Podcast Summary: How I AI — How Webflow’s CPO Built an AI Chief of Staff to Manage Her Calendar, Prep for Meetings, and Drive AI Adoption | Rachel Wolan

Host: Claire Vo
Guest: Rachel Wolan (CPO, Webflow)
Date: December 29, 2025
Duration: ~43 min

Episode Overview

In this episode, Claire Vo talks with Rachel Wolan, Chief Product Officer at Webflow, about her journey building a personal AI “Chief of Staff.” Rachel details the practical, hands-on ways she uses AI to manage her executive workflow, from calendar triage and meeting prep to team enablement and adoption of AI in her organization. The episode is packed with specific workflows, technical tips, personal anecdotes, and actionable strategies for any executive looking to operate as an “AI native” leader.

Key Discussion Points & Insights

1. The AI Native Executive: Rachel's Approach (02:27–05:09)

• While the industry often focuses on the “AI native PM/engineer,” there’s little on what it means to be an AI native executive. Rachel represents this new breed by not just using but building her own tools.
• Rachel shares her tech journey: learning to code at 16, taking a coding hiatus, then rekindling hands-on building with AI tools (e.g., Vibe coding, Claude code) for both personal and professional use.
• Quote:

  “I started coding when I was 16... when all the new app gen tools came out, it felt magical. Here we are a year later and now I’m sitting in Claude code all day... This is my daily driver.” (Rachel, 03:31–05:09)

2. Building the AI Chief of Staff: Personal Software for Productivity (06:40–10:11)

• Rachel iteratively built an AI assistant tailored for her "N of 1" needs, focusing on repeatable, high-impact workflows: calendar triage, meeting prep, and email management.
• Her process:
  • Multiple agent instances/terminals running Claude, each for specific contextual threads.
  • Ad-hoc, on-demand executive summaries and recommendations (e.g., prepping for this very podcast).
  • Emphasis on building ephemeral, hyper-customizable micro-apps.
• Quote:

  “You may never look at this Q4 roadmap after Q4 again… Software has become as accessible as documents if you lean into some of these tools.” (Claire, 07:22)

3. Calendar Triage and 'Brutal Truths' (10:11–18:57)

• Rachel uses her AI chief of staff to analyze her calendar, surface areas for improvement, and help with delegation.
• The AI doesn't just summarize—it calls out missed opportunities (like not spending enough time with customers) and advises on energy management, sometimes in a blunt, “mean” style at Rachel’s request.
• Triage includes:
  • Suggesting meetings to make async
  • Suggesting delegates
  • Drafting delegation messages
  • Providing a “brutal truth” about time allocation
• Quote:

  “You’re a CPO with no regular visible customer contact. Fatal flaw.” (AI Chief of Staff via Rachel, ~11:10)

• Quote:

  “Your chief of staff is very mean.”
  “I tell it to be mean to me. I want it to keep me in line.”
  (Claire/Rachel, 16:36–16:43)

Timestamps

• [10:11] — Morning triage workflow
• [11:22] — Technical setup: Google API tokens, permission scopes, guardrails
• [13:23] — Daily calendar review and finding delegation opportunities
• [16:32] — Custom note card UI and design delight

4. Practical Design and Technical Details (15:08–17:37)

• Custom, joyful UI for her apps: note card design inspired by Mark Andreessen’s “top priorities” system.
• Iterative design driven by personal happiness and efficiency, not corporate standards.
• Use of Markdown files to store knowledge, prep docs, and context snippets, allowing agents to reference and generate dynamic, context-aware outputs.

5. AI for Meeting and Social Prep (23:32–28:18)

• Rachel uses her AI to prep for CXO dinners:
  • Takes a screenshot of a guest list, uploads it, and has the AI cross-reference each name with LinkedIn and the web.
  • Generates quick profiles, suggests priority conversation partners and topics, and logs everything in a Markdown-powered “Dinner Research” tab.
• Markdown as a universal backend for both storage and easy retrieval across use cases.
• Quote:

  “What you can see is I’m like, can you add it to my dinner research tab? Everything that’s in Dinner research is actually a markdown file.” (Rachel, 26:02)

6. Building AI Fluency & Adoption Across Teams (29:56–36:10)

• Rachel leads by example to drive AI fluency and experimentation within Webflow.
• She runs organization-wide “Builder Days”—hackathon-style events for rapid prototyping, tool exploration, and cross-team learning.
  • Outcomes: 80+ prototypes, cross-discipline engagement (design, product, engineering, UX, analytics)
  • Success factors: hands-on building, prize incentives, leadership visibility, support channels, and both top-down and bottoms-up motivation.
• Quote:

  “I tell my team, ‘Hey, you can’t get into a meeting with me without a prototype.’ So there’s a mandate, but also a bottoms up.” (Rachel, 33:26)

• Quote:

  “People found it fun, empowering, motivating, and eye opening. I don’t think people understood what was possible... all these people, I call it getting blue pilled.” (Rachel, 36:09–36:28)

7. Practical Advice for Executives & Teams

• Hands-on building is now a “hard skill” for leaders.
• Running AI-powered personal software locally helps with security and customization, bypassing third-party cloud risks.
• Builder days can be a scalable, repeatable mechanism for AI adoption.
• Custom Markdown+agentic tooling can be a foundation for individual and team productivity.
• Quote:

  “This is the era of the hard skill. ... There is just no substitute for getting your hands on these tools.” (Claire, 38:10)

8. Is This a Product or Personal SaaS? (39:04–39:47)

• Personal software is hyper-specific, but there’s likely a product(s) or platform(s) based on these patterns in the future.
• Ecosystem will grow, but one-size-fits-all solutions have limits—extensions/customization will be essential.

9. Hiring, Evaluating, and Advancing AI Fluency (40:06–41:10)

• Rachel incorporates AI fluency into talent frameworks, rewrites career ladders to reward not just understanding but leading and pushing technical boundaries.
• Reinvention and adaptability are key executive/leadership skills in the age of AI.

10. Prompting Strategies for Agents (41:45–42:12)

• When prompts “don’t land”:
  • Clear history/context and try again
  • Use quantifiers: “Be 10x harsher” or “100x more detailed” to elicit better outputs
• Numbers and calibration in prompts work well with LLMs.
• Quote:

  “My prompting technique is... I’ll be like, be a hundred x more this thing that I want. Or, you know, be 10x.” (Rachel, 41:45)

• Quote:

  “These models like numbers… quantify it. Great tip.” (Claire, 42:12)

Notable Quotes & Memorable Moments

• Rachel, on brutal advice from her AI:

  “It’s very, like, dramatic. ... Fatal flaw. And I’m like, oh, gosh.” (11:10)

• Claire, on executive improvisation:

  “The number one skill you need as an executive is improv: you are just dropped into a wide variety of contexts. You need to be able to think on your toes.” (09:14)

• Rachel, on the joy of building:

  “There’s something really fun about actually getting to design again, but it does... make me really happy.” (15:50)

• Claire, summarizing the opportunity:

  “It’s never been more fun, and the possibilities have never been quite so unlimited.” (38:10)

Practical Takeaways

• Build for yourself first: Hyper-personal software maximizes productivity and joy.
• Use markdown as your source of truth: Portable, referenceable, agent-friendly.
• Delegate, triage, and prep with AI: Free your brain for higher-order work.
• Lead adoption by doing: Hands-on experimentation fosters trust and excitement.
• Run builder days: Structured, high-energy hackathons accelerate AI fluency.
• Iterate design for delight: Small bursts of UI delight matter in personal tools.
• Quantify your prompts: Use explicit numbers/emphasis cues with LLMs.
• AI fluency is strategic: Bake it into hiring, L&D, and promotional criteria.

Episode Timestamps

| Timestamp | Discussion Segment | |----------------|--------------------------------------------------------------------| | 00:00–05:09 | Rachel’s journey, AI native executive, hands-on coding | | 06:40–10:11 | Building & iterating AI chief of staff, personal app workflows | | 10:11–18:57 | Calendar triage, delegation, brutal-truth AI, technical setup | | 15:08–17:37 | Design details: UI delight, markdown, ephemeral apps | | 19:48–21:46 | Email triage and future agentic plans (Slack triage) | | 23:44–26:33 | Dinner prep agent: image parsing, research, markdown storage | | 28:18–29:56 | AI as learning platform, closeness to the codebase | | 31:03–36:28 | Team enablement: Builder Days, adoption curve, culture change | | 38:10–41:10 | Personal software vs SaaS, hiring for AI fluency | | 41:45–42:12 | Prompting tips: “Be 100x more...” |

Final Thoughts

This episode is a masterclass in becoming an “AI native” executive—hands-on, iterative, pragmatic, and unafraid to build bespoke tools for everyday advantage. Rachel’s example and Claire’s practical hosting provide a clear roadmap for executives looking to leverage AI for personal efficiency and organizational transformation.

Rachel Wolan:

• Twitter: @RachelWolan
• LinkedIn: /in/rachelwolan
• Webflow: webflow.com (check out Appgen)

Show resources:

• howiaipod.com

Key for speakers:
A = Claire Vo (host)
B = Rachel Wolan (guest)
C = Sponsor/Ad segments

[Ad slots & non-content sections omitted]