Ajay Awatramani

Pioneer
DISC Type : DSI

Chief Product Officer at Five9

San Francisco Bay Area, United States

Overview

Ajay is the Chief Product Officer at Five9, leading the AI transformation in customer experience. With over 25 years in SaaS, he has a track record of creating value at companies like Adobe and Marketo. He holds a Master of Science from the University of Southern California.

Beyond his professional focus, Ajay shows a deep personal interest in the broader societal implications of artificial intelligence. He shares thoughts on topics ranging from advanced multi-agent systems to how his own family members use consumer AI tools like ChatGPT for daily advice.

Unique fact: Ajay co-invented a patented system for sales performance management using high-performance analytics technology.

Personality Overview

Driven But Considerate

Decisive But Friendly

Friendly But Fast

They have the unique ability to win both love and respect from their team (or outsiders)  If they are convinced, they can become very strong champions for your product They combine a unique set of diverse traits where they are fast and friendly but can slow down to be thorough when needed

Topics They Care About

AI in CX
As CPO of Five9, his work is centered on using AI and the "Digital Labor Revolution" to innovate the customer experience and create operational leverage for businesses.
SaaS Value Creation
His career at Marketo, Adobe, and Cornerstone demonstrates a consistent focus on creating value through product innovation, strategic M&A, and driving growth.
Societal AI Impact
He posts about how voice AI can deliver high-quality legal and medical advice to remote populations, showing an interest in AI's ability to solve real-world problems.

Media Appearances

Ajay has no verified media appearances

Work History

10-2024
Chief Product Officer at Five9
6-2023 - 6-2025
NED at MBO Partners
11-2024
EIR at Storm Ventures
9-2020 - 8-2022
Chief Product Officer at Cornerstone OnDemand
1-2019 - 9-2020
Head of Product and GTM - B2B at Adobe

Education

Master of Science (MS) from University of Southern California

More Information

Social Presence :

Prographics :

Exp : 6 Location : San Francisco Bay Area, United States Job Level : Leadership Designation : Chief Product Officer at Five9
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Insights For Selling To Ajay

During A Call Or A Meeting

DO's

  • Ask them for a lunch or coffee once some rapport has been established
  • Mostly stick to your standard pitch and qualifying script, but add some stories or anecdotes to it
  • Use phrases like ‘your decision will’, ‘you will impact’ etc.

DONT's

  • Don’t hesitate from asking questions or pushing them, but take a formal approach
  • Avoid focusing only on the product or its ROI, keep building trust subtly
  • Don't lean very heavily into providing too much information, sharing whitepapers etc.

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ajay is

  • Nothing less than a strong combination of proof of results, relationship and high levels of professionalism is effective with them.
  • Will you ever get a clear answer from Ajay

  • They can say no while staying friendly, but can also be pursuaded to reconsider

Insights For Deal Planning

    How fast (or slow) will Ajay move?

  • They are generally fast movers and can take quick decisions
  • Can Ajay take some risk or not?

  • They have high risk-appetite but can get ahead of themselves once in a while. Observe carefully

You And Ajay

Personality Compatibility


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