HeyJaredHarder 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.
- Indexed episodes, last 90 days
- 4
- Latest publication
- Sep 2, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 29, 2026
Latest episodes
EP 59: The Truth about Voice AI – and Our Work to Perfect It (opens the original)
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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 launche
EP 58: A House Fire, a 2AM Call, and a Career in Parking with Melissa Jones (opens the original)
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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 o
EP 57: 850 Square Miles: How Peter Sherwill Runs Parking for the Biggest City in America (opens the original)
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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
EP 56: The Curb: Transportation's Toughest Puzzle with Benito Pèrez (opens the original)
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In this episode of Harder Than It Looks , host Brian Wolff sits down with Benito O. Pérez, AICP, CTP, CPM, PTMP, Section Chief for Transit Capital Statewide at the Illinois Department of Transportation. Benito’s career has moved through urban planning, civil engineering, transportation policy, curbside management, accessibility, and transit capital planning. But the common thread through all of it is connection: connecting planners and engineers, connecting agencies and advocates, connecting inf
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