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Annie Pearl

Annie is currently Chief product officer at calendly before that she was Chief product officer at Glassdoor

1 episode · 2 sourced appearances

Appearances and evidence

Short attributed excerpts only. Timestamps are approximate.

Frameworks in these episodes

Episode-linked context, not an unsupported claim of authorship.

Productivity4 steps

Commit Only to Dates Within Your Control

Roadmap the phase, not the feature: Discovery, then Solutioning, then Build, then a ship date.

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Strategy4 steps

Competitive Wargaming

Assign each squad one competitor for a quarter, then pool the intel on a presentation day.

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Entrepreneurship5 steps

Four Paths Into Product Management

Two formal and two informal routes into PM — the informal ones convert most often.

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Sales4 steps

Match the Sales Hire to the Motion and the Buyer (PLG to SLG)

Layering sales onto PLG: hire growers for inbound and department-head buyers, not CIO hunters.

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Leadership4 steps

The OPPA — Leaderless Peer Review of Problems and Opportunities

A recurring PM-only forum to spar on problems and opportunities — with the CPO deliberately absent.

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Leadership5 steps

The Three-Phase OKR Maturity Ladder

No OKRs, then siloed team OKRs, then company OKRs with cross-org dependency mapping.

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Strategy4 steps

Three-Horizon Resource Allocation Shift

Express multi-year strategy as a yearly percentage split of resources across three horizons.

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Strategy5 steps

Where-to-Play Product Strategy as the Prioritization Engine

Turn an integrated set of strategic choices into the filter that decides every roadmap trade-off.

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