Robert Dugdale

Captain
DISC Type : DS

SVP, Sales & Partnerships | Enterprise & Agentic AI at Kasisto, Inc.

New York City Metropolitan Area, United States

Overview

Robert Dugdale is the SVP of Sales & Partnerships at Kasisto, focusing on Agentic AI for the banking sector. He has over a decade of experience selling enterprise conversational AI, previously at Amelia. He holds a Bachelor of Science from Alliance University and is known for uniting teams effectively.

He is the Vice Chair of the iMason’s NYC Chapter and a Strategic Advisor at Cato, reflecting his interest in digital infrastructure. Robert values building long-term professional relationships, a principle that has shaped his career and is highlighted in his professional headline and affiliations.

In 2017, he went from taking a solo polar bear plunge to closing one of the most significant deals of his career shortly after.

Personality Overview

Long-Term Thinker

Planner & Achiever

Consummate Professional

Reading between the lines and seeing beyond your words comes naturally to them.  They might take some time to make their mind up but once they do, they don't change it easily. They are very professional in their approach and can weigh multiple perspectives together.

Topics They Care About

Agentic AI in Banking
He is leading the market introduction for KAIgentic, Kasisto's platform for autonomous AI agents designed specifically for financial institutions and their security requirements.
Enterprise AI Adoption
He spent ten years at one of the earliest AI platform companies, helping large enterprises adopt and scale artificial intelligence to achieve measurable results.
Digital Infrastructure
As Vice-Chairman for the iMasons NYC chapter and an advisor to Cato, he is actively involved in discussions about the future of sustainable data centers and power grids.

Media Appearances

Robert has no verified media appearances

Work History

1-2025
SVP, Sales & Partnerships | Enterprise & Agentic AI at Kasisto, Inc.
10-2024
HFTP Member at Hospitality Financial and Technology Professionals (HFTP®)
10-2024
Consumer Technology Association (CTA) at Consumer Technology Association
9-2020
Strategic Advisor at Cato
8-2017
Infrastructure Masons Vice-Chairman (Building the Local NYC Chapter) at Infrastructure Masons

Education

1993 - 1995
Bachelor of Science (BS) from Alliance University

More Information

Social Presence :

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Exp : 8 Location : New York City Metropolitan Area, United States Job Level : Leadership Designation : SVP, Sales & Partnerships | Enterprise & Agentic AI at Kasisto, Inc.
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Insights For Selling To Robert

During A Call Or A Meeting

DO's

  • Let them know of potential risks but suggest mitigation methods alongside
  • Use phrases like 'your team deserves', 'best in class' etc.
  • Ask them at the end if they see a strong value prop in your product; expect an honest answer

DONT's

  • Avoid putting conscious effort into relationship-building
  • Don't go over them unless you are left with no other option
  • Don't take their patience for granted, avoid long-winding sermons

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Robert 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 Robert

  • 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 Robert move?

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

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

You And Robert

Personality Compatibility


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