Sales Leadership: How to Ace Your First 90 Days

Apprehensive or excited?

Nervous or confident?

Scared or empowered?

There’s no right or wrong way to feel when you embark on your first 90 days in a sales leadership role.

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

We spoke to a panel of sales experts to get their advice on how to ace the first 90 days as a new sales leader.

So get stuck in! Choose a relevant section from the menu, or scroll through for the complete guide.

If you’re here for the first 90 days checklist, then jump straight to the end.

How to prepare for sales leadership

For Frida Ottosson, VP of US Sales at Cognism, preparing for sales leadership begins before your feet are even underneath the desk. It begins with the hiring process!

Frida’s advice is to treat the hiring process like a discovery call. She stressed the importance of engaging with stakeholders at all levels of the organisation. By truly understanding their perspectives, you gain valuable insights into the organisation and the role.

She said:

“These conversations helped me understand, ‘Okay, this is what I’m going to need, and am I the right person for this role?’” 

It’s crucial to ask the right questions during the interview process. This lets you align your skills and expertise with the organisation’s goals. You’re laying a solid foundation for sales leadership success.

Here are some good questions to ask during the sales recruitment process:

1. Can you describe the company’s overall sales strategy and how the sales team contributes to achieving company goals?
2. What specific qualities or skills are you looking for in a sales leader for this role?
3. How would you describe the current sales team’s performance? What areas do you see as opportunities for improvement?
4. Can you provide some insights into the company’s target market and the competitive landscape?
5. What are the key performance indicators (KPIs) or metrics that the sales team is measured against? How are these metrics tracked and evaluated?
6. How do you foster collaboration between the sales team and other departments within the organisation?
7. What resources or tools are available to support the sales team’s success?
8. What is the typical sales cycle or process for the company’s products or services?
9. Can you share any specific challenges or obstacles that the sales team currently faces?
10. How do you envision the sales leader in this role impacting the organisation?

What about after you’ve secured the role?

Cultural fit is another factor to consider. Alexander Irschenberger, VP Strategy & Growth at Contractbook, emphasised the significance of understanding the teams’ skill sets and personalities.

He said:

“What are you bringing to the table? Is it your cool personality? Do metrics drive you? Because it needs to match the others around the table quite well.” 

“Otherwise, you’ll end up with many discussions and mismatches in expectations.”

For Alexander, diversity is important in a sales team: 

“If the entire team you’re working with and leadership all have the same personality, that’s not great. Because then you’ll have a lot of opinions about the same things. No one will pick up on the things that you’re lacking.”

“Remember that when you’re a sales leader, you’re playing a role. You’re playing a role in that team, and that team needs to succeed.”

How can you build trust with your new team?

Alex told us the key is being self-aware and recognising your strengths and weaknesses.

How to figure out what success looks like

According to Rebecca Drew, VP UK Membership at Chief:

“Success in sales leadership is about building relationships, moving deals through the sales process, and achieving the results you set out to achieve.”

So what can you do to get there?

It’s all about the data...

Make sure that you’re tracking sales KPIs and analysing outcomes; this will help you provide a picture of success and drive improvements.

You should set clear goals for revenue, customer acquisition and conversion rates.

This is not a set-it-and-forget-it task - it’s an iterative process where you must continue to review performance and drive improvements. 

Ryan Reisert, sales consultant, said that sales leaders must understand the mathematics of sales:

“Understand the benchmark of what is possible and look at ways the company could generate more revenue. Identify the biggest improvement areas and target these first. You don’t want to do too many things at once.”

How to achieve quick wins

Quick wins are crucial to establishing credibility in a sales leadership role. However, you have to pick and choose your battles. It might be tempting to tackle all the low-hanging fruit, but they must align with the organisations’ objectives. 

New B2B sales leaders must prioritise tasks based on high-level leadership expectations. 

Frida explained: 

“Think about the quick wins the CEO cares about. Because otherwise, you could be running after quick wins all day, and they might have an impact but not the impact senior leadership is looking for. Be a little bit strategic with what you go after.”

When should you go for quick wins in a sales leadership role?

Frida said:

“Start with a couple of quick wins in the first 30 days. Because you need to build that trust with colleagues, and getting a win feels good!”

When it comes to quick wins, Jonathon Ilett, VP Global Sales at Cognism, first develops an understanding of his team’s current state. 

This includes benchmarking team performance, identifying gaps and standardising processes.

By addressing these issues and implementing improvements, you can generate quick wins that have a tangible impact on sales outcomes.

Jonathon advocated for getting into the weeds and looking at the details. He told us this is the best way to fix problems:

“I’m quite fortunate as I came from the UK, our highest performing revenue team. So I knew a lot of the sales processes the team had in place.” 

“A really quick win for us was benchmarking what a UK rep was doing and looking at the DACH counterpart in the enterprise team. It was very apparent where the gaps were from a seller motion.”

How to learn about the company culture

This is an essential thing to do in your first 90 days in sales leadership!

How best to immerse yourself in your new company’s culture?

Alexander said to reach out to other departments. Interviewing colleagues is a great way to get insights into the company’s ways of working. 

He said: 

“Let’s say that you’re stepping into a sales leadership position where you’re reporting to the CEO, and maybe there’s a Head of Marketing and head of CS that you’ll be working with.”

“I would definitely want to have a short interview conversation with them. I’d want to see their view on things and understand their vision.”

Alexander also pointed out the wisdom in seeking out multiple perspectives:

“I’ve found that quite often, a CEO or founder will have one perspective of the business, which is very much affected by their love for the business they’ve built. And it’s not always the same way that others see it.”

He warned:

“A CEO might promise you something like we have this great setup, and you need to build this scalable engine. But that’s often not the truth.” 

“The truth is a lot of things suck, and a lot of things are chaos, and that’s just real life. You want to be as prepared for that as possible. When you do your 90-day plan, you want to ensure you tackle the important things first. Not building a scalable model on top of something that’s not scalable.”

What are the best questions to ask your new stakeholders?

Michael Hanson, Founder and CEO at Growth Genie, gave us the following list:

• For CEOs - ask them about their vision and what his/her goals are for the next 3-12 months.
• For Heads of Marketing - ask them where they see challenges in sales and understand how you can integrate with them.
• For Heads of CS - ask them which types of customers are happiest using the product and what challenges you help solve for them.

How to manage communications with your sales team

Communication plays a central role in sales leadership. 

Alexander told us about a rule he follows as a sales leader:

“If you think you’re communicating a lot, do it three times as much. If you don’t think you’re communicating, do it 50 times as much.”

Despite being a very transparent and communicative leader, Alexander still doesn’t think he communicates enough.

And why is repeated communication so important?

Alexander explained:

“If we look at the sales process, it might take 28 touch points from you not knowing about us to actually wanting to book a demo. You can apply the same concept to people’s understanding of something inside the company.”

“Meaning if you’ve communicated something once no - one understood it. Twice - a couple of people probably understood. It’s not until you start repeating it the fifth, sixth, seventh or eighth time that they fully understand and believe in it.”

Rebecca highlighted the value of frictionless communication. She mentioned that:

“While working at Vidyard, Michael Litt, the CEO, was big on using video to communicate. He sent out regular updates and engaged with the team through video.” 

There’s more than one way to keep communication channels open!

How to manage the sales tech stack

For Jonathon, the size of the business is the determining factor when deciding on the sales tools his team needs.

He told us:

“If you’re early stage, all you need is a CRM, data provider and maybe a meeting booking software.”

“But as you get more advanced and need to build out enablement functions, this is when you can bring in more tools. At this point, you need to bring in sales training software and call recording so you have benchmarks.”

The core concept is that you can add to your tech stack as you scale your team - but not before that point. These efficiencies become more important with a bigger team too.

How to plan for long-term success

Startup SaaS sales is a very dynamic environment. You can have all the plans in the world, but things can change very quickly on the ground. This can make long-term planning a challenge.

But that doesn’t mean you should throw your plans out of the window! As Alexander said, in sales leadership, you need to pace yourself:

“It’s difficult to have a very long-term plan and strategy. However, I also see that people iterate too soon or even implement something too soon. Not that it’s necessarily a bad thing, but if you’re doing it fast and miss some essential items, you can end up rolling something out there’s not full backing on. Then you have to change it again - these changes affect your team quite a lot.”

“Honestly, most people don’t thrive in that. Most people like to have a clear goal and be repeating something so that they become good at it.”

When it comes to long-term success, Jonathon prizes an onboarding process that empowers reps to perform.

He explained:

“I want to be able to bring someone in and almost guarantee their performance because we have such rigorous onboarding. All the managers are singing from the same playbook about coaching the reps.” 

“Success for me is when we can plug and play new SDRs and get the expected output.”

But it’s not all about the numbers; Jonathon’s goal is for his reps to progress into sales leadership positions, too. There has to be a natural path for them to follow.

Sales leadership checklist: the first 90 days

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

Noted.

We’ve distilled these conversations into a checklist for your new sales leadership role 👇