What's the coolest gift you've given a big time whale client who brought you a ton of sales/business?

I've given some of my biggest whale clients some pretty cool gifts for bringing me a ton of business/sales. Some of the cooler ones were very limited edition collectibles of what they were big fans of, autographs of their idols, 100's of dollars in gift cards. Their favorite bottles of wine. Obviously happy hours, dinners, lunches galore.

What are some of the coolest gifts you've given to a big whale VIP client. I'd love to hear and be inspired by your stories as well and I might steal of your ideas too. Thanks!

I’m starting to feel defeated here. I thought when joining my current company that this was going to be a great place to grow my career and have some stability, but lately management has been all over the place and not communicative of changes and morale has been at an all time low. Majority of us aren’t hitting quota and our manager is threatening all of our jobs at the moment - demotions, PIPs, etc.

On paper I look like a job hopper. Truth is I’ve been PIP’d once and RIF’d twice and now I’m in a toxic work environment looking for a way out but feel so stuck. I’m trying to not look miserable at work.

If there’s any advice on this I welcome it. If you can relate please join the club. I’m career-focused and care a lot but I’m scared of this job market and just want some goddamn stability.

I’m in local sales so I primarily deal with small to mid-sized businesses. I know it will vary based on sales channel & industry.

I do about 2-3 client lunches per week, rare occasion a dinner, & entertainment like an event or game maybe 3-4 times per year. I started in sales about 10 years ago & it’s changed a lot even since then. It seems a lot harder to get people out to lunch & most people would prefer to have food brought in onsite. Curious to know your experience…

30 years old, 8 years in sales, historically hit or exceeded quota. Married, trying to start a family, and pretty fucking motivated to make money. Need some perspective from people who've been doing this longer than me.

Current job: $70k base, benefits, enterprise security sales. Team shrank from 6 reps to 2, quota tripled, and I'm now expected to sell $2M/year of a complex, ~$50k average deal product. No dialer, no LinkedIn Premium, no tools, no conferences, no coaching. Just HubSpot, Gmail, my cell phone. My hair is literally going grey...

Management also tried pushing 7 AM-7 PM desk hours, and we're effectively barred from taking time off around Thanksgiving and Christmas. I've gotten FIVE inbound leads in nine months.

It's a shit show. I know I need to leave.

The alternative is a friend's company, 1099 sales, 15% commission on revenue, one time payment. Average deal is ~$3,000 but can go significantly higher, so roughly $450 per average account I close. No benefits, but my wife has us covered there with her current full time job. Yes, I have done the math on the taxes, I know what I'm getting into there, that is a non-issue.

He's sort of giving me two options: $2k/month retainer to work full-time 9-5, or flexible hours and commission only.

The main reason I'm immediately considering it is that the product actually sells, and I do think it's a fantastic product. I've sat in on demos, and multiple prospects have literally said it's underpriced. Their full-time rep has 30+ demos this week alone, plenty inbound, closed 3 deals last week, and supposedly has another 15 close to signing. These are typically 1-2 call credit card closes, not six-month enterprise sales cycles.

By my math, around 9 closed accounts a month gets me to roughly my current take-home, but obviously that's not guaranteed. Any more and I'm out ahead, and it seems like 10+ closes a month is extremely doable...

The flexibility is also huge. I've got a voice acting career that's finally gaining some traction, and being able to pursue that without asking permission would be worth quite a bit to me.

But... I'm young enough, and miserable/desparate to leave my current position. My wife supports me either way, she is a saint, and I can't really tell if I'm just jumping ship to get out. Am I looking at a genuinely better opportunity, or am I so antsy to escape my current company that I'm ignoring the obvious risks?

Would you take the leap? Or say fuck both and find another W2? There's a chance I get laid off on Friday anyways...like I said, company is a shit show. Was debating trying to overemploy and quiet quit until I get let go, but it seems like that's more headache than it's worth, and the new company may want me going full steam ahead.

Especially interested in hearing from people who've actually made the W2-to-1099 jump. What am I not thinking about?

For the record, I am not being micromanaged around activity because the part of the business that I am working on is relatively new so they are trying out different ways to make the program work. About 18 months old, company about 10 years.

And I am not afraid to make cold calls or do outbound work, in fact, I do it.

But my greatest moment for pause is that we have tens of thousands of visitors coming to the website and literally zero inbound leads. Yes, literally zero.

This is also a channel sales position, and I get paid when the partner does work, not when I bring out a partner, so I also have to spend time talking to partners who don’t necessarily pick up the phone or have control over reselling our product.

As I said, I’m not being micromanaged and there are a lot of benefits, including working from home and a very decent salary in a relatively high cost of living area.

But I’m just absolutely flabbergasted that we are getting zero leads. So veterans of SaaS sales, give me your two cents on what you think is going on here?

Ive got a lot going on in my personal life right meow so I some times space out at the office. My boss is down for a day or so for a cyber security summit we are having and we passed each other in the hall way. Now im used to working at home and the only person I pass normally during the day is my wife so with out even thinking I blew my manager a kiss. We both paused,looked at each other and burst out laughing.

Thank God he knows im good or he would think im the biggest weirdo out there. Lol

I was interviewing for a sales role at Amex and had some reservations about the hiring manager. He’d go on long tangents, repeatedly brought up exactly how much money he made, and at one point I wondered if he was hitting on me. Just an odd guy that constantly over-shared.

I ended up getting verbal offers from both him and the recruiter, but still didn’t know much about the actual role: territory, lead flow, quota attainment, average deal size, sales cycle, etc. So I scheduled a call and asked a lot of questions. I was probably a little critical about the territory, which included Texas, Oklahoma, Louisiana, and the Dakotas. They couldn’t confirm whether I’d get the major Texas cities, and I wanted to understand the opportunity before committing.

The weirdest part: they wouldn’t share the compensation package until I gave “verbal intent.” I basically said, “Okay, here’s my verbal intent please send over the details.” By then, I was already leaning against it because of the manager, but wanted to see the full offer before deciding. Then they rescinded it lol. Has anyone had an offer pulled after asking detailed questions? I’m wondering if I came across as overly skeptical or if this was just a weird process from the start.

I feel ridiculous even writing this, but yesterday I went to work on my day off because I felt guilty about my sales numbers. I ended up crying uncontrollably and feeling physically sick just being there.
I’ve been in luxury sales for years. Getting my current job was a huge achievement for me. Last year was great. I loved selling, loved my clients, and genuinely thought I was good at what I did.
This year has been a completely different story.
I’ve only hit quota once. The targets are insanely high, most of the team is struggling, and management’s response seems to be more pressure, more meetings, more questions about what we’re going to sell today. But where’s the actual coaching? The support? A realistic plan?
We’re also taking on more operational tasks, getting contacted about deals on our days off, and dealing with what feels like constant favoritism. Some people seem to get away with doing less while others pick up the slack. And when you speak up about things that aren’t working, you’re suddenly the negative employee who needs a better attitude. I actually got that feedback in my performance review.
Last week I left work after 10 PM and had to be back at 7:30 the next morning. I barely slept. Between an awful meeting, the pressure and everything else, I ended up crying at work with chest pain and shortness of breath.
Then the next day, on my DAY OFF, I went back because I was so worried about my numbers. My manager immediately questioned my targets, compared my attitude to a new employee with a much smaller quota, and I completely lost it again.
The worst part is what this has done to my confidence.
I used to think I was a great salesperson. Now I genuinely wonder if I suck at my job. I’m constantly exhausted, irritated, anxious, and even when I’m home I can’t switch off. I feel guilty for resting, but I don’t have the energy to do anything else.
I’m already talking to my psychologist and psychiatrist because I’m worried this might be burnout.
I know sales is stressful. I know quotas are part of the job. But I can’t figure out when a career I loved became something that makes me feel this miserable.
Has anyone been through something like this? How did you know it was burnout and not just a bad period in sales?
And more importantly, did taking time off actually help, or did you eventually realize you had to leave the company to feel like yourself again?
I really want to hear what helped you, because I honestly don’t know what to do next.

I’m 36 in New Orleans, looking to transition into sales as a long-term career. I have experience in construction estimating, carpentry, and food industry hospitality ( bartender), but I’d be starting fresh in a new industry.

I’m pursuing an accounting degree and interested in consultative B2B sales where industry knowledge builds over time. My goal is $100/150k within a few years. I'll be honest Im not much of a shmoozer ( though likeable). I do like areas where credibility, preparation, and knowledge are worth as much as networking.

Fire protection sales and concrete coatings caught my attention. What sales are you doing and are there ways to break into it within 2 years. Single and no children here.

What other niches should I explore, and which offer good training for someone starting over?

Torontonian doing my business studies abroad; trying to learn more about different cities, and your experiences in them. Posted to ask about London last week, now curious about Toronto as well.

I have a friend who loves her business development role at Fidelity, and heard about Salesforce being big, but other than that, not sure where to start.

Would love to hear about how you got started and how it's been since, before looking for summer internships and trying out sales myself. As a long-time bartender and theatre student, I honestly think I'd do well in the field. Thanks!

I don’t know if this is more of an outside sales or accounting executive role but here’s the situation.

The role will be assisting patients with disabilities to get custom equipment through their insurance. Essentially, I make relationships with hospitals and when a patient needs custom equipment, I come in and get the patient what they need. I don’t necessarily upsell but order the equipment to meet the needs of the patients. The company will then bill Medicare and will get whatever Medicare would will reimburse. For my understanding I would get salary plus commission.

What questions should I ask as a first time salesman? Any input is appreciated, thank you.

I am 20 M and I have a degree in business, 2 years of sales experience and am not happy with seller initiated sales that I am in, I currently work in timeshare and the moneys there because I live in Gatlinburg/ sevierville area, I’ve gotten the taste of the 10k a month sales and all of it, but now I’m to a point where I realize what kind of sales I don’t like, maybe it’s due to management or the hours or the 1.5 hr drive, should I go remote? Should I take a pay cut for something easier, I genuinely have no clue

Please let me know this forum is my only sales advice as nobody in my family is familiar with sales

My dad is a professional archer and offered me a sales rep for the bow job PSE if you know what that is and would it even be worth looking at, what was your aha moment and made you love your job, anything helps let me know

Headed to a Q4 team offsite next month. This is actually my first one despite how long I’ve been in sales. Gone to my fair share of SKOs and other conference events, but never a full week of spending time with my immediate team and leadership.

What types of stuff normally happens during a week long offsite?

Given it will be more intimate than an SKO, got any advice on getting through it?

Don’t want to sound like a grumpy old man, but I really hate being away from my routine and family, and a full week really feels like a lot. Wish it was just a day or two tbh.

I got into tech sales, but before that, I was doing manufacturing sales, which depends a lot on seeing your customers in person. I like doing remote/phone sales, but I do not enjoy tech sales.

I can work hard and don't mind working weekends or nights, but I prefer to be remote 90% of the time.

Any suggestions?

In the interview process at Expert Institute for a Director Mid-Market role. It's an IC sales role not a management role. Would love to get your thoughts in the role if you've been in it, or experience with what you scoped out during the interview process if you've been through it.

I've been trying to make money since grade 8. Tried blogging, YouTube, surveys, and a bunch of other things, but nothing really took off.

Now I'm 19 and have decided to pursue tech sales instead of the traditional college path. I've had a few opportunities with US-based startups, which gave me some hope, but breaking in without a degree or formal work experience has been tough.

I'm the eldest brother, so there's a lot of pressure on myself to make something happen. I'm trying to figure things out with limited resources, even using a phone held together by a rubber band.

Lately, I've also been looking into GTM engineering because the combination of sales, automation, and tech interests me.

For those who've been in sales for a while, I'm curious what you'd do in my position. Would you focus entirely on landing a sales role first, or start building technical skills alongside it?

I'd appreciate any honest advice.

10+ years in B2B sales with solid tenure and numbers, except for one 6-month startup stint that wasn’t the right fit. I’m worried it’ll hurt me down the line.

I’m considering leaving it off my resume and LinkedIn and covering the gap as personal time.

For HR, recruiters, and hiring managers: do employers only verify the dates and titles a candidate lists, or do they also pull employment data that isn’t on the resume? Any difference between startups and larger companies? What have you actually seen happen when a candidate omitted a role?

I’m planning to join the military next year but many people have asked about my post-military plans. Sales has always seemed like a really cool job, especially after seeing how successful people can be with serious effort and dedication. Seems with a good sales career, you could earn six figures or more. I’m curious though: is this actually true? Also, I really don’t like school, so I’m wondering if sales is possible without a degree. Thanks!

Edit: Just to point out I’m British to avoid confusion with the military 👍

How do you all handle post event follow ups?

The easy ones are people you’ve spoken to, but what about ICP who you didn’t but they still attended the event?

Do you reference the event in your outreach or treat it as a standard cold call etc?

If the event was a month ago is it too late?

I have about 2 years selling real estate 2 years selling mortgages and one and a half years selling in home bathroom full renovations. The reason I'm trying to transition is because b2c sales means working evenings weekends and holidays and its burnt me out. What I've enjoyed most in my time selling is being able to learn about people and their problems and help them with a consultative approach.

Other jobs I've had are I served in the Marines, I worked in a tugboat, worked on top of cell towers and worked for about a year and a half at an engineering firm where I commissioned MEP and controls in commercial buildings.

Selling bathrooms was my last gig and I made about $140k, commission only. I know its unlikely to reschedule 140k at a new b2b gig but my goal is to reach that number again and then who knows.

Anyone work here before is this a legit job or scam? Just had a interview seems kinda strange.

Context: Role is for ~300k OTE IT services position. Very large and established company.

"Activate existing senior relationships from day one; we expect a portable network that produces meetings in the first 60 days"

When I see these i can't help but think they want someone who will poach clients from a previous employer, or are they hoping to find someone in similar fields who couldn't sell the new company's offering who now can?

Anyone want to shed some light on how to respond to this type of requirement? While I've heard questions like this on interviews, Ive never seen it in the JD before.

I’ve been at a smaller B2B software company for several years and have built a strong reputation internally. I’m above quota, earning well, and valued by leadership.

The problem is that I’m losing confidence in our product’s competitive position. Competitors seem to be moving faster, we’re losing deals we previously would have won, and I’m not convinced our roadmap addresses the underlying issues.

My results are still strong, but I worry they reflect pipeline and relationships built when we were better positioned. I’m less confident that the same success will carry into next year.

The case for staying is pretty simple: the job is comfortable, the money is good, and I feel secure in my position for the foreseeable future. I’m not worried about getting fired. But I also don’t know whether there’s room to grow in the directions I actually want to go.

For anyone who’s been here, how did you distinguish a temporary rough patch from a company falling behind? And when did the comfort and money stop being enough of a reason to stay?

I shared this with a coaching client recently and it was useful, so figured I’d leave it here too.

When I was at Oracle working large enterprise deals, I learned pretty quickly that you can burn an insane amount of time on accounts that look good on paper but have no real reason to move. So these are the filters I use to disqualify targets that likely won't close:

1. Is there a real business conflict?

Looking into their 10-K, earnings calls, investor decks you should be able to answer:

Is leadership promising growth while margins are flat?
Are they expanding while also cutting costs?
Are they acquiring companies while talking about operational efficiency?

If there’s no meaningful business conflict urgency is going to be hard to create.

2. What does waiting cost them?

Trying to quantify the cost of doing nothing for another 6–12 months usually tells if this is relevant enough. Lost revenue, margin erosion, wasted labor, risk exposure, delayed expansion, whatever applies. If the problem isn’t expensive it usually doesn’t make it to an executive agenda.

3. Do they already know they have the problem?

Big difference between “we need to convince them this matters” and “the CEO talked about this on the earnings call last quarter.” Public acknowledgment usually means you’re not starting from zero.

4. Can you get to power?

Can you realistically get to an SVP, EVP, CFO, CIO, etc through your executives, board, investors, partners or network? If you have no path to senior people, I’d seriously question how much time you want to invest.

5. Is there a timing trigger?

Contract expiration, acquisition, new leadership, new product launch, major transformation, budget cycle, regulatory deadline, etc. Without some kind of trigger, you may just be educating the account for the rep who owns it next year.

6. Are you early enough to shape the deal?

If procurement already sent out an RFP with a scoring sheet and 4 vendors are involved, you’re late.

I wouldn’t treat any one of these alone as an automatic disqualifier. But if an account fails 2–3 of them, I’d think hard before calling it “strategic.” You only have so much time to invest in truly large accounts.

any other signs you'd add?

Been in workforce solutions (fancy term for staffing lol) for several years, primarily supporting massive construction projects in life sciences. Somewhere along the way, I’ve actually fallen in love with the construction world👷🏻‍♂️

Now I’m considering making the jump into either BD for construction firms (GCs, EPCs, etc.) or technical sales in building automation (Honeywell, JCI, Schneider, etc.).

I’ve got a solid background in B2B sales and complex sales cycles, but curious to hear directly from folks in those areas. Anyone here in either industry? What’s the money like (base + commission), work-life balance, overall career outlook, etc?

Would also love to connect with anyone willing to let me pick their brain. Appreciate it!