Podcast EP 20 Rewind: Parking Pros and Marketing Must-Knows

October 21st, 2024 | Courtney Cooper

“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 20: Parking Pros and Marketing Must Knows with Dani Crain, John Conway, and Kyle Lacy.

In Segment 1 of this episode of Harder Than It Looks, we welcome Dani Crain and John D. Conway, industry legends and podcast hosts of ‘All Things Parking with Dani and John,” to share their experiences, hot industry takes, and diversity and supporting women in parking. 


In Segment 2, Heidi Barber, our VP of Marketing, sits down with Kyle Lacy, CMO of Jellyfish, who shares his journey in marketing growing and scaling leading tech companies. In his segment, we discuss balancing creativity with revenue, the alignment between marketing and sales, personal branding, and strategies to avoid burnout. 

Meet Our Guests:

Dani Crain

Senior Director Parking & Mobility, Oakview Group

Dani Crain lives in Denver Colorado with her beloved pup Axl. She’s a small-town girl from New Mexico who had big dreams to change the world, little did she know she would be doing just that, one parking space at a time. Dani has been in the consulting space for over 10 years; she successfully ran her own business in Denver for 4 years before moving into the wonderful world of parking and mobility. She has been in parking going on 7 years, her expertise is in parking operations with an emphasis on parking technology. When she’s not traveling coast to coast, she spends her time with a good book and glass of vino.

    John Conway

    Co-Founder, Chief Business Officer, Parking Revenue Recovery Services

    John D. Conway is a parking industry veteran with over 29 years of experience in transportation and parking operations. He is a founding member of Parking Revenue Recovery Services (PRRS) and contributed significantly to making PRRS the industry’s leading compliance and data analytic services provider. John serves as Chief Business Development Officer and Executive Vice President at PRRS and continues to be the company’s visionary as a member of the Board of Directors. Previously, he served Denver Mayors Wellington Webb and John W. Hickenlooper as a commissioner on the Denver Parking Commission and was appointed by both administrations to serve two consecutive three-year terms. Recently he served on the Board of Directors for the Cherry Creek North Business Improvement District. John is in possession of a vast parking industry knowledge, and he can’t wait to share it with you!

      Kyle Lacy

      CMO, Jellyfish

      Kyle is currently serving the Jellyfish team as their CMO. Before joining the Jellyfish ‘bloom,’ he had the pleasure of building a company called Lessonly. Lessonly employed over 230 people and changed the lives of many more after their acquisition.

      Kyle has also been fortunate to lead teams at Seismic, OpenView, Salesforce, and ExactTarget teams. Most importantly, he’s the father of two wonderful boys, an energetic dog, and one too many books on World War II.

        You Won’t Want to Miss These Clips:

        Segment 1 with Dani and John:

        • Dani’s Dog Axel (02:37)
        • Dani’s Career Path: From Radio to Parking (05:04)
        • John’s Career Path: From Military to Parking (11:23)
        • The Origin of ‘All Things Parking’ Podcast (19:05)
        • Challenges and Sacrifices in the Parking Industry (35:45)
        • Hot Takes: Smart Cities and EVs (41:56)
        • Empowering Women in Leadership (50:47)
        • Addressing Industry Biases (51:32)
        • Personal and Professional Struggles (56:14)
        • Podcast Crossover and Future Goals (01:05:36)

        Segment 2 with Kyle Lacy

        • Marketing Insights with Kyle Lacey (01:09:16)
        • Sales and Marketing Alignment (01:20:28)
        • Personal Branding and Writing (01:24:00)
        • Lightning Round (01:35:11)

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        Courtney Cooper

        Events + Community Manager

        Courtney is the Events + Community Manager at Parker Technology and has 8 years of marketing experience in marketing campaign management, events, copywriting, and podcasting.

        She is currently a member of the Indy American Marketing Association Chapter, and is an associate member of Pavilion.