Calendly AI Platform & Chat

Building Calendly's foundational AI platform and conversational assistant.

Staff Product Designer + Interim Product Manager

Role

Initial tiger team of 3 Engineers + cross-functional partners

Team

MY ROLE

Leading product & design from strategy through Beta

I led the AI tiger team's product and design work, including PRDs and roadmap planning, research and testing, interaction and content design, resourcing, and cross-team coordination.

OPPORTUNITY

Connecting fragmented meeting workflows

Our primary users—busy solopreneurs and small business owners—were using 3–4 tools across scheduling, CRM, meeting notes, and AI to manage their client relationships. The result was constant context switching, fragmented workflows, and missed follow-ups.

EXISTING EXPERIENCE

AI Notetaker was valuable, but limited to individual meetings

Users were already finding value in Calendly's AI Notetaker, but they couldn't search across multiple meeting transcripts or take action directly from their recaps.

This pointed to a broader opportunity: make Calendly's meeting context useful across the entire relationship, not just one meeting at a time.

RESEARCH

Mapping the highest-value AI use cases

Using customer research and feedback, I mapped needs across the meeting lifecycle to focus the MVP on three areas: preparing for meetings, acting on follow-ups, and understanding patterns across the business.

STRATEGY

Building a shared AI platform

I pI partnered with engineering to scope a reusable AI platform that combined Calendly data, model reasoning and guardrails, and agentic tools—with AI Chat as its first user-facing experience.

The MVP prioritized scheduling, meetings, recaps, and contacts, with actions for sending email and creating or updating meetings and contacts.

PROOF OF CONCEPT

Testing the core experience in 60 days

The first working prototype let users ask questions across their Calendly context so we could test whether the concept was useful before investing further.