Your First 90 Days as VP Sales — What to Audit, What to Fix, What to Leave Alone

A VP Sales who starts a new role and announces changes in the first week is usually destroying value, not creating it. The instinct is understandable: there is organisational pressure to demonstrate decisiveness, and the problems that prompted the hire are often visible and urgent. But changes made before the new leader understands why the current system works the way it does — including why things that look broken are actually functioning — frequently create new problems while solving old ones incompletely.

The more productive framing for the first 90 days is diagnostic rather than prescriptive. The goal is not to implement your playbook. It is to understand the org well enough that your playbook, when you do implement it, is calibrated to the actual situation rather than the situation you assumed you were walking into. These are rarely the same thing.

The Five Audits That Matter Most

Pipeline quality. Before you can forecast anything, you need to know what is actually in the pipeline and what it is worth. Pull all open opportunities and look at three things: when the close date was last updated, how many times each deal's close date has been pushed, and the date of the last substantive two-way interaction with the prospect. Deals where the close date has been pushed more than twice without a documented reason, and deals with no two-way prospect engagement in the last 14 days, are not pipeline — they are noise. The real pipeline number is almost always smaller than the reported one. You need to know by how much before you can make any credible commitment to leadership.

CRM configuration and data quality. Log into the CRM and look at it the way a rep does, not the way a manager does. What does a rep see when they open an opportunity record? What fields are required? What automation fires on stage changes? Which fields are routinely left empty? The gap between how the CRM was configured and how reps actually use it tells you everything about whether the current configuration serves the team or serves reporting requirements. Both can be true, but often they are in tension — and that tension is where adoption problems come from.

Forecast methodology. Ask whoever assembles the current forecast to walk you through the process in detail. How are deals included or excluded? What is the definition of commit versus best case? How is confidence assigned? Is there a structured data layer underneath the qualitative judgements, or is the process primarily rep narrative plus manager intuition? Most forecast processes are significantly more subjective than they appear. Understanding how much subjectivity is built in tells you how much you can rely on the current number — and how quickly you can improve it.

Playbook existence and adoption. Does a sales playbook exist? If so, where does it live, when was it last updated, and what percentage of reps know what it says? The honest answer to the last question — get it from reps, not from enablement — tells you whether the playbook is a real operating document or a filing artefact. If reps don't know what the playbook says, it does not exist in any operationally meaningful sense, regardless of what lives in the Notion page.

Rep capacity versus quota. Take each rep's current pipeline and project it forward using the win rate you calculated from the pipeline quality audit. How many reps are realistically on track to hit quota given their current pipeline? A rep with $300K in pipeline and a 20% win rate against a $100K quota is not on track — they need $500K minimum to have a realistic shot. Running this calculation for every rep tells you where the quarter is going before the quarter is over. It also tells you which reps need additional pipeline urgently, which ones need deal support, and which ones may have been carrying quota that was set without reference to their actual capacity.

What to Leave Alone — For Now

There is a category of things in a sales org that look like problems but are actually load-bearing structures — they exist because someone solved a problem with them, and removing them creates a different problem. Commission structures fall into this category. So does the way meetings are run, how deals are reviewed, and often how the CRM is configured. These things may need to change eventually. They should not change in the first 90 days without a very clear understanding of what they were solving for and what happens when they are gone.

The rule of thumb is: if you cannot articulate why the current system was built the way it was and what specific failure mode it was preventing, you should not change it yet. Ask instead. The person who built the commission structure, or configured the CRM in the way it is, or runs the pipeline review the way they do, usually has a reason. It may be a bad reason. But knowing whether it is a bad reason or a good one requires asking the question.

The Diagnostic Document — Your Most Valuable First-90-Days Output

The most useful thing a new VP Sales can produce in their first 90 days is not a new strategy document. It is a diagnostic that records what is actually true about the sales organisation they inherited — what the real pipeline number is (not the reported one), what the real win rate is (calculated consistently), how the forecast is actually built, which playbook steps are being followed and which are not, and where rep capacity and quota are out of alignment.

This document serves two purposes. First, it gives you a factual baseline from which to measure progress. Changes you make in months 4 through 12 will only be attributable to you if you know what the numbers were before you arrived. Second, it gives you the credibility to propose changes with specificity. "Our pipeline close rate from stage 2 is 19%, which implies we need 5.3x coverage — we are currently at 2.8x" is a much more persuasive basis for requesting additional resources than "I think we need more pipeline."