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The Word doc that became a $2B company
EvenUp co-founder Saam Mashhad speaks at Best Of on April 13
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Saam Mashhad spent years as a litigation attorney watching the same thing happen. Personal injury clients with real cases would walk away because the paperwork was crushing. Demand letters took weeks. Settlements stalled. People gave up.
In 2019, he co-founded EvenUp with Rami Karabibar and Raymond Mieszaniec to fix it. The wedge was simple: AI that drafts demand letters in hours, not weeks. For Raymond, it was personal, his father was permanently disabled after being hit by a car, and the family lived through how slow and unfair the process is.
In October 2025, EvenUp closed a $150M Series E led by Bessemer at a $2B+ valuation. Total raised: $385M. According to EvenUp, the platform has helped resolve 200,000+ cases and secured over $10B in damages, and is now used by 2,000+ firms, including 20% of the top 100 personal injury firms in the US.
The story we keep coming back to: Saam showed an early version to a client who said no. Two weeks later, buried in files, the same client said yes. That's the wedge. Find the workflow people hate, build the thing that removes it, wait for them to come back.
April 13 at Toronto City Hall, TechTO's Best Of brings 400+ builders, founders, operators and investors together for one night of unfiltered stories.
The wins, the pivots, the decisions that didn't make the press release.
Saam is on that stage, and his thinking on how to build vertical AI that actually sticks is part of the night.
When you think about your AI product's defensibility, what are you betting on: the workflow, the data, or the distribution? Hit reply with your answer.
Three roles worth knowing about this week…
JSOC Cybersecurity Specialist, Digital Threat Hunting at Questrade
Questrade is one of Canada's largest independent brokerages - this role sits at the intersection of OSINT, digital fraud investigation, and brand protection.
Head of Programmatic & AdTech at Wattpad
Wattpad reaches 155M monthly active users globally - this is a senior seat rebuilding their ad tech stack into a high-performance revenue engine.
Senior Solutions Engineer (Pre-Sales) at Geotab
Geotab is one of the world's largest telematics companies - this role owns the technical side of large enterprise deals across their global partner ecosystem.
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