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

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

How I AI · Dec 29, 2025

Webflow's CPO showcases her personal AI Chief of Staff and reveals her playbook for driving organizational AI adoption through "Builder Days."

"Vibe Coding" with AI Rekindles Executives' Passion for Hands-On Building

AI-assisted development, or "vibe coding," is re-engaging executives who coded earlier in their careers. It removes the time-consuming friction of going from idea to MVP, allowing them to quickly build personal tools and reconnect with the craft of software creation, even with demanding schedules.

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

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

How I AI·2 months ago

Use Vision Models on Guest List Screenshots for Automated Dinner Prep

For rapid meeting preparation, simply screenshot the guest list and input it into a vision-enabled AI model. The AI performs OCR to extract names, then triggers an agent to automatically search the web and LinkedIn for each attendee, generating a comprehensive prep document with minimal manual effort.

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

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

How I AI·2 months ago

Webflow's CPO Built a Personal "AI Chief of Staff" to Manage Her Workflow

An executive created a custom AI agent to handle repetitive tasks like meeting prep, calendar triage, and email. This "chief of staff" provides analysis, suggests delegations, and even offers blunt feedback, demonstrating how AI can be personalized to augment executive functions.

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

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

How I AI·2 months ago

Use Markdown Files as a Simple "Database" for Personal AI Applications

Instead of a complex database, store content for personal AI tools as simple Markdown files within the code repository. This makes information, like research notes, easily renderable in a web UI and directly accessible by AI agents for queries, simplifying development and data management for N-of-1 applications.

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

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

How I AI·2 months ago

Embed AI Fluency into Your Team's Career Ladder to Formalize Expectations

To ensure AI adoption is a core competency, formally integrate it into your team's operating system. Webflow is redoing its career ladder to make AI fluency a requirement for advancement, expecting team members not just to use tools but to lead, own, and push the boundaries of AI in their work.

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

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

How I AI·2 months ago

Use Numerical Multipliers like "100x More" in Prompts to Escalate AI Responses

To correct an AI's output when it's off track, use numerical multipliers to signal a dramatic shift. Instead of vague feedback, prompts like "be 100x more direct" or "make this 10x more creative" give the model a quantitative instruction to escalate its response, leading to more significant adjustments.

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

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

How I AI·2 months ago

Webflow Drives AI Adoption with "Builder Days" That Mix Mandates and Support

Webflow accelerates AI tool adoption using company-wide "Builder Days." This combines a top-down executive mandate (e.g., "no meetings without a prototype") with bottoms-up enablement, including tool access, support channels, and prizes. The goal is to move the entire organization up the adoption curve, not just early adopters.

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

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

How I AI·2 months ago

Program Your Personal AI Agent to Be "Mean" for Unfiltered, Brutal Feedback

To get truly honest feedback, Webflow's CPO programmed her AI chief of staff to be "mean." The AI delivers a "brutal truth" section, criticizing her for spending time on tasks below her role. This demonstrates how AI can serve as an unflinching accountability partner, providing feedback humans might hesitate to give.

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

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

How I AI·2 months ago