The GTM due diligence checklist.

Not all ARR is equal. The first job is to find out how much of the revenue is durable, contracted, and diversified - and how much is a handful of accounts on legacy terms.

FROM THE DATA ROOM · revenue by account by month (three years), the contract register with renewal dates, price book history.

RED FLAG · top accounts renewing within months of close, on terms the deck itself calls legacy.

Retention metrics are the most massaged numbers in any deck. The test is whether they can be reproduced from raw billing data, and whether churn has been studied or just counted.

FROM THE DATA ROOM · the churned-account register (reason, tenure, last billed value), cohort retention by start quarter, the stated NRR and GRR methodology.

RED FLAG · retention numbers that nobody currently employed can regenerate from the raw data.

Expansion revenue flatters growth. The thesis usually depends on winning strangers - so the diligence question is whether the machine that wins strangers actually exists.

FROM THE DATA ROOM · new logos by year with attribution evidence, the win and loss log, bookings by rep.

RED FLAG · a growth story carried by expansion while the new-logo count is flat or falling.

Pipeline is the number most likely to be quoted and least likely to be scrubbed. Businesses are routinely healthier or sicker than their own CRM says - the point is finding out which.

FROM THE DATA ROOM · a full opportunity extract with stage history and timestamps, forecast versus actual for the last eight quarters.

RED FLAG · a pipeline that has never been scrubbed - the truth could be good or bad, but the forecast inherits the mess either way.

Deal narratives are written by the winners of internal arguments. The raw record - who was beaten, by whom, and why - is where the actual competitive position lives.

FROM THE DATA ROOM · raw win and loss records, deal reviews for the largest recent wins and losses.

RED FLAG · every loss explained as price - the explanation that means nobody asked.

A market slide is a claim about strangers. Diligence replaces it with named accounts, observable buying signals, and whitespace that is measurable inside the existing base.

FROM THE DATA ROOM · the TAM build with its assumptions, a target-account list with signal evidence, product usage by module across the base.

RED FLAG · a market model that never names an account.

The question is not who appears on the landscape slide. It is who takes deals, who loses them, and whether the threat is a feature gap or a structural squeeze.

FROM THE DATA ROOM · the deal log with competitor fields populated, churn destinations, pricing versus alternatives.

RED FLAG · a competitor matrix in which the company wins every row.

Marketing is where deck and reality diverge fastest: tools quietly discontinued, campaigns paused, attribution fields at war with each other. The engine must be inspected running.

FROM THE DATA ROOM · channel spend and sourced pipeline by month, working analytics access rather than screenshots, a martech inventory with live status.

RED FLAG · attribution fields that are empty or contradict each other across systems - nobody knows what works.

Strategy is what the compensation plan pays for - everything else is a slide. The org chart question is whether the team described in the deck exists, ramped, and aligned.

FROM THE DATA ROOM · compensation plans, the org roster with roles and tenure, bookings by rep, key-person dependency map.

RED FLAG · a comp plan that rewards renewals while the investment case depends on new logos.

Every number in this checklist flows through the systems. If the systems are untrusted, every answer above is provisional - which is why this dimension gets tested first in practice.

FROM THE DATA ROOM · CRM admin access or a full extract, field history on source and stage, the exact reports leadership uses.

RED FLAG · metrics in the deck that cannot be regenerated by anyone still at the company.