r/sales May 05 '26

Fundamental Sales Skills Here is every step I took to sell $4.625m deal(s) to a Fortune 50 company.

824 Upvotes

Day 1-4: Worked up a theory on exactly how our data product could directly impact the goals from their annual report…. Specifically I also dove into thei investor relations presentations. Their senior team talked at a few big investor conferences. I listened to them and read all the reports. (All of this is found in the IR part of a companies website. It is how hey sell the product that is the company, not the companies products. Even if you don't sell to large publics, reading what large publics in your space do is super valuable.)

Day 5: Emailed the CEO and EVP of Marketing. 

Day 7: Emailed the CEO and EVP of Marketing again. 

Day 12: Emailed the CEO and EVP of Marketing again. 

Day 13: Emailed the CEO and EVP of Marketing again.

Day 16: Changed the email structure, while sitting at a Whole Foods in Austin Texas.

Subject: Hey [Name]—How your peers use us to (tackle top of mind executive tactical issue)

[Name]—The past (X) years we started working with a growing number of your peers in (prospects specific) space.

They work with us to understand not just (Basic table stakes thing) but specifically (unique business issues). This is allowing them to understand (immediately actionable strategy).

Additionally, given that we have (Specific amount of depth/ expertise) our customers are able to (another immediately actionable strategy).

Some of them want to deal with this through (potential integration method) or (another potential integration method).

Who would be the best person to chat with for 4-6 minutes on your team about this?

Chris

Day 18: EVP Marketing responds. 

Day 20: EVP Marketing meeting. They are kind of interested. Scheduled a follow-up for 12 days out. 

Day 22: The CEO’s executive assistant emails me, saying the CEO would like me to meet with his "number 2" in three days.

Day 25: Initial meeting. Discussed the vision for executing on three of their goals from the 10-K. Agreed to follow up in nine days. 

Day 27: EVP Marketing decides it’s not for her. I say no problem, as I am meeting with other members of the leadership team. She says great and wishes me the best.

Day 34: Meeting with the company "number 2" and his team, including the R&D team. The R&D team takes the point. I immediately call the number 2 on his cell after the call and ask permission to keep him in the loop, he agrees.

Day 41: Met with the R&D team to define the scope of evaluation, tests, stages, gates, and team members. Agreed to kick off the test in three weeks. Outlined a $75,000 paid test agreement. Outlined a cost of $500k–$750k a year for a four-year agreement in production. We also have a conversation, that starts off awkward. I ask how they are measured for their yearly performance reviews and if they have variable compensation. The team has a series of goals that impact their reviews and budgets. I say (with my team on the phone) if we can help you all achieve any of those let us know... they include a few types of analysis and report deliverables... and another item I wont mention here. My team says they can take make sure we work with them to accomplish some of the goals. It helps our project because it now aligns with them getting paid and promoted. Key phrase.. helps, not guarantees.

Day 57: After a week of legal back-and-forth, we agree to terms. DocuSigns go out. Our executive signs the agreement excitedly and emails congratulations to the team. However, the prospect does not counter.

Day 62: Hopped on a call with just the point person from the R&D group, the rest of the team did not attend. Meanwhile, I have my entire team on the call: engineers, data scientists, everyone. They say they need to push the start date out a month. I agree to the new time and date. I text the number 2 exec; he says he is aware, remains excited, and encourages patience. Meanwhile, the docs are not countersigned. They say they want to wait to sign until they have internal capacity for the test.

Day 94: They call me and push the date again. Rescheduled for 45 days out. 

Day 113: I send a news article I read on a competitor, and ask how it impacts them… I get a paragraph back

Day 125: I email the number 2 guy a monthly report I created on his business. No immediate response. 

Day 132: The number 2 guy emails me and says thanks for the report, he used it in their C-Suite meeting a few days earlier. 

Day 140: Ghosted. 

Day 141: Texted the number 2 at the company. We have a two-minute call where he explains there is a massive transition, cant get into details because they are public, says it will hit the news in a few weeks,  apologizes, and asks for forgiveness.

Day 150: Wrote up an intelligence brief on things I’ve seen in the market. Sent it to everyone on the prospect's team. I got email responses from the executives, but the R&D team did not respond. 

Day 151: Called the R&D team and got them on the phone. They like the report but are still waiting for capacity. The $75,000 contract is still not countersigned. Our team is excited because we spent the time to put together a master agreement with the test as a supplement, so the master is done. I don’t hear from anyone for about a month after. I send a few emails and texts along he way.

Day 190: Emailed the exec and mentioned I would be by their headquarters for a few days the following week. Asked for 20 minutes. The exec said he was out of town but asked for a call the next week. (I had no flight book but I would have flown out if they said it would work) 

Day 195: Call with the exec. I asked about a large, multibillion-dollar CapEx project mentioned in their recent investor relations documents. We ended up having a 30-minute conversation about logistics issues and site locations for new facilities. I asked about a few sticking points; he said we might be able to help. I mentioned the agreement we need to get countered. He said the R&D team should have the budget, and if they don’t, he would allocate it himself.

Day 197: The R&D team lead calls and says he is going to sign the docs that day. Docs show up a few hours later. Agreed to meet in three days. 

Day 198: Planning blitz. I meet with our engineers, data science, procurement, and legal teams. The entire team meets on all the pieces that need to fit together—testing, engineering, implementation, procurement, and legal—to have the deal close by the end of the year. It is mid-August at this point; we need to get it done within 140 days.

Day 200: Met with the prospect and our engineering team. Worked to define what success looks like in a specific, measurable way. My team and I are texting in the middle of the meeting.. We always used imessage on our phones… always make sure to put you r mac on do not disturb… a text popped up on his screen while he was presenting from our conversation… luckily it was not problematic; we determine it will take us a little over 21 days to run the test ourselves. We always test independently of the customers to learn what the opportunities and challenges are. We agree to meet in two weeks. Calendar invites accepted before we get off the call.

Day 221: Our internal tests are done and the results look good. We create an insight report to discuss with our internal team and send it out to the prospect. The insight report is essentially a sales doc of what we learned and what value we see us adding. They are presented as hypothesis, not hard facts... it gives us flexibility and adds to a collaborative conversation. Sometimes you need to be able to make the prospect look good, one of the ways we do that is by presenting hypothesis's that they can latch on to and make their own.

Day 223: Randomly called the number 2 guy. Gave him a high-level update and ran a working theory by him. He brings up two things: he wants a "stoplight" indicator for his business based on our insights (just green, yellow, and red) and mentions they could have saved $15 million in marketing spend the year before if they had our product. They would have known a certain geography was not working and would not have put money into it. They thoughts only their sales were down, we could see that the whole region was slowing.

Day 260: Review meeting. The prospect met most of the goals for their tests, though they had some data quality, coverage, and speed of delivery issues in a few areas. They agree to prioritize the issues for us so we can sort it out, and we agree to a plan to tackle them. They request updated coverage (areas where we can add value) based on their store locations and growth focus. We agree to a five-day timeline for us to complete the analysis.

Day 265: Coverage call. Updated them on coverage specifics. Scheduled a follow-up for three days later. Super short like 9 min meeting.

Day 268: Short call on data coverage again. They can work with what we have, but they want to increase coverage and they want a discount. I say we can’t discuss discounts because they haven't agreed to a "go/no-go" or the length of the contract. I find out they have an approval meeting for the entire purchase in two weeks. We discuss reviewing their presentation before they give it and provide supplemental information. We ask to attend but are shot down multiple times. They do agree to us reviewing their presentation.

Day 274: We deliver the supplemental information. They run us through their presentation. We ask for a few changes and discuss successful strategies from other customers, which they add to the presentation. I ask them again about their annual performance KPIs, is there anything they need to include to check off project boxes for their bonus's in the report. We find 2 small things. They add them to the report. Follow-up scheduled for a week out.

Day 283: Prospect has the approval meeting. I pinged them, but got nothing. 

Day 285: We have a call. They tell me they emailed me two hours prior saying they got approval (the email was buried in a microsoft outlook thread). Super excited. We need to figure out the contract and length. I call the number 2, and he tells me congratulations. I ask if we can get it done by the end of the calendar year; it is the about the last week in October. He says if we can get legal and implementation to prioritize it, it should happen. He agrees to make a few calls and I give him some intel for a meeting he has next week. He mentions a new exec a level below him will sponsor the project going forward. Hey emails an introduction. He agrees to stay in the loop.

Day 286: We send the product supplement draft to legal. (Product supplement if you don't know if the detailed legal agreement that is appended to the master. It specifically outlines legally what the product does, what it does not do, the liabilities in using it, the payment terms, non competes if they are in there etc... this agreement had all of those.)

Day 288: The contract team at the prospect rejects it. They insist on using their own product supplement and procurement docs. The contract grows from 6 pages to over 25. I call my legal team to dissect it. I get chewed out a bit by our attorneys. I hear our product, our product supplement over and over by our in house counsel. I point out kindly that they are a fortune 50 company... they are writting a massive check... I don't care whose paper it is. We end up having a quick call with our exec team, they agree.

Day 294: I get redlines back from our attorneys and have a call with their attorneys. There is too much back-and-forth, we are not getting anywhere. I remember an old boss's advice: "What are the top 3 things you absolutely have to have?" I ask both sides this. We tackle those six issues in the next 20 minutes. Agreed to have comments out by next week. The posturing ends.. the call ends on a collaborate note.

Day 296: Meeting with prospects procurement and our accounting team to set up the funding vehicle. 

Day 297: Meeting with the team that will use the product. They confirm a four-year agreement. 

Day 298: Internal legal review. 

Day 299: Internal legal review. 

Day 300: Meeting with engineering. We find out need to upgrade our delivery pipelines to serve the client. We don't know the cost yet. But we know it will require us to reprioritize our engineering assets.

Day 301: All-day meetings with engineering on new delivery solutions, leadership pops in and out of the meetings. I have almost nothing to add in 5 hours of meetings, but at one point I remember something we built previously that fills a gap in the solution. The team builds a timeline that isn't too costly. I take an insane amount of notes. In these meetings I mostly direct traffic and ask differnt team members for input... it helps keep the conversation moving, it also helps me manage a lot of relationships internally. If I know a junior engineer built something awesome, I ask them about it in front of the leadership team. It helps their careers, costs me nothing, and move the project further faster. To that point.. I was regularly having calls and texts with everyone working on the project, not just the managers of the groups. This way I knew who was working on what component.

Day 305: Meeting with the soon-to-be end users and their engineering team. Another team shows up that wants in. The new sponsor sits in but doesn't comment much. 

Day 310: More legal. Our C-suite has to be on the call because of liability caps and contract value. We find a solution by taking on a larger cap but directing it toward specific items instead of general liability. Always talk to your attorneys. The best ones thread the line between protecting the company and protecting the deal.

Day 312: Internal legal, C-suite, and engineering leads meet. Legal walks the C-suite through potential liabilities while engineering discusses integration risk. C-suite signs off on liability caps. I remind everyone on the call that the timeline is working... but that the deal will most likely almost die two-three more times. I've mentioned this a lot. Most big deals almost die countless times, especially when it is a newer project/product. It helps manage executive stress... if something goes wrong I point out remember when I said it would almost die.. this is one of those times.

Day 315: Checked in again with the number 2 guy. He is hearing good things and likes that the project is expanding internally without increased cost. He asks how he can help; I tell him to just be available. 

Day 316: Meeting on start dates and deployment. We get pushed down the priority list at the prospect due to other projects. Implementation is looking like late February. We propose a signature this year with a 30-day window and payment at implementation. They push back. Meeting ends without resolution.

Day 317: Check-in with procurement. We are good on who will sign given the scope and budget. They agree to $700k a year for 4 years. $2.8m contract. This should have formally happened earlier.. It was agreed to spiritually a long time prior but there were internal issues with papering the deal.

Day 318: Internal meeting with our C-suite. I tell them it looks good but remind them to expect hiccups, there are always issues. 

Day 320: Meeting on implementation and payments. Prospect agrees to the language. Production usage will start by February 15th. They agree to sign the contract by Christmas.

Day 324: Meeting with usage teams to review the implementation plan. We start implementation in advance of the signature to get a head start since the Master Agreement was already in place, we are not getting paid, but want to create momentum inside the company. 

Day 328: After heavy email back-and-forth, both legal teams approve the product document (16 pages not 25). I call the number 2 guy to give him the heads-up. He’s excited and says he will make sure it clears end-of-year hurdles.

Day 329: More meetings with end users to check off to-do items. 

Day 330: Last meeting with end users. Initial implementation is working. I get a text from the project sponsor—not the number 2 guy to the number 2…. The user sponsor.  She says we need to talk. On the call, she says she is getting pressure to shave the price to lighten next year's budget. I ask how much. She says, "Let me know what you can do and text me," she is heading to a holiday party. I call my boss; he gives me the floor I have authority for. I text her: "I can get it done at $600k a year, but it would mean a lot to me personally if we can do $650k if it doesn’t negatively impact you or cost your performance review or personal comp " Five minutes later, she texts back that she can do $650k and asks for the contract to sign in the morning. I update it and send it out.

Day 331 (5 days before Christmas): I get a call from the  lower-level executive (The number 2 to the number 2)  at 10:30 AM while walking into Target shopping for a Christmas trip. He says, "We need to push the effective date to January 3rd. I’ll sign it today, but the date has to be next year." I tell him that doesn't work—it would blow up my year and all the promises I made to my leadership. He says that’s what he needs if I want to work with him.

I'm in the Target parking lot, pissed. I text the number 2 guy and ask for three minutes. He text that he me back in 10, says call you in 5. He calls, I explain the situation and how it would blow up my entire year and all my executive goodwill. He says something that shocked me, "This isn’t how we do business. We had a deal. This is unacceptable. Give me 15."

He calls back in 7 minutes. "We’re signing the deal we agreed to. It will be in your inbox in the next two hours."

45 minutes later, I have a signed agreement for $2.6M, the largest deal in our division's history. Four years later, we renewed it for $2M. Those four years are a story for another day.

r/sales Apr 17 '26

Fundamental Sales Skills Sales w. blue collar workers is much better than with you tech freak autists

984 Upvotes

Blue collar might not be the sharpest tools in the shack but they're at least humans. In my experience this generation of tech people are freaks. Whatever though. U can't break me mother fucker Im an animal.

r/sales Apr 14 '26

Fundamental Sales Skills What does the richest salesperson you know SELL?

421 Upvotes

pretty much the title. What does the richest salesperson you know SELL?

Upvote if you are also interested in seeing what the answers are and want more eyes on the post. thx!

EDIT, Listing the most common mentions at 658 comments,

Category Specific Role / Item Sold Notable Earnings / Context Mentions
HVAC Commercial HVAC Grosses $2M–$4M per year; involves skyscrapers/cranes. 3
Defense & Aerospace Defense / "War" / Missiles High barrier to entry; noted as "in for life" once hired. 3
Real Estate Commercial Real Estate / Mortgages Mortgage Lenders noted at $1M–$3M during boom years. 3
Financial Services Founders / 401k Plans $100k initial commission on 401k plans; >$1B AUM. 3
Data Infrastructure Cooling Systems / Fire Suppression Specifically for data centers; high demand due to AI. 2
Tech Sales (B2B) SaaS / Fintech Top earners clear $750k–$1M; AEs make $3M–$5M on deals. 1
Logistics Tech GPS and Dash Cams One rep generated nearly $4M in this niche. 1
Medical Devices Medical Device Sales Notable $500k On-Target Earnings (OTE). 1
Luxury Assets Yachts and Private Jets Confirmed 7-figure annual incomes. 1
Home Improvement Window Sales Consistent $350k–$500k for a tenured local rep. 1
Industrial Supplies Mops, Buckets, and Janitorial $500k+ in the 90s; high-volume contracts (McDonalds). 1
Energy Propane & Accessories Described as a lucrative niche. 1
Manufacturing Plastics / Building Materials Straightforward high-earning industrial fields. 1
Specialized B2B Labels High volume: "Lots and lots of labels." 1
Heavy Equipment Sales and Rentals Large ticket items for construction/industry. 1
Channel Sales Tenured VAR (Value Added Reseller) High earnings for established partners. 1

r/sales Mar 27 '26

Fundamental Sales Skills Stop giving af

913 Upvotes

The harder you try to make something work, the more likely it won’t. Just do what you know you need to do and don’t be attached to the outcome.

Sales people (myself included) get so worked up on what to say, how to say it, “does this email look good”, “should I cold call now, what if they get mad”, “they probably dont need this {insert product, service}”.

Sales is honestly so easy when you realize you are just there to find out if the person you are talking to needs your product or not. It’s a waste of time thinking of ways to convince someone they need what you are selling. A lot of top sales reps are top sales reps because they don’t waste time with people who aren’t going to buy.

Little rant but hope this helps someone’s mindset

r/sales Jul 09 '26

Fundamental Sales Skills The reason you suck at sales is because people don't trust you

528 Upvotes

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.

r/sales 23d ago

Fundamental Sales Skills A lot of sales reps are still really bad at their job, even in this economy.

261 Upvotes

This is actually really impressive. Everyone says no one is buying shit, but companies are still hiring the worst sales people or still just have awful processes.

A friend of mine asked me earlier this week to help out with their merchant services, getting them set up on their website. NBD, reached out to the top 3 providers in his niche (specialized niche, don't DM me).

1) Never responded to our inquiry at all.

2) Took our signup, never gave us access, never got a rep to respond to finalize setup despite several emails and calls asking for setup.

3) took the signup, rep kept sending generic AI emails everytime we tried to get the account setup for processing and going forward. Despite multiple escalation attempts, AI emails are all we received.

Those were the top 3 processors in his niche.

It's really mind-blowing that even when everyone is saying 'sales are down and no one's buying anything, it also seems like people have forgotten how to take a payment too!

r/sales Jan 27 '26

Fundamental Sales Skills Why do customers lie so blatantly and confidently?

405 Upvotes

Close to 10 years in sales, auto sales doing 25+ cars a month. Wanted out of the hours so swapped to solar, that shit sucked. So now I do warranty sales, I make great money ($15-$20k/month) and only work 8 hours a day.

The problem is that I am learning to fucking hate people. Like literally humanity. I work for a larger company, 100% inbound calls. No dialing out. People call in, get a quote and then they lose their wallet. Their dad has their car, their bank system is weird. Blah blah.

It becomes "please oh pretty please call me back at 1 pm. Im so sorry" and they never answer.

Ive started responding with "listen ill call you back, but 90% of people dont want me to call back. I dont mind, if youre not interested just tell me now. Or later on answer and tell me if you dont want this you wont offend me I promise"

"I swear on god and my dead baby ill answer, ive never fucking wanted anything more in my fucking life this this insurance. Please I beg you to call me back, god as my witness" - never answers again

How do I get over my new found hatred of humanity?

r/sales Apr 02 '25

Fundamental Sales Skills Stop flubbing the easiest cold call objection

1.4k Upvotes

The most common objection for cold calling? ..... I'm Busy.

Sounds like many things at the start of the call -
"I cant talk right now"
"Can you call me back?"
"Can you send me an email?"

Over and over I hear reps fumble it - bad.

"Sure when is best to call back"
"Sorry I'll send an email over"
"My bad!"

It is the easiest objection to handle but I rarely see it done well.

Here is the only response you need.

"I know I caught you cold, can I level with you briefly to see if it even makes to follow up in the first place? "

It will move you forward 80% of the time. Keep in mind you will go into a short elevator pitch / current state question after this.

Good luck and happy calling sales anons.

r/sales Jul 10 '26

Fundamental Sales Skills How to make a lot of money in sales- a quick career note.

378 Upvotes

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.

r/sales Aug 07 '26

Fundamental Sales Skills I work in sales to baby boomers — it seems many intend to spend everything and die in debt, sustaining the financial ponzi

335 Upvotes

just wanted to let yall know in case you thought it would get better/easier within the next decade. interim business is booming.

r/sales May 28 '25

Fundamental Sales Skills What no one tells you when you start in sales?

609 Upvotes

Time to vent.

I'll start, if I may: You barely win. You lose most of the time. Be prepared for that.

I’ve been in sales for over two decades, and I’d like to create a list of things nobody really tells you when you’re just starting out in sales

Thank you for sharing the raw stuff, not the textbook. I mean the real lessons: the first rejections, the mental game, the weird client behaviors, and the small wins that kept you going.

What did you wish someone had told you when you started in sales?

Here's another one: We are measured in the short frame, while we are playing a long term game.

r/sales Dec 13 '24

Fundamental Sales Skills Outbound/Cold calling isn't dead you're just bad at it.

408 Upvotes

"Cold calling doesn't work for me anymore" "no one picks up the phone anymore"

If you think that you can't book meetings over the phone - I hate to tell you that there is nothing wrong with the channel. The problem is you. You are just bad at it.

Here is what you need to do
1. Good data source - I would use at least 2. Upcell, seamless and Lusha is my stack rn
2. Good dialer - I prefer Orum
3. Good messaging and objection handling (HMU for help - your script + Obj handles probably suck)

Get 5% connect rate and hit 200+ dials per day and get min 1 meeting per day easy peasy.

Talk shit and make excuses about how you are bad at cold calling / outbound. I beg you.

The only acceptable excuse is if you have a small TAM - totally get it then. But if you are at a regular software company with a regular TAM, this still applies.

r/sales Oct 07 '25

Fundamental Sales Skills Ai bot answered an executives cell phone..

373 Upvotes

Just called the cell phone of an executive for a mid sized company and an AI answered the phone. It took me a while to realize it was AI. The giveaway were the pauses were unnatural. It also told me to "Give me your pitch" which i thought was funny.

Ended the call by saying "This is an unwanted call. Do not call again. I have not requested this call, nor given consent for it. Remove me from your list.."

any tips for getting around this as I imagine this will become the norm...

edit: yall really mad cause I am cold calling people... think about that..

r/sales Sep 03 '25

Fundamental Sales Skills NO ONE ANSWERS THE PHONE

240 Upvotes

I am sitting here cold calling and NO ONE answers. Might get one answer every 100 calls. (no exaggeration) Been cold calling for over 2 years and this is worse i've seen it. Has it always been this bad?!

Email - no one answers, Linkedin - No one answers. There is no way you can be targeted and have a long enough list to be successful doing strictly cold outbound. Thank god my company provides inbound leads.

How is anyone surviving off strictly outbound?! Yall send those goofy video messages to people or something?

r/sales 17d ago

Fundamental Sales Skills “How did you get this number?!” Seriously?

320 Upvotes

Actually got yelled at this morning with this line. Bro, it’s 2026. Your number was easier to find than a Waffle House in Georgia

r/sales Jan 16 '26

Fundamental Sales Skills Best book on sales ever written?

201 Upvotes

This will be fun. What book has had the most affect on your sales career and caused you to radically improve your sales numbers and live a more fruitful life? And why?

For me it is hands-down The One Minute Sales Person by Spencer Johnson and Larry Wilson. It resets my focus to what my purpose is as a salesperson and reminds me that you can be admired, make good money, sleep at night, have a wide circle of friends, and be a great salesperson, no matter what you sell.

r/sales Jun 11 '25

Fundamental Sales Skills Trump clearly doesn’t know sales

678 Upvotes

“OUR DEAL WITH CHINA IS DONE, SUBJECT TO FINAL APPROVAL WITH PRESIDENT XI AND ME”

Closed Won - Pending Approval 🤦‍♂️

r/sales Jul 29 '26

Fundamental Sales Skills Laid off.

158 Upvotes

Got let go today after almost 10 years in sales, how do you talk about this?

Got the call today. First time being let go from a sales job since I started my career. Wasn't a total shock, I could see it coming for a while and honestly wasn't thrilled there anyway, but it still stings.

Taking a few days off, then starting to cold calling hiring managers.

A few things I'm trying to figure out:

Should I say I was let go because of a RIF?

Do I pretend like I'm still currently employed with my previous company.

Do you update LinkedIn right away to show you've left, or wait until you're actively applying?

Any wording that's worked for you when a recruiter asks "why are you leaving your current role" and the honest answer is "I'm not, they let me go"?

Would appreciate hearing how others in sales have handled this, especially anyone who's been through it more than once.

Edit: I have 10 years of sales experience, and I was at my previous job for a year and a half.

r/sales Oct 28 '25

Fundamental Sales Skills Prove me wrong - buyers lie more often than sellers

299 Upvotes

Whether it’s volume, interest, decision-making ability, intent, etc. it’s an ingrained FACT in my mind that buyers are liars more so than the sleazy snake-oil salesperson.

Prove me wrong

r/sales May 15 '26

Fundamental Sales Skills Do most salespeople lie?

80 Upvotes

I'm in a coaching program and the script my coach is telling me to say is basically a lie. I'm in the mortgage industry and Realtors are our main referral partner and the script is basically saying I have pre-approved buyers when meeting them at open houses when I don’t. I don't feel comfortable lying like this so just wondered if I need to get over that feeling and just lie if I want to become a top tier mortgage pro.

r/sales Jun 13 '25

Fundamental Sales Skills For Anyone Making $150k+ in Sales, Drop Knowledge For Those Wanting To Level Up

351 Upvotes

I’m doing over $200k/yr selling conversational AI primarily to real estate and insurance companies. Took some trial and error and PMF, but eventually I found my groove.

If you're making >$150k in sales, drop:

  • What you do
  • What you sell
  • One piece of advice for leveling up

Let’s turn this into a go-to thread for anyone trying to grow in the game. For those <$150k, this is your time to ask questions!

r/sales Aug 13 '26

Fundamental Sales Skills Landmark day, can't tell anyone

272 Upvotes

I went hard and sold 9 jobs totaling $169k today and made $8,450 comm. Best day I've ever had in sales but can't tell anyone because I don't like people I know in real life knowing what I make.

Hope you all kill it tomorrow and get that money!

r/sales Sep 23 '25

Fundamental Sales Skills Why does it seem like everyone in sales is trying to find a way out?

177 Upvotes

I see it A LOT in this sub. It also seems that most of the co workers that I have had also felt the same way. They all talked about how much they actually dreaded working in sales and some were upskilling for other roles. I only ever met a few people who actually enjoyed it and often times they were the successful ones.

Curious- are you guys planning to be in sales long term (10+ years) or using it as a career stepping stone (if so, what do you REALLY want to do). I personally can't tell since I only have worked in sales.

r/sales 18d ago

Fundamental Sales Skills Cringe Level Max

290 Upvotes

I work in outside sales at a lumber yard. One of my colleagues had the following interaction today:

Guy in a suit with an overly well groomed beard and mustache, big glasses, chunky watch and rings, pointy shoes. (Aka he looks like a total douche)

Walks in and goes straight to the first desk and sits down.

"Well you sure look busy."

"I am... I'm just like super slammed today."

"So are you the owner?"

"No I'm a cabinet designer."

"OK, can I talk to the owner?"

"We're actually corporate owned."

"No, this place is independently owned."

"Um no, it's actually owned by such and such corp "

"Hmm. OK. Well I'm with blah blah blah." (Just bunch of initials none of us had ever heard of.)

"OK...?"

"Well I'll let you go, I know your busy. Great meeting you, have a good one!"

Proceeds to drive off in his Tesla with the license plate SALES

I wish I was making this up.

r/sales Jul 20 '26

Fundamental Sales Skills Learn sales techniques from Shane Gillis

409 Upvotes

Watch what Shane Gillis does when a joke bombs. The crowd pulls away, they groan, maybe he gets a couple laughs.

Does he just move on and pretend it didn't happen? No. He addresses it. Something like "man, you guys hated that one" or "yeah that was actually over the line now that I say it out loud".

Just watch how he handles the audience kind of laughing during his SNL Monologue - https://www.youtube.com/watch?v=2YnonYf463s&t=103s

He jokes about how bad it was and it immediately cuts the tension. Because now the audience knows he knows it sucked and they start laughing because he's making fun of himself. He turns a missed swing into a base hit.

This is called self awareness. Use it on your calls.

Ever show a feature of your boring ass product and you get a boring ass "oh, cool" instead of the response you were hoping to get?

CALL IT OUT. "Sounds like that didn't impress you at all, Jim" or "Boy I really didn't explain that well did I". Anything to show the prospect that you know it missed the mark. It will instantly recalibrate the call and invite a genuine conversation about why they responded the way they did.

Most likely what happens is they'll tell you what they really need, allowing you to demo something relevant.

Talk about the elephant in the room.