Your first 90 days in a new sales leader role

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The average tenure for a sales leader is just 17 months.

So setting yourself up for success is incredibly important. And leveraging that time before you start a new opportunity can be a real difference maker (depending on what you can and can’t do contractually of course). 

My main recommendation is accessing and reviewing data. Obviously this depends on how much the company is willing to send before employment officially starts. But either reviewing data or instead meeting the sales team on a social level to not just get to know them individually, but understand where their blockers are, their personal challenges, and their personal goals. All of this will really set you up for day one.

Your 90 day plan

You might have covered your 90 day plan in the interview process, but if you haven’t, then create one.

As a sales leader, it’s really important to deliver value really quickly. And what I mean by that is getting to a point where at the end of the first month you’re president the founders and the VCs with a clear audit on:

  • What you’ve found
  • What you’re doing to deliver
  • How you’re going to deliver it

Consider your first 30 days as a consultant or advisor and come away from that first month with real tangibles. Of course, it’s important to deliver value quickly in those first 30 days. For example, It could be that you implement something, maybe could be basic things like you’ve seen that calling is low, you’ve implemented calling hours or whatever, basically, or there’s a deal that’s been stuck for ages and you’ve helped move it through a stage, whatever it might be.

The first 30 days

It’s those small wins make a difference, because in the first 30 days employers are always thinking, have we made the right decision? Have we made the right decision? So you’re just looking to eliminate that really early and you do that by delivering value and then at the end of the month showing them what you’re going to do basically on an ongoing basis, come up with a really clear, specific plan based on what you’ve seen type thing and it’s okay. You get way more respect as well. If you identify potential challenges in the team, it could be that there’s maybe a person that isn’t a fit that you’ve identified. It’s best to come out with that early and potentially make some quick decisions. If there’s some big red flags that you’ve seen early on, basically you just get respect. And people want to buy a leader at this point, so they want to see someone acting and thinking like a leader. And this is at this point, the founder wants to pass over sales to this person. So getting that trust really early is really important so that they’ve made the right decision and we can trust that this sales leader is now going to take the reins and I’m going to trust them to make repeatable, basically.

Importance of observing

I believe the first month in a new role should be focused on listening and learning. It’s tempting to want to make big changes right away, but that can be counterproductive. Instead, spend the first month really observing – listen in on calls, attend meetings, get to know the team. Soak up as much information as you can without trying to push your own agenda. Use this time to truly understand the business, the customers, the challenges. Then after a month, you’ll be equipped to thoughtfully develop a plan forward based on your learnings. Come in with humility, ask lots of questions, and resist the urge to make sweeping changes in the beginning. Take notes, listen, learn the landscape. Then you can thoughtfully chart the path ahead in a way that will set you up for longer term success.

My failures as a sales leader

As a sales leader, I’ve definitely made mistakes in my first 90 days in roles. The one that was a massive learning for me was in me thinking everyone had to sell like me. I was essentially trying to create mini-me’s. And if they didn’t sell like me, I was trying to coach them to sell like me. But that isn’t the way that sales, or management, works. At the time, that came down to inexperience on my part. 

I also remember a time where I actually focused too much on sales in the first 30 days. It was my first sales leader role and I’d just moved from a salesperson to a sales leader and my default was to impress by selling and getting deals over the line. 

But actually, as a sales leader in those early days in a new role, as counterintuitive as it sounds, sales isn’t the most important thing. It’s far more important to build structure, to build playbooks, and to build repeatability. 

Once you get into the thick of the job, from months probably like month two and three onwards, it’s very hard to go backwards and be that observer. You can’t justify a month of observing in your fourth month because you should have created a process by now and you will have a target to hit. 

The importance of focusing on repeatability

The early days are not purely about closing deals. And if you do that, you can actually drive the wrong expectation with the founder because they then see you as someone that is just closing deals. That isn’t your job. Your job is to build repeatability. 

Of course, part of that will be helping and moving opportunities down the line, but it isn’t always just about converting deals. Sometimes it might be pipeline velocity or moving opportunities through different stages. It’s okay to move opportunities from the discovery stage that have been stuck at the demo stage. That’s great. But it doesn’t mean the immediate expectation is to close them. Focus on your lagging metrics and the process you have in moving them along. That’s how you create repeatability. And that’s what a founder wants in a sales leader.

What I would do differently

I’ve thought a lot about how I’ve approached my first 90 days in different sales leader roles. And what I’d do differently. My key points are:

  • Listen, observe and ask as many questions as possible in those first 30 days
  • Remember you’ve been hired as a sales leader, not individual contributor
  • Repeatability trumps immediate deals
  • Build the playbook
  • Embrace the differences in your team, everybody sells differently, don’t try to create mini-me’s
  • Structure is essential. In fact, over structure in the early days. Have clear structures for one to ones, pipeline reviews, what you expect from people, creating targets etc.
  • Use tools to make you more efficient in delivering sales and repeatability in building playbooks – because you need a single source of truth for sales excellence – you won’t build repeatability without it
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