Travel Advisor Success Story: Pasindu Wewegama, Carlisle Travel Management

Claudette Covey
by Claudette Covey
Last updated: 11:00 AM ET, Sun May 3, 2026
Travel Advisor Success Story: Pasindu Wewegama, Carlisle Travel Management

Pasindu Wewegama (Source: Pasindu Wewegama)

Travel Advisor Success Stories focus on accomplished advisors and how they achieved success. Here’s a look at Pasindu Wewegama, a travel advisor with Carlisle Travel Management.

How did you get your start as a travel advisor?

I came from a software engineering background and got my start as a travel advisor during the pandemic. With travel largely on pause, I saw it as an opportunity to learn the industry so I could be ready when demand returned.

Before that, I had been planning trips for friends and family for nearly a decade and eventually realized it could become something more. I joined Carlisle Travel Management after meeting its president, Jerry Saxe, who encouraged me to combine my passion for travel with my background in technology.

Early on, I focused on adventure travel, particularly on the national parks of Utah and Arizona, and learned the business through hands-on experience.

Over time, I expanded my focus and built a more structured approach to planning and servicing clients.

How did you build your business?

I built my business by taking every opportunity early on and treating each trip as a learning experience. That gave me exposure to a wide range of clients and helped me understand both the creative and operational sides of the business.

Over time, I refined my focus toward more detailed, experience-driven travel. As my business evolved, I became more intentional about building it around the types of trips I’m most passionate about creating and the clients who value that level of care.

What characteristics make you a successful advisor?

I’m very detail-oriented and focused on how a trip feels from beginning to end. I want every travel experience to be thoughtful and seamless, not just logistically, but emotionally.

I also place a lot of importance on relationships – with my clients and with the partners I work with. I only recommend experiences I truly believe in, and those relationships help ensure my clients are well taken care of.

That combination of attention to detail and trusted partnerships allows me to create more consistent and personalized experiences.

What have been your greatest challenges?

One of the biggest challenges has been balancing client availability with the need to continue learning through travel. To stay current and provide value, I want to be constantly exploring new destinations and experiences.

At the same time, I’m committed to being available to my clients, especially while they are traveling. Finding the right balance between those two issues has been an ongoing challenge.

What are your greatest accomplishments?

One of my biggest accomplishments was reaching over $1 million in sales by my third year while serving fewer clients than I did early on. That was important to me because it reflected the kind of business I wanted to build – one focused on quality over quantity and long-term relationships.

I’m also proud of being selected as a panelist for USTOA early in my career and contributing to the development of the Carlisle Travel website, combining my technology background with my experience as an advisor.

What tips can you provide to advisors new to the industry?

Focus on what you’re genuinely passionate about. It makes learning the business more effective and allows you to speak with confidence when working with clients.

It’s also important to understand what makes you different and lean into that. Clients are often buying into your perspective as much as the trip itself, so developing your own voice and approach is key.

Over time, consistency, relationships and attention to detail will set you apart.


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