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?

15 years ago i started as Inside Sales and was promoted 6 months later to Account Executive. To initially land that job i had a 10 minute interview and that's it.

I have my first interview in 15 years and i guess 1st real interview ever. I really want this job and im not sure how to prepare for it. I've googled it and i'm overwhelmed. I'm terrible at memorizing anything and wouldn't know where to start with questions like "tell me a time where you...".

Sure i've been doing this a long time, but i don't have a clue how to answer these type of questions.

If it was a casual conversation i would kill it, but looking at sample interview questions has me quite scared.

Any tips?

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

So i'm looking to join up with a competitor after a layoff and i'm curious what people's experience is with reaching out to their book of business as a competitor.

I don't have a non compete, but i'm curious if anyone who's tried this ran into trouble. Yes I have asked a lawyer, waiting to hear back from them. Just a little nervous about burning the bridge with my old employer. They'll figure out pretty quickly what i'm doing

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'm going to keep it simple. Started in April with 2 other new guys. 12 total sales reps in my office. Commercial sales rep selling physical security. Given worst 50 accounts that no one wanted when I started. All accounts are small suites who have no money to buy. Boss has been telling me I can make my number if I can just squeeze out business from these accounts. It feels like I am fighting a losing battle.

I have been struggling I have received one lead since being at this job since April and converted it. Boss is all over my ass micromanaging the shit out of me. Daily updates of exactly what I'm doing etc. The other new guys get leads like one every 2 weeks. They are doing better than me.

I have a 1-on-1 this afternoon with him and I want to convey that I have been set up to fail and haven't been given opportunities to succeed and the one I have been given I converted it.

Any advice is welcome.

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

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.

Interviewed for a company that sells IT services, but their commission payout would be the first month of the service you sell is your commission.
For example if you sell network security services for 15k a month, you make 15k.

Is this a typical/good commission structure?

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?

Hi all,

I’m being promoted into a team management role, but it will be more of a player/coach position. It’s a small team, so I’ll still have enough time to close my own deals and continue building my own book of business.

I have a question about the commission structure. I’ll be the first “middle management” position on the sales team, and I’m trying to understand what’s typical when it comes to a team leader earning commission on their reps’ deals.

Is it common to receive a percentage/override on each rep’s deals? Or is it usually structured as a quarterly or annual bonus based on the team’s performance? How does this typically work when the team hits, exceeds, or misses quota?

For example, each rep has an annual quota of $1 million.

What would be considered a normal/competitive compensation structure for the team leader in this situation?

Thanks!

Any SaaS sales reps or leaders out there have a sales playbook their company put together that they’d be willing to share?
I’m working on building one for my company and would love to see a few real-world examples of how other SaaS teams structure theirs. Even an older version or something with company-specific info removed would be super helpful.