gainsight
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Josh Schachter and the value of getting the wrong email
A mistaken message led to a $10,000 investment. The UpdateAI founder’s career has often advanced the same way: by paying attention to people before deciding what to build.
AI Is Splitting the Customer Success Stack
New systems can read customer risk in hours. Established platforms can turn that signal into governed work, but buyers still have to prove either approach changes retention, adoption and the cost of serving a portfolio.
Your Support Queue Knows Who Will Churn
The Gainsight-Zendesk integration turns everyday support activity into shared context for customer success. Its real promise is not another dashboard, but a faster route from a warning signal to a human response.
You Don't Own the Community You Built
Skool, Circle, Discourse, Gainsight, Salesforce and Gravyty are all selling the same thing - a place for your people to gather. The difference is who keeps the keys.
UpdateAI
The AI notetaker that turned every customer call into a searchable, actionable record - and quietly became the brain behind Gainsight's push into agentic AI.
The Land Grab for Communities the Algorithm Can't Touch
Zapnito, Almabase, Disciple, XenForo, Gainsight and CMNTY are quietly selling brands a way to own their audience instead of renting it from a feed. Here is how one market splits into six very different bets.
Totango vs Hook and the Rewiring of Customer Success
Two companies are betting on opposite futures for customer success software - one consolidating the old dashboard playbook, the other handing the work to AI agents. Here is what the split says about where retention revenue is headed.
UpdateAI Beat Gong, Then Gainsight Bought It
The post-sales notetaker that customer success managers swore by went head-to-head with the giants, won a loyal following, and got absorbed into Gainsight's AI push in July 2025. Here is how a discovery interview turned into an acquisition.
UpdateAI Listened to Every Customer Call, Then Gainsight Bought It
The conversational-intelligence startup spent five years turning customer meetings into signal for post-sales teams. In July 2025 Gainsight acquired it to power Atlas, its agentic-AI bet, and put founder Josh Schachter in charge.
Cast.app
Automate your Customer Success. Drive onboarding, usage, & adoption. Minimize account & revenue churn. Influence renewals & revenue expansion. Stream referrals from promoters. Scale without scaling teams.
Barr Moses
Barr Moses is the co-founder and CEO of Monte Carlo, the company that created the data observability category and built one of the first end-to-end platforms for catching what she named 'data downtime' - the stretches when data is wrong, missing, or simply not trustworthy. A Stanford-trained mathematician and former Israeli Air Force intelligence data unit commander, she went from Bain consulting and a VP role at Gainsight to building a data reliability company valued at $1.6 billion. She co-authored O'Reilly's 'Data Quality Fundamentals' and is one of the most cited voices on why enterprises should treat broken data like broken software.
Spencer Applegate
Spencer Applegate is a technology operator and investor who built three software companies before becoming Vice President of Strategy & Business Operations and Chief of Staff to the CEO at Gainsight, the leading customer success platform. With a foundation in nuclear engineering from Georgia Tech and an MBA from Harvard Business School, he has moved fluidly between founding startups (Verusen, REscour, PainTheory), deploying capital at growth and buyout funds (M33 Growth, Pacific Lake Partners, Vector Capital), and now running strategy at a $1.25B enterprise SaaS company in San Francisco.
Nick Bonfiglio
Nick Bonfiglio is the CEO and Co-Founder of Syncari, a platform pioneering Agentic Master Data Management for enterprise AI initiatives. With 28+ years in enterprise software, he shaped product strategy at Marketo (acquired by Adobe) as EVP of Global Product, co-founded Aptrinsic (acquired by Gainsight as Gainsight PX), and now leads Syncari through a $45M total funding journey to help Fortune 1000 companies build trusted, AI-ready data foundations. A co-author of 'Mastering Product Experience in SaaS,' Nick has been a driving force behind emerging enterprise disciplines like RevOps, Marketing Ops, and Customer Success Ops.
Nick Mehta
Nick Mehta co-founded Gainsight in 2013 and spent 13 years as CEO building the defining customer success platform - growing it from a startup into a $1.1 billion unicorn acquired by Vista Equity Partners, and in the process creating an entirely new job category of Customer Success Manager now held by hundreds of thousands of professionals worldwide. A Harvard-educated biochemist turned serial entrepreneur with a penchant for Taylor Swift parody rap videos, he stepped down as CEO in August 2025 to make way for his hand-picked successor while continuing on the board.