Jason Cincotta

Questioner
DISC Type : c

Founder & CEO at Kismet

New York, New York, United States

Overview

Jason Cincotta is the Founder of Kismet, an AI platform transforming how travel is sold. His expertise is rooted in his past role as a hotel developer at The Cincotta Co. , where he built boutique hotels. He holds an MBA from Columbia Business School and has a consulting background from McKinsey & Company.

Originally from Boston, Jason is a dedicated recreational runner and an NBA basketball fan. He is passionate about cities and enjoys buying books faster than he can read them. He is happiest when wandering a city with his family, iced coffee in hand.

His career in real estate development began when a property he had under contract burned down, and he successfully convinced a bank to finance a larger project on the site.

Personality Overview

Price-Sensitive

Value Seeker

Cautious & Analytical

They generally do not appreciate an overfriendly approach and prefer to stay to-the-point.  While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters. It is quite likely of them to ask for pricing or other concessions.

Topics They Care About

AI in Hospitality
As the founder of Kismet, he is building an AI platform to reshape hotel distribution and is a frequent speaker on the topic of AI agents in travel.
Hotel Distribution
His work focuses on helping independent hotels use AI to increase direct bookings and compete more effectively with online travel agencies (OTAs).
Real Estate Development
He has extensive experience developing boutique hospitality and residential projects, notably leading the team that built The Sarasota Modern hotel in Florida.

Media Appearances

Everything AI in Travel – chats to Jason Cincotta from Kismet about getting discovered by AI agents. Featured in Apple Podcasts

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Kismet - 2026 Company Profile, Team, Funding & Competitors. Featured in Tracxn

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Hot 25 Travel Startups for 2026: Kismet. Featured in PhocusWire

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Work History

12-2023
Founder & CEO at Kismet
12-2023
Investor at The Cincotta Co.
6-2022 - 8-2022
Associate at McKinsey & Company
2012 - 12-2023
Principal at The Cincotta Co.

Education

Master of Business Administration - MBA from Columbia Business School
BA from Pomona College

More Information

Social Presence :

Prographics :

Exp : 12 Location : New York, New York, United States Job Level : Leadership Designation : Founder & CEO at Kismet
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Insights For Selling To Jason

During A Call Or A Meeting

DO's

  • Back up any claims with data and numbers
  • Keep some extra margin in hand as they will likely negotiate the pricing
  • Tell them that you will come back if you don’t have a good answer for a question

DONT's

  • Don’t try to be too friendly or informal with them
  • Don’t depend too much on anecdotal evidence, it reduces their confidence
  • Don’t overhype the product/pitch, keep it measured

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jason is

  • Ensuring that the product delivers ROI, cost-effective pricing and process compliance are very important for them.
  • Will you ever get a clear answer from Jason

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Jason move?

  • If they have the information that they need, they can move fast at making their decisions.
  • Can Jason take some risk or not?

  • If they believe that they have analyzed the situation well, they can take a little risk.

You And Jason

Personality Compatibility


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