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Wolan crafted an AI chief of staff using NLP and ML, automating tasks like calendar management and meeting prep to streamline her workflow and boost AI adoption at Webflow.
Webflow's Chief Product Officer, Rachel Wolan, has taken a unique approach to integrating artificial intelligence (AI) into her daily work. In a recent episode of the "How I AI" podcast, she detailed how she built an AI chief of staff to manage her calendar, prep for meetings, and drive internal AI adoption within Webflow.
Rachel's AI chief of staff is a custom-built solution that leverages natural language processing (NLP) and machine learning (ML) models. Here’s a breakdown of the key components:
Building personal AI software is a powerful way for executives to grasp the potential of AI. According to Rachel, the most significant outcome from these efforts has been the "eye-opening" experience for participants. She describes this as being "blue-pilled," where individuals suddenly realize the vast possibilities AI can offer.
Rachel emphasizes the importance of "builder days" in driving organizational adoption of AI. These are dedicated sessions where employees experiment with building their own AI tools, fostering a hands-on understanding and enthusiasm for AI technologies.

To build her AI chief of staff, Rachel used a combination of pre-trained models and custom training on internal data. Here are some implementation notes:
Rachel is exploring ways to scale this approach across Webflow, with a focus on:
Rachel Wolan's initiative at Webflow demonstrates the practical benefits of personal AI software. By building an AI chief of staff, she has not only improved her own workflow but also inspired a broader adoption of AI within the organization. This approach serves as a valuable model for other companies looking to leverage AI for greater efficiency and innovation.
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About the author
Kai built ML infrastructure at a Bay Area startup before developing an obsession with transformer architectures and inference optimisation that eventually pulled him out of product work entirely. A stint at a compute research lab sharpened his instinct for what actually matters in a model release versus what is marketing. He writes from the inside — from the perspective of someone who has debugged the systems he is describing at three in the morning. He is allergic to hype and instinctively drawn to the unglamorous plumbing questions that everyone else skips over.
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2 January 2026
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