technology team can be found at Booth 400 at NPA this year.

2. 

   26 Aug 2026

   EP 58: A House Fire, a 2AM Call, and a Career in Parking with Melissa Jones

   In this episode of Harder Than It Looks, host Brian Wolff sits down with Melissa Jones, PTMP, Director of Customer Experience at TEZ Technology. Melissa’s road into parking wound began with a career in counseling and crisis work with at-risk kids and families. That work taught her how to sit with people in the middle of a crisis, big or small, and help them work through it. These skills ended up translating directly into leading teams and supporting customers who call in with their own version of an emergency. Counseling and parking kept pulling her back and forth until it finally stuck for good, taking her through managing parking at Class A office buildings, a stint at Parking Soft that turned into a decade at T2, and now her role at TEZ. Melissa and Brian dig into how that unlikely combination of backgrounds quietly built the leader she is today. The conversation covers building trust quickly in high-pressure environments, creating health conflict without ill will, what it takes to lead technically strong but low-EQ team members, and how the industry’s growing number of strong woman leaders are changing the game. Key Takeaways 1. Your background is never wasted. Melissa’s years in counseling and crisis management, and her work as a fitness coach, translate directly into how she leads teams and supports customers today. 2. Bedrock leadership is about openness, not skill. Melissa can teach anyone the software or the job. What she can’t teach is flexibility, empathy, and a willingness to learn. Those traits must come from the person. 3. Healthy conflict starts with relevance.  Melissa’s approach to hard conversations is simple: make it relevant to the person in front of you and ask how you’d want someone you love to be treated. 4. Trust is built by walking the walk. Having answered the phones and taken the heated calls herself, Melissa leads by showing up in the lane, owning it when things go sideways, and never throwing her team to the wolves. 5. The industry has changed – and so have the leaders. As From hauling a coin canister through snowy parking lots to today’s technology and customer experience standards, Melissa has watched the industry raise its bar, along with a growing wave of strong women leaders shaping its future. Episode Highlights [02:00] Melissa shares how she got started in counseling and how a friend first talked her into taking a parking manager job at a community college. [04:00] The career pull between parking and counseling, with a journey through both. [06:00] A move to a Class A office building in downtown Atlanta reintroduces Melissa to parking, this time falling in love with the managerial and people side of the work. [9:00] Melissa’s journey from Mardi Gras parking to T2. [12:00] Melissa lands at TEZ Technology as Director of Customer Experience, overseeing implementation and customer experience. [14:00] Brian and Melissa discuss leading technically strong but low-EQ team members, and the importance of meeting people where they are. [24:00] The story of a tough property manager in Atlanta who became Melissa’s best friend, and the servant leadership lesson she taught Melissa. [32:00] Melissa’s 20-year parking journey, and the lessons she’s learned by being a woman in parking leadership. [38:00] Lightning round: Melissa’s go-to phrase, the hardest thing she’s ever done, and what she’s most proud of. Notable Quotes “I can teach anybody the software. I can teach anybody the job. What I can’t teach you is to be flexible and empathetic and open to learning. – Melissa Jones “If I rise because of you, then that means somebody else can rise because of me.” – Melissa Jones “We’re never going to be alone and trying to figure out things. That’s work or personal. I’m right there… you can’t get rid of me.” – Melissa Jones About the Guest Melissa Jones, PTMP, is the Director of Customer Experience at TEZ Technology, where she leads the implementation and support teams. She is a PTMP member and an active contributor to multiple IPMI communities. Melissa’s career spans more than 20 years across account services, and customer support, including roles on community college campuses, in Class A office buildings, at events, and in valet services. She joined Parking Soft’s training department before its acquisition by T2 in 2017, where she spent multiple years before moving to TEZ Technology. Before her parking career, Melissa worked in counseling, supporting at-risk youth and families through behavior management and substance abuse challenges. She is also a fitness coach and CrossFit instructor, drawing on both backgrounds to build empathetic, resilient teams.

3. 

   12 Aug 2026

   EP 57: 850 Square Miles: How Peter Sherwill Runs Parking for the Biggest City in America

   In this episode of Harder Than It Looks, host Brian Wolff is joined by Peter Sherwill, Chief Public Parking Officer for the City of Jacksonville, the largest city by land area in the contiguous United States. Peter brings more than two decades of parking and mobility experience spanning valet, event parking, municipal operations, and private sector contracts, and now oversees a system of garages, surface lots, on-street parking, and enforcement across 850 square miles. Peter walks Brian through his winding path into parking, starting as a high school valet attendant and working his way through event parking at venues like Red Rocks Ampitheatre, municipal operations in Denver, and a private sector stop in Fort Myers before landing in Jacksonville. Brian and Peter dig into how Peter keeps a lean 40-person team motivated without a formal appreciation budget, how the department earned a seat at the table for major city projects, and how Jacksonville is modernizing decades-old technology while preserving the ambassador-like role of enforcement staff. They close with a look at the next big challenges facing curb management as downtown Jacksonville grows. Key Takeaways 1. Motivation doesn't require a big budget. Without funds for employee perks, small gestures, such as dedicated a employee break room, new uniforms, "Win Wednesday" recognition meetings, have transformed a once-fragmented enforcement team into one that has each other's backs. 2. If you want a seat at the table, you have to take initiative. Parking teams are often the last to know about city projects that affect the curb. Peter changed that in Jacksonville by proactively reaching out to other departments and showing up as a problem solver, not an afterthought. 3. Modern technology should remove friction, not remove people. Jacksonville is rolling out multi-space meters, online permitting, and updated LPR systems, while intentionally keeping staff visible and approachable so automation doesn't replace the human side of the customer experience. 4. The Curb is everchanging. As downtown Jacksonville adds housing, a rebuilt stadium, and more nightlife, the parking team expects to expand enforcement hours, add residential permit programs, and manage rising demand from rideshare and delivery traffic. Episode Highlights [02:00] Introducing Peter Sherwill and his origin story. [04:00] Learning municipal parking in Denver and expanding paid parking in Fort Myers, Florida. [06:00] The surprise twist that turned a different job interview into an offer for Chief Public Parking Officer. [12:00] Keeping a lean team motivated without an appreciation budget - break rooms, new uniforms, and "Win Wednesday". [17:00] A technology rundown: multi-space meters, online permitting, new LPR systems, and upgraded garage equipment. [19:00] Stakeholder stories: booting a city council member's car and creative curb solutions for a century-old downtown business. [30:00] Cross-departmental collaboration on downtown revitalization, the new Jaguars stadium, and micro-mobility expansion. [36:00] How Peter earned parking a seat at the table early in major city projects. [38:00] Balancing automation with a human touch by turning enforcement staff into downtown ambassadors. [43:00] Looking ahead: curb demand from deliveries and rideshare, micro mobility, and expanding enforcement hours. [48:00] Lightning round: Peter's go-to phrase, hardest career challenge, and what he's most proud of. Notable Quotes "It's just parking, it's not rocket science. We can figure anything out." - Peter Sherwill "I will carry the baton for whatever project it is as far as I must, to hand it off to the next person. I don't just wait for that baton to come back - I take the next one." - Peter Sherwill "If you need something to be successful at your job, let us know what it is. As long as it's reasonable, we're going to get it for you. I don't think I've said no once." - Peter Sherwill About the Guest Peter Sherwill is the Chief Public Parking Officer for the City of Jacksonville, overseeing a comprehensive system of parking garages, surface lots, on-street parking, and enforcement across 850 square miles - the largest city by land area in the contiguous United States. Peter has more than 20 years of experience in municipal and private sector parking operations, including event parking for sports and entertainment venues, short-term garage and valet operations at Denver International Airport, and municipal parking leadership in Denver and Fort Myers. He is recognized for optimizing revenue, developing high-performing teams, enhancing the customer experience, and advancing smart mobility technologies. Additionally, Peter currently serves as Secretary for the Florida Parking and Transportation Association.

Who has been a guest on Harder Than It Looks: Parking Uncovered

Names identified in recent episode analyses. Showing up to five guests.

• Jeff Pinyot
• Kenzie Coulson
• Rick Serra
• Mike Simmons
• James Paden

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

7 ratings

Spotify

5.0 / 5

7 ratings

Podcast Authority Score: 49 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

69

Social presence

0

YouTube

0

Engagement

71