Rob Boll

Collaborator
DISC Type : is

VP of Engineering at Datadog

Brooklyn, New York, United States

Overview

Rob Boll is the VP of Infrastructure & SDLC at Datadog, focused on transforming the companys infrastructure for the AI era. A graduate of Stony Brook University, he is a recognized leader in cloud infrastructure and developer platforms. Colleagues describe him as knowledgeable, collaborative, and a passionate leader.

Outside of his formal roles, Rob is described as a "true techie" who enjoys exploring new tools and technologies purely for fun in his free time. This reflects a deep and genuine passion for the world of software engineering that extends beyond the office.

He is a frequent speaker at major industry conferences like KubeCon, sharing his expertise on the complex challenges of running Kubernetes in large-scale environments.

Personality Overview

Consensus Builder

Good Listener

Fair-minded

They are more likely to opt for solutions that are proven in the market.  Unlike D or C types, they are calm as well as friendly and can give the impression of being more receptive than they actually are. Scenarios where both sides can come out as winners appeal to them greatly.

Topics They Care About

AI-Ready Infrastructure
His current mission at Datadog is to transform the company's infrastructure and Software Development Life Cycle specifically for the AI era.
Kubernetes at Scale
He has delivered multiple conference talks on the challenges of running Kubernetes in large-scale environments with over 1, 000 nodes.
Developer Experience
His work focuses on developer platforms and he has emphasized the importance of improving developer experience and reliability in his team's hiring efforts.

Media Appearances

Rob has no verified media appearances

Work History

2-2026
VP of Engineering at Datadog
5-2023 - 3-2026
Senior Director of Engineering at Datadog
11-2020 - 5-2023
Director of Engineering at Datadog
7-2019 - 11-2020
Engineering Manager at Datadog
1-2018 - 7-2019
Engineering Team Lead at Datadog

Education

2007 - 2011
BS from Stony Brook University

More Information

Social Presence :

Prographics :

Exp : 9 Location : Brooklyn, New York, United States Job Level : Senior Designation : VP of Engineering at Datadog
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Insights For Selling To Rob

During A Call Or A Meeting

DO's

  • If possible, involve their colleagues in the sales process
  • Take time to make them feel comfortable before getting to the main pitch
  • Use testimonials, case studies to show them why it is a low-risk, high-value decision

DONT's

  • Don’t push them to make decisions very fast, let them take their time
  • Don’t give the impression of being unproven or risky
  • Don’t sound very transactional

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Rob is

  • Relationships can play a major role, followed by low risk and strong market validation.
  • Will you ever get a clear answer from Rob

  • They are not very direct, and unlikely to say no to your face.

Insights For Deal Planning

    How fast (or slow) will Rob move?

  • They can take their time to make decisions, even if they are constantly involved and friendly.
  • Can Rob take some risk or not?

  • It is unlikely that they will take many risks.

You And Rob

Personality Compatibility


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