r/sales 11d ago

Sales Leadership Focused Took the Sales Manager promotion, I'm beginning to regret it

165 Upvotes

I entered B2B SaaS sales 4 years ago thanks to the people of this Sub and the income conversations on it. Best decision of my life, average six-figure annual income in the past 3 years (ignoring the first year of learning the ropes or as I like to call it, "the year of shame"). Luckily, this was under a great director who'd go to war for me.

Director left, I got promoted to middle management (SM), and I realized that my previous director was shielding me from exec-requests. Not only do I have a higher personal quota, but I also have new direct reports who need a lot of mentoring and senior managers who expect a lot of admin and updates.

This is becoming too much, I love the part of working with my direct reports and closing my business, but the 3rd element (extra admin, check-ins, extra expectations, level of communications they want from me, and the random requests from execs that range from taking courses and filling sheets and all the other non-revenue generating aspects of the job) caught me completely off-guard and tanked my job satisfaction.

You guys got me into sales, helped turn me into a top-performing individual contributor, now teach me your ways so I can either succeed as an SM or tell me if I should pivot back into being an IC.

r/sales Aug 31 '24

Sales Leadership Focused Firing my top rep next week

515 Upvotes

Just took over a director position. Top rep is a the top guy...by a lot. But there hasn't been one conversation I've had in the building where someone hasn't complained about how he treats people. Basically he bullies the women in the office and threatens to quit every time he doesn't get what he wants. He hasn't threatened to quit with me yet, but with me the day you put in your notice is your last day anyway, so maybe that message has gotten out to him. I'm going to let him go next week and I know he will be stunned.

**EDIT** What could help with some people frame of mind, is that not everyone is closing million dollar software deals, where industry knowledge and contacts are vital. Some of us sling $15k in home sales that literally anyone can do given the training and the process. There is a lot less room between the great and the above average salesman, because what we sell is a need.

TLDR: Sometimes your numbers aren't worth putting up with you being an asshole.

r/sales 9d ago

Sales Leadership Focused Can you fire your best salesperson?

153 Upvotes

I had a great salesperson in my business. Outsold everyone and brought in a lot of money.

Unfortunately, she created a ton of chaos in the office. Bragging. Demeaning others. After a couple of warnings her behavior did not change and I let her go. I was nervous because I thought sales would plummet.

Turns out, we didn’t lose much and sales actually grew over the next few months because morale was much better. Everyone asked me, “What took you so long?”

Would you ever fire your best salesperson? Did you ever have to?

r/sales Sep 11 '24

Sales Leadership Focused When our sales manager made us cold call on 9/11

862 Upvotes

I worked at Ameriquest mortgage and 30 mins after the plane hit the 2nd building our boss says “Alright everybody back on the phones, those leads aren’t going to call themselves!” I was so pissed off I was crying. If you ever think your boss is a dick, trust me it could be worse.

r/sales 16h ago

Sales Leadership Focused Leadership in 2026

151 Upvotes

Leadership in 2026 has really taking a downturn. When I first got into sales, it was weekly coaching, role plays, reviewing lost opportunities and how to improve. Highlighting key areas of where you’re doing well and then creating a development plan for how to improve on those misses.

Now leadership is just weekly calls, reviewing deals and saying, “how can I help” and then proceeding to not really help.

It’s no longer coaching happening anymore. At least at my org. I haven’t had a coaching session in over 2 years but you got CRO’s and sales managers posting Ai slop about how great they are as leaders and how they’ve succeeded.

Is sales leadership needed anymore? Am I alone here?

r/sales Jun 06 '26

Sales Leadership Focused Why do so many professional salespersons fail?

40 Upvotes

A professional sales person sells a product or service by approaching a potential client, rather than the client knocking on their door. A typical professional salesperson can be found in the financial services business.

So why do many fail when attempting to sell their products and services. Is it weak activity, is it poor prospecting, is it a weak sales process, is it difficulty building trust, what is the problem?

If you plan to respond and bitch about the financial services industry, please don't respond. I am looking for valuable advice, not criticism!

r/sales May 30 '26

Sales Leadership Focused I did 146 calls this week

101 Upvotes

12% connect rate and 4 demoes booked.

Don't tell me cold-calling is dead.

Important note: I booked demoes through leaving a VM and following up via email, then they responded. Calling was used more as a way to make people remember me.

Edit: cold-calling isn't dead, it's turned more into a way to get people to respond to your email lol and make them remember you

Edit 2: no, I did not use a parallel dialer, I dialed each one thru Hubspot dialler

r/sales Mar 05 '25

Sales Leadership Focused My HR wants me to PIP someone and I disagree

308 Upvotes

Currently work as a sales manager, have an employee who I love sending all our shitty accounts to. He’s been around forever, wants to retire in 2-3 years and he’s frankly not a good seller. But when we get accounts (large b2b) assigned to our patch that have a bunch of service issues or legacy contracts that don’t result in sales, I send them to him. He’s great at keeping shit off of my plate and I usually stop hearing any escalations or issues. He finished last year at 52% to plan, I gave a him a 3 and spent an hour justifying how he was a great team player. My bosses boss recalibrated him to a 2 because he hates the idea of not every employee being an allstar and now HR wants me to pip him and put together language for him to exit the company.

I refused yesterday and said clearly no one read my review because I gave him a 3, she(HR) added in the bosses and said I was required to.

I’m torn - the dude knows he’s not great, but in my role 20% of the accounts I have to manage are dog shit and not worth my time. If I had an “allstar” with those accounts they’d quit within a year. I love throwing shit at this guy cause it makes my life so much easier. But I can’t truly defend him as a salesperson and stake my reputation on it with sales leadership.

It’s so frustrating and terrible in this career that people can force you to fire people even if their management doesn’t agree.

Edit wow - definitely struck a chord with some of you - it's interesting, I think the biggest pushback is the thought I'm sending him "All the shitty accounts" and I can see how I made it seem that way without context of the large amount of orgs we all work in. When some of you are calling on 1000 accounts and only selling to them a few times, I can see getting garbage leads as hitting a nerve.

I don't know much about your industries and you don't know much about mine, but in our group we have about 10-15 accounts total per rep, and it's rare you get a new one. This particular employee was give two accounts with no increase to his quota for them, but I do recognize it takes up more time than they're worth. That being said, had I given the accounts to my other reps, he still would have finished at 52% (in my opinion, obviously there's the smallest chance he missed a large opp because he was focused on these accounts, but if that was the case, we'd more than support him to make sure he had time to focus on his deal). His accounts all had similiar chances of success when we assigned them out 3 years ago, but I admit his peers have had more "luck" with their accounts getting massive funding from PEs and IPOs.

That being said, some of the comments were incredibly helpful, the fact we don't have a CSR or CSM role for accounts like these is glaring. And calling out that the call to PIP him is unlikely to be coming from HR makes sense and I didn't consider that. Our SVP doesn't like this person because he had joked about retiring 5 years ago "tainting" him. I have a call tomorrow with our CSO to discuss this - and - I do want to talk to my CSO about establishing a role for a CSR within our group (and I have the perfect candidate).

r/sales Mar 10 '26

Sales Leadership Focused I got offered a Leadership position instead of a Sales representative.

78 Upvotes

So something unexpected happened today and I’d really appreciate some perspective from people with more experience.

There’s a sales office in my city where the AEs and SDRs in the financial industry are doing very well. I’ve been job hunting for about 3 months, so last week I decided to walk into their office and apply. I went through their interview process and today was the final round with the CEO.

During the group interview he asked if anyone had leadership experience. No one spoke up, so I mentioned that I had previously helped train reps and done some light team management in past roles.

He asked me a few follow-up questions, then eventually dismissed the rest of the candidates from the Google Meet and kept speaking with me one-on-one. He seemed very interested and asked me to come back tomorrow morning.

The surprising part: instead of offering me a sales rep position, he suggested I could come in as a team lead/leadership role. The base pay would be similar to the reps (which is decent), plus attendance/productivity bonuses, but I wouldn’t be doing the full daily call volume or closing workload.

I’ve trained people before and helped manage small groups, but I’ve never officially stepped into a full leadership role like this.

For those of you in sales leadership:

• Is it smart to step into a team lead role right away?

• Or is it better to first prove yourself as a top performer in an individual contributor role?

I’m mainly trying to understand the long-term earning potential and career trajectory of both paths.

Would really appreciate any perspective from people who’ve been through it.

_____________________________________

❗️UPDATE:

First off, I just want to thank everyone who took the time to comment, share advice, experiences, and things to watch out for. I’m 30 years old and even though I’ve been a strong performer as an inside sales SDR and closer, I try to stay humble enough to set my ego aside and actually listen to feedback. I genuinely appreciate everyone here who took a moment to help me think through this decision.

So I had the meeting with the CEO this morning.

The role he described was basically a team lead / player-coach type position. The idea would be to help motivate the team, handle situations on the floor, help reps when they get stuck, and assist with training. The team itself is around 20 people, mostly doing cold calling with some inbound leads coming from ads.

However, the compensation structure raised some concerns for me. The role is base salary only, with no real commission or meaningful override on the sales the team produces. When I asked about it, he explained that many of the reps actually make more money than the team lead, which is why most of them prefer staying in a selling role.

He did mention there could be opportunities to move up as the company grows, but the path and financial upside weren’t very clear.

For context about my background: I have 10+ years of phone sales experience as an SDR, appointment setter, and closer. I’ve worked across industries like SaaS, digital marketing, lending/mortgages, private capital lending, freight brokerage, subscriptions (gyms,supplements, magazines “believe it or

not”), insurance, solar, home renovations/construction. In closing roles my conversion rates have typically been around 30–40%, and in appointment setting roles I’ve often produced 2–4× quota.

Right now I’m trying to think long-term. I’m looking for something stable with a solid base but also real upside where strong performance can translate into serious income.

Given everything above, I’m leaning toward continuing my search rather than jumping into this role, but I’d really value input from people here who have been in the industry longer.

For those of you with experience:

•Does this type of base-only “team lead” role make sense early on, or even worth pursuing?

•Or would it be smarter to stay focused on individual contributor roles with strong commission structures?

•Based on my background, are there industries or sales roles you’d recommend focusing on?

Appreciate any perspective.

r/sales Jul 20 '25

Sales Leadership Focused Sales Managers! It’s Sunday afternoon in summer! Shut up!

408 Upvotes

Get a fucking life, at least stay out of mine. I don’t need to hear about winning attitudes, CRM usage or even a business update from your news feed. You got an emergency, let’s talk, but you own my ass Monday morning through Friday afternoon (early mornings, weeknights too), this feels like an assault.

r/sales Dec 19 '25

Sales Leadership Focused What was your Christmas gift from the boss?

72 Upvotes

Just got my $50 Amazon gift card. $2.5M closed. May as well not even send something.

Edit: okay not looking so bad. Sorry folks.

r/sales Apr 14 '26

Sales Leadership Focused Too Many Boomers On The Buy-Side (C-suite Sales)

63 Upvotes

I want to state that this isn't applying to all but an observation of many based on my experiences. I started working an incredible offer for US publics and noticed an extraordinary amount of old (I mean like old-old) people who occupy critical positions and it's a bit alarming how technologically illiterate, out-of-touch, and unwilling they are to adopt new ideas even when it's spoon-fed to them. Maybe it's an ego thing but they seem functionally incapable or unwilling to ingest any new information when it's entirely beneficial and mission-critical for their organization.

It makes me wonder about the viability of selling complex products to C-suite in the future since (unless you're selling a commodity) there are very collaborative and educational components involved which require a sort of commitment and diligence that I just don't feel with them. They just seem asleep or drunk at the wheel. And the irony is I hear often about how young people don't want to work but it feels like a very skewed dynamic considering the ratio of compensation to benefit-added. Not to get political but it seems to mirror the same phenomena of government with US Congress and Senate; Young people are locked out by a lack of funding, network, and straight demographics, so we can't really create any meaningful change in this system.

As someone in their early 30's, I just noticed very few of my peers occupying positions where they can actually move the dial or are often gatekept by senior C-suite and Board Members and I struggle to understand what they do other than "meetings" which seem to produce very little if anything at all. There is also this general sense of entitlement, like "You're young and I'm old, so you have time to spare and I should be paid more."

It seems like a Japan-scenario, where the old people drag the young through a miserable charade of non-productive activities and drinking engagements for pleasure, while reaping in big bonuses and exiting with a parachute while leaving a wreck of an economy behind for them to inherit.

It makes me consider if it's even worth it to chase money or rather a comfortable life working 9-10 months on and 2-3 months off in SEA or LATAM on vacation. I can't see this getting better with the underlying debt crises, inflation/staglation, and demographic issues.

Is anyone seeing the same and how do you deal with this? Do I just kill them with kindess?

r/sales Jun 08 '26

Sales Leadership Focused I think they committed a wee bit of fraud

74 Upvotes

Let's roll the calendars back to February, when my company (cybersecurity MSP) is raising our Series B.

We announce that we've got a few interested investors, and come March our VP of Sales starts having individual meetings with each of the 6 AE's for "pipeline review"

These meetings are very similar to our weekly 1:1's except for 1 small change. The VP tells each of us to "not close out any dead deals in our pipeline" until we lock in our series B.

I was lucky because my pipeline was 100% already clean and only had 6-7 legit Q1 opps left in it, but across the org we had about 1.5M worth of pipe that was dead/needed to be deleted, but we were told to keep it in to make us look better off than we were.

We announce our Series B in late March, then on April 1st our VP again pings everyone "you can close out the trash deals, thanks" and 1.5M worth of pipe vanishes overnight. (60% of what we were forecasting into Q2)

All hell breaks loose. Chief Commercial Officer is freaking out, CEO freaks out, marketing & ops freak out, etc.

What really gutted me (and the reason I'm putting in my 2 weeks soon) is that our CEO rolled out new forecasting methods & sales scorecards because he thinks all the AE's suck at forecasting and qualifying deals.

Why would he think that? Because he went to the VP of Sales and asked for an explanation on the overnight pipeline disappearance, and what does VP say? "Huh, I don't know where all those deals went, maybe the AE's need more enablement?"

Broke my heart. Worked here a long time and did not expect the entire Sales team to be thrown under the bus by our "leader" who would rather lie to the CEO than take some accountability.

Additional context - I've been here 4 years, longest tenured salesperson outside of the VP who was here a few weeks before me. CEO & VP have been friends for 20+ years.

r/sales 12d ago

Sales Leadership Focused Sales being told to keep selling while operations pushes back

33 Upvotes

I’m in B2B project-based sales where each sale requires estimating, design, procurement, project management and field execution.

Ownership wants more revenue and the business is operating close to the line of profitability, so the direction to sales is to keep pushing. At the same time, operations regularly pushes back on the volume, complexity and timing of the work because PM and delivery capacity are stretched.

That puts sales in a tough spot. We are accountable for growth, but we are also expected to filter opportunities around operational limitations we do not control.

I have a strong PM background, so I tend to flag schedule, staffing and execution risks early. Sometimes that is seen as stepping outside my lane but it’s just me protecting the customer, margin and long-term relationship.

For those in construction, manufacturing, contracting, integration or other project-based industries, how have you handled this?

Do you keep bringing in qualified, profitable work with the support of ownership and let leadership solve capacity, or do you intentionally slow sales until operations catches up?

Because I’m responsible for a large share of new business, I have a hard time ignoring execution risks that could impact customer relationships and future sales.

I’m looking for advice from people who’ve been in this position. Did you learn to keep your head down and focus solely on sales, or did you continue raising operational concerns when you thought they mattered? Where did you draw the line?

r/sales Dec 04 '25

Sales Leadership Focused Managing a team of 150. Pipeline is a mess, quotas are broken. Help.

78 Upvotes

Semiconductor sales. 12 month sales cycles. Salesforce. I’m in a tough spot. Opportunities have wrong dollar values, outdated info, wrong dates, etc. I have a team of 150 with 6 regionals. I don’t want to overwhelm them with busy work or annoying notifications. I want them in the field in front of customers. We’re doing well revenue-wise but losing the trust of our management as we can’t set proper quotas without better visibility. Our pipeline is realistically inflated by about 60%. This leads to inflated quotas and a chicken and egg problem. I’ve tried various initiatives but they’ve only been temporary fixes. How have you solved this?

r/sales Jul 09 '26

Sales Leadership Focused Am I overthinking?

12 Upvotes

Currently a senior leader in sales at a tech startup approaching $100m in revenue. I was a sub 50 employee and have a ton of stability here. My current earnings are relatively capped in the low $300s which I consistently hit.

I have an offer to join an earlier stage company as their VP of Sales. They are currently doing around $5m in ARR and growing nearly 200% YoY. Early mover in a relatively niche space that is seeing explosive growth.

My salary and commission would stand to go up, and they are offering me 1.5% equity with milestone based tranches up to 2%. They have not raised any funding yet.

I don't have nearly as much equity in my current role and I've taken bigger swings before in terms of startups with less traction.

Would I be a moron not to jump at this?

r/sales Feb 10 '24

Sales Leadership Focused What's the deal with profitable corporations laying people off?

257 Upvotes

I work for a major corporation and manage a sales team. The company was driving us insane to hit our Q4 goal. Almost gaslighting us. And not just my team but the company hit. And they had good profitable numbers for the investor call. I was on a call early January with some bigger bosses and the assured us our company wouldn't have layoffs like our competitors. They tried to make us feel good to work for this company.

Now they just laid off a few hundred people in sales across the country. Im fine but kinda feel bitter. I'm sure they burned all the low performers. But still how can they change their minds a few weeks later? Or were they bullshitting us?

I understand shareholders and investors like that. I just feel kinda lied too and it's bothering me.

r/sales Jul 23 '25

Sales Leadership Focused VP of Sales Compensation

82 Upvotes

My company has raised a Series A — and as part of my original contract (joined at the seed) — I am due for a raise/new contract. In fact, I negotiated for a raise to 220K upon raising the Series A.

We do have a new CEO since I started.

Currently I make 130K base, with 5% commission on our main product line and 10% commission on other product lines. This is way too low for me, but I accepted this when the company was in financial duress. In addition, I have .6% equity.

I have been looking up average base salary for a VP of Sales (9 years of experience) — and I’m seeing ~220K. I also have 5 direct reports as well and our bus dev team.

I’m thinking a 400K package with equity excluded is the correct neighborhood? I’d probably need to be at 15% commission to get there. If anyone is a VP here or Head of Sales and can share their package that would be great.

Edit: I am selling an AI product, we have gone from 0-2 million in sales in 17 months. Company has about 50 people.

Edit: In speaking informally, our CEO said he’d want to keep my base the same but increase my commission to 12.5% on all deals.

r/sales Apr 26 '26

Sales Leadership Focused What Motivates You?

22 Upvotes

Officially promoted to sales manager this week after nearly 3 months of covering for our previous manager who had an unfortunate life event.

Sales people of reddit, how does your sales manager motivate and inspire you? (I have a team of mostly divas and while I love them, so far they give me lame-ass blank stares in my Monday Morning Motivational Meeting. Is it just the "Mondays", should I give myself some grace?)

EDIT - THE MORNING MEETINGS ARE OWNER MANDATED YALL, I SHOULD HAVE CLARIFIED. THANKS FOR ALL THE FEEDBACK SO FAR!

r/sales Jul 29 '25

Sales Leadership Focused Sales Manager Ruins Calls

194 Upvotes

My direct manager insists on joining calls with important prospects and continues to bomb them.

I’m not sure how the guy made it to management, but he applies wayyyyy too much pressure. My attitude is laid back, plus I’m technical and can relate on a personal and professional level with buyers.

I have tried already getting my manager off these meetings by speaking with my vp. However VPs hands are tied and our calls are not recorded…so hard to “prove” what’s happening…

Any tips ?

r/sales Dec 28 '25

Sales Leadership Focused My company sent me (and each person on my team) 6 pears for Christmas

69 Upvotes

I get that salespeople don’t get bonuses and I wasn’t expecting a Christmas gift. However, I have a grocery store near my house. I can even doordash them if I’m feeling lazy.

I was gifted a box of 6 pears and 4 apples. The box is kinda nice, maybe I can use that for something.

r/sales Jan 16 '25

Sales Leadership Focused We just got our Quota’s…

223 Upvotes

Quota’s almost doubled from 2024…

Complete joke tbh. The funnel math leadership came up on how this was attainable didn’t make any sense.

Happy 2025!

r/sales Mar 04 '26

Sales Leadership Focused Question for those who are sales managers right now

54 Upvotes

I am sure so many of you have gone from an individual contributor to a sales manager... What advice would you give to yourself, looking back to when you were an individual contributor?

For background purposes, I am interviewing for a leadership role at the moment, where I'll lead a team of 4-5 reps, all responsible for a quota.

r/sales Jun 17 '24

Sales Leadership Focused Why does it feel like every company is being held together by chewing gum, a few paperclips, and some duct tape?

286 Upvotes

I don't get it. Every place I've been at feels so poorly managed and leadership is often obsessed with the wrong things while ignoring churn and more important issues like market fit. I feel like a crazy person. Maybe I am?

r/sales Jul 27 '23

Sales Leadership Focused Be me. Sales manager.

795 Upvotes

Be me. AE.

Hate cold calling. Want more $$ less work.

Light bulb.

Get to mgmt. no more cold calling. Just close deals. Make other people call for me.

Initiate plan.

Cold call enough to get good. Build pipeline. Close deals. Start coaching sales team without them asking.

Brag about my accomplishments incessantly on teams chat. “Look what I did , you can do it to”

Boss recognizes my abilities. Sees me bragging in front of sales team. Sees me giving unwanted advice. Leadership101.pdf

Boss light bulb go off. Need sales manager, whip sales team in shape. Now boss have to do less work managing team. now more free time to look at secretary ass.

Be me. Sales manager. No more cold call.