Cyclist on a winding Tuscan road at golden hour

Concrete Ideas for Trek Travel's Next Chapter

Six actionable proposals to strengthen margins, retain talent, expand the mission, and position the brand for what's coming.

Charlotte · March 2026

The Premise

AI is reshaping the economy. That changes who your customer is and what they'll pay for.

White collar income volatility is accelerating. The younger demographic TT wants to reach is the most exposed. Meanwhile, TT's core clientele (affluent, 55+, North American) is the most insulated. The macro trend doesn't threaten Trek Travel. It clarifies where the durable demand lives and what the brand should double down on: irreplaceable, human, real world experiences.

The question isn't whether to use AI. It's how to use it to make the human experience even better, protect margins, and fund the mission without diluting the brand.

A note on perspective

These proposals are based on external observation. The internal reality of how TT operates day to day would change my priorities. If guide scheduling runs on spreadsheets, or the marketing funnel has a 60% drop off at inquiry, those are higher ROI fixes than anything below. The first proposal addresses exactly this.

Aerial view of cyclists on a coastal road with support van

The Proposals

Six ideas, each with a concrete first step

Ordered from quickest win to longest horizon. Each can be pursued independently.

Map the current state of guide scheduling, vendor management, guest communication, and bike logistics. Identify where manual processes, communication gaps, or outdated tools are costing time and money. The output is a prioritized list of quick wins.

Key diagnostic questions

  • How are guides assigned to trips? Centralized system or spreadsheets and calls?
  • How are hotel/restaurant confirmations tracked and communicated to guides in the field?
  • What does the communication flow look like between Waterloo HQ and a guide team in Tuscany?
  • Where are the biggest drop offs in the sales funnel from inquiry to booking?
  • What is the repeat booking rate, and is there a systematic re-engagement strategy for lapsed guests?
  • What are the most common friction points in post trip surveys? Patterns vs. one offs?

First step

Four to five focused 45 minute interviews with team leads across operations, sales, and the guide team. Structured question set prepared in advance. Findings document delivered within one week.

A cycling guide helping a guest in a European village
Wine glass and cycling map on a terrace overlooking vineyards

Where to Start

Three projects I can begin immediately

01

AI Discoverability Audit

Test TT across every major AI assistant for 25+ travel queries. Document where you show up, where you don't, what competitors do. Prioritized action plan.

1 week
02

Guest Briefing Pilot

For one departure, create AI synthesized guest profiles for guides using existing booking data. Measure impact via post trip surveys from guests and guides.

Next available departure
03

Booking Data Deep Dive

Three years of data to identify demand patterns, price elasticity, and customer segmentation. Foundation for any pricing or expansion decision.

2 to 3 weeks

Happy to start with any one of these. Even a single conversation to pressure test the priorities would be a good use of an hour.

Charlotte