Ashok Kalyanswamy

Trailblazer
DISC Type : DI

Managing Director at Two Sigma

New York, New York, United States

Overview

Ashok Kalyanswamy is a Managing Director at Two Sigma and a seasoned CIO/CTO leader specializing in digital transformation for the financial services industry. Colleagues describe him as a visionary, inclusive, and inspiring leader with a talent for building high-performing global teams. He holds an MS from Syracuse University and champions a cloud and API-first approach to technology.

Passionate about people development, Ashok has invested in his own growth by earning leadership and performance coaching certifications. He actively promotes a positive team culture, recruits top talent, and advocates for diversity and inclusion, which he considers foundational to a companys success. He also serves on the advisory board for an HR tech firm.

Unique Fact: He holds formal certifications in "Next Level Coaching" and "Leadership and Performance Coaching, " reflecting a deep personal commitment to mentorship and leadership development.

Personality Overview

Achievement-Oriented

Charismatic

Values Relationships

They are more likely to be open to unproven but exciting technologies.  They are charming and have the ability to align others behind their decisions. If they come to believe in your value proposition, they will be your champion.

Topics They Care About

Global Team Building
His profile and posts consistently emphasize building and leading global teams. He actively recruits, promotes a positive culture, and serves as an advisor to an HR tech company.
Digital Transformation
A core theme in his career, he frequently speaks on moving technology stacks to the cloud and using AI/ML to drive efficiency and business growth in financial services.
Leadership & Growth Mindset
He holds multiple coaching certifications and has stated in interviews that having a "growth mindset" is the most important trait he looks for in a leader.

Media Appearances

Ashok has no verified media appearances

Work History

10-2022
Managing Director at Two Sigma
7-2022 - 10-2022
Relocation at Career Break
1-2017 - 8-2022
Senior Executive Vice President and CIO (Chief Information Officer) at Saxo Bank
10-2013 - 10-2016
Division Director at Macquarie Group
4-2013 - 10-2013
Managing Director, Global Head of Markets Execution Services IT at Nomura Securities

Education

BS from BIT Mesra Student-Industry Relations Cell
MS from Syracuse University

More Information

Social Presence :

Prographics :

Exp : 16 Location : New York, New York, United States Job Level : Mid-senior Designation : Managing Director at Two Sigma
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Insights For Selling To Ashok

During A Call Or A Meeting

DO's

  • Use phrases like ‘your decision will’, ‘you will impact’ etc.
  • Help them visualize the impact of their decision
  • Talk about yourself and some of your achievements at the start of the conversation

DONT's

  • Don’t hesitate from asking questions or pushing them, but take a friendly approach
  • Avoid unnecessary negativity or slowness
  • Don’t force involvement of other stakeholders unless it is critical

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ashok is

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

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


Insights For Deal Planning

    How fast (or slow) will Ashok move?

  • If you earn their trust and they develop faith in the product, they can make decisions quickly.
  • Can Ashok take some risk or not?

  • They can take risks if necessary.

You And Ashok

Personality Compatibility


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