Safara Secures Undisclosed Funding and Acquires Skipper to Empower Independent Hotels with Advanced Technology

Doug Schuessler, a seasoned entrepreneur with an innate drive that has fueled his ventures since childhood, is once again at the forefront of innovation in the hospitality sector. His journey, marked by the launch of two prior startups and a stint at Square to immerse himself in a "real rocket shop" environment, has culminated in the strategic expansion of Safara, a company poised to revolutionize how independent hotels operate and connect with travelers. This latest development includes an undisclosed funding round led by prominent venture capital firms Sequoia and Defy.vc, alongside the significant acquisition of Skipper, an established online booking engine catering to independent hotels. This dual move propels Safara’s total funding to $14 million, signaling a strong belief in its vision.

Schuessler’s passion for entrepreneurship is a constant thread throughout his career. After experiencing the dynamic environment at Square, he moved on to become the chief revenue officer at Resy, the acclaimed restaurant booking platform. His tenure at Resy provided invaluable insights into the intricacies of the consumer-facing technology landscape, particularly within the realm of reservations and customer experience. The pivotal moment for his current venture came after Resy was acquired by American Express. This strategic shift allowed Schuessler to delve deeper into the hospitality technology industry, and it was during this exploration that he found himself captivated by the unique challenges and opportunities within the hotel sector.

"Independent hotels really need the help," Schuessler stated emphatically in an interview with TechCrunch. He elaborated on a long-standing trend that has increasingly marginalized independent lodging establishments. Decades ago, a significant majority of hotels across the nation were independently owned and operated, fostering a diverse and unique lodging landscape. However, the relentless expansion of major hotel chains has led to the acquisition of numerous smaller, independent properties. This consolidation has intensified competition for the remaining independent hotels, forcing them to navigate an increasingly complex market with fewer resources and less collective bargaining power. Schuessler recognized this significant gap in the market, an opportunity to provide a much-needed technological and strategic advantage to these beleaguered businesses.

Fueled by this realization and drawing upon his extensive experience, Schuessler, alongside his co-founder Cody Rose – another former Resy colleague – established Safara. The core mission of Safara is ambitious yet straightforward: to create a comprehensive platform that empowers travelers to book virtually any hotel worldwide, irrespective of whether it is a global chain or a cherished independent establishment. This inclusivity is central to Safara’s value proposition, aiming to democratize the booking experience and offer travelers a wider array of choices while simultaneously supporting the independent hotel ecosystem.

The Safara platform distinguishes itself through a curated selection of hotels, meticulously assembled from a blend of consumer data and invaluable community-sourced recommendations. This dual approach ensures that both popular and hidden gem properties are discoverable by travelers. Furthermore, Safara has implemented a robust rewards program designed to incentivize bookings. Users who book through the platform receive cash back, which can then be applied towards future travel, creating a compelling loop that encourages repeat engagement and fosters customer loyalty. For independent hotels that integrate with Safara, the benefits are even more pronounced. They gain access to the platform commission-free, a significant cost-saving measure that directly impacts their bottom line. While the platform is particularly advantageous for independent properties, it is technically open to any hotel seeking to expand its direct booking channels.

"Think of it as another direct channel alongside their website," Schuessler explained, drawing a parallel to how hotels currently manage their online presence. "We then connect these two products to elevate the guest experience by enabling direct web guests who book directly on the hotel’s site to manage that reservation in the Safara app." This integrated approach is a key differentiator, allowing Safara to bridge the gap between direct bookings made on a hotel’s own website and reservations facilitated through the Safara platform. By enabling guests to manage all their bookings within a single, unified application, Safara enhances convenience and provides a more seamless travel experience. The company envisions a future where direct bookings are not only managed but also enriched with personalized offerings and services through the Safara ecosystem.

The acquisition of Skipper represents a significant strategic acceleration for Safara’s growth trajectory. Skipper, an online booking engine specifically designed for independent hotels, shares Safara’s core mission of empowering these properties. The introduction of Skipper into the Safara fold was facilitated by a mutual investor who recognized the strong synergy between the two companies’ visions for the hospitality industry. The co-founders of Skipper are expected to integrate into the Safara team, bringing their expertise and established relationships within the independent hotel community.

"We actually made a pass at the deal earlier in the year," Schuessler revealed, indicating that the acquisition was not a spontaneous decision but rather a carefully considered strategic move. "But the stars eventually aligned." This sentiment underscores the importance of timing and alignment in successful acquisitions. "Both companies have a much better chance at achieving the shared vision together than they do apart," he added, emphasizing the complementary strengths and shared ambitions that make this merger so potent. The integration of Skipper’s booking engine technology will allow Safara to offer a more comprehensive suite of tools to independent hotels, streamlining their operations and enhancing their direct booking capabilities.

Safara’s overarching strategy is to differentiate itself from existing players in the market by providing a holistic solution. This includes not only offering sophisticated software tools to hotels but also developing consumer-facing products that directly benefit travelers. The company believes that true innovation lies in creating a symbiotic relationship between hotels and guests, where technology serves to enhance the experience for both parties. "The magic is going to come in 2025 when we connect these two products more deeply to create new experiences for both hotels and guests," Schuessler, who serves as the company’s CEO, articulated with palpable excitement. This forward-looking statement highlights Safara’s commitment to continuous innovation and its belief that the most impactful advancements are yet to come.

The funding round, led by Sequoia and Defy.vc, underscores the significant potential that investors see in Safara’s business model and its leadership team. Schuessler shared insights into the process of securing these key investments, noting that he met his investors through warm introductions, a testament to the power of networking and reputation within the venture capital landscape. Alfred Lin, a partner at Sequoia, was described as the company’s "first major believer," even though he initially passed on the opportunity. Schuessler recalled Lin’s prescient words: "Maybe we can become partners in the future," a statement that initially seemed like polite deferral but ultimately proved to be prophetic. This long-term perspective and relationship-building approach are hallmarks of successful venture capital partnerships.

His connection with Brian Rothenberg, a partner at Defy.vc, was forged through the AngelTrack network. Schuessler described an immediate rapport with Rothenberg, highlighting his exceptional support and shared perspective. "He is extremely supportive through good and bad and we tend to see the world through a very similar lens," Schuessler commented, emphasizing the crucial alignment of values and vision that is essential for a productive investor-founder relationship.

The newly acquired capital will be strategically deployed to fuel Safara’s ambitious growth plans. A primary focus will be on scaling product development, ensuring that the platform remains at the cutting edge of hospitality technology. Simultaneously, the company aims to significantly increase the number of hotels utilizing its product, expanding its reach and impact within the independent hotel sector.

"Our focus of 2025 and beyond is really to empower independent hotels with the same technology and network advantages as chain hotels," Schuessler declared, reiterating his core mission. This ambitious goal speaks to Safara’s commitment to leveling the playing field in the hospitality industry. The company believes that by equipping independent hotels with advanced tools and a robust network, they can not only survive but thrive in an increasingly competitive market.

Schuessler’s vision extends beyond mere technological parity. He believes that by empowering independent hotels, Safara will unlock novel and enriching guest experiences that are currently unavailable. "If we get this right, not only do we help these hotels succeed, but the types of experiences that will unlock for guests are things that frankly don’t exist right now," he stated, painting a picture of a future where travel is more personalized, authentic, and memorable. "And if we accomplish both of those things, the sky is the limit for Safara as a company," he concluded, expressing a profound optimism for the future impact and growth of his venture. Safara’s strategic funding and acquisition of Skipper mark a significant step towards realizing this transformative vision for the independent hotel industry and the broader travel landscape.