About Us

Enabling people everywhere to discover and share memorable experiences together, beginning with travel.
Made with ❤️ in Canada

It all started with an idea.

"Social networks" became "social media".

That they abandoned connections and instead focused on content consumption.

It became selling you ads, selling your data, and doing everything they can to keep you online, out of the real world.

They don’t care about your relationships, they care about revenue.

They don’t facilitate memories, they manufacture the fear of missing out (FOMO).

This sparked an idea, what if social technology was used to enable real life experiences, not impersonate them?

Social connection, not social media.

Experiences, not ads.

Friends, not followers.

The future of social technology shouldn’t be a metaversal black hole of never-ending, creepily targeted, ever-present ads.

This technology should be tools to foster connection, and enable experiences.

Using bits to connect atoms, not more bits.

That’s why we started Pilot: to enable people everywhere to discover and share memorable experiences together, beginning with travel.

We’re building a Social Trip Planner to help you discover, plan, book, and share experiences with friends, not followers, in the real world.

Together we can build a world where everyone feels fulfilled by their connections and experiences.

Because the biggest predictor of life expectancy at age 80, is the quality of your relationships at age 50.

Happier lives through shared experiences

We hope you like it as much as we love building it.

We invite you to share this experience with us!

With love ❤️the Pilot crew. 

Click or scroll through to learn why Pilot was founded, and what we stand for.
March 2019
The idea for Pilot was born

from founder Connor Wilson while on an ATV overlooking the Aegean Sea from a mountaintop in Greece during a backpacking trip through Europe.

May 2019
The not-yet-incorporated company is named HappyHour

to represent quality time with friends, and is registered on the domain name “happyhr.app”.

September 2019
HappyHour’s first idea

to address the problem of social connection with a Personal Relationship Management tool. This is quickly ruled out as too inorganic and not social.

November 2019
Founder Connor Wilson is recruited to join the NEXT Canada

a startup accelerator. He is flown to Toronto for the weekend and HappyHour joins the program.

December 2019
Connor Wilson recruits a former colleague

from a previous college venture he ran, while on another backpacking trip through Europe Founder, Reine Donnestad, to start working on an idea for a “local experience marketplace”, HappyHours second product idea.

March 2020
COVID-19 hits the world

before Reine and Connor could make any tangible progress, and local experiences everywhere were shut down completely. Reine leaves the business, but Connor decides to persevere, and pivot to trying something else.

April 2020
Connor recruits a new Co-Founder

Madi Wood, to help him incorporate the business, now focused on travel under the expectations of pent up demand due to COVID. Now, with a longer time horizon to build a social platform, and to recruit and manage a team of interns in a uniquely early stage and ultra-flexible, part time learning opportunity: To help build a startup.

May 2020
HappyHour Services Inc. is incorporated on May 6th.

The team is devastated they missed Cinco De Mayo by one day, instead dubbing our incorporation date as Sixto de Mayo. Founding Team members Taher Kathawala and Abigail Udvari join HappyHour, eventually becoming Product Team leads for Pilot after also doing brief stints working at Tesla (Taher) and Snaptravel (Abi).

June 2020
Madi Wood cannot continue and departs

due to conflicts with her full time enterprise sales day job. Connor is once again a solo founder, but with a solid founding team of less-than-part-time interns to help him.

Summer 2020
The team meets with hundreds of young travelers and backpackers

to co-create and brainstorm literally hundreds of product and feature ideas, systematically eliminating them through constant testing, iteration, and critiquing.

August 2020
The Social Trip Planner is chosen as the optimal solution

to build a platform for discovery, planning, and sharing of social experiences, and the long term roadmap and strategy is defined. Pilot continues to follow and execute on this plan today.

September 2020
HappyHour’s initial engineering team is hired

to help build the platform. Founding Team Member Avinash VK, who had been coding since he was 12 years old, joins the team. Development on the Alpha version of the product begins. Avinash will go on to build most of the initial app.

October 2020
HappyHour rebrands, changing its name to Pilot

to better inspire and empower travelers to make the most of every trip. Pilotplans.com is launched.

February 2021
Pilot’s extremely buggy but technically functional private alpha is released.

Through growing pains, the team tested the interface with users, and, as expected, discovered that a different user interface and experience is needed.

March 2021
Connor's other startup is acquired in an 8-figure exit, and Yu-Wei Hung joins Pilot

as a marketing intern and Founding Team Member, later becoming Pilot’s first full-time marketing hire and Growth team lead. He grew Pilot’s monthly organic website traffic from a few hundred to a few hundred thousand within a year. Meanwhile, Connor’s other company, a marketing software company where he still worked full-time as the business/growth head, is acquired in a multimillion 8-figure deal after being bootstrapped for 3 years.

July 2021
Connor leaves Paystone

a +$90 million/year revenue company that acquired his previous venture, to focus 100% of his time on Pilot.

August 2021
Pilot’s new interface, with a list & map based view, is released

and tested in a private beta with a small group of friends and family.

November 2021
Founder Connor Wilson opens a “friends and family” fundraising round

funding the company’s development of the early beta, and resulting in multiple full-time hires. Nearly all of the people he worked closest with at his previous company invested in Pilot.

January 2022
Pilot slowly opens its beta to the public

focusing primarily on catching and fixing bugs and making the platform simpler and more responsive.

May 2022
Connor does a second friends and family round

now with a beta version to show, raising more cash, including from several high net-worth “angel” investors.

June 2022
5,000 users now use Pilot to plan their trips

55% of them say they’d be “very disappointed” if they could no longer use the platform. Exceeding the 40% that is typically considered “product-market-fit.”

September 2022
Pilot joins the “Creative Destruction Lab”

startup accelerator, a shark tank / survivor type hybrid program. Pilot’s performance leads more angel investors to invest in Pilot.

November 2022
Pilot receives government funding

covering 80% of most salary costs for the next 8 months.

January 2023
Pilot grows to 12 full-time salaried employees.

Pilot quadruples its growth team size, hires more designers and marketers.

February 2023
Pilot launches its new website

after finally finding a design agency who can "complete" the long-winded rebrand from "HappyHour" to "Pilot". Some pages, including this one, are not yet been "brand optimized".

March 2023
15,000 members now use Pilot to plan their trip, and gets more investment.

The “Mentor of the Year” at the Creative Destruction Lab invests in Pilot.

April 2023
Pilot graduates from the Creative Destruction Lab

Pilot is one of only a small handful of companies that “graduates” from the Creative Destruction Lab, making them one of the most promising companies in Canada this year.

May 2023
The Pilot team flies to Colombia to test the app live with travelers.

The exercise is great, and helps the team (especially newer team members) understand the deeper nuances of what discovery and booking problems travelers are facing.

Our Values

How we're building a world-class team.

Love Your Work

If a decision isn’t a HECK YES it’s a NO. We want to be passionate about the work we do, and have fun doing it. This means loving our team too.

People First

We want to be humble leaders, meaning we don’t think less of ourselves, we just think of ourselves less, always striving to do the right thing in service of others.
friends at a pool party
Pilot crew having fun!

Take it Further

We challenge the status quo, and work hard to make big dreams reality. We're always learning, staying curious and going beyond what is expected of us.

Move Fast with Data

We make decisions based on data and constant experimentation, don't over-analyze theory, and instead focus on assessing results to stay adaptable, and learn quickly.

Like what we're doing?

Explore Careers
Explore Careers
Feature image
group selfie in an airport terminal
selfie of two males with a mountain backdrop
pilot team selfie at a rubgy sevens game
colleagues enjoying lunch at a cafe

Fly with us @PilotPlans