TL;DR: If you’ve Learned all you can, Earned all you’re going to, Been Burned, or have Concerns about leadership, culture, or direction… it might be time to ghost your current gig—professionally, of course. But how do you know when to leave a sales job?
This is a topic I get asked about every single week. Credit to Scott Leese for the original framework, and I’ve added a fourth piece I think too many people overlook.
The “Should I Quit?” Framework (When to Leave a Sales Job):
Learned. Earned. Burned. Concerned.
Let’s break them down:
- Learned – Have you learned everything you can from your leader, the company, or the role? If your brain’s on cruise control, you’re stagnating and it’s time to start setting a new course.
- Earned – Have you maxed out what you can make in this role? Salary, commission, equity, promo track? If there’s nothing left to earn, it’s time to earn it elsewhere. Pro Tip – If you’ve finished your 2nd or 3rd year of vesting, don’t think you need to stick around for the remainder to vest. It’s now time to optimize for income streams as Scott likes to say.
- Burned – Have they broken promises about comp, territory, title, promotions, or even just basic respect? We’ve all probably been in a relationship for 6 months too long before. You’re not paranoid if they’re really screwing you.
- Concerns – Gut check: Do you trust the leadership team? Is the company viable? Does the culture suck or feel ethically sketchy? If so, don’t ignore it, find a place you’re happy. Pro-Tip, sometimes we feel burned out from the politics of the org even when we are doing well. This is a combination of 3 & 4. Make a mental note.
Leaving a job is an emotional decision. It affects every other part of our lives. It affects our finances, it affects our friendships, it affects our career path and it affects our personal relationships. And sometimes those personal relationships are within the company and sometimes they are external to the company. And in most cases it’s both.
✳️ Just remember, you don’t need to hit all 4 to justify leaving. One is enough. But it helps bring logic to an emotional decision.
Before You Go Full “I Quit” on Slack…
There’s a smarter, more strategic way to walk out the door (ideally with a little extra in your pocket). Here’s what to do:
🔄 1. Update Your Resume
Obviously, yet most people wait too long. Don’t. Be sure you highlight your numbers, quota attainments, people managed, deal sizes, sales cycles. Anything with a number that shows success. Leave the diatribe after 5 bullet points of numbered success on your resume.
🤝 2. Quietly Network
Let trusted sales leaders and ex-colleagues know you’re on the hunt. The best way to say it is that “I’m discreetly looking.” They will understand what that means, and you’d be shocked how fast word spreads in a good way.
💼 3. LinkedIn: Quiet Glow-Up
You don’t have to scream #OpenToWork. And by all means, don’t ever use that anyway. It’s tacky and makes you look like your desperate. Just quietly optimize your profile. Pro tip: Link it back to your skills in sales training, sales enablement, or whatever niche you’re crushing.
🎤 4. Take Every Interview
Even the ones that seem like a waste. Why?
Because finding a job is just like sales. And yeah, I would even take sales interviews for roles that are beneath my current title as well. It’s a discovery skills process, and we all know we have to role play our sales skills to get better at them. The same thing holds true for improving your interviewing skills. Here’s a few specific reasons.
- You need reps telling your story.
- You need reps answering “Why are you looking to leave?”
- You need reps negotiating compensation.
- You need practice in uncomfortable conversations
Interviews are your free negotiation training. Take them all the way to the stage—even if you know you’ll say no. It’s a rehearsal for the real one. Remember, you are not negotiating salary. You are negotiating an entire employment package. That includes compensation, it includes options, it includes health benefits, it includes vacation, it includes a gym membership, cell phone plan, WFH office equipment. IT INCLUDES EVERYTHING, not just your base salary and commissions.
Just curious, how many of us have EVER been trained on how to negotiate an entire compensation plan? Yeah, exactly like I thought, zero-point-zero as Dean Wormer likes to say.
💰 5. Negotiate Your Exit
Yes. This is a thing. Most states are “at-will” which means an employer can terminate you at any time for any reason. And this also means, you can terminate your employer at any time for any reason just as easily.
Now of course, it’s proper to give a two week notice period. I firmly believe that.
And it’s not unusual for a sales person to offer two weeks’ notice and the employer immediately walks them out the door with an email to the group, “____ is no longer employed here effective immediately. We wish them all the best in their future endeavors.”
So offer your two weeks, but that doesn’t mean you have to do anything more than what you’re job description originally stated.
You do not owe them free transition support.
“Oh, you want me to stay 2 more weeks to help onboard or document stuff? Cool. Pay me.”
“Oh, you want me to transition my accounts over to Bob, who’s gonna get my bonus next month because the company policy is that I have to be employed on the date of the bonus to receive it? Oh, I see, yeah, you’re gonna have to pay me for that.”
In this case there probably is not a “severance” in the traditional sense of the word.
What can you ask for?
- Extra PTO payout (especially if they have the “take as much as you want” nonsense policy)
- A few extra months of COBRA extension
- Resume writing or LinkedIn help
- Interview skills coaching
- Equity acceleration (with proper tax convo)
- Pipeline commissions and bonuses. I’ve even said, I’ll take half so Bob can get the other half
- Letter of recommendation
- Anything that helps YOU transition smoothly
They won’t give it all—but now you’ve got levers to pull and things to concede. That’s negotiating, baby.
🛑 6. SIGN NOTHING. (Read That Again.)
The NDA and non-disparagement agreement? That’s not “standard paperwork.” That’s hush money.
They are paying you to keep your trap shut. Forever. For free. Hard pass.
Your line:
“So you’re trying to bribe me into silence? Hmm. I’m not sure I’m comfortable with that.”
And when they threaten legal action? Here’s your script:
“So let me understand this—you want to force me to sign something, and when I politely decline, your first move is a legal threat? You really think this company wants to spend money, time, and legal resources just because I gave two weeks’ notice and said no to a gag order?
That’s what you’re going with?
You want this dragging across HR, sales leadership, and dissemination through the entire ranks of the organization? You’re really signing up for that kind of distraction? Umm, ok, if that’s what you really want.”
Then pause. Let it hang. They’ll blink first.
👻 6a. And Remember…
You’ve got leverage. Even one bad Glassdoor or RepVue review can ruin their next hiring cycle.
You don’t even have to say anything directly—they know the risk.
If you don’t sign, they can’t silence you. That’s not petty. That’s power.
Also: Check your state laws. In most places, the only thing a former employer can legally say is your job title and dates of employment. Some can’t even answer “Would you rehire them?”
📃 7. If You Do Sign Something…
Make sure:
- It’s mutual – meaning they can’t say anything about you either.
- It’s bi-directional it protects both of you equally.
- And everyone in the company agrees to the same thing. They will claim they can’t control what other employees say, and you can say, “How is that my problem to solve? Legally, I can tell my spouse everything, I guess I can’t stop them from saying stuff about you either then, right?”
Even if you get NOTHING mentioned above. No additional severance, no Cobra, no nothing. YOU DEMAND THIS! Don’t ask, demand.
That’s table stakes. I’ve walked from companies over this alone.
🗓 8. Quit After the First of the Month
One more day = One more month of health insurance in most cases. You’re welcome.
Health insurance ain’t cheap. Believe me, I pay for mine directly.
💬 9. Maybe Be Less Snarky Than Me
…But then again, would that be as fun?
⚖️ 10. Talk to a Lawyer (or ChatGPT)
I’m not your lawyer. I don’t even play one on TV. But I can suggest asking ChatGPT about state-specific employment law as a starting point. And when in doubt, definitely ask a real lawyer. And now, a lawyer on Reddit does not count. And if you really want more of my advice on this, you can even ask RichardGPT here for FREE.
🤖 11. Use AI to Your Advantage
Your boss is now your customer. They are now your ICP. And we all know we have to pre-plan our sales calls in relation to our ICP and the topics to be discussed.
Upload your boss’s LinkedIn, yours, your goals, your talking points—and have ChatGPT help you plan how to bring this up based on their personality.
Also, have it tell you what you need to look out for based on your own personality so you can be better prepared for the flood of emotions you are going to feel when doing this.
This is consultative selling. But the product is you.
🧠 12. Roleplay the Exit
Ask ChatGPT to play your boss. Rehearse saying what you need to say. Practice staying calm.
This is why roleplay matters. (Which we also teach in sales coaching, btw.)
🏁 Final Rant
You’re not weak for leaving. You’re strong for staying until you’re sure it’s time to go.
You’ve:
- Learned all you can.
- Earned what you could.
- Been Burned.
- Or have Concerns worth listening to.
So go get what’s next—with confidence, leverage, and a little snark in your back pocket.
So now you know when to leave a sales job. But need help scripting your exit, practicing your pitch, or navigating the next big move?
👉 As you can tell, I get fired up over this stuff! Schedule a free consultation.
📱 Or call/text me directly: 415.596.9149
Because this is exactly the kind of sales training we do—for people like you.
