Ross Osborne

Trailblazer
DISC Type : ID

UK Chief Executive Officer at Rippling

United Kingdom

Overview

Ross Osborne is the UK Chief Executive Officer at Rippling, a senior corporate risk leader with extensive fintech experience at firms like ClearBank, Bitpanda, and Wise. Described by colleagues as an "inspiring leader, " he specializes in business transformation, risk strategy, and navigating complex regulatory environments across global markets.

He was appointed as Ripplings first-ever UK CEO in January to lead the companys strategic expansion.

Personality Overview

Achievement-Oriented

Persuasive

Values Relationships

They are more likely to be open to unproven but exciting technologies.  They like to keep things under control. They are charming and have the ability to align others behind their decisions.

Topics They Care About

European Expansion
He is actively hiring key leadership roles, including a CEO for Ireland, to strengthen and scale Rippling's payments capabilities and operations across Europe.
Fintech Risk & Compliance
As a former Chief Risk & Compliance Officer, he has deep expertise in enterprise risk, financial risk, and navigating the ever-changing regulatory landscape for financial services.
Strategic Leadership
He recently moved into the UK CEO position to drive Rippling's strategic business in the region after holding various leadership roles in risk and compliance.

Media Appearances

Ross has no verified media appearances

Work History

1-2026
UK Chief Executive Officer at Rippling
9-2025
Compliance Risk Officer (Group) at Rippling
6-2024 - 1-2026
Chief Risk & Compliance Officer MLRO (UK) at Rippling
1-2024 - 6-2024
Director of Digital Assets Risk (Interim) at ClearBank
7-2023 - 6-2024
Head of Operational & Technology Risk at ClearBank

Education

1996 - 2001
Education details unavailable from St. Ninian's High School

More Information

Social Presence :

Prographics :

Exp : 5 Location : United Kingdom Job Level : Leadership Designation : UK Chief Executive Officer at Rippling
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Insights For Selling To Ross

During A Call Or A Meeting

DO's

  • Address your competition clearly and confidently
  • Keep your pitch focused on the impact but nurture the relationship too
  • Help them visualize the impact of their decision

DONT's

  • Don’t hesitate from asking questions or pushing them, but take a friendly approach
  • Do not look like someone who doesn’t know what they are talking about
  • Avoid unnecessary negativity or slowness

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ross is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Ross

  • If they are not convinced, they will say no albeit in a friendly manner.


Insights For Deal Planning

    How fast (or slow) will Ross move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Ross take some risk or not?

  • They can take risks if necessary.

You And Ross

Personality Compatibility


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