Waqas Sheikh
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Product Builder · Org Architect · Systems Thinker

For two decades I've built products and platforms used by millions - across SaaS, marketplaces, e-commerce, and fintech, from global scale to 0→1 - always attuned to the real, diverse needs of users of all stripes. Enduring impact never comes from a single feature or launch; it comes from the systems that continually produce it - product, org, and strategy bound into a compounding engine. And those systems only endure when the human ones are built alongside them: leading with empathy through change, holding hard tensions instead of collapsing them, and building teams with trust at their core.

2024 - present
Thumbtack
Thumbtack · Sr. Director of Product

AI-Native Hiring Experiences

The home services industry struggles with uncertainty for both homeowners and pros when it comes to getting jobs done. We are redesigning matching and the end-to-end hiring experience with AI at the core to bring more confidence to both sides: homeowners can describe a problem or project in their own words, a photo, or their voice; and in parallel, we are getting sharper at learning each pro's real capabilities and the jobs/customers they're best for - with proprietary AI matching at the center. This is a full-stack 0→1 transformation of our core product & platform; not just AI bolted on, but a new Thumbtack for homeowners and pros alike.

Innovation · 0→1Marketplace
2022 - 2024
Thumbtack
Thumbtack · Sr. Director of Product

Core Marketplace

Led the core of Thumbtack's ~$500M marketplace connecting millions of homeowners with 300,000+ pros. My teams ran across the whole system: search and matching, monetization and pricing, payments and trust & safety platforms, and the data platform beneath it all. Consistently drove 20%+ Y/Y product-led growth through superior matching, optimized marketplace dynamics, and value-indexed monetization systems.

Growth · MonetizationMarketplace
2021 - 2022
Routable
Routable · Director of Product

Cross-Border Payments

Paying partners and vendors across borders is one of the last genuinely broken parts of business - slow, opaque, expensive, and stitched together from banking rails never meant to work fluidly across geographies. At Routable I led the creation of the company's first cross-border payments product, opening access to a new $35T market: the user experience, API products, and banking integrations that enabled enterprises to seamlessly run mass-payouts internationally. I also built a new PM team around this area from the ground up.

Innovation · 0→1FinTech
2016 - 2021
Dropbox
Dropbox · Group Product Manager

Billing, Engagement Platforms

Hypergrowth doesn't scale on one-off features - it scales on platforms that let a company innovate on pricing, packaging, and experimentation quickly and safely. At Dropbox I founded and led two business platform teams from the ground up, back to back: the Billing platform (pricing, packaging, freemium, and promotions) - which helped grow paid subscribers more than 4X and opened new Channel, Reseller, and Enterprise sales motions - and the Engagement platform for experimentation, personalization, and in-product messaging, used by the majority of the product and growth org to run thousands of concurrent tests. And I did it moving fluidly between individual contributor and manager roles (twice) - working hands-on to build from the ground-up, and then hiring + growing teams based on strong early momentum.

Platform · GrowthSaaS
2008 - 2016
Expedia
Expedia · Manager, Technical Product Management

Best Fare Search

Behind every flight search is staggering complexity - fares, availability, and rules changing by the second across dozens of airlines. For eight years I helped build Expedia's proprietary Best Fare Search engine: the flight-search core behind every brand and global entity in Expedia Group, including Travelocity and Orbitz as the company acquired them, at 5.5B transactions a year. I kept it fast and accurate with predictive caching and machine learning, and led the integration of a major new fare-distribution partner, Amadeus, into the North American business - a disruptive shift that became a lasting competitive advantage. My time at Expedia was the foundation of my craft: where I learned to build for scale, and grew from IC into leading a team of technical PMs and airline-industry experts.

Scale · PlatformTravel

Leadership Principles

Durable impact comes from the conditions that reliably produce good outcomes - team dynamics, feedback loops, aligned incentives - not one-off fixes. Build the right systems, and teams and products rise on their own.
Leading through change is the core of the job, not a nice-to-have. Build the systems and trust that carry teams through uncertainty without losing momentum.
The hardest tensions - strategy vs. execution, speed vs. quality - are false choices. Rather than pick sides, manage them as ongoing polarities and find the frame that serves both.
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