How to not lose your VP of Sales for your SaaS startup.

Founders: 5 Ways to Retain Your VP of Sales


The market is competitive – especially for highly sought-after roles like the VP of Sales for SaaS startups. 


Sales turnover is nearly 3X higher than any other industry.  Not to mention, it’s one of the hardest roles for startups to fill


Startups Highest Priority Executive Hires




If an opportunity isn’t providing everything a VP of Sales needs to grow the business and thrive, they’re going to be ripe for the picking.


And they don’t have to try too hard either.  The market has reached a fever pitch with countless opportunities proactively coming their way daily with enticing statements to try to woo them to their company.


Yes, it’s great to get an offer signed.  But that’s only the first step toward developing one of the most important relationships for the future of your company. 


If you’ve worked so hard to hire someone, why let them dangle in the wind and not support them?  All that does is increase your odds of losing someone you worked so hard to hire in the first place.  


This is why it’s so important to focus on retaining this mission-critical person.


Top 3 Reasons Sales Leaders Leave


1. Issues with the Founder or Company Leadership


Alignment is the new loyalty.  The relationship between the founder and VP of Sales is critical to the company.  This hire catapults your business forward or sets it back.  How you work together makes or breaks what happens.


One point of contention that I see often is the language barrier between first-time or technical founders and sales.  Founders focus on the outcome, sales leaders and people think about the why’s how’s, and what’s to get there. 


It’s a common breakdown in communication that can lead to the wrong assumptions, disagreements, and misunderstandings down the line.  Big disconnects between a founder and sales leader are bound to spell disaster if it’s not worked out early.  It’s why I’m a big advocate of setting the stage early and often for expectations together.


If a sales leader doesn’t agree with the direction a founder wants to take the company, they’re not included in the strategic planning process, or simply doesn’t jive with their personality after several difficult conversations, they’re going to start looking elsewhere. 


This is why it’s crucial to make sure that the VP of Sales you hire is a good fit BEFORE you send them an offer.  


Pro tip:  Use a hiring scorecard to drastically reduce your margin for hiring error.


2. Poor product to market fit


The market speaks the loudest.  Have you taken the time to listen to it before spinning up a sales team?


Many founders make the mistake of hiring a sales leader without validating the product or looking for a shortcut fooling themselves that it’s a leader’s job to find PMF (product-market-fit).


It doesn’t matter how excited you are about your product.  If there’s no demand for it, nobody will be able to sell it – not even the strongest sales leader with the most impressive track record.


PMF is a key milestone BEFORE you start the hiring process for a VP of Sales.  The more you understand your market, buyer, process, gaps, etc., the stronger you will be to understand the right work that needs to be done to hire an outstanding VP of Sales when the time is right.  


The second a VP of Sales realizes that there’s no product-to-market fit, they know the company is in trouble.  And that’s when they start taking calls from people like me with opportunities that do have PMF.


Remember, honesty is always the best policy.  The truth is always revealed and it’s a heck of a lot easier to talk about it now than later when it’s beyond painful for everyone involved.  The interview is not the time to tell tall tales. 


3. No opportunities to grow and thrive in the role


It’s table stakes for sales leaders to want a true seat at the table.  It’s one thing to say you’ll give it to them, it’s a whole other ball of wax to pull out the chair for them. 


When they feel left in the dark, like their input doesn’t matter, and they’re being glossed over when it’s time to make important company decisions that translates to them not feeling valued or respected by the company. 


Strong leaders will leave if they feel like their position has stagnated without an understanding of the true bigger picture.


Leaders crave being productive.  All too often, factors out of their control get in the way.  According to HBR, “the average company loses more than 20% of its productive capacity – more than a day each week to ‘organizational drag,’ the structures and processes that consume valuable time and prevent people from getting things done.”  the VP of Sales is no exception to this dilemma.


Retention begins with a bulletproof hiring process

How to create an A+ Hiring Process


Finding the perfect hire is a myth.  Nobody is going to be perfectly aligned with your business and ready to accelerate growth from day 1. 


Your hiring process should focus on filtering candidates for their raw skills, drive, and motivation to succeed, while leaning into your startup at the same time.  Once you confirm you’ve found this in a VP of sales, HIRE THEM and support them…  the opportunities for growth are endless.


So don’t get caught up in the big statements of metrics from a sales leader’s past experience.  What are they bringing to the table today?  How would they do what they claim?  Is that the right work that you need to accomplish?  And How does that translate to their potential for long-term success in the future? 


You want to make it clear during the hiring process that you’ll be there to support their growth in the role. 


Ask questions like:

  • Why does this matter to you?  
  • Given what we’ve talked about, what do you think?  
  • And most importantly, how can we help you get there?


Get as close to the real work that needs to be done versus hypothetical, theoretical, behavioral-based questions that don’t really tell you much about the merits of what a person brings to the table.  


Fun fact:  With so many communities, slack channels, and articles written on the topic of interviewing, it’s easy to ace a presentation or behavioral-based question.  You can’t game a real conversation to peel back the layers together to get to the brass tacks of how and why.


Look at the interview process as the beginning of the relationship with any candidate.  Kick things off with open, honest communication instead of trying to sell them on the role.  When you’re aligned, you won’t have to do the hard sell.


A hiring scorecard is your North star to stay things on track so you get the hire right the first time to avoid a seven-figure dilemma later. 


What to do AFTER the Hire


Button up your onboarding process


The contract getting signed is only the beginning.  It’s up to you to welcome them into your company with open arms while creating a smooth onboarding process that brings them up to speed.  


That means not going radio silent between the offer signing and their actual start date.  Co-create a plan together to make sure the hot buttons and priorities for both parties are addressed and included.  Introduce them to other members of the team, provide company resources for them to explore, keep them in the loop on updates and key projects, understand what they need to get started, make sure they’re clear on benefits, etc.


First impressions carry a lot of weight.  What you put into this critical part of your journey together will be what you get back.


A few other onboarding tips:


  • Make your new VP of Sales feels wanted and welcome.
  • Give them realistic time to get up to speed. 
  • Use the details uncovered in the hiring process as a guide for what you’ll work on together.
  • Set expectations early and often.
  • Make sure they have access to all company resources.


Invest in professional development opportunities


94% of employees surveyed via LinkedIn’s annual Workplace Learning Report said they’d stay at a company longer if it invested in their professional development. 


If there’s no effort made to support growth, a VP of Sales committed to being at the top of their game is going to feel like they’re falling behind.  If you hire a VP early on, make it clear how they’ll be able to advance their career at the company.  Invest in leadership training.  Hire a coach for them.  


If something falls short, figure it out together with them.  And who knows, that might mean hiring a new leader to get everything in sync. 


Pro tip:  be clear about this in the hiring process.  It will make you stand out as so many Founders refuse to invest in their leaders like this.


Give your sales leaders a seat at the table


The best VPs of Sales want to know that their input is respected, valued, and desired when it comes to key company decisions.  Leaving them out of the conversation sends a message that you don’t care what they think.


Always keep them in the loop and make it clear that they’re appreciated and recognized at every step of the way. 


A VP of Sales is an incredibly important role in the continued growth and success of any company.  So once you hire someone, make sure you put them in a position that maximizes their impact. 


Communicate early and often


It starts from the top.  As a Founder, you set the tone.  It’s important to be proactive to understand what’s happening with your people and what’s falling short. 


It’s important to establish open and honest communication right from the start.  Create a culture of accountability and transparency.


Show them that you’re open to all feedback in your conversations – good, bad, or otherwise.  


Research illustrates the power of psychologically safe workplaces.  Those that lean into this are more resilient, productive, and you reduce burnout for your employees reducing churn.


Psychological danger versus psychological safety

If a sales leader feels like they have to hold back critical information to avoid offending you, it creates a harmful barrier.  


Even if you disagree, set the example from the start and they’ll always feel comfortable asking for what they need and pointing out issues when they see them.  It’s okay to disagree, it’s the ability to understand why that’s powerful and where progress happens.


These conversations are also a great place to ensure that your expectations, goals, and objectives are aligned.


As a Founder, this is the flywheel you want to create.  The compounding effects will create stability, continuity, and trust across the company AND your customers. 


Show appreciation


66% of employees say they would quit their job if they felt unappreciated.


Take the time to show gratitude and a genuine interest in the hard work your VP of Sales and team are putting in – even if you’ve hit a rough patch.  Being stressed out from the job AND feeling underappreciated is a recipe for burnout. 



Be genuine and specific in your appreciation and take the time to really check-in and connect with your sales leader on a regular basis.  


The same rules apply if things are falling short.  Understand what it is, be specific, avoid absolute statements, and seek to understand.  I realize I’m mentioning this under-appreciation.  This is a form of it when you care and show up to pinpoint challenges BECAUSE you appreciate them versus sweeping it under the rug to only fester and grow.


I can’t stress enough how critical this relationship is to the success of your startup.  Give this executive the time, respect, communication, support, and appreciation they deserve.


Wrapping Up


Above all, people want to be seen, heard, understood, and valued.


Appreciate your newly minted VP of Sales, provide support and opportunities for continued career growth, and put effort into developing a mutually beneficial relationship with them.  That’s how you retain your sales leaders to achieve sustainable growth while defying the turnover odds.


The fallout from losing a VP of Sales can be disastrous for a startup – be proactive and it won’t happen to you!


Remember, when you show up and take care of your people, they show up and take care of your business, each other, and your buyers.