How do you go from 25 customers to $110M ARR and a $500M deal? - Daniel Chait [Greenhouse]

Today on BILLIONS, I’m sitting down with Daniel Chait, co-founder and CEO of Greenhouse, the hiring platform used by more than 7,000 companies. Daniel has spent more than 27 years as an entrepreneur and built Greenhouse from an idea VCs initially dismissed into a $100M+ ARR company. Now, hiring is being disrupted again. Candidates are using AI to apply to more jobs and make every resume look better. Companies are responding by using AI to filter thousands of increasingly similar applications. Daniel calls it the “AI doom loop.” And Greenhouse is betting that the answer to AI breaking hiring… might actually be better AI. In this masterclass, we break down: → The 25-customer test Greenhouse used to prove product-market fit → The fundraising hack that turned investor rejection into demand → Why Greenhouse cut 30% of its team during COVID — only for hypergrowth to return weeks later → How the company crossed $100M ARR and brought in TPG as a majority investor → Why AI has made hiring worse for both candidates and recruiters → Why resumes are becoming a worse signal for identifying great talent → Greenhouse’s acquisition of Ezra AI Labs and its bet on Voice AI interviews → Why Daniel believes every candidate could eventually get a first conversation → How AI could actually remove some of the most biased parts of traditional hiring → Why SaaS pricing is moving from seats, to usage, and eventually outcomes → Why founders shouldn’t hire a sales leader before figuring out how to sell → How to hire great executives for jobs you’ve never done yourself We also discuss startup hustle, acquisitions, surviving market cycles, the future of resumes, whether candidates will accept being interviewed by AI, and what the next generation of hiring software could look like. If you want to understand how AI is changing hiring — and how a $100M+ SaaS company is trying to reinvent itself before someone else does — this is the episode. TIMELINE: 00:45 – Building Greenhouse and why hiring was broken 03:41 – Getting rejected by VCs and ignoring startup hype cycles 06:34 – The fundraising hack that got investors to say yes 09:40 – The job fair hustle that gave Greenhouse its first insights 11:29 – The 25-customer product-market-fit test 13:14 – Cutting 30% during COVID — then hypergrowth came back 16:45 – Buy vs. build: how Greenhouse thinks about acquisitions 18:14 – Acquiring Ezra AI Labs and betting on Voice AI 20:21 – The “AI doom loop” breaking hiring 23:25 – Do we still need resumes and job applications? 25:35 – 3 bets made by Greenhouse 27:45 – Will candidates accept being interviewed by AI? 31:55 – From SaaS seats to usage and outcome-based pricing 33:55 – Bigger mistake : why founders hire sales leaders too early 35:45 – How to hire for a job you’ve never done yourself