Validated traits
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In October 2013, HubSpot's Chief Product Officer David Cancel asked me and Andy Cook to create "startup within a startup" after HubSpot acquired Andy's company, Rentabilities. He gave us just three guardrails: build something that helps small businesses do marketing make it free or cheap use orange in the logo. The rest was up to us. Over the next two years we built Leadin, a free lead-generation and CRM Wordpress plugin that tens of thousands of people came to genuinely love. I worked closely with an engineering team based in Dublin and it taught me product and design skills I couldn't have gotten anywhere else. Leadin was announced on stage in front of thousands of people at HubSpot's Inbound conference in 2015 by Dharmesh Shah, one of the founders. Leadin grew to over 100,000 plugin installs and eventually transitioned to become "HubSpot Marketing Free", HubSpot's first freemium marketing product. Leadin was the capstone of that HubSpot chapter that gave me th confidence to leave and co-found my own company, Tettra, in 2015.




Our AI Slack bot, Kai, had become a critical bottleneck in our sales process. We weren't closing any new customers because prospects testing the bot during trials were getting too many unanswered questions, prompting them to choose competitor tools instead. With customer conversions at a standstill, improving Kai's answer rate became an urgent priority. I worked closely with our sales team and prospects to identify exactly which questions weren't being answered. Through this investigation, I discovered the root cause: we had recently migrated our search infrastructure from Algolia to Typesense, and the new platform wasn't properly tuned for our AI bot's needs. I led the effort to heavily tweak the search configuration, refine the RAG (Retrieval-Augmented Generation) prompt, and optimize the prompt context to better serve our users' queries. The results were immediate and dramatic. Kai's answer rate more than doubled from approximately 30% to over 60%, and new customer conversions resumed. This work directly unblocked our sales pipeline and restored confidence in our product during the critical trial phase when prospects evaluate whether our solution meets their needs.
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Founder & CEO at Trove
CTO at Tettra
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