Overview Summary
Mitch Bach talks with Josh Halpern and Ben Sann from TourOptima about how to stop treating operations as a cost center and start using it to drive revenue. The session covers specific tactics for upselling, cross-selling, protecting reviews, retaining revenue through disruptions, and communicating with guests across the booking lifecycle, all built around what happens after the booking instead of before it.
Key Takeaways
1. Your biggest revenue opportunity is not more marketing, it is better operations (02:49)
Operators default to spending more on top-of-funnel ads when revenue stalls. Josh argues the bigger return is looking inward at what happens after the booking. Smarter communication, better timing, and fewer missed opportunities inside your existing guest flow will outperform another round of Google Ads for most operators.
2. Use audio guides to triple your OTA listings for the same search term (05:11)
List a self-guided audio tour, a small group guided tour, and your main guided product on the same OTA. Three listings instead of one. The audiences are different and do not cannibalize each other. You can also use the audio guide slots to upsell people into a guided tour as the departure gets closer and you see which time slots are filling.
3. Offer a free audio guide as a lead magnet to capture contact information (09:22)
A free “top 10 food spots” or “intro to the city” audio guide gives people a reason to hand over their email and opt into marketing. It costs you almost nothing to produce. You then funnel those contacts into paid guided experiences. Ben describes operators in Florence doing exactly this.
4. Audio guides in underserved languages are low-hanging fruit (09:35)
Josh lived in China for seven years and says most operators shy away from the Chinese market because they do not have Mandarin-speaking guides. A Mandarin audio guide solves that. You do not need the full infrastructure. You just need to be the one operator who actually speaks to that audience.
5. Keep OTA and agent communications utility-only, and upsell back into their platform (11:26)
Viator is running secret shoppers to check what you send their customers. If you upsell, make it another product that lives on the same OTA. That builds trust. Blasting promotional messages to an OTA’s customers will get you flagged. For luxury agencies, limit yourself to day-of logistics unless the agency explicitly agrees to more.
6. When disruptions happen, offer a rebooking before you offer a refund (15:31)
Ben puts it simply: the first thing you do is offer another date. Not a refund. If you have already built personal connection through a guide intro, a free audio guide, or personalized messages, guests are more likely to stick with you through weather cancellations, bus breakdowns, and no-show guides.
7. Put a real person’s name on every message (16:30)
Small operators try to look big by sending from “Rome Tours LLC.” Big operators spend money trying to look small. Guests want to hear from Maria, not a brand. It does not have to be the actual guide. But a real name makes the experience feel personal, and it makes cancelling feel a little rude. Josh says if you have not added names to your messages yet, do it today.
8. Time your upsells to two windows: 24-48 hours after booking, or 72 hours before arrival (18:57)
Those are the two moments when guests are either excited to enhance or planning logistics. Outside those windows, upsells feel like spam. Inside them, you are helping someone plan a better trip.
9. Profile three guest types and map a unique upsell to each (19:30)
Families get kid-friendly add-ons. Couples get evening experiences. Large parties get private upgrade offers. Your booking system already sends PAX data (adults, children, infants) via webhooks. Use it. If you do not have a unique upsell for each of your top three guest profiles, start building one.
10. Sell the private upgrade when seats will not fill (20:20)
A family of four booked on a semi-private van of ten. Six seats are empty and you are 72 hours out. Sell them the private experience on the same vehicle at a premium. You recover revenue on seats that were going to go empty anyway. Do not send that offer to guests still inside the free cancellation window.
11. Lunches, alcohol upgrades, and audio guides are the top-performing upsells (31:43)
Ben names these specifically. Lunch upsells hit 42% conversion when sent to the right tour, at the right time, with the right group. For cross-sells, pairing your tour with an evening activity like a flamenco show works well, especially when you can guarantee the timing between experiences.
12. WhatsApp and in-app messages get 80% read rates versus 20% for email (23:13)
Ben pulled the numbers the same day. SMS is hard to measure, but mobile channels overall are at 80%. If you are relying on email for pre-tour communications, four out of five guests are not reading them. One caveat from Josh: if your audience skews older, email still works for that group.
13. Preempt known pain points before guests discover them (24:15)
If the line at the Colosseum is always 20 minutes at 5pm, tell guests before they arrive. Offer a trivia quiz or an activity to fill the wait so the experience starts when they get in line, not when they get through the door. Josh says misaligned expectations cause more negative reviews than bad experiences.
14. Check in with guests before the OTA review request hits (35:36)
Ask a quick “how is everything going” before the platform sends its automated review prompt. If someone flags a problem, you have a window to respond, apologize, or offer a discount. Sending every guest to leave a public review without knowing their sentiment is a gamble. Josh says you can automate it: anyone who gives one star gets 20% off their next trip and an apology note.
15. Build a pre-check-in step like airlines do (28:29)
Let guests check in before the tour. If they do not, ping them with a reminder. If they miss the window entirely, send an automated message offering to rebook for a fee. Most guests assume a missed tour means the money is gone. Telling them it is not changes the outcome.
16. Send a guide selfie at the meeting point, not just a pin on a map (28:50)
Map every guide to every location to every tour. Automate a photo of the guide at the exact meeting spot going out to guests before they arrive. It cuts “where are you” phone calls and gives guests three trust cues: a name, a face, and a specific location detail.
17. Shorten every guest message by 30%, then cut it again (30:30)
Josh says people are not reading long messages. Write it, cut a third, then cut another third. If you have not done this exercise on your current pre-tour and post-tour messages, it is the fastest free improvement you can make.
18. Cross-sell other operators’ products, not just your own (34:43)
You do not need to own boats and vehicles to grow revenue. Partner with a complementary operator and sell linked packages. Some operators white-label delivery for each other and the guest never knows the difference. Join the OTA’s affiliate program and you can cross-sell partner products through the same platform.
19. Private transfers sell at around $80 and convert well for parties of three or more (40:51)
Guests pay for certainty. Missing a tour because they could not find a taxi costs them hundreds in non-refundable tickets. For larger parties, the per-person cost drops fast. If you already employ drivers and own vehicles, this is revenue on assets you are paying for anyway.
20. For regional instability, communicate proactively and honestly (38:28)
Do not whitewash the situation. Acknowledge it, explain what you are monitoring, confirm the tour is still on schedule, and give them an emergency contact. Josh says the knee-jerk reaction to present a positive face without acknowledging reality does not land well. Guests want honesty and a plan, not reassurance.
21. Opt-out rates on pre-tour messaging are under 0.3% (43:39)
Ben pulled this from one of the largest operators in the world. The only spike in “stop” replies came from post-trip surveys. Before that, guests want the updates. If you are holding back on pre-tour communication because you are afraid of over-messaging, the data says you are leaving money and experience quality on the table.
22. Keep guests on your app after the tour with photos, audio souvenirs, and return discounts (44:16)
Group photos from the guide, cooking class recordings, 10% off the next booking, and exclusive audio content all give guests a reason to keep you on their phone. Josh adds that geolocalization can ping returning travelers when they arrive in another city where you operate. If you stop adding value, they delete you.
23. Build a pre-trip group chat for multi-day tours weeks before arrival (29:31)
Introduce the guide in an automated message and let guests start talking to each other before they land. Guides usually are not paid for pre-trip communication, so the office handles the early touchpoints and automates reminders about passports, medical forms, and logistics. Once the group is connected, they build relationships that increase stickiness and lifetime value. Josh says this elongated brand experience is one of the biggest drivers of repeat bookings on multi-day.
24. Start mobile messaging from booking confirmation, not just before the tour (46:07)
Ben says the switch from email to SMS or app-based messaging should happen at booking confirmation. Do not wait until the week before departure. The earlier you move guests onto a mobile channel, the higher your read rates and the more touchpoints you have to personalize, upsell, and build trust before they arrive.
25. Turn post-tour photo montages into a referral channel (45:23)
Catalog every photo by tour, guide, and guest. A month after the trip, send a montage back to the guest with a “share with a friend for 20% off” offer. It works as a souvenir, a re-engagement trigger, and a referral tool in one message. Josh says the montage is one of the simplest ways to turn a past guest into an affiliate for your business.