Quit VP Sales Startup

How To Tell When It’s Time to Quit Your Job as a VP Of Sales in a Startup


Is it time to quit your job as a VP of Sales in a startup?


If you’ve already invested a good chunk of time in this company, you may be hesitant to walk away from what you’ve built.


Or what if you value your position so much that you’re not ready to give it up, despite the warning signs you should bounce?


While I can’t decide for you, I can show you some red flags to pay attention to and a few tips about what to do before you call it quits. 


So don’t even think about handing in that resignation letter before you read this article. What you should be thinking about is whether you’ve seen these:


14 Telltale Signs It’s Time To Quit Your Job as a VP of Sales in a Startup


Keep an eye on how many of these telltale signs you’ve either seen, felt, or thought. The more red flags you pile up, the more you know it’s time to consider parting ways seriously:


1. The Role or Startup No Longer Aligns With Your Values or Inspires You


I’ve said it before, and I’ll say it again, alignment is the new loyalty.


Maybe the company’s values were once the same as yours. But people change, and you’ve likely evolved in your thinking.


It’s going to be impossible to show up every day and perform your best if your current role:


  • It no longer inspires you
  • Isn’t connected to anything you’re passionate about
  • Doesn’t align with your current values
  • Doesn’t mesh with your future goals


Motivating and inspiring your team will also be impossible if you feel this way, making this one telltale sign you can’t ignore.


2. You’re Underutilizing Your Skills 


If you find yourself bored and feeling unchallenged in your day-to-day activities, it’s likely not the right role for you anymore.


Maybe you were promised one thing when you were initially brought on, or perhaps the role has changed over time.


Whatever the case, not using your skills, growing professionally, or tapping into your full potential will hurt you in the short and long term. So if you’re feeling this way, it may be time to make your next move.


3. There’s Too Much Focus on Non-Revenue Generating Activities


Being weighed down by too many non-revenue generating activities can whittle away your drive and motivation, especially if it continues too long.


You signed on to increase revenue, right? So why is your day-to-day filled with tasks that aren’t remotely connected?


If you realize you’re in this position, it may be time to evaluate your options and find a role that lets you do exactly what you’re good at.


4. You’re Struggling To Fulfill Job Responsibilities


If there’s one thing we all know about startups, it’s that things are constantly changing. 


This never-ending state of flux may mean that your role starts morphing, sometimes for the better and sometimes for the worse.


If your new job responsibilities seem out of your wheelhouse, you might:


  • Feel overwhelmed and unprepared to handle your day-to-day tasks
  • Dread showing up for work, knowing there’s another tough day ahead
  • Find yourself unsure of what to do next more often than not


You have superpowers and skills, but not being able to master these new tasks may start to eat away at your confidence. 


That’s a huge deal considering how valuable and vital confidence is to VPs of Sales, so don’t let this slowly erode.


Speaking of confidence… 


5. You’re Lacking Connection With or Confidence In Leadership and Staff


Another big issue you can’t afford to ignore is confidence in and connection with your leadership and team members.


Do you truly believe in your leaders at the helm?


Are you connected with them?


What about your team?


It’s critical to be honest here because there’s no faking this stuff.


People will immediately see if you’re in alignment or out of step. And if you’re not on the same page, it’s going to feel off for everyone involved… making it hard to make an impact, especially when the going gets tough.


Instead of dragging this out, try to fix it, seek help, or it may be time to jump ship.


6. Major Changes at the Company


Ultimately, you can’t control everything that happens at the startup you’re working for. 


Changes pop up due to new investors, product pivots, supplier issues, marketplace dynamics, and more. Maybe your company tried remote work during the pandemic, and now the CEO wants everyone to return to the office.


No matter what waves of change you’ve been riding, at some point, you have to step back and consider whether they’ve made your work life better or worse. 


Have these significant changes altered your productivity, selling ability for the team, leadership, buyer journey, customer experience, etc.?


While change can be good, don’t be afraid to admit it when it’s not. It’s worse to stay somewhere that no longer serves you (and vice versa).


7. New Leadership or a Disrespectful Boss


A change of leadership is another strong reason many VPs of Sales leave for greener pastures. A disruptive new executive leader on the team who refuses to play well with others can send people running for the hills.


Sometimes you just don’t jive with someone, and there’s nothing you can do about it.


As we will share in a later point, it could be that the new GM doesn’t align with how you work. Or worse, they’re so disrespectful in their approach that the situation is unfixable.


No matter how much you fight it, you’ll be wasting time and energy here. And you could be putting both toward finding a better fit.


8. You’re Stuck with Outdated Technology and Processes


Another red flag is when you know you can do so much more in your position, but you’re limited by outdated tech that your Founder refuses to change, with no budget, and stuck with processes that hinder everyone’s performance.


This is a frustrating roadblock VPs come across, and unfortunately, there’s not much you can do if your startup is mired in its old ways. Without the right tech stack, repeated attempts to improve things to no avail, and a Founder that refuses to enable you and the team, it’s hard to keep the momentum alive or hit those lofty goals.


9. You’re Feeling Burned Out and Overworked By the Unhealthy Work Environment


Being chronically stressed, overworked, undervalued, and burned out is the last thing anyone needs right now. 


It’s a recipe for poor mental, emotional, and physical health in the short and long term. It also tanks productivity, motivation, engagement, and job satisfaction.


Yes, startups can be stressful and require a lot of hard work. But like anything that functions well for the long haul, it requires striking a balance. 


If you’re driving yourself into the ground in a thankless job, it may be time to consider something new.


10. Dysfunctional Culture and Toxic Work Environment Vibes


Poor company culture creates unhealthy work environments where people rarely thrive.


Whether it’s a culture of “sales is a necessary evil,” a revolving door that loses remarkable people, moving the goal post constantly, or an icky board… a dysfunctional company culture can wreak havoc on the entire business and everyone along the way, including you.


So even if your values align with this company, but the culture is starting to raise more than enough red flags, take a hard look to understand what’s happening, why it’s happening, and if you can fix it or not.   


Remember, Lt. Gen George Flynn, USMC (ret.) said it best, “Culture = Values + Behavior.”


11. The Situation is Unfixable


It’s natural for us to want to fix things. It’s human nature.


But sometimes, you can’t change a poor culture, disrespectful leadership, or mismatches in personalities and work styles. 


Some situations are just unfixable, and that’s okay. But it’s best to walk away when you come to this conclusion. We’ll talk about how to work through this situation a bit later.


12. Your Ethics are Being Compromised


This one seems straightforward — why would you want to work for any company that compromises your ethics?


But the reality isn’t quite so black and white.


It may start with small things here and there that you disagree with. Yet you choose to take one for the team and follow orders. 


However, those mismatches might snowball and get worse. Then you can’t deny that something in your gut is telling you things are off.


Those gut-instinct nudges wake up your brain to situations or decisions compromising your ethics. So when your North Star seems far off from the company’s, it’s time to find a startup that doesn’t force you into those situations or compromise your integrity. 


13. You’re Being Under Compensated


Not being paid enough is another good reason to raise an eyebrow.  


  • Do you understand how you’re getting paid?
  • Do the incentives align with the work and outcomes?
  • Are you at fair market value?
  • What is your upside?
  • If the market is shifting and the business is suffering, are there programs to make up for it later?
  • Have you had challenges getting paid on time?
  • Does your compensation plan constantly shift (not for the better)?


If the answers to these questions are not in your favor, it’s time to do your homework, have a serious conversation, and let that discussion determine what happens next.


Please bring this up before just walking away. 


Already had this conversation? If you know your company is maxed out on cash, you’ll need to ask yourself whether you’re comfortable performing at this level despite the mismatch in pay. What else are you gaining, and is it worth it? 


Big picture > Small picture


14. The Company’s Future Doesn’t Look Bright


Are you questioning the stability of your company right now?


Are irreconcilable issues or bad decisions coming to a head that could change the future you envisioned for this startup?


If the future in earnest seems more bleak than sunny, it might be time to dust off the scorecard.


Before You Decide To Call it Quits, Answer These Questions


What happens now that you’ve racked up a few red flags? 


Have you tried to fix what’s broken?


Should you start searching for another position?.. If so, what does that look like to ensure you get it right?


Is the grass really greener on the other side?


Is this just a hard season, or is it truly irreparable? 


Before you do, it’s best to take a step back and look at the big picture… listen to yourself in earnest; my approach to journaling is an excellent way to do this.


Answering these questions can help you see things more clearly:


What changed between your initial expectations and what’s currently happening? What can you learn from this?


Which of the 14 telltale signs mentioned have you witnessed or felt? Write these down so you can dive deeper into each one specifically. Ask yourself:


  • What’s different?
  • Why is this change not working?
  • How is this affecting me specifically?
  • What’s my part in the story?
  • If I stay, how can I make it better?


These answers will help you uncover the heart of the issues you’re dealing with. Then you might brainstorm possible solutions to save you from having to quit and start all over again.


If the situation is unfixable, ask yourself what you can learn from this experience.


Thinking about this question ensures you don’t repeat these same mistakes or take a role where you’ll be in a similar position.


Journal about these for a bit before moving on to the following reflection questions.


What have you done to keep your seat at the table? Or did you let it get taken away?


It’s one thing to get the seat, it’s a whole other ball of wax to keep it.  Not having a voice is a huge reason to dislike your current role. Yet many sales leaders I talk to are afraid to speak up.


But guess what? No one has your back more than you do.


And if you haven’t done everything you can to speak up about the red flags you’re experiencing, you’ll likely regret it later.


You shouldn’t have to lose a good opportunity just because you didn’t want to make waves. So do some soul-searching and give this some thought.


Think about using your voice and taking back your power instead of locking both inside of you. You’ll strengthen your fortitude and boost your self-confidence along the way.


Even if you don’t stay in this role, you’ll take this type of personal growth with you into your next position.


As a VP of Sales, it’s your job to be a leader.  Not a follower.


Where are you hoping to go? Is it worth walking away from what you built?


It’s easy to lose sight of how much time and effort you’ve put in when all you can see is a sea of red flags.


But you can’t lose sight of the fact that you’d have to start over from scratch somewhere else. So you need to make sure it’s worth it first.


Get intentional about a potential career move by using a job scorecard


This rating system can help you evaluate how your current or future job stacks up against your ideal role. This allows you to discover what works for you, not what everyone else tells you is a “great opportunity.”


Take a look specifically at these items to gauge whether it’s possible to get the job done right:


  1. Runway
  2. Run Rate
  3. Product-market fit
  4. Ability to drive change
  5. Resourcing to get your job done with tools and budget
  6. Realistic expectations about the GTM (go to market) strategy


Remember, the grass isn’t always greener. You could be in for more trouble or a different set of red flags when you jump ship.


But you might also land a VP of Sales role at the startup of your dreams.


Decision Time: Is It Time To Quit Your Job as a VP of Sales at a Startup?


To be clear, I’m not suggesting you run away at the first sign of trouble… in fact, it’s quite the opposite.


But you shouldn’t ignore the clear signs that things aren’t working well either.


Instead, it’s time to get intentional… sit down, reflect, and journal on what’s going on.  And dismiss the shiny objects and crappy advice while you’re at it.  


Then you can clearly see whether it’s time to quit your job as a VP of Sales or make improvements to avoid that from happening.


Now you have everything you need to make this decision confidently.


My job scorecard and the tips in this article will help you work through what’s going on, what you need, and what fuels you. Then you’ll know exactly what to do from there.


Remember, you got this!