Socrates.AI
An AI-powered chatbot SaaS product for the HR/Benefits & Employee Engagement space.
HR AI for the Enterprise
While at Espressive, I was asked by a VC on our board — who was impressed with the work I had done — to lead design for a similar company in their portfolio: Socrates.AI. Socrates had a similar chatbot interface, but on the HR and Benefits side of the enterprise.
My Role as Head of Design
- Product management: waterfall to agile — bringing Socrates to customers
- Branding and naming
- Chatbot personality development
- Website and messaging (v1, v2)
- Sales and board decks
- Mentorship and people management
- Board management & reporting
What happened: I came in through the board after Espressive, into a company with a strong engine and a story nobody outside could follow. I rewrote the value proposition with the sales team, redesigned the website around it, and shipped a run of improvements to the core product that customers noticed and said so. The company was later merged into Simppler (2023). The lesson I took from it is in most of my work since: an enterprise AI product is a trust problem before it’s a UI problem, and the design job is deciding what the person sees when the system is doing something on their behalf.