Building a global customer-facing business: Headout’s unique journey

Summary

There are few playbooks for finding success in global B2C expansion. Headout, a leader in curated travel experiences, offers a roadmap for founders looking to expand their horizons beyond their home markets. The company, in over a decade of operations, has perfected its understanding of new markets to achieve PMF, consolidating fragmented supply, and empowering operators with technology-driven insights. There are valuable lessons for entrepreneurs in Headout’s navigation of global B2C complexities and sustainable growth strategies.

Founders are naturally restless, and their ambitions limitless. They are always watching out for the next horizon. Whether it is expanding the scope of their offering, or transcending domestic borders to replicate their success in new markets. However, navigating the waters of a cross-border B2C business can be tricky. While success stories are many, established playbooks are scarce. This is why Headout’s journey is a valuable case study for entrepreneurs. 

Headout is an online platform for travellers to discover curated tours, excursions, day trips, and last-minute tickets to major tourist attractions, museums, shows and events in several global destinations. 

Headout exists in a market that has exploded in the past decade. Recent reports state that travel is at an all-time high with a market size of $11.1 trillion in 2024. Naturally, Headout needs to earn the trust of its customers (no one wants a ruined vacation) while also building and maintaining a moat. In 2014, Headout spotted the moat: the value of curated and managed experiences.

“Experience booking is fairly complex because these activities are diverse, complex and have no recognisable global brand,” - Suren

In addition, their operators are extremely fragmented, so a big part of Headout’s focus has been to create convenience for the customer by simplifying and aiding their decision making. 

For example, say a traveller is looking to experience the Eiffel Tower in Paris. Instead of an overwhelming list of 100s of tours, Headout offers distinct curated options from top, vetted operators for the landmark.

Headout set out to be a cross-border business from the very beginning. And so the challenges in their journey were many. From understanding the cultural landscape to the differences in the customer mindset to the country-specific guideline protocols and regulations. 

Suren walks us through the intricacies and thinking behind building Headout as a truly cross-border enterprise over the years. 

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Expanding markets with a supply-first lens

Headout's international ambitions were clear from the outset, but navigating this complex path required careful consideration of various factors:

1. The business
2. The customer 
3. The scope of the solution

The trick here, says Suren, lies in understanding that the way to achieving PMF can differ significantly across geographies. Cultural preferences, pricing sensitivities, regulations, and technology adoption all vary, and require a nuanced approach. 

“The key is in knowing how well your current PMF translates to another market. If the core market characteristics that make your product successful in a certain market translate to other markets, then it is easier to expand internationally,” he explains.

He should know. Headout has established a presence in over 130 global destinations within a decade. Over time, Headout has perfected its playbook, approaching market expansion from a "supply-first lens", which in their case means destination-based expansion. 

Suren enumerates some factors that guide their expansion strategy:

• Market Size: Bigger markets, though competitive, offer greater potential growth.
• Fragmented Supply: Navigating the fragmented markets, Headout offers a curated selection of experiences.
• Technology Adoption: Headout seeks markets where operators are tech-adept.
• Customer Patterns: Headout prioritises destinations where travellers stay for extended durations and aren’t simply transiting through 

Suren adds that once the market is identified, Headout initiates the hiring process in these new geographies. He emphasises the crucial role of local teams in navigating the cultural and operational nuances of new destinations.

So, how is PMF achieved in each new market? Understand which metrics really  indicate PMF before you expand aggressively in a new market, explains Suren. For Headout, this means starting with a limited set of 10-20 experiences focused around the top two to three points of interest or themes in a city and then building a certain size of business with profitable unit economics, high NPS, and strong customer retention with this. 

“This triggers a growth flywheel, so hitting this point is our focus in the first few months of launching a new market,” he adds.

Customer needs are paramount 

In customer-facing businesses or any B2C business, the end-user is the most important stakeholder.

With the kind of business Headout has built, with a global customer base of over 25 million people from over 180 countries, Suren and his team have figured out the thing that sets them apart in the market. They have learnt how to address customer pain points like information overload and lack of trust. To solve this, Headout offers hyper-personalised choices. A hyper-personalised product is a deliberate, strategic choice for Headout. It helps the customer feel seen and understood. 

“Hyper personalisation is where a product feels like it is built just for you. Or it's customised in a way that it perfectly meets your needs,” - Suren

It does so by ensuring that its offerings fulfil the four main components of hyper-personalisation:

• Quality products
• Convenience
• Value
• Relevance for customers 

To achieve this, it works closely with partners, ensuring consistent quality and competitive pricing. The collaborative approach benefits all stakeholders. Operators gain access to a global customer base and simplified operations. Customers enjoy a curated selection of experiences that still offer sufficient depth and diversity of choice. 

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Pricing strategies for a new market

With a multitude of options available to choose from, and an increasingly competitive landscape, pricing for the global customer is a science that requires a careful mix of technology, data-driven insights, A/B testing and experiences. 

Headout does this by leveraging existing cost structures for similar products in a particular region to establish a baseline. This gives Headout a sense of what customers might be willing to pay. It then experiments with different price points to identify the sweet spot that maximises demand. Over time, as Headout accumulates data, its model now automatically suggests optimal pricing for new products based on location, cost structure, and past performance of similar experiences.

The idea is to delight customers with a value-for-money offering that fosters loyalty and repeat business. A fundamental principle, true for all businesses, be it B2B or B2C. 

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Shared success: customer feedback and partnerships

For any consumer-facing business, word-of-mouth is the lifeblood, and customer feedback reigns supreme. This becomes even more crucial when serving a global audience, where trust is paramount.

“We actively solicit customer feedback and monitor user behaviour on our products. This plays a huge role in driving our product roadmap and the experiences that we build because, this is who we're building for,” - Suren

Headout leverages this feedback to constantly refine experiences and partner with reliable operators based on quality, tech adoption, and local accreditations. This win-win approach benefits everyone—customers, operators and the company. 

Yet running a cross-border business is no mean feat. Suren says that one of the most complex aspects is dealing with regulations that vary from country to country, whether it is related to data protection or payments. “We rely very heavily on experts in those areas to help us navigate the ever-evolving regulatory landscape,” he adds. 

International expansion is not a one-size-fits-all approach. The business model, customer needs, and the market are all important factors. While staying on top of every minor skirmish is impossible for any company, Suren recommends staying informed long enough to resolve customer concerns. 

“At the end of the day, our job is to create the best customer experience we can,” he signs off.