The first time I read a VP of Sales' 30-60-90 day plan, I approved it in about ten minutes. It had phases, milestones, a hiring timeline, everything a plan is supposed to have. By day 70 I realized I'd graded the formatting, not the substance, and the plan had nothing in it that would actually tell either of us if the hire was working.
That mistake is common, and it's not really the founder's fault. A well-written 30-60-90 plan reads like competence. Polished formatting, confident language, and a tidy structure will get past almost any first read. The problem is that the plan's job isn't to look complete, it's to give you a way to catch a bad hire in week six instead of quarter three.
Why the standard plan fails you
Most 30-60-90 templates are written for a VP joining a company with an existing sales motion to learn, not one they have to build from close to nothing. Generic templates emphasize "ramp up, meet the team, review the CRM." None of that tells you whether the person can actually generate pipeline, close a deal themselves, or diagnose why your last ten deals stalled. A plan can hit every generic milestone and still not prove the one thing you're paying for: whether this person can do the job at your stage, not a later one.
What to actually look for, phase by phase
Days 1-30: listening, with proof of listening. A vague plan says "shadow calls and meet the team." A real one names how many customer and prospect calls they'll sit in on (aim for at least 15-20), commits to a written summary of what they heard from your last five lost deals, and includes at least one live deal they're personally working by day 30, not just observing. If the plan has no deliverable you can read by day 30, you have no way to catch a slow start until it's already cost you a month.
Days 30-60: a specific point of view, not a strategy deck. By day 60, the plan should force them to commit to something falsifiable: a named ideal customer profile they'll prioritize, a specific change to the pitch or pricing conversation, or a hiring plan with a headcount number and a hire-by date. "Refine the go-to-market strategy" is not a milestone, it's a placeholder. Push for the actual sentence they'd write in the plan, and if they can't produce one in the interview, they won't produce one on day 60 either.
Days 60-90: a number, and who owns missing it. The plan needs an actual pipeline or revenue target for day 90, agreed with you before they start, not set by them alone once they're in the seat. If the plan avoids a number entirely, or the number is so soft neither of you could call it a miss, that's the plan protecting the hire instead of informing you.
The three red flags that matter more than the format
No named deals. If the entire 90 days is process, hiring, and dashboards with no mention of a specific deal they're personally trying to close, they're planning to manage a team you don't have yet instead of learning how your company actually sells right now.
No number they're accountable to. A plan with milestones but no day-90 target that could actually be missed isn't a plan, it's a narrative. You want something you can point back to in the quarterly review and say "we agreed to this."
Priorities that were never ranked against yours. The single most common reason a VP of Sales hire fails in year one isn't a skills gap, it's that the founder and the VP silently disagreed on what mattered most and never found out until the numbers were already off track. Before you sign off on the plan, force-rank your top five priorities for the role and have them do the same, independently, then compare lists. If they don't match, that conversation needs to happen before day one, not after day 70.
If the plan they hand you is vague
Don't rewrite it for them. Send it back with three specific questions: which deal are you personally closing by day 30, what number are you accountable to by day 90, and what would make you tell me by day 45 that the plan isn't working. How they respond tells you more than the original document did. A strong operator will tighten the plan in a day. Someone who pushes back on being pinned down at all is showing you, before you've paid them a dollar, how they'll handle accountability once they're running your revenue.
Frequently asked questions
Should the VP write the plan alone or with me?
They should draft it, but you should review and negotiate it together before their start date, not after. A plan approved unilaterally by either side tends to protect that side's interests when things go sideways.
What if they're still deciding between VP of Sales and Head of Sales titles?
The 30-60-90 evaluation works the same either way, but the title question itself comes down to a stage question, and it's worth settling before you finalize comp or the plan.
How specific should the day-90 number really be?
Specific enough that a third person reading it later could say clearly whether it was hit or missed. "Build momentum" fails that test. "$150k in new pipeline with two deals in late-stage" passes it.
What if they miss the day-90 number but the reasons seem legitimate?
A missed number with a clear, specific explanation and a revised plan is a very different signal than a missed number with a vague one. The plan's real value is giving you a baseline to tell those two situations apart.
A good 30-60-90 plan isn't a formality you approve on the way to onboarding, it's the first real test of whether this hire can operate at your stage. Reach out if you want a second read on a plan before you sign off on it.