A Canadian startup’s journey from inception to success demonstrates the resilience of entrepreneurship and the vibrant dynamic of the tech industry. Pilot, born from founder Connor Wilson’s contemplative ATV ride on a Greek mountain in March 2019, was initially registered as HappyHour, a representation of quality time with friends.
The nascent company initially planned to tackle social connection through a Personal Relationship Management tool. However, this idea was soon dismissed as too mechanical for social engagement. Wilson’s resolve saw him join NEXT Canada, a startup accelerator, in November 2019.
In December 2019, the tide turned for HappyHour as Wilson reunited with former colleague Reine Donnestad. The duo, reconnecting during another of Wilson’s European backpacking excursions, brainstormed about a “local experience marketplace.” However, their plans were brought to a grinding halt by the COVID-19 pandemic, which forced a shutdown of local experiences worldwide.
The pandemic saw Donnestad exit the company while Wilson, undeterred, brought on board Madi Wood, refocusing the venture on travel in anticipation of pent-up post-pandemic demand. May 2020 saw HappyHour Services Inc. incorporated, missing Cinco De Mayo by a whisker and humorously acquiring the nickname “Sixto de Mayo.”
Unfortunately, by June 2020, Wood left due to her full-time job obligations. Nonetheless, Wilson soldiered on with the support of a part-time intern team, which he had enlisted. This team spent the summer conducting extensive surveys with young travelers and backpackers, sparking hundreds of product and feature ideas.
By August, they had zeroed in on the Social Trip Planner as the optimal tool for sharing social experiences and planning discoveries. HappyHour, rebranding to Pilot in October 2020, continued to execute on this idea. The team, now bolstered by a hired engineering team including coding prodigy Avinash VK, started developing the Alpha version of the product.
The Social Trip Planner
Pilot is an all-in-one travel planning platform designed to make the process of organizing trips easy, efficient, and enjoyable.
The platform allows users to collaborate with their companions on their dream journey through comprehensive travel itineraries, according to the BC startup.
In a single view, users can plan their days and routes using Pilot’s map feature. They can also decide on and vote for different activities to include in their itinerary, adding a democratic element to the planning process.
One standout feature of Pilot is the ability to obtain travel eVisas in just three clicks, streamlining what can often be a complicated and time-consuming task. The platform also provides users with up-to-date travel requirements for any destination, assisting travellers in navigating the sometimes confusing landscape of international regulations.
Users can chat and collaborate on travel tips, share their experiences, and create exceptional memories together. They can find, save, and share places that match their specific preferences, utilizing dozens of filters to discover unique things to do on their journey.
Pilot doubles as a travel organization tool. Travellers can use the platform to store and share critical information like flight times, itineraries, and expenses. Securely import and share travel documents, save notes, make packing lists, and add to-dos—keeping all important travel details in one location.
Early 2021 was marked by growing pains for Pilot as they grappled with an alpha version fraught with technical issues. Then Wilson’s other venture, a marketing software company, was acquired in an eight-figure exit deal. This allowed him to bring on board Yu-Wei Hung, who dramatically scaled up Pilot’s organic website traffic.
With his other venture successfully sold off, by July Wilson was able to dedicate his full attention to Pilot. A revamped user interface was unveiled in August 2021, and the company started seeking outside funding in November. Notably, almost all of Wilson’s colleagues from his previous company invested in Pilot.
Last year saw Pilot’s beta slowly opened to the public, with a focus on debugging and improving responsiveness. By June, the platform had attracted 5,000 users, the majority of whom expressed significant disappointment at the prospect of not being able to use it. This positive feedback prompted a second fundraising round, which included several high net-worth “angel” investors.
Pilot joined the Creative Destruction Lab accelerator in September, attracting further investment due to its impressive performance. By November 2022, it had obtained significant government funding, covering most salary costs for the following eight months.
The start of this year witnessed Pilot expand its team with more designers and marketers, reaching a total of 12 full-time salaried employees. A rebranding process culminated in a website overhaul in February, finalizing the transition from HappyHour to Pilot. By March, membership had ballooned to 15,000, attracting more investment, including from the “Mentor of the Year” at the Creative Destruction Lab.
April saw Pilot graduate from the Lab, earmarking it as one of the most promising companies in Canada. And in May, the team flew to Colombia for a live test of the app with travellers, providing insights into the discovery and booking challenges faced by users.
This month, the startup is a New Ventures BC Competition finalist.