Piero Sierra

Inquisitor
DISC Type : Ic

Chief AI Officer at Skyscanner

London Area, United Kingdom

Overview

Piero is the Chief AI Officer at Skyscanner, leveraging 29 years of experience from Microsoft and Skyscanner to shape the future of travel with AI. A Princeton graduate in Computer Science, colleagues describe him as super smart, passionate, and charismatic, with a focus on traveller-first innovation.

Beyond his executive role, Piero is a passionate software developer. He recently channeled this passion into a deeply personal project, building and releasing a Mac application as a tribute to his late father, showcasing his drive to create meaningful and heartfelt technology.

He personally built and launched a slideshow app on the Mac App Store, "SoftBurn", in memory of his father.

Personality Overview

Curious

Value Driven

Assertive

They are generally good communicators and can be hard to convince.  They can sound friendly and charming but can quickly change gears to become inquisitive and probing. They often ask many questions and rely heavily on information and documentation.

Topics They Care About

AI in Travel
As CAIO, he is accountable for Skyscanner’s AI vision and strategy, focusing on making travel planning more personal and seamless for millions of users.
Consumer Product Strategy
Previously Chief Product Officer, he grew Skyscanner's audience nearly tenfold by leading with a strong, traveller-first product culture and vision.
AI Ecosystems
He analyzes how brands can integrate into the broader AI ecosystem, drawing parallels between today's AI platforms and foundational tech partnerships of the past.

Media Appearances

Fireside Chat with Skyscanner CPO, Piero Sierra. Featured in YouTube

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Rethinking travel search with AI – Sponsored Interview. Featured in Phocuswire

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Work History

9-2025
Chief AI Officer at Skyscanner
12-2015 - 10-2025
Chief Product Officer at Skyscanner
1-2012 - 12-2015
Partner Director of Product – Microsoft / Skype at Microsoft
1997 - 2012
Group Program Manager – Windows, Internet Explorer, and MSN Messenger at Microsoft
1992 - 1993
Software Developer – Pirelli Telecom at Pirelli Cables

Education

1993 - 1997
Bachelor of Science (B.S.) from Princeton University
3-2023 - 6-2024
Certificate in Finance from London Business School

More Information

Social Presence :

Prographics :

Exp : 31 Location : London Area, United Kingdom Job Level : Leadership Designation : Chief AI Officer at Skyscanner
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Insights For Selling To Piero

During A Call Or A Meeting

DO's

  • Persuade objectively how your product will help them achieve their goals
  • Build rapport, it will come handy to handle hard questions later
  • Ask them questions to understand their needs better while staying affable

DONT's

  • Don’t try to rush them into a decision, provide all necessary information first
  • Avoid making offhand commitments
  • Don’t be too objective but make sure to pad your storytelling with data points

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Piero is

  • Clear proof of product value matters to them, followed by others' testimonials and rapport.
  • Will you ever get a clear answer from Piero

  • They are practical and friendly, don't expect a clear-cut response often.

Insights For Deal Planning

    How fast (or slow) will Piero move?

  • They like to perform full analysis and can take time to make any decision.
  • Can Piero take some risk or not?

  • They systematically evaluate all decisions and are unlikely to take many risks.

You And Piero

Personality Compatibility


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