How to hire a VP of Sales in SaaS | CEO Guide

Every SaaS company reaches a point where they hit the ceiling and need help overcoming their unique sales challenges. I want to help.

Every SaaS company reaches a point where they hit the ceiling and need help overcoming their unique sales challenges.

You’ve got the business to at least $1m ARR or close to it.

The conditions seem right you accelerate pre-existing sales and have a growing sales team closing deals. Your sales strategies and tools are perhaps less imaginative but effective. It’s not just repeatable – but repeating, so it’s ready to scale, finally.

You’ve appeared to do all the right things. Then suddenly, you do not see the results you need any more – and you need leadership to step up.

Maybe you have a VP of Sales already, and they can’t get you there. Perhaps you are finally ready for your first VP. Either way, it is your most challenging hire. Most expensive hire and possibly the worst hire you will ever make. A high failure rate is inevitable. I want to help you.

I am going to be honest with you. There are a million things that I can say on this topic, but the most important thing is that each business, including SaaS companies, is different, meaning someone with a creative approach at the helm who gets it is a must – or you’re steering a sinking ship.

So, if you have specific questions about your VP of Sales, sales tactics, or sales function, reach out to my team and me. Otherwise, keep reading and see if I can help you.

INSIGHTS IN THIS GUIDE

SaaS VP of Sales Comp Packages

sales team and sales leader in a sales meeting

I hate starting here. When you start thinking about your first VP Sales and getting the right person, it is not about your sales comp, but it is often the first thing that stops founders in their tracks writing that job description.

The unfortunate realities that startups face outside SaaS are not dissimilar to that faced by other businesses:

The woeful lack of competency and the severe talent shortage is ripe among the VP of Sales.

However, while business outside of SaaS struggles to come to terms with the reality that they need to recoil from potential hires wanting anything less than a $150k base, the SaaS startup world is often throwing crazy money at people they think will fix the problem. And it’s not that they were hired and hit some obstacle along the way, but actually, they were never going to be the person to fix it.

SaaS companies are throwing everything at SaaS VPs who can talk and not even have to walk. It’s crazy.

But let’s get real. You will have to pay them a base salary. They usually need some commitment when they work the enterprise customer deals, plus over-rides on their team, bonuses tied to specific metrics, and equity.

All said and done, you are looking at a $500k+ comp package on a good VP Sales.

Is it an expensive hire for someone who won’t sell most of your deals? Yes, but necessary – if you get the right one.

If you get the wrong one, it is your most expensive mistake.

Honestly, I have seen worse, and this is just what someone at this level expects. And did I mention that this assumes you can lure a VP of Sales to leave?

There is a reason why the average tenure of a VP of Sales is falling daily. In today’s competitive markets, people have no clue how to sell, close, or what it takes to be a true VP of Sales.

In short, most people are soft. You need to know where to find someone and how to ensure you don’t choose the wrong person – stop focusing on what you’re going to pay them and focus on getting the right one.

Where to find a VP Sales for SaaS

This is easy to answer but is hard for any CEO or founder. It may take you six months to find and close a VP of Sales – perhaps longer. 

This is because you can’t compromise, and they likely have a very comfortable role, perhaps not as a VP, but they are already valued somewhere.

So do everything to find them. Hound your network – Angel List, LinkedIn. Stalk your competitors. Pay recruiters.

Rose garden quotes
A great VP of Sales is 100% accretive.

Jason Lemkin

SaaStr

Be relentless and suspicious.

Don’t take advice at face value for such a crucial hire. While paying recruiters can be helpful, I’m also skeptical of anyone claiming to have the perfect candidate.

It is not uncommon to meet 20+ candidates. Just know the more you encounter, the more you learn what you want, especially if this is your first VP Sales hire.

One last thing: Always court great candidates. Meet all of them. And drive to see them. You want to show these people that you want them and want to invest in them. Never forget that value is a great motivator – and like any sale, you need to inspire.

It may take up to six months to find and close a great one. You can’t compromise. Otherwise, they will squander your precious lead generation, capital, and time.

So, do it. Do all of it. And start now.

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

VP Sales Types in SaaS

There aren’t three, six, or twenty-six types of VPs; there are two.

  1. Good VP Sales that know what their job entails and what they have to do;
  2. Then the rest.

One ancient idea relative to the SaaS sales was three types of VP sales: The Scientist, The Engineer, and The Operations Managers.

The basic gist:  The Scientist experiments. The Engineer builds a repeatable sales process. The Operational Manager executes.

The current stage of your business also requires a specific type.

I have talked to many thought leaders in this space about the over-simplification of the VP of Sales. Most know that it is not that simple and that content is content…

So, here are my thoughts about: The Scientist, The Engineer, and The Operations Managers:

The scientist

The scientist is a Sales Ops Manager; if you hire this person, you will have a very regimented and efficient sales process, deal management, and buyer journey.

It will be clean, documented, and logical. It will lack personality; no sex appeal to sell.

You will hit quota if it’s set low enough. You will maintain a good business and only sell profitable deals. Your sales organization will be a good core group of salespeople with no HR issues.

This lead is always careful not to scale too quickly.

The Engineer

sales leader or sales team speaking to prospect

The Engineer is serious about data. Constantly require customization and optimization to get 0.1% better.

But this person is so far in the weeds that they completely miss the forest from the trees – data-driven VP Sales equals poor planning.

You will have high salespeople turnover because their approach will be abrasive. They will constantly talk about SPIN Selling and Challenger Sales Methodology.

They will get you to deal with large organizations and enterprise customers, perhaps close one every year but will burn almost all the smaller (cash flow) deals.

This person will want you to constantly pay for new tech, loading up your tech stack because he NEEDS to keep track of everything.

If you ever say no to something, they will blame everything on ‘lack of insight into the numbers.’

They will grow the team slowly until they hit the benchmarks for one quarter and then want to go on a hiring craze. Scale rapidly and then quickly lose control.

The Operations Manager

Is a lazy idiot – do not hire them.

sales leader and sales reps

Look, there is no full-proof predictor of success in a VP of Sales role. You have to be willing to make the mistake of getting this wrong, but there are ways to avoid a complete catastrophe. I have never seen someone get this right on the first try – especially without my help.

Saas VP of Sales traits

Solutions-focused & results-driven

The sales director is your buffer from everyone else in your organization who believes you’re overly ambitious. It’s an unwavering commitment and mentality ​​–– “there’s always a way.”

Do not hire The Engineer that produces data and reports to explain away missed targets and projections.

Data is good, but you need to be results-driven, not data-driven – thus, your sales leader is solutions-focused.

Solution-focused means that your sales leader needs to be creative and strategic in their sales strategy and then put the measures in place to execute.

Cultivating sales culture

Above all else, your sales leader systemically cultivates the sales culture. This is true of even the worst VP of Sales because culture is formed whether you are actively seeking to develop it or not.

In sales, culture is essentially the way things get done in your organization – and this needs to be based on accountability and transparency.

Accountability includes:

  • Meeting quota.
  • Meeting targets.
  • Aligning yourself to the company values and mission.
  • Playing your part in the sales team.

It is the sales leader’s job to enforce that accountability and therefore uphold the culture of the entire sales team.

Suppose the sales leader is beholden to everyone accountable to standards. In that case, they must be capable of achieving those standards as well – this links to their selling capabilities which we will get to shortly.

sales hiring and sales team

Talent recruitment & development

A significant component of sales culture is the hiring and development of each salesperson to meet the specific needs of the sales organization.

Suppose a salesperson or sales rep feels they get limited value from the sales leader. In that case, they will not utilize the sales leader to their fullest potential because they won’t feel confident in the leader’s abilities and training.

When the leader isn’t beholden to any particular rep, they can push the boundaries and make the sales representatives achieve more. This also creates the need to have crucial conversations while also implementing the forcing functions that keep the team in line without constant hand-holding.

The leader must prioritize sales hiring to build and scale a team of the right people and retain highly accountable, professional salespeople while consistently weeding out unimproved low performers.

Sales talent

All sales leaders need to succeed as sales representatives in their past. Prior experience and previous roles are irrelevant.

I want hard proof that they can sell because, on paper, a VP of Sales with experience in a big company does not mean they can drive revenue upwards.

There are myriad factors for revenue growth: competitive market, marketing strategy, and founder skills, to name a few.

In SaaS, the leader knows:

  • what they are selling and what their customers buy (software, hardware, services).
  • the market you’re selling to (industry, geography, role, people)
  • how you’re selling (SaaS vs. On-Premise; high-volume, low price vs. premium).

You may be thinking: but my VP of Sales shouldn’t be closing deals with the rest of them; they need to be leading.

I agree that your VP of Sales is most likely not pulling in all your deals. They are hiring, culture developing, and scaling your processes in an ideal world.

But your sales representatives need to aspire to a leader that can sell. Think about the power imbalance. If your top performer weren’t your VP of Sales – you would have mutiny.

As a founder, I need to know a VP of Sales can close a deal versus allowing solid sales teams to experience failure as a learning opportunity. Only high-performing sales experience provides you with this insight.

sales team and sales leader in a sales meeting

Interview Process & Questions

The interview process can be long and arduous. Expect to interview your candidates formally, informally, and thoroughly courtship. Since when have you learned everything you have needed to know about someone in one hour.

Take them to lunch… take them for a drive… get them out of their comfort zone.

Interview questions

Sales Talent

First and foremost, your sales manager must be able to sell. Your sales leader is the best salesperson on the team – no question.

So, what questions do you need to ask yourself and the candidate? These are my top five areas:

  1. Discovery process
  2. Pitch & Positioning
  3. Closing
  4. Negotiating

Ask yourself:

  • Will the candidate ask questions that get the prospect talking about the challenge you solve?
  • When the candidate completes their discovery process, is it clear what the prospect’s challenges are and what solution should be proposed to earn the prospect as a client?
  • Will they tie your SaaS solution back to specific pain points?
  • Do you believe that the candidate can position your SaaS solution where your prospect will perceive your solution as more valuable than any competitor?
  • Does your candidate pitch? Do they motivate and inspire the prospect to WANT to move forward?
  • How frequently will the candidate “wait” for the prospect to make a decision?
  • When the candidate has a prospect choice to go with a competitor, will you have a tangible reason why you could not work with the prospect?
  • Will the prospects be able to negotiate the price down?
  • How frequently do you believe the candidate will sell deals above the listed price?
  • Will this candidate be the ‘go-to’ person in the office for dealing with client concerns?
  • Will this candidate be able to approach clients with complex requests and get them resolved in favor of the company without any ill will towards the company?

These are just some of the questions you may ask yourself and your candidate to prove. Always consider, how do you know this to be true?

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

Strategic & Creative Thinking

Can your next VP of sales find a window when a door is closed? And you must test their ability to produce creative solutions when all else fails.

So, what questions do you need to ask yourself and the candidate? These are my top four areas:

  1. Behavioral
  2. Decision making
  3. Feedback loop
  4. Structural

Ask yourself:

  • How frequently will the candidate look at a salesperson’s mistakes as an opportunity for growth?
  • When a prospect cancels a meeting, is this candidate’s initial reaction to reschedule the call?
  • Will the candidate want the revenue difference subtracted from the monthly goal when a salesperson quits?
  • When a challenge is posed to the candidate, can they make a decisive decision when all the facts aren’t available?
  • When they have two options in front of them that seem desirable, do they select the option that requires more work?
  • Does the candidate watch/listen to their own sales calls? What was an example of a sales call that went wrong, and why?
  • How frequently do you feel the candidate admits they were wrong about a decision?
  • How often will the candidate test incorrect hypotheses to validate their current known system?
  • How frequently will the candidate look to improve methods to see if they can find a new edge?

Lastly, before answering any of these questions, always consider how you know this to be true?

Sales culture development

Great sales leaders value sales culture and actively build an accountable and transparent culture in sales teams.

So, what questions do you need to ask yourself and the candidate? These are my top five areas:

  1. Clear expectations
  2. Accountability
  3. Crucial conversions
  4. Forcing Functions
  5. X-Factor

Ask yourself:

  • Will the candidate make it clear what kind of sales culture they want?
  • Will the candidate communicate the repercussions of not adhering to the required results?
  • Will the candidate hold everyone accountable to the same standard (Results, KPIs, Activity, Policies + Procedures, etc.)?
  • Will the candidate show sympathy (not empathy) when a salesperson is struggling?
  • When the candidate has to correct a salesperson’s behavior, will the candidate come back with a “middle-ground” solution?
  • When the candidate is asked to handle a difficult conversation, are you confident that they will do as well as, if not better than you, in that conversation?
  • Will the candidate tie in incentives to extraordinary efforts and results?
  • Will the candidate communicate that the required tasks are the ‘price of admission’ to work there?
  • Will the vibe/intensity/mood more vibrant and upbeat when the candidate is in the office?
  • Will everyone in the company (not just the sales team) respect and want to impress the candidate?

Lastly, before answering any of these questions, always consider how you know this to be true?

sales team

Recruitment & Development

The sales hiring process is the VP of Sales responsibility: they recruit to fill gaps and attract and retain top talent.

So, what questions do you need to ask yourself and the candidate? These are my top five areas:

  1. Sales team vision
  2. Hire the right people for the right seats
  3. Developing the talent
  4. Retaining the talent
  5. Transitioning the low & unimproved salespeople

Ask yourself:

  • Will the candidate consistently go back to their plan of what the team should look like in job functions?
  • Does the candidate have a track record for hiring successful salespeople?
  • Will the candidate use behavioral, functional, or personality assessments to vet candidates before hiring?
  • Will the candidate spend one-on-one time with the new hires on their team?
  • Will the candidate clearly understand each salesperson’s strengths and weaknesses on their team?
  • Does the candidate have a systematic way of measuring who is happy, fulfilled, and engaged in their role?
  • Does the candidate provide every person a reasonable path to succeed?
  • Will the candidate have difficulty terminating a sales team member who isn’t putting in the necessary efforts to get better?
  • Will the candidate take decisive action when a salesperson’s attitude harms the morale of the rest of the team?

Lastly, before answering any of these questions, always consider how you know this to be true?

Interview questions

3 VP Sales traits you want

Here are some things to look for in a VP of Sales who may work out:

Has a humble cocky attitude

Stick with me because there is a clear distinction between cocky and humbly cocky.

The key difference is they don’t brag about themselves.

Ask a bunch of questions

They ask you a bunch of questions from the start. It may seem like they are uninterested in the position and more interested in what the company is doing right now: a genuinely positive sign.

They don’t ask you what or why you are looking for someone. They don’t need to twist themselves into something that will satisfy the role: they are the role.

sales team sales leader success

Makes you feel good while evoking pain

Highlighting flaws is good because it evokes pain; you never get the sale without it.

But the best type of salespeople are the ones that expose you raw but make you feel good about it.

It’s a type of sex appeal and finance – that is a particular type of gift in a sales leader.

If they don’t have it in the interview, they won’t have it in front of the client.

Scale your SaaS Sales department right

There are probably a million more things I could tell you to look for and watch out for, but I’m getting lazy.

If you still have many questions on the subject, it’s time to call in some outside to help shake things up.

Rose Garden Consulting will light a fire under your team and redefine your process into a SaaS sales experience.

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.

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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