Elaine Montilla

Sharpshooter
DISC Type : DC

Chief Technology Officer at Pearson

Hartsdale, New York, United States

Overview

Elaine Montilla is a C-Suite technology executive with over two decades of experience leading large-scale digital transformations in the edtech sector for organizations like Pearson and CUNY. She is a recognized leader, speaker, and published author focused on human-centered technology and inclusive leadership. Colleagues describe her as inspirational, authentic, and thoughtful.

As the founder of 5xminority, she is a passionate advocate for empowering women, LGBTQ+ professionals, and people of color in tech. A proud Latina immigrant from the Dominican Republic, she uses her platform to speak on resilience, authenticity, and creating inclusive workplaces. Outside of her executive roles, she enjoys photography, dancing, and traveling.

Interesting fact: Elaine taught herself English after moving to the United States at 17, viewing education as the one thing no one could ever take away from her.

Personality Overview

Rigorous & Demanding

Thorough Evaluator

ROI Driven

They put a lot of effort into ensuring personal success.  They are less concerned about the product and more about its potential impact. They like to stay in control of the negotiation or defining of the terms.

Topics They Care About

Inclusive Leadership
She founded 5xminority, a platform dedicated to empowering women, LGBTQ+ professionals, and minorities in tech, and speaks frequently on creating equitable and inclusive cultures.
Human-Centered Technology
A core philosophy in her work, she believes technology should improve lives by being people-centered and serving everyone, not just a select few.
AI Transformation
She completed an Applied Generative AI program at MIT and often speaks on navigating AI's impact on work while keeping humanity and empathy at the center.

Media Appearances

The Importance of DE&I in Technology: Elaine Montilla, Pearson. Featured in YouTube

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Elaine Montilla - Chief Technology Officer at Pearson. Featured in Chief In Tech

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Elaine Montilla - Forbes Technology Council. Featured in Forbes

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Work History

8-2022 - 1-2025
Chief Technology Officer at Pearson
12-2019 - 12-2023
Official Member at Forbes Technology Council
9-2017 - 8-2022
Assistant Vice President for Information Technology/CIO at The Graduate Center, City University of New York
8-2011 - 9-2017
IT Director of the Division of Client Services/Deputy CIO at The Graduate Center, City University of New York
8-2005 - 8-2011
Manager of User Services/Help Desk Manager at The Graduate Center, City University of New York

Education

3-2024 - 4-2024
Applied Generative AI for Digital Transformation from MIT Professional Education
2-2022 - 4-2022
Professional Certificate from BrainStation

More Information

Social Presence :

Prographics :

Exp : 19 Location : Hartsdale, New York, United States Job Level : N/A Designation : Chief Technology Officer at Pearson
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Insights For Selling To Elaine

During A Call Or A Meeting

DO's

  • Help them weigh the risks by sharing objective proof points without becoming too analytical
  • Hold your ground without indulging in one-upmanship
  • Speak about competitive differentiation that your product offers

DONT's

  • Do not spend too much time focusing on product tech or features
  • Don't try too hard to forge relationships with them
  • Do not hesitate from asking counter questions, just avoid challenging their authority

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Elaine is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Elaine

  • If they are not convinced, they will say no without any hesitation.

Insights For Deal Planning

    How fast (or slow) will Elaine move?

  • If convinced, they can reach decisions quite fast.
  • Can Elaine take some risk or not?

  • They do not shy away from taking risks, but can be quite binary about them.

You And Elaine

Personality Compatibility


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