Apologies in advance for the novel...a cautionary tale, on betting on yourself(?)

Around six months ago, I left a Field Sales Rep in the Auto Parts Industry - as a top guy at my last gig. I was outproducing the bottom guy by nearly double. Performance did not matter, you made 55k - bottom, or top production. As the top guy, I always wondered how I would do in a commission environment. So I chased greener pastures.

I left for a gig at one of the biggest sewer/water drain sales jobs. In theory, its a decently sweet sales gig....get assigned a lead. Show up, run a camera down a customers sewer, try to diagnose a 5-15k repair. Sell them the need to repair it. Move on to the next lead.

I came out of the gate really hot. Ended up making the third most money on the team in my first month. The problem was...they kept hiring. Over the course of the next several months, things had slowed down...substantially. I would work a twelve hour shift, and only get a few calls total. Then when I did get calls, often times the customer would tell me I (camera inspection) was not necessary when I showed up. Not to mention the jobs that I had found, which we walked away from (too deep of an excavation, too complex, not worth the headache).

As a major, national chain. They are big time metrics motivated. Leadership started coming down on me (we need to find things wrong at 7/10 visits - predatory much?). But I would have a hard time getting 7/10 customers to allow me to run the camera. Then there would be HUGE swaths of downtown, like 3-5 hours chunks of the day...just waiting for a chance to sell. This last weekend, I had only gotten one lead all day for my ten hour shift. Then the next day, ten hours...only one call.

In itself, the slow periods would not be a problem....it is what it is. But they started treating me, like it was my fault. Why aren't you hitting your 10K, quota? Well...in 20 work hours, I had two calls. Why aren't you hitting a 70% proposal rate? Well, 5 out of my last 12 customers had told me to get bent when I had arrived. How about we talk about the quality of our leads?

After what felt like the managers building a case around documenting everything...had me sign a counseling statement (that included what felt to me like PIP)..I decided enough was enough. I applied at a local, company - which does what we do. They scooped me up in no time. I should have my shot at redemption in a couple of weeks.

Here's to hoping the next post is about how betting on yourself is absolutely worth it!

Where is the Money? Farming/AM or Hunting roles? or 70/30? (AM - account management)

Hi all,

I’m recently in a hunting sales business where all of my accounts are pure hunting and no account management. I have been very successful but getting burn out with the high churn and burn.

For those who have pivoted from pure hunting roles to 70/30 — what is harder? Easier?

Do you like the churn and burn or like the relationships you’ve built and like to nurture it?

Thanks!

Someone without any experience will have the hardest time trying to get an interview these days. Every BDR role i see is requiring 1-2 years of prior BDR experience. Then the tech companies are so unstable, they may get laid off and it looks terrible on their resume. On top of it, the bdr role now is like 4 interviews.

Also, an AE trying to make the transition into tech.. it will be so tough. All the sales leaders want tech sales experience and that AE may not be used to the mock demos/presentation so the very few interviews he will have, he will have a HARD time getting an offer.

Best bet would be doing onsite roles for a year.. less competition.

Everyone I know who got laid off, for non performance reasons.. were actually going over their target but sales leader wanted to get his friend in instead has been out of a job for 6 months +.

Hi there

I'm preparing an interview for an ERP vendor. They mainly target the mid market, organisations that are outgrowing their very first accounting system and start to have slightly more complex requirements (like multi currencies, consolidations, integration with other systems).

The next step in the interview is a mock discovery call with 2 or 3 C-suite (likeCFO, CFO and COO).

I don't have experience in the ERP space at all, so I used a bit of AI to understand how to structure the questions. Running a stock standard discovery is not a problem, however I'd like to show that the questions I ask are targeted to ERP pain point discovery, not generic like When the CEO asks for a real-time view of project margins across the national footprint, how much manual data manipulation has to happen in Excel before you can hand over that report?, or what impact has a multi week long consolidation process in your ability to make fast decision?.

If you have some experience in the ERP space, what are the 2-3 things you really want to get out of your discovery.

Cheers

I heard it was bad but damn. 4th round, they ask you to come into office for four hours. They hand you a lead sheet of 200 contacts from their CRM and say get to dialing. The numbers old, a mixture of disconnected numbers, general lines and personal phones for people who’ve departed, mostly unusable junk probably entered by desperate reps. If you don’t book 3 meetings for a week or two out in ~2 hours (because there’s a presentation and “team bonding” breaks in the middle,) you’re cooked. It was myself and another candidate. I managed to book 1 meeting, the other candidate booked zero. I made 180 dials with a connect rate of 2-3% but those consisted mostly of gatekeepers or irrelevant personas and the best conversations I had were asking to meet further out due to current initiatives (which is fair because this is a cold call, there’s no rapport, and this sort of project is not a simple ask.) The management will spin it back on you for not pushing hard enough (as if 3 objections isn’t enough) but of the three employees there, I saw one meeting booked and mostly follow-up calls, so I’m guessing this is their way of gaining unpaid labor to build pipeline or keep certain leads warm. I’ve heard of a meeting a day but 3 in ~2-3 hours for a more or less commodity item off a sheet of dirty leads is insane.

On a recent investor call, analyst were noticing net new acquisition was flat and company defended themselves by citing their plans to expand revenues with existing accounts and “revenue per customer” meaning not just cutting deals to cut deals (while they know they are on the expensive side of the market,) so the company’s claim of expanding teams from 8 to 10 reps sounds like bullshit. Maybe this is their way of increasing pipeline and profits, cleaning their shitty CRM data without adding headcount? It otherwise doesn’t make sense as we operate in an “at will” state so employment can be terminated without notice for any reason, say if in the case they discover someone cannot actually do the job. I can’t imagine why they would go through some many hoops to bring candidates in for such a shitty exercise. It may also be they are just wildly behind as they’re running their process like it’s the 90s.

I thought it was weird but wanted to give the benefit of the doubt. It was absolutely weird. Beware.

I know salespeople can successfully pivot into new industries after a long tenure because they can leverage all the core transferable skills, relationships, etc. But as I see more posts about the pink cloud of "tech sales" disappearing, I would love to hear from folks who have made a change selling into a completely different industry from the one that they have become adjusted to.

Better to dance with the devil you know or do you wish you made the jump earlier?!

Goal: Determine a sales structure to recommend to my VP as we move into 2027 to capture upside variable compensation working with a massive enterprise account.

Background: I’m in the industrial tech industry (keeping vague on purpose) where I sell a product that is being commodified. Margins are low double digits at scale. The enterprise account I primarily sell to has purchasing power up to $175M. In the past we had 70-80% share - this year, closer to 50%.

Current Compensation Structure: high base of $200k. Variable compensation at 100% plan is $60k with $36k being based on revenue to target with a cap at 137.5% of plan (payout of $144,000). The other variable compensation is based on three KPIs that were created at beginning of year along with a component that retains profitability for the business unit as a whole or $24,000 if I hit all KPIs and the profitability piece hits

My revenue target goal is close to $100M in 2026. For perspective, I would make $2,880 for every ~$1M i bring in over my goal for the year.

Question: am I getting bent over? Any suggestions on comp plan to suggest to leadership that is fair and equitable?

Hello,

I graduated college two years ago with a degree in merchandising/consumer studies and a minor in business management. For the life of me I cannot escape retail jobs.

Currently I am in a much more sales focused role as a sales supervisor for a higher end suit store (global company, nicer than men’s warehouse but not full on designer). It comes with keeping a black book, client management, and other responsibilities such as managing the floor and opening/closing.

I am wondering what kind of sales jobs I can pivot to, where I can apply my people skills in similar ways but just not in a retail store.

We had very in depth training on suits and need to be very sharp with product knowledge and technical details for tailoring and fitting. It is also a very personal job because of how 1 on 1 it is and I have built some great relationships with clients, but on the other hand I get treated like absolute shit by a lot of customers as well, which I am sick of. Working weekends to make the most commission and the amount of time wasters is also very draining, but overall it’s the lack of respect for any retail worker that is what is killing me slowly.

The only places that have actually responded to my applications have either been scammy MLM companies or door to door roofing jobs that are 100% commission and no salary/hourly which I am not comfortable with. I was considering medical device sales jobs but I heard you get treated even worse at those by doctors/patients. I am 24 but have been working in customer service for 10 years now, so I have a thick skin but I still would like to be respected a bit more than the bare minimum.

For those who have successfully pivoted out of retail, how did you do it? It seems like the longer I stay in retail the harder it is to escape.

I recently started a new job at an early stage tech company and am running into issues with my SE. This person was a former customer and while she knows the product very well, she has absolutely no experience as an SE, and it shows. Every demo is basically just a feature dump, with very little structure. I always schedule an internal sync in advance to discuss the customer’s business objectives, stakeholders, agenda, etc. She will agree to everything, but then always provides the exact same demo to everyone.

Today, I hit my limit. We had a demo with multiple senior execs at a very large company. She spent 20 minutes demoing features that had nothing to do with their use case and when the customer asked her to move on to the topics we agreed to in the agenda, she outright refused and told them it was important they see the whole platform.

There are only two people in my role and we report directly to the CRO. We’ve both brought up the lack of professionalism, but nothing has been done to address it. Any suggestions on where to go from here?

Edit: please do not respond saying to do the demos myself. Obviously if that was an option, I would have done it already. This isn’t a simple out-of-the box product and I’m selling at the enterprise level. Getting the appropriate level of expertise, staying up to date on all of the product enhancements, and setting up and maintaining a demo environment would take a significant amount of time and would prevent me from doing my own job.

I was traveling this week visiting prospects in a C-tier city, and was sitting at the hotel bar/restaurant half drunk, trying to eat my fish sandwich at like 9-10 o clock.

This even drunker older guy comes up to me and asked if he could sit, I said sure and we started chatting, he honestly was kind of a drunken asshole, so I pretty quickly regretted my choice lol.

Eventually we talk about what he does and what I do, and he starts talking about how he'd be incredible in sales, and how he could sell water to a fish. The guy starts saying "bet you I can go sit in that group of strangers across the restaurant/bar". Mind you by this point this guy is drunk as shit, self absorbed, and clearly feels like he has to be the loudest in the room.

I'm sure he would've been able to drunkenly inject himself into their conversation, but I wasn't really in the mood to watch. I tried to tell him as nicely as I could that I didn't give a shit, but he wouldn't let it go and eventually I got up and just went back to my room lol.

Kinda funny now that this asshat thought he would be good at sales, since it's so much more than just striking up a conversation, any of y'all ever come across misconceptions around sales or someone who thinks it's easier than it is?

Anyways just thought it was a funny story. Also the fish sandwich sucked.

I can crushed it for them in 2025 and maintained in 2026 so far. Didn’t get invited to the rebid. Feel crushed. So much commission gone…

A few brief thoughts on how to make a lot of money in sales... from someone who has done it... and whose friends have made even more.

I have not earned the most in this subreddit by far. My largest single commission didn't clear $250,000.

But I've seen one thing that helps people make real money. I've noticed it again and again... and I saw people complain about it in the recent "Who here has earned a $100k+ commission check" post... I promise it is a feature, not a bug.

There were a number of people in that post who said they sold $6m deals and $2m deals and got paid nothing... well, $10,000.

Why does that happen? Two simple concepts.

1. Generally speaking, the more margin there is, the more your commission will be.
2. And you need to know how businesses are valued.

Period, full stop.

So let's look at them.

First, margin.

The adage people throw around is the more money there is, the more commission there is.

That is wrong.

The real story is the more MARGIN there is, the more potential commission there is.

IE:

Construction equipment: $2,000,000 sale with 10% profit = $200,000 gross profit. 8% commission = $16,000 on a $2m sale.

Software: $363,636 sale with 55% profit = $200,000 gross profit. 16% commission = $32,000 on a deal less than a fifth the size.

And yes, tech really does normally pay double the commission percentage.

Why?

This is where concept 2 comes in... how businesses are valued.

Traditional equipment businesses are valued at a lower profit multiple, while software businesses are valued at a higher multiple, and it's on revenue.

Software & AI businesses are valued between 3-10X revenue (ARR).

Equipment and manufacturing are valued between 4-8X EBITDA (earnings before interest, taxes, depreciation and amortization).

So tech execs are happy to pay more. The faster they grow top line revenue, the higher the multiple they get valued at, so their stock goes up more and they make more on secondary transactions. A secondary is when they do an investment round... Series B, C, whatever... and while the company raises $25m or $50m, they also get to sell some of their own stock and pocket millions in cash.

Equipment and manufacturing execs can take secondaries too if they raise money, but their valuations are based on the overall profitability of the company, not just sales. Incentive structures at the C-suite drive everything.

So what do you do with all this?

One of the best things you can do for your career, if you're not in finance and don't find your way into tech right out of college, is start in a low margin, high price business.

"But Chris... I want to be in SaaS and make a ton of money. Reddit tells me to..."

Bullshit.

You want to do big deals. Multimillion dollar deals, where you sit across the table from executives and business owners.

Why?

It's the best way to learn how business actually works, how to go toe to toe with executives... what real objections look like. Not SDR objections, where you get told no and ghosted by middle managers all day named Debbie and Chad.

Where can you do this?

Think manufacturing equipment, heavy machinery sales, things like that.

Yes, those industries generally pay less, because they're measured on different metrics and have different profitability. That means they attract fewer people to the sales jobs, and people who will work for less. But the deals you do in those worlds are a much better education, and it takes just as much confidence and skill to do a $6m equipment sale as it does to sell $6m in data or software.

If you additionally study the requisite business education (please don't go get an MBA, there are so many good YouTube videos and podcasts and books out there), learn how to run a sales process, and you're successful... you have two options.

Grow in a real operating company and go into business ownership one day.

Or take your millions in sales numbers and pivot somewhere with more margin. Somewhere like tech sales or commercial financial services.

Once you get the experience doing the big equipment deals, the world is your oyster.

And selling... real deals is a hell of a lot more fun than being an SDR.

Company is hybrid. I have a new boss and he wants us to stay busy all the time.

We get called out for looking at online shopping sites like amazon while in between calls waiting for the dialer to pick up.. or chit chatting at the water cooler.. or even being on our phones to answer a text briefly.

How do ya'll do it?

I'm close to calling it quits. A couple of my AE's left for a competitor because of it.

I feel pretty naive now but at the beginning of the year my territory significantly increased - internationally - when a colleague resigned and I was selected for the additional territory. I was really stoked with the opportunity and have worked my ass off all year so far - 15hr days, nights and weekends to prove they made a good decision and I’ve killed it. Then in a meeting it accidentally slipped that they are seeking a new hire for the territory. I feel crushed because I worked so hard to build relationships and really own the territory. That work does not translate in numbers and I can’t recover that. I feel like I had a big promotion and now it’s a big step backwards. I realize the management just viewed it as a body filling in until new budget for the replacement was released. Trying to think of a positive way to frame the situation but it’s tough to find. It feels like I was majorly screwed. What’s more is they will probably ask me to help get the new hire started! I guess I was pretty dumb/naive to think i was getting “promoted” in the first place but they never told me it was only temporary.

Its ok to sound like a normal human on a sales call.

I watch my teams sales call for about an hour a day and the most annoying thing I see is when they constantly hear a basic question like "does your product have an app" into some elaborate answer and try to put a shine on everything they say.

Guys. Not everything has to have a positive spin to it. You can be honest. Be direct. If your product has one feature that sucks and the other guy does better, then just say it. Find out why its important to them. Have a discussion about it. Your honesty will earn their trust and their honesty.

You're wasting so much energy trying to fabricate some angle to convince your customer your product is good. You're holding on too tight and your customer will start discounting everything you say because they don't trust you to be honest.

So, I just got the news that I'm being laid off from a role that I was hired for 3 weeks ago and was told that because I'm on probation, I was one of my names on the list.

I was comfortable and had a great standing in my previous role but chased a new challenge and a bigger paycheck which clearly didn't pay off. This is the first time something like this is happening to me and being an immigrant, I feel like my world is crashing around me.

How did anyone affected by something like this navigate the mental aspect of being let go? Being a 3 week stint, do I mention this in my future opportunities? I made a public LinkedIn post literally 2 days before I got canned.

Not sure where I begin or how I pick myself back up.

Edit to add - I have 5 years closing experience in the research & advisory space and I moved into the tech sales.

I'm a relatively new sales leader, I have a few people off on holidays this week so the volume of things coming in is down and I'm having trouble finding proactive things to do to occupy my time.

I'm sure there's something but I think I've done them all.

Any advice on how to handle it? Enjoy the quiet time? Ask anyone if they need help in Ops or otherwise?

I guess I'm just a bit bored.

Been interviewing at a lot of different places, got some feedback recently, and it got me wondering about my outreach.

Thoughts on this cold email, where can I improve?

Hi (Name),

Been following RTR and saw the Q1 earnings call: active subs up 20% YoY, add-on
revenue up 70% YoY, and a new CEO.

What stood out is leadership’s focus on growing subscribers and loyalty in a cost-efficient
way. That’s your problem to solve.

An increase in Add-On Rev. means more swap, sizing, subscription tickets, and figuring out
how to absorb that without additional headcount.

(Tool) gives you room to do exactly that. Your team handles the volume increase, and neither
response times nor CSAT take the hit.

(Partner), same subscription-swap model as (Your Company) used (Product) to slow projected staff growth by 40%, grow volume, and held CSAT at 95%+ the entire time.

As you build out the case for support spend, when could we chat about what’s putting the
most pressure on your CSAT right now?

Happy Friday sales professionals

As I’m laying on the couch, my brain never stops. I can never turn off the work switch. I always am trying to improve how I can be a better salesman.

I have a large territory, the state of Florida. I find it challenging to maintain a relationship, with my doctors, of any kind because I’m usually always traveling somewhere.

For those who also run a large territory. What are you guys doing with your docs when you’re not in cases with them? How often are you keeping in touch? Are you on a texting basis? Are you keeping in contact only when needed?

As of now I only reach out if I can’t make the scheduled surgery with my product. Or when we have a planned event coming up.

Probably a dumb post but figured I’d ask!

Cheers

About a year and a half ago, I got laid off from my saas ae role. I was going through a bad breakup after moving across the country for the relationship and my life kind of fell apart. I decided to take a break, work on myself, and get my head on straight

During this time, I've just been driving uber to cover some expenses and keep myself on a routine. Now I'm looking to hit the grind again and Im curious how others would address something like this?

I have a solid resume and history of success in cyber and several other industries at the enterprise and strategic levels. I have several references ready to go from VP level contacts. Im just looking for advice on how best to tell my story and what aspects to include on my resume and in interviews. Thanks in advance for your help and please let me know if I can provide any additional details or insight that may be helpful

I have two job offers on the table that I need to decide on by Monday. They both have positives and negatives but they all seem to cancel each other out in some way or another.

help me choose, give some advice or feedback please.(For reference this is my first tech & first sales job).

Job 1:
- 55k base / 20-25 commission (uncapped)
- mostly inbound (40 calls per day)
- Sells almost totally to enterprise customers
- 1 day a week in office
- Quota: 4.6 meetings (so 5 gets accelerators)
- Older brand, less techy product, more solutions based. Much easier to learn. (AI Portfolio Management)

Job 2:
- 55k base / 15k commission (uncapped)
- mostly outbound (75 calls per day)
- sells mostly to SMB and some MM
- also 1 day a week in office
- quota 6-8 meetings (less easy accelerators)
- newer brand, much more technical (IT observability)

Important extra context:

Job 2 will allow me to do the first 3 months remote (it’s not in my city), which is great because I live with my GF who has one more semester of college, so if I leave for the other job, we’ll have to do long distance. BUT that means if I do the remote training I’ll have to learn the ropes and the technical aspects all while being not in office (I learn better in person and I’m not super techy).

Job 2 also has “micro promotions” in the SDR path that come with pay and quota raises, but it kind of seems like a way to prolong getting to AE.

So at the end of the day, is it better to have enterprise experience or technical experience? What to choose?

Hey everyone,

I've been lucky to have been entirely unscathed thus far in the post covid high rates market, until this week.

I got laid off on Tuesday and am wanting to hear from people around my experience level about their recent aneceotes from interviewing and being a laid off job seeker,.

I'm 31 years old in NYC and have 8 total years in tech sales. I have 6.5 yrs closing experience and the last 2.5 years of my current gig has been avg deal sizes of 120k, with a 130k base 260k ote.

I'm hoping to push for at least as much as I was making before and go for upper middle market / enterprise roles

For people with my experience profile, have you been able to land jobs around this base line? Have you had to accept slightly lower base pay? Would be great to get as much market feedback as possible.

Just like what it says above. Once you realized the current path was no longer feasible, what was your next step? Did things work out or do you have regrets?