Harry Dixon

Questioner
DISC Type : c

CEO & Co-Founder at Checkmate

Los Angeles Metropolitan Area, United States

Overview

Harry Dixon is the CEO and Co-Founder of Checkmate, an AI-powered marketing platform. A Forbes 30 Under 30 honoree, he has a background in commerce and economics from UCLA and The University of Western Australia, with prior experience leading strategy and partnerships at EasyPost and Skyryse.

Outside of his entrepreneurial ventures, Harry has been deeply involved in surf lifesaving. He served as a Head Trainer for Bronze Medallion Courses and a Unit Leader for a youth cadet program, demonstrating strong leadership and community commitment within the North Cottesloe Surf Life Saving Club.

Unique fact: Before founding his tech company, Harry was a certified IRB (Inflatable Rescue Boat) Crew member and held an Advanced Resuscitation certification.

Personality Overview

Value Seeker

Price-Sensitive

Systematic

It is quite likely of them to ask for pricing or other concessions.  They generally do not appreciate an overfriendly approach and prefer to stay to-the-point. They prefer to do thorough analysis of any situation.

Topics They Care About

AI-Powered Marketing
He is building an AI marketing platform, Checkmate, to create personalized buying experiences and recently unveiled its core AI engine, "Haptics".
Startup Growth
As a co-founder who was previously the first business hire at another startup, he is focused on product roadmaps and learning from eCommerce industry veterans.
eCommerce Loyalty
He has moderated panels on customer loyalty in the beauty sector and emphasizes the importance of brands listening to their community to build addiction to their products.

Media Appearances

Harry Dixon (Checkmate): Personalization & Cashback Innovation in .... Featured in Spotify

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Checkmate! Perth Founders Raise US$15M For Their Discount Shopping App. Featured in Startup News

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The online shopping start‑up that's banked millions for Silicon Valley – Aussie mates bank millions for Checkmate. Featured in Australian Financial Review

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Work History

5-2022
CEO & Co-Founder at Checkmate
7-2020 - 5-2022
Partnerships Director at EasyPost
12-2019 - 5-2022
Business Strategy Lead at EasyPost
8-2019 - 12-2019
Senior Manager, Strategy & Partnerships at Skyryse
8-2018 - 12-2019
Manager, Launch & Strategy at Skyryse

Education

2011 - 2014
Bachelor of Commerce (B.Com.) Bachelor of Economics from The University of Western Australia
2014 - 2014
Bachelor of Commerce (B.Com.) from UCLA

More Information

Social Presence :

Prographics :

Exp : 16 Location : Los Angeles Metropolitan Area, United States Job Level : Leadership Designation : CEO & Co-Founder at Checkmate
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Insights For Selling To Harry

During A Call Or A Meeting

DO's

  • Back up any claims with data and numbers
  • Emphasize on objective proof of ROI, help them do a thorough evaluation
  • Share as much information as possible regarding your product

DONT's

  • Don’t depend too much on anecdotal evidence, it reduces their confidence
  • Don’t try to be too friendly or informal with them
  • Avoid rushing them, be polite and patient

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Harry 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 Harry

  • 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 Harry move?

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

  • They can take some risk if they are confident that they have analyzed the circumstances well.


You And Harry

Personality Compatibility


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