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

“Harder Than It Looks: Parking Uncovered” is our podcast that we use 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.

Today, we’re rewinding and recapping Episode 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 roughly 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 a dedicated 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 ever-changing.
   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.

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 have to hand it off to the next person, and 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 jpb, 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 ever said no once.” – Peter Sherwill

Meet Our Guest:

You Won’t Want to Miss These Clips:

Episode Highlights:

• Introducing Peter Sherwill and his origin story. [02:00]
• Learning municipal parking in Denver and expanding paid parking in Fort Myers, Florida. [04:00]
• The surprise twist that turned a different job interview into an offer for Chief Public Parking Officer. [06:00]
• Keeping a lean team motivated without an appreciation budget – break rooms, new uniforms, and “Win Wednesday”. [12:00]
• A technology rundown: multi-space meters, online permitting, new LPR systems, and upgraded garage equipment. [17:00]
• Stakeholder stories: booting a city council member’s car and creative curb solutions for a century-old downtown business. [19:00]
• Cross-departmental collaboration on downtown revitalization, the new Jaguars stadium, and micro mobility expansion. [30:00]
• How Peter earned parking a seat at the table early in major city projects. [36:00]
• Balancing automation without a human touch by turning enforcement staff into downtown ambassadors. [38:00]
• Looking ahead: curb demand from deliveries and rideshare, micro mobility, and expanding enforcement hours. [43:00]
• Lightning round: Peter’s go-to phrase, hardest career challenge, and what he’s most proud of. [48:00]

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