What a Great VP Sales Does In Their First Week. Watch For It. | Saa Str AI

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What a Great VP Sales Does In Their First Week. Watch For It.

One of the most controversial things I’ve said over the years on Saa Str is: You know within 30 days if you hired a VP right.  Especially a VP of Sales.

Not at 90 days. Not at 6 months. By day 30, the split is visible. And if you’re not paying attention, you’ll miss it.

Just about every founder and CEO that has been through it agrees with this.  A lot of executives challenge it.

But it’s just as true today in the Age of AI.  Maybe even more so.  As there just isn’t enough time to scale slowly, or hope someone that is scaling slowly … will eventually get there.

Great VP of Sales, first week: – brings 2-4 great sales execs in ASAP. often week 1 – identifies top existing talent, does what it takes to keep them – begins to move out underperformers – jumps into all critical deals Mediocre VP of Sales, first month: – has no one to bring… — Jason ✨👾Saa Str. Ai✨ Lemkin (@jasonlk) June 30, 2026

– brings 2-4 great sales execs in ASAP. often week 1 – identifies top existing talent, does what it takes to keep them – begins to move out underperformers – jumps into all critical deals

— Jason ✨👾Saa Str. Ai✨ Lemkin (@jasonlk) June 30, 2026

This is not a maybe. This is not a plan to hire. This is day one through day five. The great VP has already been building their network. They have 3-4 people they’ve worked with before who know them, who know they can close, and who are ready to move.

Ron Gabrisko joined Databricks as CRO when it was under

Matt Plank, who was employee #5 at Rippling, built out the early sales team by focusing on network hires first: “Your first few hires will typically be from your network.” He scaled Rippling to over $1B ARR.

Ashley Kelly joined Brex at $2M ARR and immediately brought in three experienced SDRs from her previous company.

The network hire is not a nice-to-have. It’s the job. If they don’t have this network, they are not a great VP.

Ever single great sales leader I’ve ever worked with, and this includes stretch ones, ones that want to be a VP Sales … is cultivating their network.  They’re constantly making sure the top 2-5 sales execs they know are ready to join their next thing, and they’re constantly recruiting one way or another.  Constantly.

Just don’t hire anyone for a leadership role that doesn’t have a few excellent sales execs to come with them. Trust me. And talk to them (the ones that will join) to confirm it.

2. Identifies top existing talent. Does what it takes to keep them

Week one they’re doing 1-on-1s. Not group meetings. Not all-hands listening tours. One on one with everyone, if the team is small.  With all your top performers if it’s larger. They’re asking: What are you doing that works? What’s your close rate? What’s your deal size? Why are you still here? What would make you leave?

The top performers get direct attention from day one. Not later. Not after the process is built. Now. The message is clear: the best people get the best leader’s time

Ron Gabrisko’s core lesson from scaling Databricks: “Talent beats everything. Culture beats everything. If I could go back, I’d tell myself to invest even more aggressively early on.” This means retention conversations with your top reps happen in week one. They make retention offers to these people. Not because it’s nice. Because losing your top rep means losing 20-30% of pipeline and breaking morale for everyone else.

Bad sales reps don’t get better. They get slower. They take pipeline from people who can close it. They make the whole team accept mediocrity.

The great VP starts this conversation in week one or two. Not cruelly. But fast. “I’m seeing X. Here’s what I need to see. If this doesn’t change in the next 30 days, we’re going to make a change.” No second chances. No process that will fix them. No hoping they turn it around.

4. Jumps into all critical deals.  Doesn’t wait to get “a lay of the land”

They spend the first two weeks in deal reviews, and in actual deals. Not strategy sessions. Not CRM reviews. Actual deals. The ones stuck. The ones that should have closed. The ones where something is broken.

They’re asking: Why is this deal here? Who’s the buyer? Have we talked to them? What’s the objection? Is there a competitive threat? How much revenue is this? Is your rep actually trying?

They’re not running the deals. They’re learning the problems and helping deals close their first week, often their first day. They’re seeing which reps know what they’re doing and which ones are winging it. They’re identifying the patterns. By end of week two, they know what’s broken in your sales process.

They show up with no network. No one who will move with them. So they immediately start recruiting, which means they’re building a plan instead of executing.

They spend weeks 1-2 writing a hiring plan. A sales process. A CRM framework. A training program. They’re trying to fix what’s broken through systems instead of people.

If this is your VP, you’ve already made the hire wrong.

Your A player is watching. They see that the new VP doesn’t know anyone. Doesn’t have gravity. Is focused on meetings instead of deals. They get a call from a recruiter on Wednesday and take a coffee on Friday.

Your top revenue driver sees a founder at a competitor who moves faster. By week two, she’s seriously looking. Your third-best person hasn’t heard from the new VP at all. They’re wondering if they matter anymore.

By day 21, you’ve lost one person or are about to. If you ask them why, they say “I’m just looking for something new” or “The opportunity came up.” What they’re actually saying is: I don’t trust this hire.

3. Tries hard to keep everyone, including low performers

The mediocre VP focuses on retention because that’s what you asked for. “Jason left, we need to keep people happy.”

So they build retention plans. They promise more coaching. Better commission plans. More training. They try to make the process so good that people don’t leave. But they’re not fixing the real problem: underperformers are still here. Pipeline is still stuck. They’re still building process instead of executing. So people who could win somewhere else stay just long enough to see that nothing is changing, then leave anyway. And people who are costing you money stay forever because there’s no accountability.

Week 1: Sales process documentation. Week 2: CRM cleanup and reporting. Week 3: New comp plan proposal. Week 4: Training schedule.

Nothing about this is wrong. It’s just not the job of a VP of Sales in their first month. The job is: fix what’s actually broken, move the right people into place, and get the organization moving.

2-3 underperformers either gone or have 30-day exit plans

Your top performers have had real conversations about why they’re staying

1-2 critical deals have moved or are close to moving

Your sales team believes this person knows what they’re doing

No new people hired yet, but lots of job reqs posted

Everyone is still here, including the people who can’t close

You have a new sales process doc and a meeting schedule

Your sales team is wondering who this person is and what they’re trying to do

The great VP can even make you uncomfortable. They move fast. They make hard decisions. They do things without consensus.  They are confident by the end of Week 1 at least in 2-3 things that truly will move the needle, and they can tell you exactly why.,

The mediocre VP makes you feel heard. They listen. They build lots and lots of plans. They’re professional.  They often are pretty darn good at selling up.  They do a lot of listening tours to start. Your board and investors may even love them.

By month two, you’ll know which one you hired. You’ll even know at the end of Week 1 if you really listen and watch.  The hard part is: most founders hire the mediocre one because they seem competent in the interview, and often have the best Linked In. The great one often seems reckless.

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Most Great VP of Sales Were Fired Once In Their Career

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Key Takeaways

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

• AI Agent Playbook Free e Books

    e Book: Hiring a Great VP of Sales
    e Book: Raising Capital
    e Book:  The First $1m ARR
  

• University All Posts Podcasts The Top CROs VC Fundraising Top Videos Q&A Best of Saa Str #1 Bestselling Book Search Everything Join the Community

• Free e Books

    e Book: Hiring a Great VP of Sales
    e Book: Raising Capital
    e Book:  The First $1m ARR
  

• AI Annual 2026 Events Overview Sponsors

    Event Sponsorship
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