Jimmy Fitzgerald

Enigma
DISC Type : icd

Chief Executive Officer at Paddle

United Kingdom

Overview

Jimmy Fitzgerald is the CEO of Paddle, a payment infrastructure provider for SaaS companies. With over 20 years of experience scaling tech businesses, he previously held senior roles at ServiceNow, including SVP of Customer Outcomes, where he specialized in international expansion. He holds an MBA from Helsinki School of Economics and is described by peers as a strategic, focused, and strong leader.

Interesting fact: Jimmys focus on culture is so strong that Paddle created its own book called "Paddle Compass," which serves as the companys guide to high performance.

Personality Overview

Challenger

Persuasive & Assertive

Fast Follower

They are generally strong communicators and are not easy to convince.  They can sound friendly and charming but can quickly change gears to become inquisitive and probing  They are likely to ask many questions and look heavily for supporting proof as well as information.

Topics They Care About

SaaS Growth Strategy
He focuses on helping software businesses scale sustainably, moving beyond the 'growth at all costs' era by leveraging payments and billing as a strategic growth lever.
Global Market Entry
He has extensive experience leading international expansion, particularly in the Asia-Pacific and Japan region during his tenure at ServiceNow.
Customer-First Mindset
His leadership background in 'Customer Outcomes' at ServiceNow shows a career-long focus on ensuring customers achieve success and see real economic impact from the products they use.

Media Appearances

Mastering international markets, from ServiceNow to Paddle – lessons from Jimmy Fitzgerald. Featured in Now We Build Podcast (Spotify)

See Now

Paddle CEO Transition: Christian Owens Hands Over to Jimmy Fitzgerald. Featured in Paddle Blog

See Now

Who is the CEO of Paddle in 2026? Jimmy Fitzgerald's Bio. Featured in Clay

See Now

Work History

4-2023
Chief Executive Officer at Paddle
4-2021 - 4-2023
President and COO at Paddle
1-2019 - 2-2021
Senior Vice President, Customer Outcomes at ServiceNow
1-2018 - 12-2018
Global Vice President, Professional Services at ServiceNow
4-2013 - 12-2017
Vice President and General Manager, Asia Pacific and Japan at ServiceNow

Education

2002 - 2004
MBA from Helsinki School of Economics, Singapore (2004)
1992 - 1995
Commerce from University College Cork

More Information

Social Presence :

Prographics :

Exp : N/A Location : United Kingdom Job Level : N/A Designation : Chief Executive Officer at Paddle
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Insights For Selling To Jimmy

During A Call Or A Meeting

DO's

  • Use phrases like ‘clear evidence’, ‘data-based results’ etc.
  • Be prepared for a mix of questions and inquisitiveness, answer them in the tone in which they have been asked
  • Let them lead the discussion, create opportunities for them to speak if they are not very forthcoming

DONT's

  • Don’t rely excessively on your relationship with them to win the deal even if you come to form one
  • Don’t try to rush them into a decision, provide all necessary information first
  • Avoid long presentations and just 'high-level' value proposition, dive into the details

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jimmy is

  • Proven value, strong objective evidence are important for them, rapport can impact decisions a little.
  • Will you ever get a clear answer from Jimmy

  • They are practical and friendly, but can give a clear response with a little prodding

Insights For Deal Planning

    How fast (or slow) will Jimmy move?

  • They like to be detailed, so unless they develop strong conviction, they can take their time to arrive at decisions
  • Can Jimmy take some risk or not?

  • They evaluate their decisions systematically and do not take risks that often, unless you can get them to develop strong conviction

You And Jimmy

Personality Compatibility


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