Jamie Cosgrove

Captain
DISC Type : DS

Vice President Financial Services at Databricks

Greater Chicago Area, United States

Overview

Jamie Cosgrove is a technology executive leading the Financial Services sales organization at Databricks. With extensive experience at AWS, Salesforce, and Podium, he specializes in go-to-market strategy and helping financial institutions transform using data and AI. Colleagues have described him as a strategic leader and one of the greatest managers, leveraging his leadership to develop his teams.

Jamie earned his Bachelors degree from Truman State University, where he was a member of the Sigma Phi Epsilon fraternity. His professional interests include major technology companies such as Microsoft and Cisco, reflecting his deep engagement with the tech industrys ecosystem.

He has built a distinguished career by consistently focusing on the financial services vertical across several of the worlds top high-growth technology companies.

Personality Overview

Decisive But Calm

Output-Driven

Consummate Professional

They exhibit a rare combination of being result-oriented but patient at the same time.  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.

Topics They Care About

Financial Services Tech
He leads the Financial Services vertical at Databricks, has held similar roles at AWS and Podium, and speaks at industry events on banking transformation.
Enterprise Data & AI
His role and public posts focus on how the Databricks platform enables organizations to scale their AI and data capabilities for business growth.
Strategic Account Planning
As an expert panelist on the topic, he advocates for rigorous planning and executive alignment to win major accounts in enterprise sales.

Media Appearances

Jamie Cosgrove - Data + AI Summit 2025 - Databricks. Featured in Databricks.com

See Now

Work History

5-2023
Vice President Financial Services at Databricks
1-2022 - 5-2023
Senior Director of Sales - Financial Services at Databricks
11-2020 - 1-2022
Vice President of Enterprise Sales at Podium
11-2020 - 1-2022
Head of Enterprise Verticals - Financial Services, Professional Services and Auto Services at Podium
11-2019 - 11-2020
Strategic Customer Engagements - Amazon Web Services at Amazon Web Services (AWS)

Education

1991 - 1995
Bachelor's degree from Truman State University
Education details unavailable from Crystal Lake South

More Information

Social Presence :

Prographics :

Exp : 28 Location : Greater Chicago Area, United States Job Level : Senior Designation : Vice President Financial Services at Databricks
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Insights For Selling To Jamie

During A Call Or A Meeting

DO's

  • You can spend time on BANT (or other qualification methodology) but keep it to the point
  • Come across as a trustworthy professional and be respectful, they usually know their game
  • During followups, use phone or text if needed, they should be fine

DONT's

  • Don't focus too much on mutual contacts or bother about other stakeholders, focus on them
  • Don't shy away from asking hard questions, but be extra polite
  • 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 Jamie 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 Jamie

  • 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 Jamie move?

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

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

You And Jamie

Personality Compatibility


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