A — Their world
[3]- 01What kind of operations have you run/worked — restaurant, hotel, hospital, event? Which do you know best?
- 02On a typical Friday night: how many cars total? How big is the worst rush (cars in 15 minutes)?
- 03How many valets per shift? How are they paid — hourly + tips? How bad is turnover?
B — How it works today
[4]- 04Walk me through one car arriving, step by step — who touches what, from pull-up to key on the board.
- 05Paper tickets or software? If software: which one, what does it cost, who chose it?
- 06How does a guest get their car back today — hand back a ticket, text a number, call? What’s the average wait, and what wait makes guests angry?
- 07How do you track where a car is parked (lot / row / spot)? How are keys organized? What happens when a key can’t be found?
C — Pain (the gold — go slow here)
[5]- 08What goes wrong most often? Lost tickets, lost keys, wrong car pulled, guest disputes?
- 09Damage claims: how often do they happen, what’s the process, what does a typical claim cost the operator? Would timestamped check-in photos have saved real money?
- 10Describe the worst part of a peak rush — first from the valet’s point of view, then the manager’s.
- 11How much payment is still cash? How are tips split — pooled or individual? Ever seen tip disputes or shrinkage?
- 12Cell signal in the garages/lots you’ve worked — does anything phone-based actually work down there?
D — Money & buying
[4]- 13Who decides what software a valet company uses — the owner, an ops manager, or does the venue dictate it?
- 14What would an operator realistically pay — per month per location, or per car? What does the current tool cost them?
- 15How do valet companies win venue contracts? Would hard data (average wait time, damage claim rate, guest ratings) help win a bid?
- 16Have you seen Oobeo, SMS Valet, CVPS, or Flash in the wild? What did people actually like or hate about them?
E — Kill questions (be brave)
[3]- 17If this tool existed tomorrow, would operators actually switch? What stops them — contracts, hardware, training, “we’ve always done paper”?
- 18What single missing feature makes this a non-starter for an operator?
- 19Is there anything about this industry that would make you tell a friend not to build software for it?
— deep dives —
F — The lot itself
[4]- 20When a guest is waiting and the valet who parked their car is mid-run, how do you find it?Listen for stories, not policy.
- 21How do you decide the lot is full, and who makes the overflow call? Ever gotten it wrong?
- 22Do you stack? How do you pick what parks behind what, and what happens at shift change?
- 23If you sketched your lot on a napkin for a new hire, what would you draw — named areas, rows, numbered stalls?
G — Connectivity & the podium
[6]- 24Name specific sites where phones die. Underground, or mid-deck too? Which carrier held out longest?
- 25What does the crew actually do today when signal dies — radios, paper backup, shouting up the ramp, a hotspot taped in a window?
- 26Where does the podium physically sit relative to the structure — street-level curb, or inside the deck itself?
- 27Does venue Wi-Fi exist, and does anyone get to use it? Who pays for hotspot plans today?
- 28Have you seen a valet app fail underground? What happened to the tickets?
- 29Would a ~$500 preconfigured connectivity kit plus a small monthly fee be a relief or an objection?
H — The venue’s POS & payments hardware
[2]- 30What POS runs at the venue — Toast, Clover, Square, Micros? And does the valet operator take payments on their own terminal or the venue’s?
- 31Would one handheld that does tickets, payments, and stub printing appeal — or do crews want their phones and nothing else in their pockets?
I — Damage claims & photos
[2]- 32What’s the longest-delayed claim you’ve seen actually stick — and did any ever go legal?
- 33Do garage-keepers insurers specify how long photo evidence must be kept?
J — Paper tickets & the hybrid
[5]- 34Who prints your tickets today, what does a book cost, how often do you reorder?
- 35If the same stub had a QR that let guests ping for the car and tip by card — what, if anything, would your crew have to change?
- 36What share of your guests would scan vs. just hand the stub back? Would you put a tip QR on the stand sign tonight?
- 37Would you let guests pay from their phone while in line, or must a human always collect?
- 38When the system is down or signal dies, what does your crew do today?
K — Devices, apps & the stand
[6]- 39Whose phones run the stand — valets’ own, or company devices? Who pays for the data plan?
- 40Would your valets install a work app on their personal phones — and would you ask them to?
- 41Is there a tablet or phone that lives at the podium on a charger?
- 42When you’ve evaluated valet software, did “is there an app in the App Store” matter to anyone who signed?
- 43How much of payment/tips happens at the stand vs. the guest’s phone? Would tap-a-card-on-the-attendant’s-phone matter?
- 44For hotel/hospital prospects: does vendor onboarding involve a security review or questionnaire?
After the calls, we should know
- Beachhead segment (where the network is warmest)
- What operators will pay, and who signs the check
- The 3 must-have features and the 1 deal-breaker
- Whether offline mode is essential on day one
- One named operator willing to pilot
- Whether “my guys just know where cars are” — lot zones as a wedge, or just a settings page
- Where the podium sits, and whether a connectivity kit is a relief or an objection
- The right default ticket mode — digital / hybrid / paper — and a guess at guest scan rate
- How long after pickup claims actually surface, and any insurer retention minimums
- BYOD vs. company devices, and whether a missing app-store listing gates any deal
Three live screens — stand, guest phone, ready board — running on demo data. Nothing to install.