PracticeProduct Judgment

decideDifficulty 3/3~15 min

Two roadmap bets, one team

The artifact

Context: You run product at Kelvin, a 14-person B2B analytics company. One engineering team is free next quarter. Two proposals are competing for it. Both were written by their sponsors. A third document — this quarter's cohort retention chart — is attached because you asked for it.


Proposal A — Salesforce integration

Sponsor: Diego (Sales)

Three accounts have asked for a native Salesforce integration in the last six weeks: Halverson Group (renewal March, $84k ARR), Northline (in procurement, $60k proposed), and Bexley Analytics (expansion conversation, currently $31k). Halverson's champion has said in writing that the integration is "a significant factor" in the renewal conversation. Northline's technical evaluation lists it as a requirement.

Scope estimate from engineering: one team, most of a quarter, with a two-week tail for the OAuth review.

If we ship it, we protect $84k, materially improve the odds on $60k, and open a credible expansion path at Bexley. Sales believes it also unblocks a segment we currently disqualify ourselves from — we've passed on four RFPs this year that required it.

This is the lowest-risk revenue work available to us next quarter.


Proposal B — Rebuild activation

Sponsor: Maya (Product)

New workspaces currently require a user to connect a data source, define at least one metric, and invite a teammate before anything in the product does something useful. We know from session data that a large share of new workspaces never complete all three.

The proposal is to rebuild the first-run experience: sample data pre-loaded, one starter metric generated automatically, and the teammate invite moved out of the critical path.

Scope estimate: one team, roughly a quarter.

Expected impact is harder to attribute than Proposal A. Maya's argument is that activation compounds — every cohort from here forward is affected, and the current experience is a tax on every dollar of acquisition spend we make. She notes she cannot promise a number.


Attachment — Cohort retention, last four cohorts

Percentage of workspaces from each signup cohort still active at week N:

CohortW1W2W4W8W12
March100%61%38%19%11%
April100%58%35%17%9%
May100%63%40%21%12%
June100%60%36%18%

Monthly new workspaces have grown from 190 (March) to 340 (June). Paid acquisition spend over the same period rose from $9k to $22k per month.


Your task

Decide: which proposal gets the team next quarter? Commit to one, and defend it. Say explicitly what your choice costs and how you'd handle the consequences of not choosing the other. Aim for 300–500 words.

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