A bit about me
I started at 21. Nobody told me how any of it actually worked.
So I spent twenty years finding out — at Amazon, at Microsoft, from individual contributor to Principal Engineering Manager, and now leading engineering at a security startup. This is the guide I wish someone had handed me.
A journey rooted in experience
I dove headfirst into tech at twenty-one — into a world of innovation, ambiguity and people who seemed to know something I didn't. Over the years I gathered insight across engineering, product and program organisations at two of the most demanding companies in the industry, and spent the last six building and leading security engineering teams.
Today I am Director of Engineering at a startup. Before that I was a Principal Software Engineering Manager at Microsoft, and before that a Software Development Manager at AWS. I have written promo packets, sat in calibration rooms, run hundreds of interview loops, and made the call on offers. I have also been on the receiving end of every one of those processes — including the times it did not go my way.
That is the part most career advice is missing. It is written by people describing a room they have never sat in. I will tell you what actually gets said when you leave the interview, what actually decides a promotion, and what actually separates the person who gets the offer from the four who did not.
Your success, my priority
We all face the same time constraints, so my coaching is built to deliver maximum value inside the hour. I am not going to spend it on generic encouragement. I am passionate about helping people excel in interviews and navigate the intricacies of a career — securing the role, uplevelling the skills, climbing the ladder.
Your success story starts now. Let's work together to unlock your full potential.
One honest caveat. I cannot offer you a job, and helping people who are not in a position to help themselves is beyond the scope of my expertise. What I can do is make sure that when the opportunity comes, you are unmistakably ready for it.
The track record
Twenty years, in order.
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Now
Director of Engineering
Security startup
Leading engineering at a startup, six years into security engineering. The problems are the same ones Big Tech has — with a fraction of the people and none of the cover.
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2021 — 2025
Principal Software Engineering Manager
Microsoft · Cloud Security
Owned Athena, an ML service for reducing time-to-mitigate, and the Key Management Service Provider behind Azure Key Vault. Latterly responsible for data intelligence across business, partners and product.
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2019 — 2021
Software Development Manager
Amazon Web Services · Textract
End-to-end engineering and operations for the AWS Textract control plane.
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2016 — 2019
Senior PM Manager
Microsoft · Azure Customer Experience
Built the first Azure online support team and shipped the first chat experience on the Azure portal. Grew the team from 2 vendor resources to 38 globally; roughly $10M in cost savings over two years.
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2012 — 2016
Software Development Engineer → SDE II
Microsoft · MSN & Windows
Built the Toast Notification Service for iOS, Windows and Android — adoption reached 2 million devices. Sole liaison between editorial and seven engineering teams.
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2006 — 2010
Software Engineer
Aditi Technologies & Bally Technologies
Web products across healthcare, finance and telecom. New Grad Star Performer award. Later, MS in Computer Science at UT Dallas.
Who I work with
Different roles, same hard questions.
Software Developers
Breaking in, levelling up, or finally getting the scope that turns into a promotion.
Product Managers
Building influence without authority, and telling the impact story that gets you the next role.
Program Managers
Owning ambiguity, driving cross-org outcomes, and being seen for it.
Career switchers
Coming into tech from somewhere else, and needing an honest read on what it will actually take.
Testimonials
In their words.
Thank you so much Gurpreet for being such a great listener and an equally good and articulate speaker — and for helping me understand technical concepts in easily understandable, digestible bits. Gurpreet is not someone who says "do as I say". He is someone who says "do as I do", and talks from experience.
Software Engineer
Career transition
I really found the session very helpful and effective. The suggestions you gave to overcome my confidence issues make a lot of sense. I am looking forward to the next session as discussed.
Product Manager
Confidence & communication
I felt amazing after the session. I am so grateful for all the practical solutions you have given to set my career in the right direction. Would love to have a session again.
Program Manager
Career direction