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Sales leadership: your first 90 days

May 9, 2022

Apprehensive or excited?

Nervous or confident?

Scared or empowered?

Whether you’re feeling one or all of these ways in the run-up to your first 90 days in a sales leadership role, you shouldn’t be feeling alone.

There’s no right or wrong way to feel, and the chances are whatever you’re feeling will help you to succeed. These are the emotions that got you here in the first place anyway, right?

You can’t plan your feelings, but you can plan your journey. From preparing for the position, to gaining quick wins, to planning for long-term success.

We spoke to sales experts who have excelled in leadership positions to get their advice on the first 90 days in a sales leadership role.

Choose a relevant section from the menu below, or scroll through for the full guide. If you’re just here for the first 90 days checklist, feel free to jump straight to the end.

Preparing for the position | Establishing quick wins | Planning for long-term success | The first 90 days checklist | Building a bespoke toolkit

Preparing for the position

The first 90 days in a sales leadership position are crucial, something Cognism’s VP of Global Sales, Mark Bedard, knows well.

"It’s critical. You need to thoroughly assess the organisation, processes, personnel and culture. You need to identify the low hanging fruit and figure out which changes you can make to give you the biggest lift, with the least disruption. These early stages are incredibly important when you’re preparing for long-term success." - Mark Bedard, Cognism

And the work doesn’t begin when you turn up for your first day. Ideally, you want to be fully prepared before you start a new job. The job interview is the perfect time to get familiarised with a new company or position within your current company. Michael Hanson, CEO at Growth Genie, believes that the key is communication.

​​"One of the things that is often overlooked when you start a sales leadership role is aligning with other departments. Interview your CEO about his vision and what his or her goals for the next 3-12 months are. Then, interview marketing about where they see challenges in sales and understand how you can integrate with them, finally, talk to customer success about which types of customers are happiest using the product and what challenges you help solve for them." - Michael Hanson, Growth Genie.

This dedication to learning before suggesting changes doesn’t stop once you’re familiar with the company. Strong communication needs to be an everpresent part of your leadership toolkit.

"The best thing you do can in a new leadership role is overcommunicate. Be inquisitive. Ask a lot of folks about what’s going on. When you find a problem, talk about that problem with a lot of people within the team. You should be doing this before you’ve got a solution, because when you speak to people within the company, the solution often becomes clear."

"Also, when you’re ready to start making changes, speak openly about the changes you’ll be making. Give your staff time to raise questions or concerns about changes that are being made. Make sure your changes are positive, possible, and well communicated. This is all a part of familiarising yourself with and respecting a company’s existing culture, and it’s really important." - Mark Bedard, Cognism

If you haven’t yet familiarised yourself with a company’s culture and ways of working, find a way to immerse yourself in the environment.

"The first thing you should do is start shadowing someone who has been there for a while. How are they working here? What is their workflow like? How are they using their software? Monitor and observe as much as you can in the first 30 days." - Ryan Reisert, Cognism

Establishing quick wins

Michael Watkins is the author of The First 90 Days: Proven Strategies for Getting Up To Speed Faster and Smarter. In this book, he explains the importance of establishing quick wins in a new role.

In a sales leadership context, the importance of this isn’t to gain credibility, but to make steps towards your long-term goals. If you can achieve this, the credibility will follow naturally.

"A lot of people look to bolster their credibility early on, but this isn’t really what’s important. The most important thing you can do is identify issues and think about how you can remove them. You might be aware of them early on because you have experience from your previous role."

"Spot inefficiencies and resolve them. People will appreciate these solutions, and the company will appreciate them too. That’s how you build credibility long term." - Mark Bedard, Cognism

That’s not to say you shouldn’t be showing your team any new techniques first-hand. Demonstrations and discussions are always a good way to teach, and test new methods.

"Get in the trenches and do it yourself. Show people you’re willing to get involved and make cold calls. Don’t just run things from the top. Get in alongside your sales team and do the job, show them how your recommendations work, or don’t work, in practice. This will help you get them on your side and start believing in your processes." Ryan Reisert, Cognism

Start with the macro-level objectives, and see what you can do right away to make progress towards them. Once the basics are in place, you can plan for long-term success.

Planning for long-term success

First things first, figure out what success looks like. In some cases, this will be clearly defined in the interview process. It’s definitely something you should look to figure out before you get started.

"The average tenure in a sales leadership role is 18 months. This isn’t just because it’s a tough job. Different sales leaders will excel in different situations. Some will be better at implementing a go to market strategy, others will be better at managing a large sales team. It’s possible that you’re being brought in for a particular stage of growth and you need to know this and be honest about your suitability for the project."

"You want the board’s expectations of you to be clear when you start a new leadership role. You need to know what they’re looking for, where you will sit in the organisation, and whether their expectations are realistic. Try to understand as much as possible before you start planning for long-term success." - Mark Bedard, Cognism

If you haven’t had much guidance, don’t worry! You can do some calculations to establish your own realistic targets. Ryan Reisert, an expert in the maths of sales, has some advice.

"Start to figure out the maths of sales. Understand the benchmark of what is possible and look at ways in which the company could generate more revenue. Identify the biggest areas in which the team can improve and target these first. You don’t want to do too many things at once." Ryan Reisert, Cognism

You can find Ryan’s SDRMath tool right here.

The first 90 days checklist

“But Cognism… all you’ve given me here is a bunch of quotes and I need cold hard facts!”

Noted.

We’ve reduced these conversations down to a delicious syrupy checklist for your new sales leadership role. Feel free to screenshot this, print it out, or write it on your mirror in toothpaste.

I clearly understand the product and the market.

 

I clearly understand what success would look like in this role.

 

I have spoken to my team and understand the problems they’re currently facing.

 

I have shadowed an experienced member of the team to learn about the organisation, processes, and culture.

 

I have interviewed the CEO and heads of departments to familiarise myself with their processes and goals.

 

I have made sure my team have an easy and safe way to communicate with me.

 

I have assessed the organisation, processes, personnel and culture.

 

I have identified some early changes I can make to give us the biggest lift, with the least distruption.

 

I have a clear vision of the journey to long-term success

 

 

Building a bespoke toolkit

Long term success in sales starts with a strong toolkit.

Start by making sure the core technology is all there. The tools your team will use to make calls or send emails. They’ll use these every day so do the research and get it right!

Supplementary technology, like sales intelligence software, can make things a lot easier for your team, but they can come with a considerable price tag. Do an audit of these technologies and make sure they work from an ROI perspective.

Consider the company’s data too. If they’re going through a period of change, or have had problems closing deals, it might be time to consider levelling up your data.

You can find our list of the best sales automation tools of 2022 right here, just click the link below.

The best sales automation tools of 2022