Hiring Your 1st VP & Other Exceptional Sales Leaders

Hiring your first sales leader, or replacing that first sales leader, is something I see organizations struggle with all the time. And if you’re a growing company, picking the wrong person can set you back months to a year. 

So from my experience as a VP of Sales multiple times over and a CEO of a revenue consulting consulting who’s helped to hire sales leaders, I’m sharing my blueprint for hiring your first VP & other exceptional sales leaders.

These are the three common mistakes companies make early on when hiring their first sales leader:

1) They try to make the VP of Sales the messiah hire

2) They hire a VP/senior leader to “document” their sales process

3) They hire a VP to build out their tech stack

Read below where I break it all down starting with the first sales leader, rules around hiring a VP, and then what you should look for in great managers and directors.

But here’s the bonus: This week’s topic is two-fold. If you’re on the frontlines or a Sales Manager or Director looking to level up your career and want to get picked to lead, all you have to do is reverse-engineer this blueprint to plan out what steps you need to take in your career to get there.

Excited to get into it.??

PS - If you’re looking to hire full-time, use the blueprint in this week’s article to make sure it’s the right one. However, you might not need a full-time person just yet, but you do need strategic and expert help, consider fractional leadership. Just like Marketing, Operations, and Finance - Sales can scale with fractional resources. 

“There are three mistakes companies make early on. The first is they try to make the VP of Sales the messiah hire.”

The gold in these sessions is actually two-fold. 

If you’re a CEO or leader doing the hiring, I’ll give you the blueprint on what to look for in every type of leader you’ll consider for sales roles. Starting with your first sales leader, rules around hiring a VP, and then what you should look for in great managers and directors.

The second person I think will benefit from this is the person who wants to get picked. Everything I talk about today, you’ll be able to reverse engineer to plan out what you need to do in your career to get to the next level and get picked.

Definitely watch the recording for some stories in my own career and my peers, but I’ll summarize the important bits below. 

In part 1, I cover When to Hire Your First Sales Leader & When to Up-Level

• Three big mistakes (messiah hire) (don’t hire a sales leader to document your sales process) (don’t hire a VP to build out your tech stack)
• When/how to level up

In part 2, I cover: How to Hire/Be Exceptional Sales Leaders (From Managers to VPs)

• Three characteristics of a sales leader
• Skills of a frontline manager
• Skills of a director
• Skills at the VP level

One other thing I want to give you before we jump in is something we put together a little bit ago that not only covers people but what to look out for in terms of process and technology if you’re a smaller company growing from $0-20 million in revenue.

Download What Breaks in The Road From $0 to $20 Million 

Recap: Hiring Your 1st VP & Other Exceptional Sales Leaders

• Part 1: When to Hire Your First Sales Leader & When to Up-Level
• 2:34 – There are three big mistakes companies make when hiring their first sales leader.
• 4:52 – You should not look for a more senior sales leader until you get to 10-20 sales reps.
• 6:33 – You should not hire a sales leader to document your sales process.
• 7:32 – You don’t want to hire a VP to build out your tech stack.
• 9:20 – The sales leaders that can take a company from 0 – $100s of millions in revenue are unicorns. It’s a different skill set.
• 11:40 – First 0-20 reps, a really good manager is fine. 20-75, you need someone with a proven track record (or to get them the support they need – leaders who’ve built other leaders).
• 13:10 – Scale with the resources and people you need today.
• Part 2: How to Hire/Be Exceptional Sales Leaders (From Managers to VPs)
• 16:55 – There are three characteristics of every sales leader you hire.
• 20:15 – For frontline managers, these are the non-negotiables.
• 22:40 – In directors, it’s the two things I mentioned for managers but with this one extra layer.
• 24:40 – VPs of Sales, you are leading leaders at this point. You have all the skills and skill development I mentioned before, but at the VP level, you must be good at working with other groups in the organization. Ex. Engineers think way differently than marketing, and marketing things differently than finance, etc.

When to Hire Your First Sales Leader & When to Up-Level

3 BIG MISTAKES COMPANIES MAKE WHEN HIRING THEIR FIRST SALES LEADER

There are three big mistakes companies make early on when making their first hire.

The Messiah Hire

I like to call this VP of Sales (first hire) the messiah hire, because the perception that founders have of this person is that they are going to come in and build the foundations AND put together the reports and dashboards AND know how to manage a team of 40 AND… etc. 

Most companies don’t think about the leader they need today (the next 3 to 6 months). For example, if you need someone who can work with the reps and get on deals. Cool. You need a manager – someone who’s managed people before and is used to getting in the trenches.

You should not hire a VP of Sales if you only have a few sales reps. Instead, you need to lay some basic foundation that you can learn and iterate on. A manager type and fractional leader for more of the strategy is better at this stage. You should not be looking for a more senior sales leader until you have at least 10-20 reps. 

Hiring a VP/senior leader to “document” your sales process

You should not hire a sales leader to document your sales process. Why? You don’t need it. Most likely, it’s already built in your or someone else’s head, and you just need someone to pull it out.

You already have the process. You know what’s worked and what hasn’t, so you want a leader who can iterate and grow.

Hiring a VP to build out your tech stack

I love you, my sales leaders out there, but we have not prioritized keeping up with sales technology. We have not honed that knowledge and skill. I talk to many sales leaders who don’t really understand what the tech stack does. They know at a high level, but technology evolves quickly.

This is an issue because it’s tough to build a team that isn’t just adding more people because you can’t fathom the productivity you’d be getting from these tools if they were correctly integrated. 

So if you have a small team, haven’t documented the process, or don’t have a basic sales tech stack, you do not need a full-time senior sales leader. They will flame out.

WHEN/HOW TO LEVEL UP SALES LEADERSHIP

There is this notion that you don’t have time to mentor and level people up. And this is actually true. I can tell you from my experience that I only know maybe two to three sales leaders who have taken a company from 0 – $100s of millions in revenue. It almost never happens, and there are a few reasons for that.

One, the leap from managing 20 reps to managing 75 reps, which includes managing leaders and leaders of leaders, the complexity has grown, and many people have trouble removing themselves from the day-to-day. It’s a different skill set.

So my advice for companies out there who want their internal people to level up, or you yourself are looking to level up, is to get mentorships or advisors who have been there and done it. And not your board or people with other jobs who don’t have the time.

And I don’t mean mentorship as someone you go get coffee with, but somehow who knows your business and can say, “OK, here is what is going to happen next and what you are going to do about it. “

You need a network of coaches or consultants that you can tap into.

This is one of the only ways I’ve seen people level up within a company. 

Otherwise, as I said in the last section, you have to hire for what you need now, and most likely will be hiring different leaders and levels of leaders as you grow.

How to Hire/Be an Exceptional Sales Leaders (From Managers to VPs)

3 CHARACTERISTICS OF A SALES LEADER

These are the three general traits or skills that leaders need to have, but they can play out a little differently depending on the type of leader you’re hiring. In the next section, I’ll then break these down into a few examples of exactly what to look for in managers, directors, and VP-level.

They have a playbook

A repeatable process is the #1 thing you want to look for in a sales leader. This leader already has the playbook of what you’re trying to build.

Sales technology

As a VP of Sales, you have to know how these technologies and systems work, so when your CEO or board comes to you and says, “You have to do more with less,” you can so, “Ok, let’s go.” You don’t need to hire 45 people this next year to hit your number; you can hire 10 and set up the tech stack to make that 10 more productive using RevOps partners to help set it up.

How can you scale to hit your revenue goals if you don’t know how to do more with less?

Build your network to see around corners

Great leaders know their own limitations and invest in themselves. You have to build a network of people that are mentors, coaches, consultants that you trust, etc.

SKILLS OF A FRONTLINE MANAGER

Here are the non-negotiables for hiring a sales leader that is a frontline manager. 

The first is that a frontline manager has to be able to build trust with people. You build trust by being very good at what you do – you don’t have to be the best seller, but a good seller – and knowing how to motivate the individual. We all have similarities regarding motivation, but it’s important to be able to pull out an individual’s drive.

The second is that they have to be able to look at the metrics and come up with smart solutions to the problems. Managers who show up to a pipeline meeting and say, “Hey, we’re missing quota. Let’s do more activities.” Hard pass.

Related Content: Motivating Your Team From Top to Bottom

SKILLS OF A DIRECTOR

For a director, they also need to know how to build trust and come up with unique solutions. The extra layer is that this person knows how to remove themselves more and more and more from situations. But it’s also a balancing act.

You can check in with a subordinate of a subordinate but don’t jump in and do or take over what the rep or manager should be doing.

On the other hand, being aloof or “letting them figure it out on their own” is not a good strategy either. Maybe in certain situations, but a terrible strategy in others. A great director knows how to keep a pulse on what’s going on with the frontlines, because you’re just one level removed, but they don’t feel the need to jump in and solve all the problems. They inspect, coach, and remove themselves when needed.

SKILLS AT THE VP LEVEL

VPs are leading leaders of leaders at this point. I’m all about the skill development piece, so you have all the characteristics I mentioned before, but in addition, you have to be good at working with a lot of different and diverse groups within the organization. Engineers think way differently than marketers and finance, etc. Playing across departments is very important at this level.

So. If you were in this second group looking for advice on how to grow your career, you can also think of this as my formula to level up or move from rep to manager, manager to director, director to VP. These are the skills you need to hone and grow.