How To Hire Your First Sales Leader | Founders Guide


Think of your perfect first sales leader as a unicorn. So rare that they are likely not on the open market. If your organization were genuinely worthy of a unicorn, you wouldn’t be looking for one. You would have already found them.

So, let’s correct some genuine assumptions held by founders and startups.

How do you hire your first sales leader? First, you need to figure out what type of sales leader the organization needs. Second, you’ll need to figure out what kind of objective qualities this person will display if they are the right person. And finally, you’re going to need a process that will identify and attract this individual.

I have worked with many founders and startups, ready for the first VP of Sales hire. And many of them hold similar assumptions that are detrimental to their sales hiring process and their entire sales department.

These individuals have built a billion-dollar company, some from the early stages.

They’re cashed up.

And, now sitting on $10 million.

Founders often assume that individuals will walk off the street and ask: “would you like to hire me for your nine to five job?”

If you’re expecting somebody to come and say that to you, you’re wildly out of touch with reality.

Learn how to prepare, identify and secure your first sales leader that will capitalize on the existing market potential for your organization.

Rose garden quotes

First, you need to figure out what type of sales leader the organization needs. Second, you’ll need to figure out what kind of objective qualities this person will display if they are the right person. And finally, you’re going to need a process that will identify and attract this individual.

sales team and sales leader in a sales meeting

Your first VP of Sales is the spearhead of a company’s bottom line, not just a money maker. They will be responsible for creating predictable and repeatable revenue growth, all while building out the sales culture of the team – sometimes from the ground up.

You assume the sales leader’s role as the Founder or founding team at the beginning of startup sales.

But, you get to a point where you’ve taken your company with your founder-led sales about as far as you can. You have a few good salespeople, revenue feels stable, but you know, you can make a more significant impact on the market.

The only thing you’re missing is your right-hand man who will come in and capitalize on that market potential.

Just know now, it can’t just be anybody. Don’t make the wrong hire and kill your business before starting.

Download Our Sales Leader Hiring Rubric
Systematically assess your sales leader against measurable sales leader traits and expectations. Ensure your organization’s growth.


It’s a balancing act.

Leaving it too long and your business can drown in insufficient data and arbitrary processes. Your sales reps will devise their systems to close deals without a centralized approach.

Later, you will find it impossible to scale or onboard new team members.

Hiring too early risks your VP going on a hiring spree without enough prospects coming through and closing deals.

That sales leader will fail, and you will likely hear: “we need to focus on hiring quality salespeople.”

Far too many business owners hire sales leaders that produce data and reports that explain why they are missing targets and why the quarterly and annual projections will be missed.

If you find yourself in this position early, you need to make it abundantly clear that they need to be solutions-focused and results-driven, not effort-driven.

Get your sales leader on the phone, lead generation, and close deals.

Your sales leadership requires sales talent; the candidate must have had success as a salesperson in the past to get this position – so get them to use it.

Here are some signs you are ready for your first VP of Sales:

  • You, as the Founder, has taken the organization as far as it will go.
  • You have 2-6 sales representatives in house, who spend their time closing prospects.
  • $1-3M+ in ARR, proving your market fit.
  • You have a market incumbent and your business goal is to take them over.
  • A competitor is making some serious noise inside of your industry.

So, if the timing seems right now, you need to decide who you and your executive team need?

Rose garden quotes

Your sales leadership requires sales talent; the candidate must have had success as a salesperson in the past to get this position – so get them to use it.


So, who do you want to spearhead your company’s sales across the department?

Let me guess.

  1. You want someone who’s already been in this position before with portfolio companies.
  2. You want somebody that took an early-stage company from five salespeople, all the way to 500 salespeople.
  3. Ideally, they took it through multiple funding rounds, and ultimately, either through an acquisition or an IPO.

Your desires aren’t unwarranted. However, they are unrealistic.

sales leader or sales team speaking to prospect

Let’s be realistic and logical. And answer me this: What makes you so unique?

What’s so special about your organization that somebody at that level would want to join you?

Don’t tell me it’s your culture. Don’t tell me it’s your solution. Don’t even tell me it’s your market.

It leads to a common mistake that startup founders make: overweighting industry experience and under-valuing leadership experience. Founders overweight the candidate’s industry experience because they value the approval of their baby company.

The truth is, nobody believes that their kid is ugly. Everybody thinks that their kid is the cutest in the world as they should. And this is the same with founders and their startup organizations.

Your sales leader is rare. The right candidate you are looking for is not on the open market. If you genuinely had an organization worthy of this unicorn, you wouldn’t be looking for one; they would have already found you.

The truth is, you’re just like everybody else. And, you’re going to need to put in your hard work to develop your first sales manager.


Let’s break down how you determine what type of sales leader your organization needs.

For your organization’s first VP Sales, there are two types of sales leaders:

  • Peacetime general
  • Wartime general

To distinguish which type of sales leader you need, look at your organization’s current needs, goals, and missions and align them with your leadership role.

Your organization may be at the point where it’s stable, trending upwards. There may be no market uncertainty, and the opportunities are plentiful.

All you need is somebody to maintain and steer the ship forward.

If so, then you need a peacetime general.

On the other hand, your organization may have a market incumbent, and your business goal is to take them over.

Suppose a competitor is making some serious noise inside of your industry, and you need to destroy their momentum before it gets out of hand;

what you need is a wartime general with a particular skill set.

The type of sales leader most needed in most organizations is a wartime general who needs to be scrappy and held accountable for revenue and developing the sales culture.

Sales Leader Role Definition

Another thing to consider defining is the role of your first VP of Sales. The easiest way to find the wrong VP of Sales is to look for the perfect candidate that does it all, instead of the one who will communicate and work effectively with you, the CEO.

It is essential the head of sales and the CEO speak the same business languages. Otherwise, you risk no one else in the company knowing what is going on, including the sales team.

Generally, the role of the sales leader falls under these four categories:


Operationally minded managers are great planners. Their organizational skills help set company norms and streamline the sales process as you scale your sales team. They will have a proven sales track record, and they will want to systemically simplify your company’s sales methodology, sales tools, and sales cycle.

Ask yourself:

  • Is this person responsible for building out systems and processes, onboarding salespeople, and ensuring their success?

If so, then an operationally minded individual is what you need.

Creative Strategy Management

These sales leaders excel at strategic thinking backed by data and experience. That does not mean that only a senior leader will fit this role. What it means is that they are solutions-focused and results-driven. They have a talent for strategic thinking and creative thinking alike.

Ask yourself:

  • Do you need somebody to find your differentiator and separate you from the market?

If so, you’re going to need somebody who will develop a creative strategy.

Culture Management

Don’t ever underestimate your culture-driven sales leaders. They lead the charge integrating sales and customer success into every part of the organization. These culture managers are often operationally minded and have had experience scaling and building up sales teams outside of the organization.

Ask yourself:

  • Are you looking for somebody to build out a proper management structure with sales managers, sales operations, and all the other roles required to support salespeople?

Deal Management

Deal managers are addicted to sales and closing deals. They will demonstrate a proven sales methodology in a proven competitive environment. The rest of your salespeople greatly admire these sales leaders, encouraging others to close deals.

Ask yourself:

  • Do you need to capitalize on the market potential right now to get to the next stage?

If so, a deals-minded manager is what you need.

Define your expectations

sales leader and sales reps

Equally as important. Define your expectations for the type of support you are willing to provide your sales leader.

Ask yourself:

  • What type of support are you looking to give this person?
  • What are your expectations of what they will do?
  • Are you looking for a person to assume one sales leader role?
  • Or, are you looking for somebody who will take you to that next step by covering all of the above roles?

Be aware that if you are looking for someone to cover all the above roles, that individual will be more junior and scrappier.

In comparison, a more Senior VP of Sales will be best to build a management structure from the top down.

This is the first thing you need to know. If you don’t understand this, you can’t expect to get the right sales leader.


Now, assuming you’ve already understood what type of VP of Sales you need, you need to be able to identify this individual.

Again, there are many different sales leaders, and their attributes will vary significantly depending on your situation.

Remember: the type of sales leader most needed in most organizations is a wartime sales leader who needs to be scrappy, held accountable for revenue, and developing the sales culture.

To identify this Wartime Leader, you need to understand the characteristics they will portray.

This person is not going to call themselves a servant leader.

They may come across as slightly egotistical, but there is a difference between ego and confidence.

Ego is someone who’s looking for all the glory. Confidence is somebody looking for a challenge.

sales hiring and sales team

In the interview, ask yourself:

  • Is this person talking about what they can do or have done?
  • Are they telling you about how they would execute specific initiatives?
  • If so, does it make sense?
  • Do you like the idea?
  • Does it feel aggressive enough and as if this person is putting their neck on the line by making bold claims?

If so, you may have your wartime sales leader right there.

I’m always wary of salespeople who talk about the past. And so should you.

I don’t care what you’ve done in the past. All I care about is what you’re going to do for me today.

Somebody who’s egotistical and has no intention of delivering any results will talk a lot about what they’ve done in the past; they will offer more questions than solutions.

And their go-to line will always be: “well, we’ll just have to test it and see what the outcome is.”

As a founder, you never ask your first sales leader to test. You are asking them to execute with precision.

In the interview, ask yourself:

  • Do you know how to get results?

If they don’t, don’t waste your time.


sales team and sales leader in a sales meeting

One place they most certainly are not is on the open market.

Your future sales leader is not unemployed. This person is gainfully employed with some golden handcuffs, making a serious amount of money.

But the only reason they’ll speak to you is that they are restricted with their current leadership structure.

This means your interview process needs to recognize the fact.

If I were you, I would look to work with a sales recruiter and focus on an organization that has recently passed up promoting a Sales VP from within and brought someone in from the outside.

There, you may find some diamonds in the rough.

Now I understand that most of these people you’ll be looking at have already been passed up for promotion.

That does not mean they are the wrong person for your job.

This likely means they are not ready to lead at the level you need them.

However, many organizations pass up the right person to bring someone in from the outside.

So, while most of them passed up, rightfully so, there is a person on that list that should not have been, and they’re pissed off that they were passed up.

That’s the person I’ll put my money on.


sales leader and sales reps

Once you’ve found that potential sales leader, your instincts might compel you to immediately send an offer letter and comp package, hoping they will accept.

But you can close a lead candidate more effectively.

Remember that an interview is a two-way street. Your candidate needs to be ready.

Logic then tells us to ask them if they are ready to accept the offer.

Ensure you pencil in time before they accept the position to ask lingering questions that only you can address.

Take you and the candidate out for dinner. Get to know them and also their family or significant other.

Your candidate’s employment affects their family. You must show you understand this and build trust.

Explain the full scope of the role. Great sales leaders are drawn to growth and opportunities to scale their entire sales department. They will want to capitalize on the product-market fit that’s already in place.

When the candidate is ready to accept, make the offer in person.

My compensation for a VP of Sales is relatively straightforward, but take the time to go through it with them.

Talk about their compensation upfront.

The right Sales VP is worth it.

Remember: you have not closed this sales leader until they show up on the first day in front of you. Streamline the transition process into their new organization and their new role.

Final thoughts

So, while you may feel the ideal situation is having a unicorn walk in and take your business to the next level, the reality of the situation is you’re going to need a wartime general before you can get there.

This person may be a little bit harder to find, but they will pay off much more in the long run.

Your effort on the front end will dictate your success in the long term.

Your first sales hire – especially in sales leadership, is tricky, specially when you don’t know what it is that you’re looking for.

The Rose Garden Sales Leader Hiring Rubric categorically unroots the best for the job from the best available in the interview process. You don’t want the best known because good enough isn’t good enough.

So sit down. Be disciplined. And understand this is not an easy process.

But when you do find the right person, you’ll understand why you waited.

Download Our Sales Leader Hiring Rubric
Systematically assess your sales leader against measurable sales leader traits and expectations. Ensure your organization’s growth.
Ali Mirza

About the author:

Ali Mirza is the Founder & CEO of Rose Garden, a national sales consulting organization, and featured in Forbes, Inc, Business Insider, The Huffington Post, Business Rockstars, and The Wall Street Journal.

Ali is a highly sought-after public speaker presenting at multiple national conferences on innovative ways to accomplish transformational growth on your sales team.

Rose Garden provides unparalleled support and guidance to growth-minded founders via sales strategy differentiation, world-class sales culture creation, and exclusive playbooks, processes, and scripts to position them for limitless growth.

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