Rajendra Uppal

Enigma
DISC Type : Dic

Head of Engineering at 5day.io

Bengaluru, Karnataka, India

Overview

Rajendra Uppal is an accomplished software engineering leader, currently serving as the Head of Engineering at 5day. io. With a history at Microsoft and Adobe and an M. Tech from IIT Delhi, he specializes in building high-performing teams for B2B SaaS products, with a strong focus on AI-driven engineering productivity and exceptional user experiences.

Outside of his primary role, Rajendra is a dedicated mentor and community builder, known for providing clear, actionable feedback to help engineers grow. He is committed to continuous learning, often reading and writing about software architecture, best practices, and new technologies to stay sharp.

He once led the revamp of a backend system that resulted in a remarkable 180x performance boost.

Personality Overview

Challenger

Fast Follower

Persuasive & Assertive

They are generally strong communicators and are not easy to convince.  They can sound friendly and charming but can quickly change gears to become inquisitive and probing  They are likely to ask many questions and look heavily for supporting proof as well as information.

Topics They Care About

Generative AI
Currently hiring AI engineers to build and deploy Generative AI applications and AI agents, and has a certification in the subject.
Minimalist Products
Believes "clarity and simplicity" are essential features and is building a minimalistic project management tool at 5day. io that stays out of the user's way.
Engineering Mentorship
Highly regarded as a mentor, with people describing his guidance as "invaluable" and his feedback as "clear, actionable, and showed a deep understanding. "

Media Appearances

Rajendra has no verified media appearances

Work History

8-2025
Head of Engineering at 5day.io
1-2023 - 1-2025
Director of Engineering at Pulse Labs
9-2021 - 1-2023
Senior Software Engineering Manager at Microsoft
7-2020 - 9-2021
Engineering Manager at WorkSpan
8-2019 - 3-2020
AVP Engineering at inFeedo

Education

6-2006 - 6-2008
Master of Technology - MTech from Indian Institute of Technology, Delhi
2000 - 2002
Master of Science - MS from M. D. S. University, Ajmer

More Information

Social Presence :

Prographics :

Exp : 5 Location : Bengaluru, Karnataka, India Job Level : Mid-senior Designation : Head of Engineering at 5day.io
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Insights For Selling To Rajendra

During A Call Or A Meeting

DO's

  • Let them lead the discussion, create opportunities for them to speak if they are not very forthcoming
  • Be prepared for a mix of questions and inquisitiveness, answer them in the tone in which they have been asked
  • Leverage 'negging', or the art of asking negative questions like "you must not be convinced yet..."

DONT's

  • Don’t try to rush them into a decision, provide all necessary information first
  • Avoid long presentations and just 'high-level' value proposition, dive into the details
  • Avoid making offhand commitments, understand the root of their concerns first

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Rajendra is

  • Proven value, strong objective evidence are important for them, rapport can impact decisions a little.
  • Will you ever get a clear answer from Rajendra

  • They are practical and friendly, but can give a clear response with a little prodding

Insights For Deal Planning

    How fast (or slow) will Rajendra move?

  • They like to be detailed, so unless they develop strong conviction, they can take their time to arrive at decisions
  • Can Rajendra take some risk or not?

  • They evaluate their decisions systematically and do not take risks that often, unless you can get them to develop strong conviction

You And Rajendra

Personality Compatibility


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