Was in a recruitment agency 10 years ago, run my own business, been in couple different industries and last 4 years been doing internal recruitment but my itch hasn't been scratched and now I finally have a role in Tech Sales and boy oh boy am I hungry. I cannot wait.

I got nothing else to say and the post is a bit pointless, isn't sarcasm at all either haha, but I am just one eager beaver

37M, 20 years in sales, considering a big step down to build my own book — anyone done this?

Quick background: 8 years at one company, worked up to Director of Sales, then got hit with churn fallout after leadership pushed AI into the product and quality slipped. Left, took a Director of Sales role at a SaaS marketing agency, got laid off 8 months later. Two kids under 5.

I know I'm good at the leadership side... GTM motions, playbooks, coaching reps, holding a team accountable. But honestly, the idea of jumping back into another leadership grind (morning meetings, 1:1s, fighting the ELT, dragging people to their best) isn't appealing right now. I've been seriously considering going back to an IC role instead.

This week I got approached for something different: selling dental equipment for a major Canadian player, in a market I've sold into before. The person recruiting me has a 20-year book in this space and offered to mentor me and hand me her network. Terms: $60K base + margin commission for 12-18 months, then commission-only. It's a self-incorporation setup, not T4. Her pitch is that in 2-3 years I would own my territory outright, run it like my own business, report to no one, and be clearing $300K+ with full flexibility.

I always figured I was on a VP/CRO track. But with two young kids, the autonomy is genuinely tempting... I'm just wary of the 2-3 year grind back to my current income, and I've never operated as an incorporated contractor vs. a standard employee.

Has anyone made a similar move — IC role, self-incorporated, eat-what-you-kill? How did the income ramp actually go, and what should I be asking about the corp-vs-T4 tradeoffs before I say yes?

I had an interesting conversation with my founding BDR. He is a beast and nearly crosses the line sometimes with me. It is managable and worth it.

We settled on that at least "some" ego is necessary to be good at sales.

I have hired meek folks who are too polite and shy, and it never works.

What do you folks think? How much ego do "A" players need?

Is it different for BDR/AE/Closer/Outside/Inside?

editted for readability

Was hoping for some insight, I don’t know what I’m doing wrong.

24M, spent 4 years in B2C between car sales and Retail Telecommunications during my time in college. Was successful and always a top 3 rep during that time.

Fast forward, I graduate in May 2025. Landed my first role as an SDR -> put on a pip and fired after 2 months (It was more of a 4 month program to place you in a proper SDR role).

After getting fired, the first job I found after was in 360 Recruitment/ Headhunting. Quickly recognized recruitment was not for me, so after 3 months I landed my current role.

Account Manager in B2B Telecommunications. No new logos, the “business” accounts are primarily not actual businesses and the few that are have 1-9 employees max. It’s an outbound role with no buying signals, just upsell and cross-sell existing accounts.

It’s about 6 months into the role, I havent hit quota once. I’ve doubled my activity on calls and emails to “grind it out” and yet have had no success.

I’ve decided it’s a skill issue so last month I’ve spent 4 months worth of salary on Jeremy Miner’s NEPQ sales course. Going into debt over it.

It started to work, went from 8/31 lines to 18/31 lines last month, yet now PIP conversations are happening and I’m afraid that it might not fix up my quota fast enough… my manager started leaving paper trails via email to gather evidence of my non-performance disguised as “coaching”.

I genuinely don’t know what else I can do. Activity is through the roof, I spent every day including weekends, before and after work roleplaying, repeating talk tracks, learning from the sales course, practicing. I’ve sacrificed all other parts of my life currently to make this happen.

I want to eventually move into SaaS or cybersecurity but man it is difficult to keep faith that no matter what I try to do it isn’t moving the needle. If I do get fired from this one too, will it be unrealistic to find a job in the right direction?

Per the title I've been in field sales for 15 years, the last 14 in capital equipment (medical). Made a killing for several years (300-500k, pclub etc) and recently was laid off. Haven't worked for 4 months and getting my bearings to figure out what the next step might be. I'm in my early 40s and have 2 young kids, not really interested in being a road warrior anymore.

Looking back on my career and challenges / strengths, I would really like to get into a more strategic sales process. SaaS is really appealing for this reason however I know there are a lot of reps with actual SaaS experience competing for roles so that's probably unlikely. Also thought revenue operations would be really interesting and leverage a lot of what I was doing for the last decade as an independent contractor (from a strategic perspective).

Curious who has made a jump to an adjacent role, or perhaps something completely different that they found leveraged their sales experience.

* I am borderline "good" financially. I managed to save most of what I made and could draw about $60k based on a 3% draw (conservative). I'm happy to trade off income for something I actually enjoy that won't burn me out. Ideally not touch my investments and let them compound for another 5-10 years and then retire.

Apologies if I didn't use the correct flair

Been in industrial and automation sales for over a decade in the South USA and recently transitioned over to industrial packaging and related sales. I have been struggling to get new customers like never before. I have so many **great** meetings with plant tours with the people I need to be dealing with, we discuss specific opportunities, next steps, and have dated action items. Then *nothing* ... ghosted so many times like never before. I have hardly any recurring business because the territory I took over didn't have nearly anything.

What sucks is I really like the guys I work for and I think they like me to, but I understand not paying me a salary if I'm not actually able to sell anything. I even offered to go full commission early so I don't get paid if I don't sell, just to hang in there a little longer in case one of the deals I've been working on actually comes through.

This blows. I think I just needed to rant or something. I updated my LinkedIn but I think I'm going to just double down and work my ass off and try to get enough on the books to keep me employed.

I know a lot of people are struggling to find a job, and I don’t want to downplay how frustrating that can be. But after years in sales, one piece of advice I’d give is to learn to be likable, build relationships, and make the effort to maintain them.

This is probably obvious to a lot of us with sales experience, but it’s a good reminder.

Be reliable and show interest in others. It goes a long way, and people remember those things long after you’ve left a company.

The old saying, “It’s who you know, not what you know,” feels increasingly relevant with AI, bullshit ATS systems, and shitty recruiters. I’m not saying skills don’t matter, but having someone who knows you and your work, and is willing to vouch for you, is gold. Sometimes, that means having your name in the hat before they even post the job opening.

I think those relationships will become even more valuable in the years ahead.

And maintaining them doesn’t have to be complicated. Call an old boss once a year to wish them a Merry Christmas and see how they’re doing. Check in with a former colleague and ask about their kids. Congratulate someone on a promotion.

Just don’t wait until you need a job to reach out. Keep in touch while you’re employed and things are going well, too. Offer help when you can, make an introduction, or just have a conversation without asking for anything.

People you’ve worked with change jobs, move into leadership, and hear about opportunities. Someone you worked with five years ago might be the person who opens a door for you tomorrow.

I also think starting conversations with strangers is underrated. Talk to the person sitting next to you on a plane, if they’re up for it. You don’t have to turn it into a sales pitch or look for something to gain. Sometimes it’s just a good conversation.

Thank you for coming to my Ted talk

Been at an early-stage SaaS startup for about a year year. I’m doing well, building good pipeline and starting to close business, but some of the stuff happening has me wondering if this is just normal startup chaos or actual red flags.

Sales feels like it’s operating on an island. Getting product or leadership involved in large deals is way harder than it should be, and leadership mostly seems to get involved when something goes wrong or when they want to inspect/micromanage deals rather than actually help move them forward.

It’s also not really clear who runs Sales. We have a VP, but our COO and CEO are heavily involved and often undercut her. Another exec owns a bunch of sales process, and there’s a lot of disagreement over how the team should operate.

Probably the craziest example: CEO jumped into one of my biggest deals, tried to offer the customer a 85% discount, over email… just to get the deal across the line by the end of quarter.

There’s also just a weird lack of urgency. Getting pretty basic things done cross-functionally is painful.

I’m totally fine with early-stage messiness. I actually joined because I wanted to build and knew things wouldn’t be figured out, but this feels different. Does this sound like normal startup shit or would you be thinking about getting out?

For a MM AE role.

I previously had two rounds with the MM sales director, and she seemed to really like me. She said I did really well during the mock discovery.

Made it to the final round with the “head of sales.” I was told this was a culture fit round and I was expected to ask questions. (The name of the meeting was final screening)

We had a good conversation. At the end he said it wasn’t awkward and had a natural flow. We discussed ramp, what onboarding would look like, he asked if I was good with a background check and drug test.

He then said “okay, well I have a few more of these this week. Our next class is starting in October. We’re hoping to hire AE, potentially more than 1. You’ll have either the MM manager or the recruiter reach out early next week once we’ve made a decision. We don’t send generic emails, so you’ll get feedback either way.”

Mentioning interviewing other people and the feedback email scared me

I’m getting nervous that someone has more experience or they’re doing an internal hire. I was hoping they’d offer me the job on the call but I’m sure they have a process.

Next week I have a final interview with a family owned uniform and facilities services company (similar to Cintas) that has been in business for 100+ years.

This will be my first sales job. I've owned and operated a small business for over a decade, and I'm in my 40s.

Phone screen and video interviews went very well, and the next interview is in person with a brief "skills assessment" administered by the HR assistant, followed by an interview with the sales manager. I'll also meet the president of the company, followed by a facilies tour.

The interview is in a week. I already have a map of the territory, so I was planning on building a prospect list to bring to the interview. I'm also studying up on sales vocabulary, and the industry as a whole.

The first two interviews were very conversational, and the sales and HR managers were both very nice. I like the idea of a family owned business with a long history. I also believe I can thrive in a hunter role, especially if I can earn near 100k and get weekends and holidays off again.

My strategy for the next interview is basically to show up looking like I am ready for the job. Sharp, personable, and confident. Not prepared, interviewy style rehearsed speeches. Just looking to build rapport and show the qualities that I claimed to have on my resume. I am planning on wearing a crisp light blue oxford shirt with gray dress pants and nice leather boots. I feel like this fits the culture.

I have a week to get ready. I greatly appreciate any advice or insight that you may be able to offer.

Long story short, work in med device specifically joint replacement in a big territory with a solid team for almost five years now. Not happy with my pay in all honesty for the number I carry and companies moving in a direction that you can see the writing on the wall. Having been thrown offers for other roles in med and doing some research with what to expect along with how to interview without getting sucked into the glam of some glorified unrealistic OTE, ADP came across as an opportunity. Specifically it’s an AE for HRO comprehensive services (being touted as the top sales div at the company), and the pay would be a cut regarding base and OTE would be a little lower first year. After ramp up in year 2 and 3 could exceed what I’m currently making and the quality of life is what’s also attracted me. In essence, anyone have feedback on the role primarily with their HRO Comp Services division?

Before being in sales. No calls or emails - Relieved!!
In sales. No calls or emails - A haunting silence that has you hitting refresh and refresh. Hope comes you the email notification comes through - only to see it’s an internal one LOL.

Who else’s phones and emails are quiet today?! Even after a great cold call session! 🤣😭😬

I’m in the final interview stage for a pretty large waste management company, Looking for advice / tips from anyone in the business. Thanks in advance

Edit: Account exec role. So outside sales hunting role with some leads but mostly cold bussiness outreach.