“Jessica, thank you so much for being here. Welcome to the podcast.”
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Jessica Fain
Today my guest is Jessica Feain who's been a product leader at Box and Slack and Brightitewheel and now at Webflow
1 episode · 1 sourced appearance
Appearances and evidence
Short attributed excerpts only. Timestamps are approximate.
Frameworks in these episodes
Episode-linked context, not an unsupported claim of authorship.
Influence4 steps
Anchor the Pitch to the Exec's Incentives
Find the metric, OKR, or board pressure they own, then show how your idea moves it.
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Leadership3 steps
Follow the Breadcrumbs and Calibrate Urgency
Act fast on an exec's subtle hints, but ask how strongly they actually feel first.
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Influence3 steps
Shrink the Change to Build Trust
De-risk a scary idea into a two-week experiment with a fixed check-in date.
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Communication3 steps
Stewart Plus Two More
Never bring one option; show a Goldilocks three and hold the rest in the appendix.
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Communication4 steps
The 60-Second Meeting Reset
Buy a context-starved exec 30 seconds of orientation before you pitch.
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Communication3 steps
Themes for Discussion at the Top of the Doc
Bubble up the spiciest 3 topics live; answer the hundred nitpicks offline.
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Influence4 steps
Treat the Executive as Your Key User
Run stakeholder conversations as discovery interviews, not approval requests.
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Resources in their episodes
- A History of Burning
- Airbnb
- Amazon
- Apple Podcasts
- Atlassian
- Box
- Calendly
- Claude
- Codex
- Figma
- Gemini
- Glassdoor
- Google Calendar
- GPT
- Homegoing
- Kasa
- Lenny's Newsletter
- Lenny's Podcast
- Loom
- Lovable
- Microsoft
- Minto Pyramid Principle
- Omni
- Pachinko
- Salesforce
- Slack
- Slackbot
- Spotify
- Stripe
- Switch
- The Greek Theatre at UC Berkeley
- The Overstory
- The Pitt
- Vanta
- Webflow
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