[Portfolio Demo]Tilberry Society is a fictional community created byUpstate Web Co.— member counts, monthly fees, revenue figures, and quotes are illustrative.

The journal

Selected entries
from the archive.

A curated journal of past dinners + virtual panels + retreat sessions. Visitors read the summary; members read the full transcript. 184 recorded events across 5 years; this page surfaces the ones the founders return to.

XLII 2026-04-12 · New York

On Saying No to a Promotion

Hosted by A VP of Product at a public marketplace · Career stewardship at Director-to-VP transition

A dinner conversation about the calculus of declining a promotion that would have moved the host out of product and into a general-management role. Members discussed the long arc of staying in craft versus stepping into power.

Members: full transcript (12,400 words) Read transcript →
XLI 2026-03-29 · San Francisco

The Quiet Reorg

Hosted by A Director of Product at a Series-D fintech · Surviving (and shaping) silent restructuring

A conversation about reorgs that arrive as fait accompli — the host had walked through three in two years. Members shared the language they had used to advocate for product priorities while the org chart was still being drawn.

Members: full transcript (9,800 words) Read transcript →
XL 2026-03-15 · London

On Being the Only

Hosted by A Senior Director at a B2B SaaS at $150M ARR · The structural loneliness of being the only senior woman in the room

A panel on the experience of being the only senior woman in a leadership cabinet. Members debated whether the loneliness was a feature of progress (we are early) or a bug of structure (we are perpetually starting over).

Members: full transcript (14,600 words) Read transcript →
XXXIX 2026-02-22 · Berlin

When the IC Track Disappears

Hosted by A staff PM who declined VP for the third time · Maintaining individual-contributor depth at the senior level

A conversation about the disappearing IC track in product organizations. Members shared concrete language for negotiating staff-PM scope without ending up in management by attrition.

Members: full transcript (11,200 words) Read transcript →
XXXVIII 2026-02-08 · New York

On Leaving

Hosted by A founder who exited · The first six months after a founder departure

A conversation about the strange middle period after leaving a company you founded — too senior to take a senior role, too restless to take time off. Members compared the months between roles.

Members: full transcript (13,100 words) Read transcript →
XXXVII 2026-01-25 · San Francisco

Compensation in a Down Year

Hosted by A VP who took a flat year · Negotiating in markets that have moved against you

Members discussed the data they had each been working with privately — comp adjustments, refresh cycles, the calculus of stay-versus-go in a year when most companies were paying flat. The conversation was unusually direct on numbers.

Members: full transcript (10,500 words) Read transcript →

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