r/sales

Looking for honest advice from experienced B2B reps/managers because I’m struggling right now and trying to figure out whether I need to push through this or reevaluate the situation entirely.

I’m about 6 months into a new AE role selling for a well respect SaaS company. I genuinely like my manager, the company, and the product, but if I’m being honest, I never fully believed in the TAM/territory I inherited. I have 45% close rate on qualified opps but the volume isn’t there.

This territory has historically underperformed, and economically it’s a difficult market:

Lower social economic areas

Operators heavily impacted by economic shocks

High volatility

Slower expansion activity than stronger metros

On top of that, it feels like every possible headwind stacked together:

Saturated market

Heavy incumbent competition

Long travel for on-site meetings

Decision Makers that are difficult to reach

Existing opportunities/accounts already worked repeatedly

Lower overall density compared to stronger territories

The hard part is I’ve had success before:

Former top-performing BDR

Strong self-source background

3x President Club AE or the equivalent

So this experience has honestly shaken my confidence because effort is not translating into pipeline or results whatsoever. I’ve tried to outwork the problem:

Heavy outbound

In-person Prospecting

Creative prospecting

Expansion hunting

Networking

Offering additional cash incentives to SDRs out of my own pocket for meetings booked in my territory
And despite all of that, I’ve gained very little traction from it.

One thing I keep coming back to is:
“Territory + Timing > Talent”
Obviously talent and work ethic matter, but I’m starting to question how much even strong reps can realistically overcome a fundamentally weak TAM.
What I’m struggling with now:

At what point do you stop blaming yourself?

How do you professionally bring up territory concerns to leadership without sounding defensive?

Is leaving after 6 months a career burner if you genuinely believe the territory economics are broken?

How do you separate “push through adversity” from pure sunk cost fallacy?

Have any of you successfully turned around a historically bad territory? If so, what specifically worked?

I’m open to hearing hard truths too. If the answer is “adapt better,” I can take it. I’m just looking for perspective from people who’ve actually dealt with this before.

Looking for honest feedback from people in sales hiring or who’ve made a similar jump.

My background: I started as a BDR at Oracle NetSuite where I hit 109% quota and generated $300K+ in pipeline in under 12 months. After that I went full entrepreneur and built a mobile fleet maintenance business from scratch, solo with no playbook. Prospected and closed multiple $10K–$12K ARR fleet contracts through cold calling, door knocking, LinkedIn, and email. Scaled to $150K+ in ARR and landed a 200-vehicle fleet account with one of the largest home service companies in the city.

I shut my business down for personal reasons to move back to my hometown to be closer to family.

During that transition period, I took a remote marketing job to learn since I struggled to understand marketing platforms when I was running my business.

Just left that company back in March for a variety of reasons (high leadership turnover, promised salary increases deferred, etc.)

I want to get back into sales for the challenge and upside. Ive had two interviews so far. Both rejected. One mentioned it was because I did not come in with quota carrying or closing experience.

I know I probably did a bad job articulating that in my resume so I have opted to making a pitchfolio to send to hiring managers.

I am looking at making a LinkedIn post later this evening to see if I can get any inbound opportunities from my network.

But overall, I am just curious if I even have a chance or if I should go BDR again.

Yesterday I posted a true story that happened to me when I was a sales manager for a large financial institution in Canada. Because I used an Ai program to help me, a number of people chose to focus on the Ai version rather than the story. It is unfortunate they missed a heart breaking event in my life and hers.

At the time, she was a 50 year old grandmother who had been in been in financial sales for a number of years and had a very large client base (2,500+ clients). She was working very long days 6-7 days a week, and was exhausted and very concerns she had no time for her grandchildren.

The mistake she made was that she treated all her clients equally and was giving all of them her undivided attention. As her manager and her coach, I saw the problem immediately. After both of us calmed down, yes I was upset as well, for I cared about my team, just as I care about those individuals I coach now.

I believe we should treat all our customers fairly but never equally.

Step 1 - I had her do an extensive process to classify all her customers into three categories; A, B and C.

A "C" client would only buy from her once and not offer referrals to others.

A "B" client could buy again or give her referrals, but not both.

A "A" client could do both, buy from her again and give her referrals.

After 2 weeks of hard work with her assistant, she accomplished the task.

Step 2 - I suggest some guidelines to manage her client base fairly but not equally.

Regarding "C" clients - she is never to call them. If they call her, of course she is to respond.

Regarding "B" clients - she is to call them one per year just before their birthdays to offer an annual review or a prospecting meeting.

Regarding "A" clients - she is to call them twice a year, once for an annual review before their birthday, and one other time to socialize and build a stronger relations ship.

This took another 2-3 months to organize, quiet file some "C" clients, and approach some "A" and "B" clients.

She transformed before my eyes in this period, she worked less hours, her earnings increased by 30% and most importantly she had time for her grand kids. She had joy in her heart and re-committed to the career

So if you have a large client base, assess them and treat them fairly but never equally.

I hope whomever complained about my previous posting being Ai assisted, now get the message above.

There is a principle I live by which is "People don't care how much you know, until they know how much you care!" I hope I am judged on how much I care, for I do care!

So I’m a sales exec, left my last company about a month ago working in aviation sales, aftermarket aircraft parts, before that industrial engine parts and before that motorcycle fleet sales.

I have a background in CS, I was considering switching to tech/software sales and have been interviewing. It seems decent, I’d be going for account manager and they’re actual account manager roles, not a dressed up sales dev role.

On the other hand, there’s the opportunity to work in business dev for HVAC, I’ve heard this is a high paying, niche industry. I don’t particularly care about what I sell, as long as it’s a good product/service providing actual value for a decent company that isn’t Israeli, I’m satisfied. I won’t sell scams.

I’ve positioned myself for technical sales, my only goal is breaking £100k. What would you suggest, fellow sales people?

no reason or explanation given. i actually don't have an inkling of an idea as to why, unless they're in the red and just can't afford me anymore?

has this happened to anyone else? i am absolutely flabbergasted right now lol

How often do you have customers sending in rfis and do you respond to them? I hear quite a mixed bag of responses about this.

Almost 1 year into sales after coming from a Product Director background. Curious how sales directors / VPs would perceive this conversation with a manager:

“How do I get better? What are the biggest things I should improve on?”

Context:

- Enterprise / long sales cycle environment

- Territory expectation is realistically ~2 major deals per year

- Lots of relationship building, technical conversations, and navigating ambiguity

- Hard to know early on if you’re truly progressing because the feedback loop is so long

As someone newer to sales, I genuinely want coaching and pattern recognition from people who’ve done this a long time. But I also don’t want it to come across as insecurity or lack of confidence.

If one of your sales managers asked you this directly, how would you perceive it?

And for those in enterprise/strategic sales, what actually separates average reps from great ones in year 1-3?

Been out of a job for a minute. Have experience in Customer Success at a start up where I got thrown in the deep end. One week of training, then the only other CS person went out on baby leave. So with one week of training, I became an interim CS director.

With it being at a start up, I was pulling triple duty. CS, I was the main AE, and the "Hubspot guy". Ironically the only thing I didn't do was XDR stuff. Still had build my own pipelines and close my own deals.

Here's the fun part. This was a career change. My prior career was a hostage negotiator.

Should I be looking at CS, XDR, inside sales, or AE gigs.

Long term, I want to lean into the AE route or even do training.

Maybe im just frustrated with my job hunting pipeline. Had one interview where the interviewer wouldn't stop talking about how great Chris Voss is for sales training, then says im under qualified for the role.

Just need a reality check and what I should actually be looking for.

*If any of your sales teams needs an ex hostage negotiator, I know a guy*

Part 1 - She was 50 years old. A financial advisor with 2,500 clients. Working 12-hour days, often six or seven days a week. She had two grandchildren she barely saw. She wasn't failing. She was doing everything right.

That was the problem.

She was treating all 2,500 clients exactly the same — and it was killing her.

Here's the deal. You can treat people fairly. You cannot treat all 2,500 people equally. There isn't enough of you.

We ran a Gap Analysis together. We looked at where she was, where she wanted to be, and what was standing in the way. Then we got to work.

Two months later, she was usually leaving the office by 4pm. She was at her grandchildren's events. She was taking weekends off.

And her income was up 30%.

Not because she worked harder. Because she stopped spreading herself across everyone equally and started putting her time where it mattered most.

If you have team members who are exhausted and their results aren't improving, the problem might not be effort. It might be where the effort is being placed.

Does that sound familiar?

31M. Been working for 11 years now, started from the bottom and now managing a team of reps in a new job which I started couple months ago. (Which I'm not liking ofc)

To say that I'm burnt out is an under statement, had a baby 3 weeks back and now I'm also sleep deprived.

I want to just quit all this and go somewhere quiet but I look at the baby's face and feel bad for not being a stable father, also realizing that Sales in SMB will never be stable.

Really want to shift to Enterprise or Customer Success for some mental peace.

The sales grind is good when I'm single and without a family, this pressure is really getting to me.

Can't imagine taking a break in this shit market though.

Stuck from all angles and feeling dejected.

Please be kind in the comments.

TLDR - Burnout stress, really need a break!!

Just a bit of a rant here. I've been in sales for 10 years, I got lucky at 20 and a company hired me for a professional full cycle sales role, I hit some early big wins due to dumb luck and made like $80k for a few years. Got to travel a lot for work seeing places I'd never been to, I had to come up with creative solutions for my clients which was a lot of fun. That company dissolved during covid, it was a small business.

So since then I've hopped from job to job, having absolutely no success. A good month here or there, but that's it. You'd think after a decade of cold calling that I'd have picked up the skills to at least be average but no, and honestly I don't like it. I got laid off again a few months ago, and finding a job has been a bit tougher now, but the thought of even going back and trying this again just has me miserable.

But I'm stuck, sales is the only real experience on my resume, I don't have a degree. I'm gonna apply for jobs and cold call some hiring managers again today because that's what I know how to do, but I'm really not looking forward to it.

Our sales director has been very open about metrics recently, and that the only way our numbers are going to get hit is if we start utilizing LinkedIN and going after CEO's to sell larger package deals in comparison to just single units while cold calling.

I was interested in your opinions in this group, especially those who have more tenure than I do. Has this been the case for your sales experience? What percent of your success would you say came from company leads vs your own outreach to people through social media or your circle?

Sales has the reputation of people who are in it for the money and commission driven, which can be true.

I hate those salespeople because they are the ones who gives sales a bad name with a lot of tricks and lies etc to make a sale

I feel being able to do a market analysis and being able to identify new markets/new services is underrated.

Being able to see where a new future product or service is going to change a market means you’ll have less competition and can be the challenger to incumbents.

When SAAS first hit the market, that was a big deal and fundamentally changed how software was sold. But now it’s a standard business model and you have to differentiate in other ways.

That’s why I’ve always enjoyed selling startup services. I think it’s more interesting to find new services to sell to an existing market instead of finding existing services to sell to a new market.

What do the D2D or pretty much any outbound reps that are outside on the daily wear when it’s incredibly humid/hot outside?

Give me recommendations for your favorite Pants and shirts

I work in a professional services industry, so our "sales" is called "business development."

A person who oversees a group of business development reps recently told me his most successful people focus on building a client relationship, versus focusing on primarily just asking clients for work (the "sale").

My struggle is pretending that a relationship is genuine, when i know its really not. Its hard for me to focus on the relationship, i.e. getting lunch with a client and talking about things unrelated to work, when in reality the only reason im doing it is to get a sale in the future. Its difficult for me to try and turn each client into the equivalent of a friend, when we would never be friends if it wasn't for my future financial benefit.

Any tips?

I was let go last week, but have some time before making my next move.

I’m hoping for some guidance from guys who’ve been able to navigate the ups and downs of this thing, who’ve seen the good, bad, ugly and feel like they’ve got a handle on how to have a successful long term career. And also things to avoid!

Tech and non-tech as well.

I’ve been in tech for 6 years with only 2 companies, but am open to jumping over to outside territory sales as well.

I know this rare especially in the same company. But has anyone been able to start in SMB at one company and land a ent role at another? How was the learning curve/ growing pains etc?

A little bit about my background I’ve been an AE for 6 months now and was put on a pip warning for only having an 80% attainment for the month. If you don’t hit 100% you get a pip warning.

I’m currently leading the team this month at 75% attainment with 7 selling days left.

I say all this because there is a good chance I will be on a pip next month unless I get extremely lucky. I’ve already been applying for other jobs a month ago and the only jobs I see on LinkedIn in my area is enterprise roles.

Would making that jump be too steep at this point in my career? Has anyone made that type of jump before?

Just curious of what you think.

After the former Google CEO got booed off stage, and just the recent sentiment that is almost palpable, you can tell people are starting to sour on the side of AI.

The future looks bleak to some and uncertain to others.

My mind has been racing. For the last few years we have been building Ai agents and deploying them for SMB's.

In the past, you could speak about cost cutting, increasing margins at the expense of humans, but now, that is not a great way to position things on a sales call if you actually want to close deals.

The argument some would make is it is increasing efficiency. By installing this agent in a company, now this roofing company is not losing revenue. The downside is that a human job is gone. (We have seen it a lot with the builds, not very proud of that fact to be honest).

So on one side, one person wins. The other side, the other person wins.

After a lot of consideration here. It left me with a thought. On one side, someone loses their job. On the other side, someone becomes more efficient. Does that actually even out?

My thought is no. Not because I'm some crazed anti-capitalist, but what happened before was simply distribution. It wasn't waste due to inefficiency. If that person called x company and Linda was on the other line and missed the call, that homeowner would call the next roofing company. The money was still distributed. The job didn't just disappear due to a lack of efficiency. The home owner didn't just call Randy's roofing and give up on roof repair because Linda didn't answer.

The argument that some other country will beat us to it so we have to do it is fair, but man, that still feels like a weak case for AI.

I think it's hella fun, I just do not see real net benefit to it and I personally think humanity would have been better off without advanced technology.

I know someone will come with the argument that (X) was invented and it created more jobs, but to be honest, that is intellectually lazy and you know it. This is not a freaking typewriter. Humans were in the loop for all of those items.

So, do you think AI is a net good or net negative for humanity?

A bunch of mediocre sales people were employed and taking up all the jobs during Covid, when anybody could sell.

It feels like late 2022-2025 was rough but it’s ungodly out there right now. At this point I’m sure most people have just given up on sales and are trying something else, and newer SDRs are going to be replaced by ai

My only hope, is that at least for decently tenured reps (5+ years as AE) that we will have less competition for MM or ENT roles

How do sales ppl, who travel a ton together, who experience the highs and lows of sales together, who work out together at the hotel gym, who see each other at their hottest (looking good and sounding smart) manage to avoid affairs?!

Im really worried I’m going to fall in love with my boss. He’s married. I’d be so incredibly horrified and devastated at myself if it results in an affair (he’s married to a beautiful, kind woman).

We are around the same age. Mutual respect and admiration. Mutual attraction, I suspect. Mutual interests and lifestyles. Mutual level of intelligence and think at the same pace so it feels like we easily understand each other. If I met him on a dating app, I’d know after date one we had a strong chance of a long term relationship. It’s just easy with him.

I’ve had to dial down my normal work-self playfulness with him because I don’t want to risk facilitating him falling for me. I think he is confused because I’m ultimately friendlier to my other male colleagues than him. I dress more modestly around him to be less visually distracting. I praise and express appreciation but also tone it down too knowing how much of an effect it can have on men. I also act a little weirder and a little less cool than I am IRL, to try to turn him off. Hahahaha, good lord. Also, I don’t drink so that keeps things in check when we travel. I’m trying very hard to manage this on my end. 😅

We are building a new business together. Travelling a lot. I think we have big potential to come out as winners if we play our cards right.

I have no idea if he’s wrestling with an awareness this could happen on his side, like I am on mine but I catch his micro expressions when he thinks I’ve done/ said something endearingly cute or when he’s impressed by my brain. Otherwise, fortunately, he’s largely non-expressive which is helpful.

I want to have a rock solid relationship with him that doesn’t cross the line.

I’ve met his wife and she’s awesome and beautiful and I’d feel like the worst traitor to my fellow woman if he and I crossed a line.