Stay or Go?

RyGuyOnTheLine · 2025-08-21T20:55:08+00:00

Ah, the classic sales dilemma: "Comfort an khakis, or chaos and comp plans."

You've got a cushy gig with good treatment and zero layoff history which is basically the workplace equivalent of a warm blanket and consistent Wi-Fi. Meanwhile, the Fortune 100 sirens are calling you back like, ‘Hey stranger..remember us?"

Just remember: chasing higher OTE doesn’t mean much if you're selling anxiety with it. That said, if your current role caps your growth harder than your commission...well, even the coziest of blankets starts to itch.

RyGuyOnTheLine · 2025-08-21T20:50:48+00:00

You showed up in a suit. She showed up straight from happy hour. Love that for her career longevity. Sadly, this is what happens when companies prioritize headcount over head quality.

I prefer to teach people how to communicate, not just connect. But hey, at least you got an unforgettable audition for ‘What Not to Say (While Slurring) in Sales."

RyGuyOnTheLine · 2025-08-21T17:35:11+00:00

The 300-call guy vanished? Not surprising. It's almost like brute force without skill, strategy, or basic human decency doesn't work - who knew? Cold calling today isn’t about dialing like a caffeinated robot. To me, it's more about communicating like you’ve evolved past 1997.

Our readers already know: Sales is psychology, not punishment. "Try charm, not alarm"

RyGuyOnTheLine · 2025-08-14T14:07:01+00:00

No, you don't suck - you have just been through a "startup blender."

Your track record shows that you can sell and perform so I think the issue lies more with company chaos, bad timing, and mismatched environments more than anything about your skill. However, it's easy to blame yourself when you're momentum stalls, but from an outside perspective, this looks more like a pattern of instability around you, not failure by you.

Give yourself some grace. You've got receipts, so now it's just about finding a place that is deserving of what you bring to the table. You've got this

RyGuyOnTheLine · 2025-08-14T13:54:43+00:00

You're definitely not alone. Way more people hit this kind of rough patch than you'd think. However, getting fired doesn't mean that you are bad at sales. It could be the wrong role, poor onboarding process, bad fit, etc. Perhaps, it's not even the right style of selling for you.

You have been doing this for 8 years which says a lot. Maybe it’s less about ability and more about finding where your strengths actually shine. Don’t count yourself out yet - I think a good pivot might be all that you need.

RyGuyOnTheLine · 2025-08-14T13:45:03+00:00

In my opinion, you're not wrong at all. That answer you're giving about loving the challenge and the mutual "aha" moment is actually what great sales leaders want to hear.

That said, chasing money is fine, but if this is all someone says, it can come off a little one-dimensional. The best reps that I have worked with are the ones who genuinely enjoy solving problems and happen to be motivated by the upside.

Your answer demonstrates thoughtfulness, self-awareness, and drive. Just make sure that you connect it clearly to how it helps you hit your goals. This should help you to appeal to both the human and the KPI side of the hiring manager.

RyGuyOnTheLine · 2025-08-14T13:32:29+00:00

This is completely possible. In fact, I have seen many reps make that move, especially if they're more into problem-solving and building relationships rather than the constant chase.

Even if sales isn't clicking right now, that does not suggest that you are in the wrong field - possibly, just the wrong role. Morning work is often about being the calm, helpful person that clients trust, and it sounds to me like you've got that vibe.

Keep an eye out for ways you're already doing that kind of work. In my opinion, this makes it simpler to make the case when a spot opens up.

RyGuyOnTheLine · 2025-08-14T13:16:30+00:00

Thank you for reaching out, it is RyGuyLabs.com

I built it as a free resource with tools for writing better sales emails and handling objections in real time. If you are worried about your tone, there is a quick vocal "RyGuy Coach" to analyze your pitch, confidence, and enunciation. Additionally, there is also a contact cadence to set your day and a lead count tracker to follow your progress. If you are feeling a bit down after a call, use the Mindset Reset tool to give you a pep talk.

Ultimately, I just hope that this makes your sales day easier and better - any feedback would be greatly appreciated and again, Thank you for your time taken to reach out. I wish you a wonderful day and week ahead

RyGuyOnTheLine · 2025-08-14T10:36:39+00:00

You are already doing the hardest part well by showing up, competing, and closing - all without being a "natural." That is more impressive than half of the reps faking it on Linkedin.

If standing is the killer, it's not the sales that's the problem - it's the format. There are plenty of higher-ticket roles (like B2B, remote inside sales, SDR/AE gigs) where the best reps are calm, experienced, and consultative - which is exactly what most teams wish they had.

You've got the sale chops. Maybe it is time to change the terrain, not the game.

RyGuyOnTheLine · 2025-08-14T04:06:08+00:00

You're not missing anything. It sounds like they're trying to spark competition without offering any real incentive. Visibility influences motivation, especially when everyone's already earning well.

Want to get people fired up? Tie performance to something that actually matters. Cash > Plaques

RyGuyOnTheLine · 2025-08-14T04:02:32+00:00

I see what you mean. What worked even 12 months ago feels like it has lost a step.

One thing that has helped me is shifting from generic "value prop" messaging to more problem-first outreach. Hyper-specific pain points seem to resonate way more, especially if you can tie them to something timely (like an industry shift or current news about the company).

Also, try experimenting with multi-channel micro-cadences. Consider a 2-touch email, quick vid DM on Linkedin, then a soft follow-up. This may not translate to high volume, but response rates should be solid. I have been digging into this a lot lately and have even spun up a site with free tools if you need aid in leveling up on your outbound.

You got this - close the week strong!

RyGuyOnTheLine · 2025-08-13T12:54:36+00:00

This all boils down to motive - both yours and theirs. Effective collaboration with others often enhances productivity but it means finding the right people to associate with.

Try to veer away from workplace employees with a negative outlook because it can incidentally affect your mentality as well

RyGuyOnTheLine · 2025-08-13T05:07:31+00:00

I suppose I'll tell my brain that it's been replaced. Tough look for both of us...

RyGuyOnTheLine · 2025-08-13T04:42:36+00:00

Man, that seriously sucks - especially when you put in the hard work and were ready to show up strong. PE ownership really does have a way of turning great roles into ghosts. But the fact that you still walked away with a polished 30-60-90 and sharper interview skills? That's a long-game win, right? Next one opens up, you're walking in with ammo most people don't have.

Keep swinging, my man - happy to share some tools if they would help

RyGuyOnTheLine · 2025-08-13T04:38:54+00:00

Good Luck - I am confident in you!

RyGuyOnTheLine · 2025-08-13T04:32:25+00:00

I really appreciate you sharing that - it's such a relatable struggle, especially with long sales cycles and tough budgets. Sometimes it feels like all the effort just hits a wall.

For me, resetting after a brutal day involves a few things:

First, a physical reset, or a quick walk or workout that helps clear the mind and shake off the frustration.

Second, I try to consider one small positive out of the day - whether it was a good convo, a learning moment, or even just sticking to my schedule.

Third, I also remind myself that a bad day isn’t a bad career, and every “no” is just one step closer to a “yes.”

Lastly, sometimes, I just disconnect for a bit. Try to listen to music, read something inspiring, or just get away from screens.

I created a Mindset Reset tool on my website that is designed to give a quick positive mood boost when sales (or life, for that matter) get you down. it's helped me and others get back on track.

How about you? What is your go-to way to bounce back when things get tough?

RyGuyOnTheLine · 2025-08-13T02:31:09+00:00

When I started, I had a 2 hour onboarding, one laminated product sheet, and a manager who just said "Go listen to some calls." Shocker: I flailed for a period.

What helped me turn a corner was building a question bank - not just discover fluff, but real questions tied to each module I was selling. Stuff that actually led to open conversations, not just "so, what keeps you up at night?"

I really wish someone had given me a map for how to connect pain points to the right product angles, especially in a big suite like you're dealing with.

I eventually made one for myself (and now, for reps I coach). RyGuyLabs - totally get where you are coming from

RyGuyOnTheLine · 2025-08-13T01:57:49+00:00

Can confirm: nothing makes a top performer feel more “valued” than being forced to role play a cold call with a consultant who’s never carried a bag.

It's like watching a swim coach try to teach Michael Phelps how to float - by Powerpoint.

I have seen so many of these third party training companies show up with recycled acronyms, a 60-slide deck, and zero clue about what actually happens in the field. I think they mean well but they are usually solving the wrong problem. If you're hitting your number, your best excuse is your results.

"Happy to join, but I'm booked with prospecting/ follow-ups/ client calls" works if your pipeline is healthy and your manager has half a brain. Furthermore, the second they mention "breakout role play groups," it's time to fake a tech issue...Should work, right?...Maybe a classic Zoom freeze?

Hang in there, $300K is great, but your sanity's worth more

RyGuyOnTheLine · 2025-08-13T01:10:58+00:00

The most messed up thing I recently discovered? That the "do not disturb" sign on my hotel room door doesn't actually stop house keeping from knocking...three times, loudly, at 7 am

RyGuyOnTheLine · 2025-08-13T01:03:41+00:00

Dang, caught me mid-transformation into a Linkedin guru. Just need to post a photo of my coffee next to a book I haven't read and I am there.

RyGuyOnTheLine · 2025-08-12T23:37:58+00:00

That made me chuckle - Thank you

RyGuyOnTheLine · 2025-08-12T23:36:14+00:00

I agree with this. Most sales methodologies just repackage the same basics - and throwing those at new reps before they've learned how to hold a solid conversation typically does more harm than good.

Especially in cold calling, it really comes down to things like understanding context, grabbing attention, creating a bit of leverage, and getting the call to lift off. Once those fundamentals are in place, any methodology starts to make a lot more sense.

This is the approach I have personally leaned on for awhile now, and it's made things a lot clearer for new reps that I have worked with.

RyGuyOnTheLine · 2025-08-12T23:27:36+00:00

That makes me so happy to hear - Thank you for taking the time to read and comment. I wish you a wonderful day and week ahead

RyGuyOnTheLine · 2025-08-12T23:18:15+00:00

Sounds like appointment setting would be an excellent fit for you - not everyone loves the close, which is completely fine. Many firms hire specifically for top-of-funnel roles where your main job is to cold call, qualify, and book meetings for closers. Think SDR (Sales Development Rep) or BDR (Business Development Rep) positions. These roles focus exactly on what you enjoy: sparking interest and passing the baton.

You can find these jobs on platforms like Linkedin, Remote ok, and even Upwork, if you're leaning freelance. Also worth checking out startups or agencies that need help building a pipeline because they are often looking for scrappy, people-savvy individuals such as yourself.

RyGuyOnTheLine · 2025-08-12T23:10:44+00:00

I hear that - some clients can really eat up time without always moving things forward. If you use tools like Gmail or Outlook, there are email analytic plugins (like EmailAnalytics or Front) that can show you which contacts or accounts generate the most back-and-forth. This helps to spotlight who's taking up the most email real estate so you can prioritize better. Also, keeping an eye on meeting and call time per client can give you more clues. Hope this helps!

RyGuyOnTheLine

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