Waypoint 01 // The Road

Sahil Talwar

I'm an engineering executive, entrepreneur, and frequent traveler. I build teams and software, read widely, and like a good question almost as much as a road I haven't driven.

20Countries visited

46US states visited

1–2Books per week

NowBuilding Job Hunter

Start the journey Resume

Three US road trips and four months on the road have not cured my interest in road trips.

Waypoint 02 // The City

The work, by district

A few places where I learned to build systems, teams, and companies.

District 01

RedShelf

VP of Engineering

Feb 2024 – Oct 2025

Led engineering for a platform supporting $35M+ in annual recurring revenue, 8M+ users, and 20M API calls/day.
Reworked delivery around AI tools, human review, and better tests; velocity improved 20%+.
Redesigned teams while developing a strong pipeline of engineering managers.
Launched a new product that grew annual recurring revenue 10%; cut legacy operating costs ~25%.

District 02

Oracle

Director of Software Engineering

Apr 2018 – Jul 2022 · Manager → Sr Manager → Director in 4 years

Grew from one team to a 50-person, seven-team organization across four offices.
Led through engineering managers and saw only four departures in four years.
Ran a $150M ARR platform handling 30B daily API calls with sub-22ms SLAs.
Moved the platform from IBM SoftLayer to OCI while breaking a monolith into services.

District 03

Ungambled

Co-Founder

Oct 2021 – present · advisory since 2024

Bootstrapped the first product from an idea to market at under $10K monthly burn.
Added two revenue streams and doubled average revenue per customer.
Learned the unglamorous parts too: taxes, compliance, company structure, and three platforms.

District 04

Excella Consulting

.NET Specialty Area Lead & Senior Consultant

2012 – 2015

Led 20 engineers modernizing a pension system serving 65K people and $16B in assets.
Designed exact financial calculation engines that have run in production since 2015.
Delivered all nine milestones on time and budget while teaching and growing engineers.

Earlier

Lanetix, Senior Software Engineer, led two teams · Bitgrid, CTO, MVP in six months with an engineer and designer · Solers · GeoEye · Microsoft, software engineering intern.

Education

Virginia Tech

B.S. Computer Science + B.A. Philosophy. Minor in Mathematics.

2006 – 2010

Waypoint 03 // The Observatory

What guides me

It's a waste to drift through life without intention. You make yourself through your actions, so choose to be someone worth being.
- Sahil Talwar

How I lead

01
First Principles
Ask the silly questions, name assumptions, and understand why the system is the way it is before changing it.
02
Working Software
Define success, execute, deliver results, and measure to prove real value - not just a story.
03
Respond to Change
Raise issues transparently, immediately, and without ego; change the plan when evidence disagrees.
04
Clarity and Agency
Say the hard thing clearly, listen for real feedback and what I missed, and leave people with agency.

Personal reading // A Free Man's Worship, Bertrand Russell (1903)

Morality: We alone, amongst all of Nature's children, can see the difference between right and wrong.
Vision: We should use that vision to make this world a better, more just place.
Resignation: We must accept that we cannot change everything, and still work to improve what we can.
Compassion: We are all travelers on the same path - we should be kind to one another along the way.

This essay was formative for me. It said what I felt in my core better than I ever could, and has stayed with me ever since.

Waypoint 04 // The Archive

Notes from the margins

Travel, books, music, questions, and work in progress.

Shelf 01

Travel

Three road trips across the US, four months on the road in total. Road trips in Greece and India, too. Between trips, I climb, bike, and swim. An open road and somewhere new ahead is about my perfect day.

Shelf 02

Reading

One or two books a week. Max Gladstone for fantasy unlike anything else I’ve read. Jim Butcher for mysteries steeped in magic that grab hold and don’t let go. Isaac Asimov for wildly imaginative visions of the future.

Shelf 03

Music

Chicane, The Midnight, and ODESZA are frequent listens. The radio plays an original score generated in your browser. Press M to toggle it.

Shelf 04

Questions

I read philosophy, especially epistemology and ethics, and write essays. Lately, two questions occupy me: Does agent-written code do what we intended? How do we check it for defects? Getting the intent right and verifying the implementation are separate problems.

Shelf 05

Current work

I’m building Job Hunter, an open-source agent workflow for matching jobs and tailoring resumes. I also maintain a Job Scraper fork and have submitted changes upstream. These projects let me test agent workflows, context, and evaluations—not just read about them.

Explore Job Hunter View Job Scraper fork

Waypoint 05 // Orbit

Say hello

If you want to compare ideas, build something, or talk engineering leadership, I'd like to hear from you.

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Docking // pwep consulting

The station ahead is my consulting practice: AI adoption, engineering organization assessments, and leadership coaching.

Explore pwep consulting