How Tailormade Increased Proposal Conversion Rates to 42% Using White-Label Itinerary Software
Spain Luxury 7 users
“Wow factor matters… Tourwiter itineraries deliver higher conversions than pdfs and other software”
Sam Lister, Founder, TailormadeSummary
Company: Tailormade (Seville, Málaga, and Jerez, Spain)
Founded: 2008
Challenge: Manual proposal creation taking up to 4 days for complex itineraries, with inconsistent presentation affecting conversion rates.
Solution: Implemented Tourwriter’s white-label itinerary software for streamlined, same-day proposal turnarounds with professional branded presentations.
Results: 42% proposal-to-booking conversion rate, same-day turnaround on 15-day itineraries, 100% white-label branded proposals for agent partners.
Nearly a decade after first adopting Tourwriter in 2016, Tailormade converts 42% of proposals into bookings. Behind that number sits a deliberate strategy and the right software stack.
Results at a Glance
Before Tourwriter:
- Manual copy-paste proposal building
- Up to 4-day turnaround on complex itineraries
- Basic PDF formatting
- Inconsistent agent experience
After Tourwriter:
- 42% proposal to booking conversion rate
- Same-day turnaround on 15-day itineraries
- 100% white label branded itineraries for agent partners
- Consistent, professional presentation that helps agents close deals
The Challenge: Speed and Polish Matter When Agents Charge Planning Fees
Sam Lister describes himself as an “international mongrel”, half Kiwi, half Scot, raised across Hong Kong, Japan, and England. He landed in Seville straight out of university, drawn by Spanish studies and, he admits with a laugh, a girl from Seville.
“I wouldn’t say the rest is history. I actually married a different girl. But the whole culture, I was drawn to it.” What stuck was Sam’s unique perspective. “I feel like a local, but with the eye of a foreign traveller. I’m almost like a bridge between two worlds.”
Working for a travel and lifestyle magazine gave him insider access to Andalucía’s hidden gems. In 2008, he launched Tailormade alone, building relationships most tour operators never can. We’re talking winery owners who personally conduct tastings, local families who host travellers in mountain villages, and artisan workshops that create authentic experiences.
“So often the most lasting memories are made by the people you meet along the way,” Sam explains.
“The person who shows you around is the eyes through which you see that experience. You get a much different experience having a wine tasting with the owner of a winery rather than someone on work experience.”
The Local Knowledge Advantage
Sam’s strategy focuses on secondary destinations and rural areas where authentic Spanish culture thrives, untouched by mass tourism.
“The largest cities like Barcelona, Madrid, and even Seville have become very cosmopolitan. Whilst you do get a good taste of Spanish culture, it’s perhaps not as raw as when you get out to where people are living in a genuine bubble of local culture. It’s harder to achieve that nowadays.”
This approach became Tailormade’s competitive advantage. They provide access to experiences only available through Sam’s years of relationship building in southern Spain.
But insider knowledge only matters if you can package it professionally and fast.
The Old Way: Copy, Paste, Proofread, Repeat
Before adopting Tourwriter in 2016, creating itineraries was painful.
“It was very manual. Copy, paste, copy, paste and then constantly proofread. You had to go through it with a fine-tooth comb to make sure you’ve got everything right.”
Multi-day turnarounds were normal. Complex itineraries took even longer. And when travel agents started charging planning fees, they expected DMC partners who could move at their speed.
Tailormade needed technology that could keep up.
The Solution: Technology That Supports Quality Partnerships
Post-pandemic presented a choice. Demand exploded. Many companies hired aggressively, chasing every booking opportunity.
Sam chose differently.
“We could have grown a lot faster if we wanted to, but we don’t really have a great interest in conquering the world,” he explains. “We’ve got a very tight core team, which means everything.”
From 2021 to 2024, Tailormade grew from four people to seven, while competitors often doubled or tripled team size.
But slower headcount growth meant the technology had to work harder.
How Tourwriter Helped Tailormade Scale Quality Without Rapid Expansion
Tailormade first adopted Tourwriter in 2016, transforming their proposal process. In 2020, they upgraded to the new version of Tourwriter, further enhancing their capabilities.
The platform solved three specific problems:
1. Speed Without Sacrificing Quality
Even with Tourwriter’s supplier catalogue and templates, a complex 15-day itinerary can still take one to two hours to build properly. But that’s same-day turnaround instead of multi-day processes.
“Whilst Tourwriter is intuitive, you know, if you’re going to create a 15-day trip completely from scratch, it’s still going to take you anywhere from an hour to two hours, depending on the complexity,” Sam notes.
That combination of craft and speed matters when professional agents charge planning fees and expect quick turnarounds.
2. White-Label Proposals That Make Agents Look Good
White-label capability became essential to Tailormade’s agent relationships. Every proposal carries the agent’s branding, logo, colours, and contact information while showcasing Tailormade’s expertise behind the scenes.
3. Presentation That Drives Conversions
Sam noticed something important: modern proposal presentation directly impacts conversion rates, not just Tailormade’s, but their agents’ too.
“The aesthetics are really cutting edge. The itineraries are really beautiful to look at. When people click on the link, that initial impression they get, the wow factor, really does have an effect.”
When agents send a Tailormade proposal, the professional presentation reflects well on them. “Conversions are a lot higher compared to when we’ve exported PDFs, but also compared to a lot of other people’s trip software.”
The Quality Agent Partnership Strategy
Tailormade’s 42% conversion rate stems from a deliberate choice: work exclusively with professional travel agents who pre-qualify clients through planning fees.
“The agents we work with are very slick,” Sam explains.
“Once they’ve got a client, they’ve got a planning fee. We’ve got good relationships with them, and once an itinerary is in the planning process, it’s quite a high level of expectation that it will confirm.”
But Sam knows these professional agents have choices. What makes them choose Tailormade repeatedly?
The Two-Person Team Model
Every confirmed booking gets assigned two dedicated specialists:
Trip Designer: Works with the agent or client from first inquiry through to arrival, ensuring the itinerary perfectly matches expectations.
Operations Specialist: Handles all reservations, ground logistics, and serves as the client’s personal concierge during their trip via WhatsApp.
“I am aware that a lot of companies will just give you a generic concierge number or bounce people around the office,” Sam notes. “That’s not us.”
This model ensures continuity. The person who designs the experience is there supporting clients throughout their journey.
Why Team Cohesion Drives Consistent Agent Service
Sam’s deliberate growth approach created unexpected advantages:
Team Knowledge: Every team member knows the business deeply. No generic responses or passed around to clients.
Quality Over Volume: More time per proposal means better customisation and higher conversion rates.
Consistent Service: Travel agents receive reliable, high-quality service that builds long-term relationships.
Before scaling your team rapidly, consider whether new hires will maintain or dilute your service quality. Consistent performance attracts more agent partnerships than larger teams with variable quality.
Specialisation: How Family Travel Became a Profitable Niche
Over three years, Tailormade developed expertise in family travel. Working with specialised family travel agencies, Sam refined his approach to multi-generational groups and families with children to become a market leader in this space.
Making History Engaging for Young Travellers
The challenge: How do you teach Spanish history to children without boring them?
Sam’s solution combines movement, hands-on experiences, and food:
Dynamic Transportation: Bike tours through medieval quarters, riverboat rides, horse-drawn carriages instead of walking tours and buses.
Hands-On Food Experiences: Visiting orange groves to pick fruit, make fresh juice, and bake orange cake; chocolate and marzipan workshops instead of standard cooking classes; market tours where children select ingredients for lunch.
Interactive History: Art restoration demonstrations, flamenco lessons, craft workshops where families create pieces they take home.
“Making things a bit more engaging for the kids” isn’t just good service; it’s what drives repeat bookings and agent referrals.
Sam emphasises that customisation makes the difference: “We don’t just send a random product. We go into the detail of how each product can be adapted or a new product created to kind of suit families, particularly the ages and the individual profiles within a family group.”
Technology in Action
Tourwriter’s supplier catalogue and product library let Tailormade quickly customise family experiences for different age groups. What once took hours of manual formatting now happens in minutes, allowing the team to focus on creative trip design instead of administrative work.
5 Ways Tour Operators Can Increase Conversion Rates Using Technology
1. Match Your Operations Speed to Professional Agent Expectations
What Tailormade Does: Leverages Tourwriter to enable same-day or next-day proposal turnaround for complex itineraries.
Why It Works: Professional agents who charge planning fees move quickly. Technology-enabled operational speed means proposals arrive while clients are excited and ready to commit.
Your Action: Audit your proposal turnaround times. If complex itineraries take more than 2 or 3 business days, your technology may be limiting agent partnerships.
2. Use White Label Technology to Strengthen Agent Relationships
What Tailormade Does: Uses white label proposals so every itinerary carries the agent’s branding while showcasing Tailormade’s expertise.
Why It Works: Agents can send professional proposals immediately without reformatting or rebranding, maintaining their client relationships while accessing your expertise.
Your Action: If your system doesn’t support white label proposals, you’re creating friction with agent partners. This single feature can differentiate you from competitors.
3. Professional Presentation Directly Impacts Agent Success
What Tailormade Does: Invests in modern proposal presentation that creates immediate visual impact through Tourwriter’s interactive itineraries.
Why It Works: Beautiful, modern itineraries signal quality before anyone reads the content, leading to higher agent conversion rates and more repeat business.
Your Action: If you’re still sending PDF documents, you’re handicapping your agent partners. Look for systems that create web-based, responsive proposals with strong visual design.
4. Specialise to Become Agents’ Go-To Expert
What Tailormade Does: Develops deep expertise in family travel and in lesser-known parts of Spain and Portugal.
Why It Works: Specialisation builds reputation among agents. When an agent has a specific type of trip, they know who to contact.
Your Action: Become an agent’s first call for something specific. Deep specialisation makes you memorable and referable within agent networks.
5. Technology Should Enable Your Philosophy, Not Replace It
What Tailormade Does: Uses Tourwriter to streamline operations while maintaining personal service and human creativity.
Why It Works: The right technology amplifies what makes you unique. It doesn’t commoditise your service.
Your Action: Choose software that supports your business model, not one that forces you to change how you operate.
What’s Next for Tailormade
For Sam Lister, the next chapter is about evolution, not expansion. Tailormade is stepping confidently from a boutique operation into a refined, data-driven business that keeps its personal touch at the heart of everything.
“It’s about pairing the care and creativity we’ve always had with stronger systems, better forecasting, and deeper analytics,” Sam explains.
“We’re building the structure of a serious company while keeping the soul that’s made us who we are.”
Sam watches artificial intelligence development pragmatically and sees AI as a tool for streamlining operations and amplifying the human touch in relationship building and creative trip design.
Sustainable Tourism Leadership
Beyond business growth, Sam invests in regenerative tourism. Tailormade supports a local non-profit restoring abandoned salt marshes, creating eco-tourism experiences that fund environmental restoration.
Travel must be a force that supports local people and places. Bespoke tour operators and travellers are united in wanting tourism to leave a positive impact. Tailormade are at the front, demanding and demonstrating what this change needs to look like through their eco-tourism initiatives and tours taking in less-visited places.
The Ever Elusive Balance
When asked what drives Tailormade’s success, Sam returns to his core philosophy:
“We aren’t actually striving to be a big company. It’s more striving to find that ever elusive balance between quality, personal touch and hard work.”
In an industry where many agencies chase scale at any cost, Sam’s approach proves that thoughtful growth, high conversion rates, and deep client relationships create more sustainable success than rapid expansion.
His 42% conversion rate demonstrates that being selective about growth doesn’t limit success but amplifies it. And the right technology makes that philosophy scalable.
Frequently asked questions
How did Tailormade achieve a 42% conversion rate?
Tailormade’s 42% conversion rate comes from a combination of working exclusively with professional travel agents who pre-qualify clients through planning fees, delivering same-day proposal turnarounds using Tourwriter, and creating visually impressive white-label itineraries that help agents close deals. Their dedicated two-person team model (trip designer + operations specialist) ensures consistent, personalised service throughout the client journey.
What is Tailormade’s two-person team model?
For every confirmed booking, Tailormade assigns two dedicated specialists: a Trip Designer who works with the agent or client from enquiry through arrival, and an Operations Specialist who handles reservations, logistics, and serves as the client’s personal WhatsApp concierge during their trip. This ensures continuity and eliminates the frustration of being bounced around different team members.
How long does it take Tailormade to create proposals with Tourwriter?
Complex 15-day itineraries that previously took up to 4 days can now be completed in 1-2 hours, enabling same-day turnaround. Whilst Tourwriter streamlines the process through supplier catalogues and templates, Tailormade still invests time in thoughtful customisation to maintain quality and achieve high conversion rates.
How did Tailormade specialise in family travel?
Over three years, Tailormade developed expertise working with specialised family travel agencies, refining their approach to multi-generational groups. They make history engaging for children through dynamic transportation (bike tours, riverboats, horse-drawn carriages), hands-on food experiences (picking oranges, chocolate workshops), and interactive activities (flamenco lessons, craft workshops) rather than traditional walking tours and museums.
How has Tourwriter helped Tailormade grow post-pandemic?
What makes Tailormade’s presentation different from PDF proposals?
Tourwriter’s web-based itineraries create immediate visual impact with modern, responsive design that works across devices. Sam Lister notes that “the wow factor really does have an effect” on conversions, with Tourwriter proposals significantly outperforming both exported PDFs and other trip planning software. The professional presentation reflects well on both Tailormade and their agent partners.
What is Tailormade’s approach to sustainable tourism?
Tailormade focuses on secondary destinations and rural areas where authentic Spanish culture thrives, supporting local communities away from mass tourism. They partner with a local non-profit restoring abandoned salt marshes, creating eco-tourism experiences that fund environmental restoration, demonstrating that tourism can be a force that supports local people and places.
Table of contents
- > Results at a glance
- > The challenge: Balancing speed and polish
- > The local knowledge advantage
- > The old way: copy, paste, proofread, repeat
- > The technology solution
- > Scaling quality with Tourwriter
- > Their agent strategy
- > The two-person team model
- > Unexpected advantages
- > how the family niche become profitable
- > How to increase conversion rates
- > What’s next for Tailormade
- > Frequently Asked Questions
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