Jason (Jay) Stevens: Crafting Responsible Luxury Travel

Jason (Jay) Stevens: Crafting Responsible Luxury Travel

Jason (Jay) Stevens,    CEO

Jason (Jay) Stevens


Embarking on a journey is not just about reaching a destination; it's about creating lasting memories and immersing oneself in experiences that resonate on a personal level. This is where the allure of tailor-made luxury holidays shines, offering travellers the opportunity to go beyond the ordinary and shape their adventures based on individual interests. Recognising the transformative power of tailor-made luxury, Wayfairer crafts not just vacations but exquisite masterpieces of exploration. As a company deeply committed to responsible and more sustainable travel, Wayfairer ensures that each tailored holiday leaves a positive impact on both the traveller and the destinations visited.

At the forefront of this transformative approach is Jason (Jay) Stevens, the visionary CEO of Wayfairer. Jay's journey, spanning the corporate landscape and diverse cultures, has uniquely positioned him to lead the charge in redefining luxury travel. His passion for ethical practices and responsible, enriching travel resonates in every tailored holiday, making Wayfairer not just a travel company but a curator of unforgettable and personalized odysseys.

Jay's leadership style is defined by a genuine passion for people and their success. His commitment to fostering personal and professional growth, coupled with a team-oriented approach that embraces mistakes as integral to the learning process, sets him apart. His experiences managing ventures, working in a family-owned business, and contributing to the corporate landscape exemplify a career characterized by a diversity of challenges and achievements.

Give a brief account about your professional journey and what motivates your daily routines?

Post high school, I entered the supply chain industry, starting with UPS in New Zealand, eventually transitioning to DHL in various operational roles. My journey took me from Dubai to Singapore, the Philippines, China, and finally to the United States before parting ways with DHL.

Subsequently, I joined an Omani business (OFSAT) within the Shanfari Group, overseeing diverse ventures such as oil rig transportation, tire manufacturing, laundry services, carpentry, and shrimp farming. As the Group General Manager, I navigated the complexities of managing this Arab consortium.

Following this, I entered the corporate world again, working for a family-owned business in Singapore. The experience provided a stark contrast to my previous roles, offering valuable insights into different business perspectives. Later, I transitioned to a global role with Schneider Electric, focusing on transformation initiatives.

As circumstances evolved, I found myself in Thailand, working regionally for a Swiss company, then later with SAP. A return to DHL in an e-commerce role came next, but it became apparent that my aspirations lay beyond the corporate realm. Realizing my corporate limits, I seized the opportunity to invest in Wayfairer in 2017, initially as a third owner of a £700,000-a-year business. Quickly joining full-time as CEO, we experienced substantial growth until COVID hit in January 2020. Despite the challenges, we adapted by pivoting to PPE supplies, leveraging my network for exports from China.

My daily routine is no longer a 'routine' but a passion, working with an incredible team & deeply valuing our customers

Post-COVID, we managed a significant volume of trips, rapidly growing our team and capitalizing on the high demand for luxury travel. Wayfairer has emerged from this period stronger than ever, achieving record revenues year after year.

Now, as CEO, my daily routine doesn't feel like work; it's a manifestation of my passion. The focus on recruiting exceptional individuals and providing them with the tools they need creates a dynamic and enthusiastic environment. Our commitment to service has resulted in a 4.5-star review average, with 105 five-star reviews this year alone. It's the people, the team, and the opportunity to exceed customer expectations that drive me in leading Wayfairer.

Define Wayfairer as an organization and its position in the market.

Wayfairer is an organization that defines luxury in travel as the ability to personalize the entire travel experience according to individual hopes and dreams. By actively listening to the unique preferences and desires of each traveler, Wayfairer goes beyond conventional travel services. Leveraging extensive experience and robust local networks, the organization curates exclusive and distinctive opportunities, providing travelers with authentic interactions and uncrowded vistas that allow for a genuine and immersive experience. Wayfairer ensures that travelers have the space, seclusion, and comfort they desire, coupled with seamless support to relax and explore the most exciting destinations globally.

I would say our market position is unique, particularly in the tailor-made travel sector. Wayfairer is characterized by its dynamic and energetic approach to business. Embracing a culture that encourages learning from mistakes, we believe in continuous growth and development. We place a strong emphasis on ethical practices, especially in terms of travel and carbon impact. Currently, we are actively working on assessing the sustainability of our supplier base, engaging with local communities, and exploring innovative approaches, such as carbon offset initiatives through community farming. At the core of our values is a deep commitment to our customers—everything we do revolves around their satisfaction and needs.

As CEO, what factors guide your development of effective corporate growth strategies?

I have a golden rule of not planning too far ahead due to the unpredictable nature of events. Many companies tend to focus too far into the future, but we prioritize our customers' immediate needs and stay current with technology to drive process efficiency and improvements. Team alignment is crucial in our 40+ member organization, ensuring constant collaboration. Relevance is key in all conversations, be it with suppliers, customers, or the team, discussing technology trends and ensuring our plans are executable. It's essential to focus on the basics, execute decisions, and measure outcomes—a fundamental practice that some companies overlook.

How do you train your team to deliver services to travellers?

We seek inherently entrepreneurial individuals in our recruitment, providing significant autonomy within the business. Our support extends to facilitating new market entries and empowering our sales team to choose new suppliers, ensuring compliance with governance and ethical standards. While comprehensive training is integral to our operations—covering sales, call handling, and customer service—the essence of delivering a seamless travel experience lies in the meticulous design, execution, and handover of each trip. Sales focus on designing trips and customer engagement, while our concierge department takes charge post-confirmation, ensuring high-quality service, pre and post-travel engagement, and careful attention to detail. Continuous feedback mechanisms ensure any discrepancies are promptly addressed with our supply base, fostering a commitment to delivering a flawless customer experience.

Describe your leadership style and guiding principles.

The leadership approach revolves around a genuine passion for people and their success at all levels. Recognizing that success varies for each individual, we focus on understanding their passions, strengths, and comfort zones to foster personal and professional growth, ultimately benefiting the company. Our team operates with substantial freedom, a principle I insist on for both the executive team and myself. Embracing mistakes as a natural part of the learning process, we provide support, analyze root causes, and use these experiences for continuous improvement without blame or finger-pointing. Our organizational structure is not rigid; instead, we prioritize a fluid and dynamic approach based on culture, projects, needs, and outcomes. This agility allows us to pivot swiftly, capitalize on opportunities, and navigate the challenges effectively, contributing to our overall success.

What is the future destination you are headed towards?

In deciding to step out of the corporate world, I aimed to create an environment where exceptional individuals collaborate on meaningful projects with outstanding customers. We are highly selective in choosing our customers, avoiding those with disrespectful behaviour towards our staff. I believe in a mutual selection process, where customers choose us, and we, in turn, choose customers a departure from conventional business practices. As for my future, it revolves around travel, aligning my passion with the work I do.

What would you advice to budding industry leaders in the domain?

Age is just a number, and what truly counts are experiences the breadth of experiences acquired as swiftly as possible. In the past, the concept of job tenure held weight, but now, it's vital to move around, gaining diverse experiences quickly, especially for those eyeing entrepreneurship.

Hard work remains essential; success comes from a mix of luck, vision, and dedication. Many underestimate the effort needed for business success. It's not easy; results require hours of hard work. While luck plays a role, relying solely on it is rare. Stand out, push boundaries, and embrace challenges, particularly when transitioning from corporate to entrepreneurship.

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