Dear SaaStr: What Should The First 2 Weeks Look Like For a New VP of Sales?
The first two weeks for a successful VP of Sales in a B2B company should be laser-focused on understanding the business, the team, and the customers. All three.
Here’s what they should prioritize. If they don’t — it’s a flag.
1. Learn the Product Inside Out. Ideally, Before You Even Start. But At Least By Week 1.
A VP Sales needs to be able to demo the product themselves by the end of Week 1. If they can’t, they’ll never truly understand the sales process or be an ally to the customer. This is non-negotiable, especially sub $100m ARR or so. A VP of Sales / CRO who can’t demo the product is just a process manager, not a leader.
It’s a huge red flag today if a new VP/CRO shows up thinking they’ll learn the product after they start. The world is just too fast paced and too competitive today.
More here.
2. Understand the Go-to-Market Motion. And Lean Into What’s Already Working, At Least Partially.
They must dive deep into the existing GTM strategy. One of the biggest flags? They immediately insist on running the playbook from their last company. Especially when it conflicts with what’s already working.
Is the top current motion direct sales? Channel-driven? A mix? If they don’t understand how revenue is currently generated, they’ll be out of sync with the team and the market. For example, companies like Shopify and HubSpot rely heavily on partnerships. Missing this nuance would be a massive oversight. Too many mediocre VPs of Sales and CROs just run the playbook from their last role. Bringing some of that to a new role in is important. But they have to focus on what already works, and just level it up and improve it first.
More here.
3. Meet the Team IRL and Assess Talent
In the first week or two, a strong VP Sales meets everyone on the team they haven’t already met. And they do it in person, not on Zoom.
Not just to be a good leader per se, but also to quickly identify the top performers and underperformers. Great VPs of Sales focus on retaining top talent and moving out weak performers quickly. If they don’t, it’s a red flag. Leads are too precious to waste on reps who can’t close.
The mediocre retain mediocre talent … because they don’t know how to find better talent. This happens again and again and again. Mediocre revenue leaders retain mediocre talent. Because they can’t recruit better.
Trust me.
More here.
4. Talk to Customers. Yes, Your First Week. As Many As You Can.
A VP Sales should spend significant time talking to customers directly. Their first week.
Not planning procesess.
There is no other way to truly understand the value proposition, objections, and the competitive landscape. A VP of Sales / CRO who doesn’t deeply engage with customers in the first two weeks is setting themselves up for failure.
So just ask them during the interview process what they plan to do the first 2 weeks. If they don’t say met 10+ customers, just on 20+ calls … pass.
More here.
5. The Top VPs of Sales and CRO Recruit Top Talent. Even Before They Start.
The best sales leaders bring in 1-2 great reps within the first week or two, but the groundwork for this starts far earllier. The best revenue leaders are constantly recruiting.
If a new CRO / VP of Sales hasn’t started recruiting top talent for the new role before they start — they’re not good enough. Saying “I’ll hire recruiters” is not good enough. In fact, it’s a sign of almost 100% failure to come.
The best revenue leaders are constantly building their bullpen. Not just for their current role, but for the next one too. Because they’ll always need a team of high performers. That’s the job.
More here.
6. Analyze the Pipeline and Metrics. And Be In All The Top Deals Yourself.
They need to dig into the pipeline, lead flow, and conversion rates. Are there enough leads to hit the plan? If not, they need to address this with the CEO immediately. Signing up for an impossible plan is a recipe for disaster.
And any new VP of Sales / CRO needs to be in deals themselves week 1. Not just talking about them with the reps in those deals.
More here.
7. Leading From The Front
The first two weeks are about establishing credibility, not just “learning”.
A VP Sales needs to show the team they’re hands-on, knowledgeable, and ready to lead. This includes being visible, accessible, and decisive. And it generally includes carrying a bag and selling yourself. Nothing builds trust more quickly than when a new VP of Sales / CRO closes deals themselves when they start. Even if later, they mainly coach and support the team.
More here.
If a VP of Sales / CRO doesn’t hit these marks in the first two weeks, it’s a sign they aren’t the right fit. And that’s on you.
It’s not a strategy and playbook role. Not at least until $30m, $50m+ ARR. That’s just a small part of it, the “playbooks”.
The best VPs of Sales and CROs make an impact immediately—not by magic, but by focusing on the fundamentals.
