Hotel booking platform Safara raises $14M, acquires rival Skipper

Doug Schuessler, a serial entrepreneur with a childhood fascination for building things, has once again channeled his innate drive into a venture poised to revolutionize the independent hotel sector. His latest endeavor, Safara, a comprehensive platform designed to connect travelers with a vast array of global hotels, has announced a significant funding round of an undisclosed amount, co-led by prominent venture capital firms Sequoia and Defy.vc. This infusion of capital, bringing Safara’s total funding to $14 million, is accompanied by the strategic acquisition of Skipper, an established online booking engine specifically tailored for independent hotels. This dual announcement marks a pivotal moment for Safara, signaling its ambition to become an indispensable tool for both travelers and independent hoteliers worldwide.

Schuessler’s entrepreneurial journey is marked by a relentless pursuit of innovation and a deep understanding of technology-driven businesses. His formative years were characterized by a consistent drive to create, a passion that propelled him to launch two startups before the age of 25. Seeking to immerse himself in the environment of a high-growth, impactful company, he relocated to San Francisco and joined Square, a financial services and digital payments company. There, he gained invaluable firsthand experience observing the operational dynamics of what he described as a "real rocket shop." This period at Square provided him with a foundational understanding of scaling technology businesses and navigating the complexities of rapid expansion.

Following his tenure at Square, Schuessler transitioned to the role of Chief Revenue Officer at Resy, a leading restaurant reservation platform. His leadership was instrumental in driving revenue growth and strategic partnerships for the company. It was during his time at Resy, and particularly in the wake of its acquisition by American Express in 2019, that Schuessler found himself increasingly drawn to the intricacies of the hospitality industry. He began to meticulously study the technology landscape within hotels, a deep dive that quickly ignited a new passion. "Independent hotels really need the help," Schuessler stated to TechCrunch, articulating a clear need he identified within the market.

He elaborated on the historical context of the hotel industry, noting that decades ago, the vast majority of hotels in the United States were independently owned and operated. However, a significant shift has occurred over time, with large hotel chains systematically acquiring smaller, independent properties. This consolidation has intensified the competitive pressures faced by the remaining independent hotels, leaving them at a disadvantage in terms of marketing reach, technological resources, and booking capabilities. Schuessler recognized this imbalance as a critical opportunity to intervene and provide much-needed support.

It was this profound understanding of the challenges confronting independent hotels that led Schuessler to co-found Safara with Cody Rose. Rose, who also boasts a background at Resy, brings complementary expertise to the Safara team. Together, they conceived Safara as a solution that aims to democratize access to global accommodation for consumers while simultaneously empowering independent hotels. The platform boasts the ambitious goal of allowing customers to book nearly every hotel in the world, encompassing both major chains and boutique independent establishments.

The Safara platform differentiates itself through a meticulously curated list of hotels, compiled from a blend of consumer data and invaluable community-sourced recommendations. This approach ensures that travelers are presented with a diverse and high-quality selection of accommodations. Furthermore, Safara has integrated a compelling rewards program designed to incentivize bookings. Users who book through the platform earn cash back, which can then be applied towards future travel, fostering a cycle of loyalty and repeat engagement.

A key aspect of Safara’s strategy, particularly with the acquisition of Skipper, is its commitment to supporting independent hotels. Independent hotels that utilize Skipper’s technology can access Safara’s platform commission-free. While technically any hotel can integrate with Safara, this commission-free offering for independent properties underscores the company’s dedication to leveling the playing field. Schuessler explained this integration as akin to "another direct channel alongside their website," emphasizing that Safara aims to enhance, rather than compete with, a hotel’s existing direct booking efforts.

The synergy between Safara and Skipper is designed to elevate the overall guest experience. By enabling direct web guests who book through a hotel’s own site to manage their reservations within the Safara app, the platform creates a seamless and integrated journey for the traveler. This feature allows for a unified view of bookings, itineraries, and potentially loyalty program benefits, regardless of how the initial reservation was made.

The acquisition of Skipper is particularly significant. Introduced by a mutual investor who recognized the shared vision between the two companies, the integration of Skipper’s online booking engine into Safara’s ecosystem was a natural progression. Schuessler revealed that Safara had previously considered the acquisition earlier in the year, but the timing and strategic alignment were not yet optimal. "But the stars eventually aligned," he commented, underscoring the serendipitous yet calculated nature of the deal. "Both companies have a much better chance at achieving the shared vision together than they do apart." The co-founders of Skipper will be joining the Safara team, contributing their expertise and further solidifying the combined entity’s market position.

Safara’s overarching mission is to be more than just a booking platform; it aims to provide comprehensive software solutions for hotels and valuable products for consumers. This dual-pronged approach is central to its long-term strategy. Schuessler, in his role as CEO, articulated this vision, stating, "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." This future integration promises to unlock novel functionalities and enhanced value propositions for both sides of the hospitality equation.

The funding round was secured through what Schuessler described as "warm introductions" to investors, highlighting the strength of his network and the compelling nature of Safara’s proposition. Alfred Lin, a partner at Sequoia Capital, emerged as an early and significant believer in Safara’s potential. While Lin initially passed on an earlier opportunity to invest, he expressed a forward-looking sentiment to Schuessler, stating, "Maybe we can become partners in the future." Schuessler, initially skeptical, acknowledged the prescience of Lin’s remark, which has now materialized into a key partnership. He also established a strong connection with Brian Rothenberg, a partner at Defy.vc, through the AngelTrack network. Schuessler characterized their relationship as immediately harmonious, noting Rothenberg’s "extremely supportive" nature through both favorable and challenging times, and a shared perspective on the market.

The newly acquired capital will be strategically deployed to accelerate product development and expand the number of hotels integrated into the Safara platform. Schuessler outlined the company’s forward-looking objectives, stating, "Our focus of 2025 and beyond is really to empower independent hotels with the same technology and network advantages as chain hotels." This ambition reflects a commitment to bridging the technological divide that often separates independent properties from their larger, more resource-rich counterparts.

Schuessler concluded with an optimistic outlook on Safara’s potential impact. "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. And if we accomplish both of those things, the sky is the limit for Safara as a company." This vision paints a picture of a future where independent hotels thrive, offering unique and unparalleled experiences to travelers, all facilitated by Safara’s innovative technology and comprehensive platform. The company’s trajectory, bolstered by significant funding and a strategic acquisition, positions it as a formidable player poised to reshape the landscape of independent hospitality.