Bio
VP of Product at Webflow. Former chief of staff to two consecutive Slack CPOs and product leader at Brightwheel. Public reference voice for upward influence as a discipline distinct from politics — discovery-mode pitching, killing things to build trust, and treating agents like junior colleagues.
Operating themes
- Influence is discovery, not conviction. Treat exec conversations as discovery interviews.
- Kill things to build trust. The senior move is showing what you killed and why.
- Shrink the change. Pitch a 2-week experiment, not a 12-month commitment.
- Agents are junior colleagues. Onboard them with explicit context and philosophy.
Cards
- Treat upward influence as a discovery interview, not a sales pitch — Stakeholder conversations are discovery interviews; the pitch follows [Tier A]
- Killing your own initiatives loudly is the highest-trust move with executives — Loud kills earn the runway for the next bet [Tier A]
Sources captured
- 2026-04-28 — Lenny's Podcast, "How to influence executives (and why it's not politics)" (
raw/podcasts/jessica-fain--influencing-executives--2026-04-28.md)