Playbook · Operating

How to write a 90-day plan for a VP Sales

A new VP Sales who arrives without a written 90-day plan is operating on instinct. A new VP Sales who arrives with one written by the CEO is operating to someone else's brief. The right answer is a co-authored plan, drafted in week minus one and reviewed weekly.

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Audience

Sales leader, Founder / CEO, Revenue leader

Time on task

Ninety days

Context

Written by Rich Evans from advisory work with founder-led businesses replacing or installing senior commercial leaders. The first ninety days set the operating cadence for the next two years; treat them as the highest-leverage moment in the relationship.

Before you start

▸Signed VP Sales scorecard with twelve-month outcomes
▸Current sales org chart, comp plans and quota assignments
▸Last four quarters of pipeline, win rate and cycle-time data
▸Named CEO, CFO and CRO sponsors who will hold weekly one-to-ones with the new hire

What you will have at the end

▸A written 30-60-90 plan signed by the VP Sales and the CEO before day one
▸A weekly one-to-one cadence with the CEO for the first ninety days
▸A diagnostic memo at day thirty, a set of decisions at day sixty and the first executed change at day ninety
▸A revised twelve-month commercial plan ready to present at the day-ninety board review

Jump to a step (6)+

01Week minus one: co-author the plan
02Days one to ten: install the operating cadence
03Days one to thirty: diagnose, do not decide
04Days thirty to sixty: decide and communicate
05Days sixty to ninety: execute the first change
06Day ninety: present the revised twelve-month plan

The steps.

Step 01Two hours in week minus one · CEO with new hire

Week minus one: co-author the plan

Draft the 30-60-90 plan with the new hire one week before they start. The hire owns the draft; the CEO owns the sign-off. Both names appear at the top of the document.

Checklist

☐Schedule a two-hour co-authoring session in week minus one.
☐Use a one-page template: thirty days diagnose, sixty days decide, ninety days execute.
☐Name the three to five outcomes the hire owns by day ninety.
☐File the plan in a place both the hire and the CEO can edit.

Failure mode this step prevents

Letting the hire build the plan in their first month. They lose thirty days of operating time and arrive at day sixty without a baseline.

Step 02First two weeks · VP Sales

Days one to ten: install the operating cadence

Before any change is announced, install the cadence. Weekly one-to-ones with each direct report, weekly forecast call, weekly leadership scorecard review. The cadence is the chassis on which everything else hangs.

Checklist

☐Book recurring one-to-ones with each direct report for the next twelve weeks.
☐Adopt or replace the existing forecast call format in week one, not week six.
☐Confirm the day, time and attendees of the weekly leadership scorecard review.
☐Publish the cadence calendar to the wider commercial team in week two.

Failure mode this step prevents

Skipping the cadence because there is too much to diagnose. The cadence is the diagnostic.

Step 03Days one to thirty · VP Sales

Days one to thirty: diagnose, do not decide

The first thirty days are for diagnosis, not change. Talk to every direct report, every customer-facing function leader, the top ten customers and the top five lost prospects. Take notes in writing. Resist the temptation to fix anything visible in the first month.

Checklist

☐Schedule fifteen to twenty diagnostic conversations across the business.
☐Write a structured memo at day thirty: what works, what does not, what is unclear.
☐Share the memo with the CEO and with the direct reports it concerns.
☐Resist any change to comp, structure or process before day thirty.

Failure mode this step prevents

Announcing a restructure in week three. The team loses trust in the new leader before they have earned the right to act.

Step 04Days thirty to sixty · VP Sales with CEO

Days thirty to sixty: decide and communicate

On the back of the day-thirty memo, make and communicate the three to five decisions that matter. Comp adjustments, structural changes, hiring priorities, process changes. Decisions land before execution begins.

Checklist

☐Convert the day-thirty diagnostic memo into a day-sixty decisions memo.
☐Walk the decisions through the CEO, CFO and direct reports before announcement.
☐Communicate decisions to the wider commercial team in a single all-hands.
☐Publish the decisions in writing and revisit them at every weekly one-to-one.

Failure mode this step prevents

Making decisions in private and executing them by stealth. The team finds out from the comp run rather than from the leader.

Step 05Days sixty to ninety · VP Sales

Days sixty to ninety: execute the first change

Pick one structural change and execute it cleanly by day ninety. Not three changes, one. The first executed change is what the team will remember at year-end.

Checklist

☐Choose one change with visible impact: comp restructure, segment rebalance, leadership hire.
☐Sequence the execution week by week with named owners.
☐Track impact against the scorecard from day sixty-one.
☐Hold a day-ninety review with the CEO against the original scorecard outcomes.

Failure mode this step prevents

Trying to execute four changes in parallel. None lands cleanly and the team disengages.

Step 06Days seventy-five to ninety · VP Sales with CEO and CFO

Day ninety: present the revised twelve-month plan

The day-ninety milestone is the revised twelve-month commercial plan presented to the board or leadership team. It supersedes any plan written before the new hire arrived and is the document the next nine months are run against.

Checklist

☐Draft the revised twelve-month plan in week eleven.
☐Walk it through the CEO, CFO and chair before the board meeting.
☐Present the plan at the day-ninety review with capacity model, comp model and hiring sequence attached.
☐Confirm that the next quarterly review is booked.

Failure mode this step prevents

Letting the day-ninety milestone slide. Without it, the cadence drifts and the year never gets reset.

Common questions.

Should the CEO write the 90-day plan or should the new hire?

Co-author. The hire owns the draft; the CEO owns the sign-off. A plan written entirely by either party loses the other party's commitment.

What is the single biggest 90-day plan failure mode?

Skipping the diagnostic phase and announcing a restructure in week three. It happens because the new leader is under pressure to look decisive; it almost always backfires.

How does this plan differ for a CRO versus a VP Sales?

The structure is the same. The CRO version adds a board-level workstream and typically a comp redesign by day sixty. The VP Sales version stays focused on the sales function only.

What if the business cannot wait thirty days for diagnosis?

It can. A new senior commercial leader making decisions in week three on incomplete information is the most common cause of failed senior commercial hires inside the first year.

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