Ashok Venkatraj
Founder, Questimate
I have spent 20 years building products at PayPal, Indeed, eBay, and General Motors. I have led teams of 125+ engineers. I hold a U.S. patent. I have shipped software used by millions of people.
I am also a licensed Texas realtor. I understand what it means to win a client, lose a deal, and compete on trust. Contractors and agents face the same challenge: the first professional response usually wins.
I built Questimate because I watched skilled tradespeople lose jobs they deserved — not because of their work, but because the estimate took too long. That is a problem I know how to solve.
Why I Built Questimate
I watched my landscaper, Mario, lose jobs. Not because of his work - his work is excellent. He lost jobs because the estimate took too long to send. Or because writing in English slowed him down. He spent his evenings doing paperwork instead of being with his family.
Mario is great at his trade. He should not need to be great at documents too.
So I built something to fix that. Questimate turns a quick conversation into a professional estimate. In English or Spanish. In under a minute. So contractors like Mario can send the quote while standing in the driveway, and get back to doing what they are actually good at.
Background
Before Questimate, I spent two decades building products at scale. I led teams of 125+ people. I shipped products used by millions. I learned what it takes to build software that actually works for real people with real problems.
Some of the things I have shipped: AI tools that reduced spam applications by 90%. Payment systems processing hundreds of millions in transactions. APIs used by 200+ enterprise partners. Products that won company-wide awards at Indeed and GM.
Credentials
- M.S. Computer Science, University of Arizona
- U.S. Patent 7,865,880 (Software Development Innovation)
- CEO Award, Indeed
- One Team Award, General Motors
- Licensed Texas Real Estate Agent
What People Say
“Ashok has the rare blend of business acumen, product judgment, and execution excellence. He helped us scale our product internationally and build a team that could sustain that growth.”
— SVP, HRTech Company
“He consistently goes above and beyond to advocate for his teams and deliver meaningful business outcomes. Direct, thoughtful, and gets things done.”
— Senior Director, Enterprise Software
My Promise
I am not building Questimate to flip it or chase venture capital. I am building it because I saw a real problem and I know how to fix it.
Every feature exists because a contractor needed it. Every price is set to be fair, not to maximize extraction. I answer support emails personally.
Your trust is earned, not assumed. I intend to earn it.