Before You Start as a VP — Please, Please, Please. Do a 60-Day Plan. And Make Sure the CEO Agrees With It.


I’ve now worked with or invested in ~30 successful start-ups beyond my own companies and I’ve watched a lot of VP hire train wrecks.

Probably the most common is “the wrong VP of Sales”.  We’ve talked about that for 6+ years on SaaStr, and we’ll keep talking about it.  Hiring someone for the wrong stage, wrong ACV/deal size, or a VP of Sales that is a a stretch too far.

The 48 Types of VP Sales. Make Deadly Sure You Hire the Right One.

But the #2 mistake with VP hiring, and maybe the #1 reason VPs lose their job, is priority dis-alignment.  Most especially for VPs of Marketing, although also for all other roles.  Marketing just tends to have the most heterogeneous responsibilities (demand gen, field, corporate, content, product marketing) so the gaps between CEO expectations and VP expectations are often the widest here.

The exercise is simple:

  • As a VP-to-be, put together a real, detailed First 60 Day Plans.  Do it in Google Slides or Powerpoint, probably ideally.  Or Notion or a Google Doc (although a presentation format will almost always force you to structure your thinking more).  However you do it, just do it.  And do it in as much detail as possible, including what you’d do first, who you’d hire, what consultants you’d want to use, what you want to fix.  And what you don’t want to change.
  • And as part of the 60-Day Plan, make the summary / Slide 1 your Force-Ranked, Top 5 Priorities.  What matters most, and what you are going to attack first.
  • Go through these Top 5 Priorities for First 60 Days with the CEO (and vice-versa), and see if you are 100% on the same page here.
  • If you aren’t on the same page as the CEO, see if you can get on the same page.  Talk through the priorities openly.
  • And if after that you can’t get on the same page on the top 3-4 priorities as VP — don’t take the job.  No matter how great it looks and sounds otherwise.  No matter how cool the company seems, or how much it has raised, or how many RSUs.

You have to do a real plan, and the CEO and her VP(s) have to agree on the Top 5 priorities for each functional area.  Otherwise, no matter how great you get along personally, or otherwise, cracks will quickly develop.  Even just by $10k-$20k in MRR, most CEOs have already effectively been the VP of Sales, Marketing, Product and Customer Success, and sometimes, Engineering. That means they already have pretty strong ideas around what is working, and importantly, what doesn’t and hasn’t so far.

If you come in and your Top 5 priorities are things the CEO doesn’t believe will work, based on her experience with the first 100 customers, you won’t last.  Even if that playbook worked perfectly at your last company.  Because even by Customer 100, there’s a pattern.  Maybe events don’t work.  Or maybe they work really well.  Maybe agencies have been a waste.   Maybe Adwords is a disaster.  Maybe Facebook is a great lead gen tool.  Whatever it is, the company and CEO have already figured out how to acquire and service at least some customers well before the first VP is ever hired.  So your job is to do it better.  Not break the wheel.  Not yet, at least.

So make your 60-day plan AND as a summary, force-rank your Top 5 priorities.  Get the CEO to e-sign it for real, and you too, that those are the right 5 priorities for your role.

Then you won’t have to worry nearly so much that you are doing a great job.  But your CEO just doesn’t see it that way.

(Note: an updated SaaStr Classic post)

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