From the farm to your phone.

From the farm to your phone.

Hello, I’m Shawn. I grew up on a dairy and maple syrup farm in Canada where the cows needed milking twice a day, every day, and it takes about 40 litres of sap to make one litre of syrup. That’s still how I think about product: build consistent habits, and boil everything down to what customers truly value.

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Hello, I’m Shawn. I grew up on a dairy and maple syrup farm in Canada where the cows needed milking twice a day, every day, and it takes about 40 litres of sap to make one litre of syrup. That’s still how I think about product: build consistent habits, and boil everything down to what customers truly value.

Today I lead organisations that build products and the platforms behind them at global scale, using AI and ML where they help customers and move the numbers. For six years I led product for Booking.com’s Connected Trip, a €500M+ P&L, with a high-trust team of 200+ across product, engineering, design and analytics. We grew multi-product adoption 4x, doubled taxi and car rental bookings year on year, and built an offer platform that saves travellers millions.

Before that, I helped millions of readers find their next book at Rakuten Kobo, and helped bring Canada’s largest online retailer onto mobile at Sears.

I also mentor and volunteer with Rockstart and Techleap, supporting the next wave of Dutch startups. I’m open to conversations about product leadership opportunities, and always happy to meet new people in product and tech.

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Shawn Watt
Shawn Watt
Shawn Watt
Shawn Watt

Shawn Watt

Shawn Watt

Senior Product Executive

Senior Product Executive

Selected work.

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Booking.com

2025

Developed the Connected Trip vision for Booking.com

Architected the long-term 'Connected Trip' strategy, positioning 'the trip' as the central customer experience to build a defensible moat against emerging external AI-driven disruption. Here I'm presenting this vision to our Transportation partners in 2025.

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Booking.com

2025

Delivered critical foundations of the Connected Trip for Travellers

Created My Trips, the centre of gravity of the traveller experience. It gives travellers one place for everything they’ve booked, plus recommendations to make the trip even better.

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Booking.com

2023

Giving Travellers a Free Ride to their Hotel

Launched and scaled Booking.com’s ML-powered Free Taxi offer. It made trips easier for travellers and drove growth in new travel verticals.

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Booking.com

2018

Reinventing Booking.com on Desktop

Led the evolution of Booking.com’s desktop experience. The new design unlocked multi-armed bandit experimentation and new merchandising opportunities.

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Rakuten Kobo

2016

Laying the Groundwork for Kobo Plus

Helped shape Kobo Plus, Rakuten Kobo’s eBook subscription service, which launched after my time at Kobo.

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Rakuten Kobo

2015

Rewarding Voracious Readers with More Value

Introduced the first “buy more, save more” offer for eBooks. Readers got more value, and publishers got more volume.

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Sears Canada

2012

Putting Canada’s Biggest Online Retailer in Your Pocket

Launched Sears Canada’s first mobile apps and mobile website, when Sears was the country’s largest online retailer.

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Sears Canada

2011

Bringing the Wish Book to Life

Launched the first interactive version of the iconic Wish Book catalogue as an app. It became one of the top 3 most downloaded apps in Canada.

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My bookshelf.

Some of the books I keep coming back to, and the ideas I took from each.

Six Simple Rules

BY Yves Morieux & Peter Tollman

How to manage complexity without getting complicated through smart rules for organizational clarity.

My key takeaway

More process doesn’t fix complexity; better cooperation does. Shared goals that make teams depend on each other’s success gets more done than adding rules, committees and handoffs.

Loonshots

BY Safi Bahcall

Why great teams start killing radical ideas as they grow, and how to structure organizations so breakthrough innovation and the core business thrive together.

My key takeaway

Innovating inside a successful company is a structural problem more than a cultural one. Giving new bets their own space, while valuing the core business just as much, keeps the current success from killing the next one.

Incorruptible

BY Eric Ries

Essential reading on product integrity, resilient architecture, and maintaining core user value over long-term growth.

My key takeaway

Optimizing for the next quarter isn’t the only way to run a business. The structures a company chooses decide whether it can keep building products that make people’s lives better as it grows.

Enshittification

BY Cory Doctorow

A critical analysis of platform dynamics, digital ecosystem decay, and strategies for sustaining user trust.

My key takeaway

Products rarely get worse by accident. Once users are locked in, the pressure to extract value instead of creating it never lets up, and holding that line is part of a product leader’s job.

No Rules Rules

BY Erin Meyer and Reed Hastings

An exploration of Netflix’s radical culture built on high talent density, extreme candor, and replacing rigid controls with freedom and responsibility.

My key takeaway

The biggest insight for me was seeing how to raise the talent bar, sharing the full picture, and keeping feedback candid in every direction is what builds a high-trust team.

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Let’s connect.

Connect with me and see more of my experience on LinkedIn.

Connect with me on LinkedIn