Dear Saa Str: How Can I Become a Better VP of Sales? | Saa Str AI

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Dear Saa Str: How Can I Become a Better VP of Sales?

The hard truth: most VPs of Sales fail not because they can’t sell, but because they don’t understand what the job actually is. It’s not managing a team. It’s not building process decks. It’s not attending QBRs. It’s making your number — quarter after quarter — while simultaneously building a machine that will make next year’s number.

Here’s what separates the ones who last from the ones who don’t.

#1. You Have Two Jobs. Everything Else Is Secondary.

Hire great people. Make your existing people better.

That’s it. If you’re not spending at least 30% of your calendar on recruiting and coaching combined, you’re optimizing for the wrong things. No amount of process improvement, sales tool evaluation, or cross-functional alignment work will compensate for a weak team.

The VPs who struggle are usually the ones who inherited a mediocre team, couldn’t upgrade it fast enough, and then spent all their time managing around the talent problem instead of solving it. Don’t be that person.

#2. You Have to Keep Selling. Not “Coaching.” Actually Selling.

This is the one that trips up most first-time VPs of Sales, especially the ones who came up through enterprise or who are trying to “act the part” of an executive.

Until you’re past

20M–

30M ARR for SMB, or

40M–

50M ARR for enterprise, you are not just a sales leader. You are a closer. You need to be in every deal that matters. Not watching. Not reviewing the CRM notes. Actually in it — on calls, in emails, in rooms.

Dashboards don’t tell you that. Being in the field does.

#3. Set Goals That Are Clear and That You Actually Believe In

But here’s the part most playbooks skip: you also need to be aligned with your CEO on what success looks like before the quarter starts — not during it, and not after you miss. The VP of Sales who surfaces a forecast problem two weeks before quarter end is a liability. The one who surfaces it six weeks out and brings a recovery plan is a partner.

Set the goals. Own the goals. Give your CEO visibility early when something is off.

If you don’t have 3x pipeline coverage, you’re already behind — regardless of how confident your reps feel about their deals.

Push outbound. Always. Even when inbound is strong. The startups that rely entirely on inbound are one algorithm change or one content drought away from a pipeline problem. Build outbound as muscle memory, not a crisis response.

#5. Be a Product Expert. Not Just a Sales Expert.

This is underrated. The best VPs of Sales I’ve seen can speak to the roadmap, explain the technical architecture at a high level, and connect customer pain to product capability without pulling in a solutions engineer for every call.

Meet with your VP of Product weekly. Know what’s shipping, what’s not, and why. Know the competitive landscape cold. When a prospect asks why you can’t do X, you should have a real answer — not “let me check with the product team.”

Misalignment between sales and product is one of the most common ways early-stage companies destroy their win rates. You’re the bridge. Act like it.

This is disturbingly common. A VP of Sales who sees a miss coming and manages information instead of managing the problem.

Own the miss. Analyze what went wrong — was it pipeline, rep performance, product gaps, market timing? Communicate it to leadership before it’s obvious. Adjust.

The VPs who last are the ones who are honest when things are hard. The ones who hide — eventually get replaced.

Yes, you need playbooks. Yes, you need a consistent sales process. Yes, you need to invest in tooling and enablement.

But not at the expense of velocity. Too many VPs of Sales at

5M or

8M ARR are spending 40% of their time building process infrastructure that won’t matter until $25M. They’re optimizing the machine before the machine is producing.

Close deals first. Learn what works. Then systematize. Not the other way around.

The companies that scale fastest don’t have the most sophisticated sales processes early. They have the most clear feedback loops — between what they’re selling, what’s closing, and why.

If there’s one pattern that separates the VPs of Sales who compound — who make their first number, then their second, then earn the trust that comes with it — it’s this:

They never stop being accountable for the result. Not for the process. Not for the effort. For the number.

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Most Great VP of Sales Were Fired Once In Their Career

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Dear Saa Str: How Do I Know If My New VP of Sales is Working Out?

Most Great VP of Sales Were Fired Once In Their Career

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AI VC AI Mentor: Digital Jason + Amelia AI Startup Benchmarking