To Hire a More Senior Sales Leader Or Not? 


Insights in this guide

I have many clients who reach out to me with questions. A while back, I had a business owner ask me:

What tips would you have for hiring a seasoned VP of Sales in my field?

So, let me tell you my answer to them with a few extra thoughts.

Hiring the wrong sales leader is the single easiest & lousiest mistake you can make, and sales hiring questions are common amongst business leaders.

So, should you hire a senior sales leader? It depends on your organization’s situation. A senior VP of Sales may suit an organization in a stable place with no market uncertainty and plenty of sales opportunities. However, most organizations need a wartime general who needs to be scrappy, held accountable for revenue, and developing the sales culture; usually, they’re less seasoned sales leaders.

Regardless of whether you are looking to hire a sales manager, Director of Sales, VP of Sales, CRO, CSO, you will be wildly surprised at the lack of talent on the market.

When I say lack of talent, I mean actual ability to do the job. Sadly, most will seem impressive during the interview process, but their ability to deliver results, including those with seniority, will astonish you.

Some fundamental facts should scare you: the average senior leader has about $97k in turnover costs. So, you need to get the right person.

Continue reading to learn when a more senior leadership hire is appropriate and the potential downfalls of focusing purely on looking at seasoned candidates.


sales team and sales leader

Senior sales leaders generally have the most experience on a sales team. They guide sales representatives, ensure sales quota is met, and devise creative solutions to sales problems.

This person may be your VP of Sales, but it is also important to point out that experience does not always mean they are the best for the job.

The problem is that everyone wants that particular sales leadership experience.

  • You want someone with portfolio companies.
  • Experience taking an early-stage company all the way.
  • Experience through multiple funding rounds.
  • Ultimately, either through an acquisition or an IPO.

I’m going to be honest: you are being unrealistic.

You’re always going to need to develop a new sales leader, no matter their experience.

When I say lack of talent, I mean actual ability to do the job. Sadly, most will seem impressive during the interview process, but their ability to deliver results, including those with seniority, will astonish you.


The Current Situation

I hate simplifying and categorizing sales leaders into types. Sales leadership is not simple, and you will likely go through many candidates and numerous VP of Sales positions while figuring things out.

sales teams and sales proc

My top sales hiring tip for getting the right sales leader today is to hire one that can get you to where you want to be tomorrow.

And to do that, you need to understand the organization’s needs, goals, and missions and align them with your leadership role. So, there are two situations you may find yourself in:


Your organization may be in a stable place, trending upwards. You have your sales process, and sales funnel wrapped tight. You may have no market uncertainty, and the sales channels offer plenty of opportunities.

Your sales process is buttoned up so tight that hiring salespeople is easy because what they sh*t and eat is scheduled. Your sales reps have a clear path to follow to success. And the sales model is vetted and legit.

You need somebody to maintain and steer the sales team forward – that’s it.

If this sounds familiar, and you find yourself in this situation, you need a peacetime general; they are usually a more seasoned leader.

sales team sales leader success


Alternatively, you may have a market incumbent you develop a business goal to take them over.

Perhaps competitors are making noise inside your industry, and you need your sales reps geared up to destroy their momentum before it gets out of hand.

Perhaps you need your business to go from sales exploration to sales execution, ultimately a sales scale.

If this resonates with you, you need a wartime general with a particular skill set.

Now let me say this: most organizations need a wartime general, not a peacetime general. These people tend to have less sales management experience, will be scrappy, and are held accountable for revenue growth and sales culture development.

However, most CEOs feel that they need a senior sales manager with experience to help them run this show. It provides them with more reassurance and comfort.

Now I am going to be clear: they are wrong.

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Sales Leader Skillsets


You may need a strategic VP backed by data and experience. More senior leaders could hold this skill set, but they also may not.

They are solutions-focused and results-driven, but I am going to be honest, I have met senior leaders who do not fulfill this role.


These people with this skillset are often operationally minded and experience scaling and building up sales teams outside of the organization.

You need someone who will be firm and hold your salespeople accountable.

sales leader and sales reps


This skill set is all about getting in there and selling. They may need to do the heavy lifting, but they will also inspire the team to focus on making the sales.

Remember, your high achievers want nothing to do with low achievers. So, imagine if your sales leader wasn’t a high achiever. How will they attract top talent when they the cant inspire it themselves?

So, you need to be certain your sales leader can garner the respect of the team by showcasing their ability to sell.


The people with this skillset set company norms and streamline the sales process. It’s all about scaling your sales team.

It is essential to emphasize these people will have a proven sales track record that is verified, and they will want to bring systems to simplify your company’s process, sales tools, and sales cycle.

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

If you need someone to cover numerous skills sets and roles, you need someone more junior and scrappier than seasoned.


Pitfall 1: Previous “success” isn’t a great determinant

The problem: People get blinded by a great résumé all too easily in the sales hiring process.

Perhaps you are excited by a sales candidate’s education and qualifications, or they have previous success as a sales manager or several high-profile startup sales.

seasoned sales executive may present success with a previous company on their resume. Maybe they dazzled you with stories about their success in private companies.

Don’t get me wrong: you need a sales executive with a proven track record. But that is often much easier said than done.

Previous “success” isn’t a great determinant.

There are many factors why people and companies are successful; it’s not just sales execution. Some reasons may be:

  • marketing lead generation
  • investor relations
  • market forces
  • VC money + connections
sales hiring and sales team

The solution: Three key elements lead to a successful executive-hiring process: sales rubric, multiple interviews and vetting, and reference checks.

Be wary of any sales manager or sales rep who talks about the past. They talk about portfolio companies and revenue achievement. These people are generally egotistical.

Look, it doesn’t matter what you have done in the past. I don’t care. All I care about is what you’re going to do for my sales organization today and tomorrow.

Egotistical new hires have no intention of delivering any results and talk a lot about the past. They offer zero solutions.

They will say: “we just have to test it and see the result and outcome.”

Rule number one: never ask your leader to test. You’re asking them to execute with precision.

During the sales hiring process, ask yourself:

  • Do they know how to get results?
  • Can they execute?

If they can’t, they are not the sales team leader.

Pitfall 2: It doesn’t pay to be an optimist here

The problem: We always look for the best traits in people. Even an executive search from reputable recruiters will always highlight the accolades of other candidates.

Don’t get me wrong; I am not saying you shouldn’t use recruiters, but you need to stay objective.

The solution: Always look for the flaws or potential weaknesses in a new hire, especially a leadership hire.

You want to know what they can’t do first. Nobody can do everything, and it is dangerous to assume they can.

Isolate what they are good at by finding out their weaknesses.

sales leader speak with prospect and sales team

Use a Sales Leadership Hiring Rubric to systemically guide you to answer whether they can create a scalable system?

For example, specific elements include:

  • Behavioral
  • Decision making
  • Feedback loop
  • Structural

Remember: Isolate what they are good at by finding out their weaknesses.

Pitfall 3: Undefined strategy for the leader’s success.

The problem: Have a defined strategy for your VP Sales’ success or have the blind leading the blind.

The solution: Define your expectations for this sales role and the type of support you will provide your sales leader.

sales leader and sales rep

Ask yourself:

  • Do you need a peacetime general or wartime general?
  • What particular skill set do you need of that wartime general?
  • Or, do you need someone to cover several skills sets and roles?
  • What support are you looking to give this person?

Remember, if you need someone to cover numerous skills sets and roles, you need someone more junior and scrappier than senior and seasoned.

Rose Garden Team Assessment
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Pitfall 4: Falling for a candidate’s personality or style

The problem: It happens all the time when a CEO prioritizes finding someone who is a perfect cultural fit over a culture builder and fosterer.

Am I saying that culture is not essential? No, I am not.

The problem is that CEOs and companies don’t know the sales culture. Peter Drucker once said, “Culture eats strategy for breakfast.”

I am not going to argue with the late, great Peter Drucker, but I would say that if your definition of culture is giving your employees free sh*t, work drinks, and ping pong tables, then, of course, your execution will suffer.

The actual definition of sales culture is how sh*t gets done in your organization. It is about building a team around accountability and transparency.

So, contrary to Drucker’s statement, your sales culture can be your company’s great differentiator.

sales teams and sales leaders

The solution: While culture is an important consideration, you need to focus on your leader’s ability to foster a winning culture, not their personality traits.

Sales Leadership Hiring Rubric systemically guides you through questions with specific cultural control elements.

For example, specific culture control elements include:

  • Clear expectations
  • Accountability
  • Forcing functions
  • X-Factor

These elements need thorough exploration, so there is consistency when vetting candidates. The rubric also ensures that you put the proper importance on cultural aspects versus skillset.

Pitfall 5: Assuming a season sales leader

The problem: One of the worst mistakes you can make when hiring a sales director or sales rep is assuming they can sell.

I have already said it once, and I will keep saying it: Sales talent is woefully lacking today, and there are charlatans everywhere.

But your leader needs to be your top performer, even if you need them, especially for culture control or creative sales strategy development.

You need your sales leader to know when to jump on a deal and close it versus allowing their team to fail as a learning opportunity. Only a high-performing sales executive can give you this.

You also need your sales reps to mirror your sales director, so they need to emulate a successful and accomplished leader.

sales team

The solution: So, how can you figure out if your leader can sell in the interviewing process?

Use the Sales Leadership Hiring Rubric to systemically guide you to determine whether this new hire can close deals, focus on selling and get results.

For example, interviewing about selling abilities includes:

  • Discovery
  • Pitch/Positioning
  • Closing
  • Handling difficult client situations

If you have got it down to two candidates and you want to determine which is the better seller, I suggest this trick:

  1. Take them for a drive in your car, but don’t tell them where you are going.
  2. Get them to talk about sales and the role while having to pay attention to driving.
  3. Make sure you take them on the freeway and give turn-by-turn directions.
  4. Give them last-second directions.
  5. Determine how they carry the conversation.

Ultimately, this is what a sales call is like, and it’s the best way to emulate a sales call.

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Do you need help hiring a sales leader?

So, while you may feel the ideal situation is having a unicorn walk in and take your business to the next level, the reality 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 is tricky, especially in sales leadership, especially when you don’t know what 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.

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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