How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan

12/29/25
Source: Lenny’s Newsletter by Claire Vo. Read the original article

TL;DR Summary of How a CPO Built a Custom AI Chief-of-Staff App to Transform Executive Productivity

Rachel Wolan, Webflow’s Chief Product Officer, developed a custom AI chief-of-staff application to streamline her executive tasks like meeting prep, calendar audits, and email management. This AI tool provides real-time feedback and just-in-time information, significantly improving her productivity and decision-making. She also led company-wide initiatives to boost AI adoption by organizing “builder days” that empowered teams to embrace AI tools effectively. Wolan’s hands-on approach highlights the importance of executives leading AI integration to drive authentic organizational change.

Optimixed’s Overview: Transforming Executive Efficiency with Custom AI Tools and Leadership

Introduction to Personalized AI for Executive Management

Rachel Wolan, a seasoned coder and Chief Product Officer at Webflow, has leveraged her technical skills to build a personalized AI assistant that functions as her chief of staff. This custom application integrates with her calendar, email, and other workflows, helping her manage the complexities of an executive role more efficiently.

Core Features and Benefits of the AI Chief-of-Staff

  • Meeting Preparation: The AI app gathers and organizes relevant information to ensure Wolan is fully prepped ahead of podcasts, dinners, and business meetings.
  • Calendar Auditing: It triages and analyzes her schedule to optimize time allocation and identify productivity bottlenecks.
  • Email Management: Automated workflows help prioritize and manage incoming emails, reducing cognitive load and response time.
  • Honest Feedback: The AI provides candid insights into how Wolan spends her time, facilitating continuous personal and professional improvement.

Driving Organizational AI Adoption

Beyond personal productivity, Wolan champions AI adoption throughout Webflow by organizing “builder days,” events designed to familiarize teams with AI tools hands-on. This initiative has led to a dramatic increase in AI integration across the organization, underscoring the importance of executive leadership in digital transformation efforts.

Technical Approach and Executive Insights

The AI system is built using markdown files, API tokens, and multiple large language model interfaces, showcasing how executives can personally engage with AI development to better understand capabilities and limitations. Wolan’s approach exemplifies how leaders can blend technical expertise with strategic vision to harness AI’s full potential.