Troy Payne

Doer
DISC Type : ds

Head of Engineering at Squire

New York City Metropolitan Area, United States

Overview

Troy Payne is the Head of Engineering at SQUIRE, a high-growth startup that achieved a valuation of over $750 million. He has a strong background in full-stack and iOS development, having held key engineering roles at TripAdvisor, Stayful, and Jetsetter, where he was the first staff engineer.

He is a product-minded engineering leader with a track record of shipping polished consumer experiences. His work on the Jetsetter iOS app earned a nomination for a TechCrunch Crunchie award and reached the #3 spot in the Travel App Store, showcasing his ability to deliver impactful products.

Unique fact: The first major iOS app he launched at Jetsetter was nominated for a TechCrunch Crunchies award.

Personality Overview

Long-term Focused

Results Focused

Risk-Accepting

Reading between the lines and seeing beyond your words comes naturally to them.  They are very professional in their approach and can weigh multiple perspectives together. They exhibit a rare combination of being result-oriented but patient at the same time.

Topics They Care About

Engineering Leadership
Serves as Head of Engineering for SQUIRE, a company valued at over $750 million, and has a history of building and leading engineering teams.
iOS App Development
Has extensive experience leading iOS development, including kicking off the successful Jetsetter iPhone/iPad application which was a top-ranked travel app.
Full-Stack Engineering
His experience includes backend development in Scala and node. js, demonstrating a deep and versatile full-stack skill set in building scalable systems.

Media Appearances

Troy has no verified media appearances

Work History

2-2017 - 5-2025
Head of Engineering at Squire
7-2014 - 2-2016
Lead iOS Developer at Stayful
5-2013 - 7-2013
Software Engineer at TripAdvisor
7-2009 - 7-2013
Software Engineer at Jetsetter
7-2009 - 4-2013
Software Engineer at Gilt.com

Education

Bachelor of Science - BS from Loyola Marymount University

More Information

Social Presence :

Prographics :

Exp : 13 Location : New York City Metropolitan Area, United States Job Level : N/A Designation : Head of Engineering at Squire
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Insights For Selling To Troy

During A Call Or A Meeting

DO's

  • Suggest clear next steps with confidence, don't be vague or hesitant
  • You can spend time on BANT (or other qualification methodology) but keep it to the point
  • During followups, use phone or text if needed, they should be fine

DONT's

  • Don't get into pricing discussions early on, steer conversation towards proven results
  • Don't shy away from asking hard questions, but be extra polite
  • Avoid putting conscious effort into relationship-building

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Troy is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Troy

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Troy move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Troy take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Troy

Personality Compatibility


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