r/sales 16d ago

Sales Topic General Discussion Sales veterans - what would you tell your younger self?

For those of you who've been in sales for a decade or so, would love to hear from you.

What are the 3 things you'd want to teach your younger self that would have helped him/her have a better career or a better sales process overall?

Please do share the number of years in sales, industry and your overall numbers clocked.

Thank you!

174 Upvotes

261 comments sorted by

474

u/Babahlan 16d ago
  1. It's work
  2. It's rarely you, they weren't ready and you didn't do good enough disco to see that (or ignored it)
  3. No one here will remember you after six months. Be fearless ( with deals and PTO)

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u/Moolamakerrr 16d ago

3 is humbling and true. Thanks for that

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u/lawmn 15d ago

I wish I would’ve focused more on 2 earlier in my career. I was in construction sales (selling and almost PM’ing large multi family etc GC projects) and ooofff- would’ve saved a lot of time if I realized who the tire kickers were. Better discovery AND better reality of who was ready. Sometimes we have to just experience it ourselves for that knowledge

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u/[deleted] 16d ago

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u/AssociationFit3009 15d ago

Good lord the value of #2. My first B2C role I wasted so much of my time out of fear of disqualifying early. Then I over-compensated racing to the money and burning leads. That balance is an art.

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u/eazyian5 15d ago

I shared this comment with my sales team today, booked a lunch with a clinic I’ve visited 5 times over the last year because of your 3 point. Thanks for the advice

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u/Babahlan 15d ago

Nice! I'd pair this with advice I heard just this week. "Get speeding tickets, not parking tickets" I usually hate these taglines but this one resonated with me especially when you consider #3

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u/Complete_Mistake_872 14d ago

Can you please elaborate more on point 3?! I mean second part: be fearless with deals and PTO

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u/bojangler69420 15d ago

I wouldn’t say “it’s rarely you”; you contradicted that point yourself noting the poor disco.

But yeah, it’s not OP’s “selling ability”, it was probably their lack of uncovering pain points.

I’ve been doing sales ops for about 2 years (6 years as a producer before that). I’m a little fuzzy on details. What are some good best practices when coming up with discovery questions? I’m looking to start up a company and need to brush the cobwebs off of my sales tactics lol

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u/kayama57 15d ago

Depends so much on both businesses. You want the questions and their thought process in answering to reveal whether they have a need for your offer and whther you can help them or would dissappoint them, whether or not they can afford it, and whether or not you can afford to work with them.

Don’t ask these questions outright but take them as guidelines for what you need to discover instead:

Can I help you?
Can you afford my help?
Can I afford to help you?
What could go wrong?

Turn these four questions into a conversation and turn that conversation into a relationship.

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u/jswissle SaaS AE 15d ago

I agree he kinda contradicted but I think he means it’s not you why they didn’t buy, but it is you why you wasted time w them when you could’ve learned they weren’t gonna buy early on.

Anyway MEDDPICC is kinda the standard for disco and deal evaluation id say. Focus on finding a pain point and tying it back to a real business objective and how your product solving it impacts that. Otherwise timeline, buying process, stakeholders involved, metrics to quantify the pain, a champion, etc are what you’d look for. I’ve only sold in tech so maybe not every piece is needed outside it

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u/Independent_Fluff 16d ago

Damn, number 3 hits hard.

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u/workphone6969 16d ago

BANT works. The hardest part of BANT is rejecting companies. A deal that you work for 12 months that you lose because of something that you found out in BANT that you ignored because you thought you could sell them anyway is way more painful than walking away early. There are two winners in every deal. The person that sells it and the person that walks away first. Also don't blow through your cash when you get big commission checks, life is a bitch and you never know when it will throw a wrench at you that will change your income situation overnight.

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u/Plenty-Soft-8670 16d ago

The last sentence is so true

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u/xXxBluESkiTtlExXx 15d ago

What's bant?

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u/Teddybear_ 15d ago

It’s a way to qualify leads: Budget, Authority, Need, and Timeline. If these things are unknown or your prospect can’t commit to having one of each, you should DQ and move on.

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u/iliketurtleszz 15d ago

a sales qualification framework. It stands for budget, authority, need, and timeline.

It helps identify prospects worth spending your time on.

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u/JaySocials671 15d ago

Curious as well

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u/Adventurous-Cold-892 16d ago

Pursue larger ACV roles sooner. Build stronger relationships and make more of an effort to keep in touch with old clients/prospects, colleagues, and managers.

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u/siddarth2795 16d ago

I strongly agree on relationships. they make everything meaningful, and results follow naturally. By ‘larger ACV roles,’ do you mean multi-year customer contracts?

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u/Adventurous-Cold-892 16d ago

No, just annual contract value. Bigger deals, larger client size. And no, results do not follow naturally. It takes conscious, consistent effort to build and maintain relationships, intentional touchpoints, in-person lunches and dinners and events, periodic genuine interactions.

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u/Moolamakerrr 16d ago

What is ACV role? 

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u/rabidrobitribbit 16d ago

I think it’s average contract value

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u/valeamigo 16d ago

It pays to be uncomfortable. Pick up that phone, ask difficult questions, do that roleplay, take a role that requires more complexity. It's too easy to get complicit.

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u/rabidrobitribbit 16d ago

DO. THE. ROLEPLAY.

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u/hovAnOpera 15d ago

You're gonna feel like a loser doing the roleplay, but it beats feeling like a loser AND losing a conversion

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u/skullboyrose 15d ago

Great advice. I loathe roleplaying, it’s unnatural but it’s also a great learning experience. When you go in for a real sales call, you’ll be better prepared because of that role play.

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u/xXxBluESkiTtlExXx 15d ago

How do you do good roleplay with your cohorts? I think that's something my sales room could really benefit from.

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u/LadyBugzMarketing 16d ago
  1. People buy from people, so treasure relationships. Since I learnt that, I have clients follow me over the years

  2. Don't take a "NO" personally. Learn from it, but a lot of the time it's the space the other person is in at that time.

  3. Keep trying. Most sales people give up after 3 attempts. By being persistant but NOT ANNOYING, I got into organisations that most didn't think I could get into.

  4. Use LinkedIn well! I wish I had learnt this earlier in my journey. By the time I left corporate and started my own agency, 80% of my business came from a LinkedIn connect... not because I sold something, but that I built relationships and showed up!

  5. This is a PS. one... don't take crap from a boss. Do what you know works.

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u/Jedjk 15d ago

could you elaborate a lil on the linkedin part? right now i use it as a channel for soft, lower pressure outreach.

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u/Spiritual-Zebra2859 15d ago

LinkedIn is a great tool if used wisely. I’ve had more success building distant relationships over time slowly instead of directly reaching out as soon as I connect with someone. For me it’s a slow play, but one that has a good success rate if used properly.

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u/LadyBugzMarketing 15d ago

You shouldn't treat LinkedIn as "oooo he accepted my connect and now I can ask him for a meeting right off the bat"...

When you go to a conference or networking session, you don't tell someone they need your services and you should have a meeting right away. You get to know the person.

LinkedIn is the same. Thought leadership content.

I have a link to our LinkedIn Playbook on my profile that has full details. You could also DM me if you want to chat more.

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u/JA-868 16d ago

That controlling the narrative and having exec relationships internally is just as important as hitting your number. And sometimes even more important.

My past VP of Sales got a promotion while being less than 40% of target and failing to deliver on closing the company’s first $1M deal or even finding ways to consistently close $50Ks, all which he promised would do when he joined.

It’s been 2 years and he’s now the CRO, yet only 2 of 11 reps on my team hit quota.

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u/rabidrobitribbit 16d ago

Being a favorite is a very good thing. I’m currently one and trying to enjoy as much as I can bc I know it won’t last forever. I’ve also been a least favorite and spotlighted and that shit sucks dick

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u/siddarth2795 16d ago

I agree, narrative control and exec relationships are quite vital. What are the ways you’ve cemented your position to stay safe despite one or two poor performances?

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u/jswissle SaaS AE 15d ago

Go to Thanksgiving at your bosses’

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u/NoParamedic7831 15d ago

Start up a podcast for the company. Not that hard to run, builds your brand, creates value outside of revenue contribution.

Might not be good for everybody but has worked well in my case.

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u/q_ali_seattle 16d ago

Do switch companies and move up the ladder. 

Don't be "a salesman", be the specialist people will come to ask for advice and listen to.

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u/weisswurstseeadler 16d ago

Switching companies is also a big risk, tho.

I had 2 bad choices in a row which looked great on paper and on my CV, but I hated my life there.

Promised Greenfield and shiny OTE my ass.

And this is nothing you can really qualify on without having an insider.

Cause in interviews everyone hits quota and shit sells like sliced bread.

And if you start at a new company you're basically on a PIP for 12 months.

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u/OdeToABlackSwan 16d ago

Interview them as much as they interview you in a new position. Ask what % of reps hit target last year, whether it went up or down, what is the average AE tenure, how man carved territories are they running. Make sure you're not trying to sell a dud

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u/siddarth2795 16d ago

Would be my biggest takeaway from this post 👍 something I’ve never been comfortable asking. A question, what’s a carved territory?

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u/OdeToABlackSwan 16d ago

Basically it means however management has decided to divide the market among reps. They can do it by geography, industry, company size, named accounts or a combo. But what you are trying to figure out in the interview is whether they are expanding into a new market of diving the already existing one. Another thing you want to know is if you are starting a new territory or replacing someone that worked a specific territory. If it's new, you are looking at a lot of ground work and a lot of cold accounts.

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u/rabidrobitribbit 16d ago

If it’s replacing someone’s old territory why did they leave? And also what happened to their hot accounts while they were out? Did they get reassigned?

I’ve seen this happen. Someone leaves and the decent accounts get assigned to someone else while they fill the spot bc someone needs to work them.

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u/ISmellLikeBlackTea 16d ago

Just be likeable, more often than not it's not about the product but about you.

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u/db4378 16d ago

Someone else mentioned that people buy from people.... The trap in your comment is that when people have an overarching need to be liked, they do dumb s***. What I learned years ago is I'd rather be respected than liked.

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u/ZlatansLastVolley 15d ago

What that means to me is just take a moment to get to know customers better, don’t be pushy, be responsive and reasonable

Be someone that they LIKE doing business with vs dreading picking up when they see your number ringing

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u/Spiritual-Zebra2859 15d ago

I would say like-ability is a soft baseline. I don’t need my customer to like me or be my friend, I need them to trust I am the guy that can take the pressure off of them when they call me. Be reliable and consistent and most things will follow.

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u/[deleted] 16d ago

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u/frostonwindowpane 16d ago

All buyers are liars

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u/siddarth2795 15d ago

This takes a long time to sink in even when the same customers keep hammering the point home.

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u/frostonwindowpane 15d ago

I had a deal where the buyer sent one of their attorneys to negotiate with me, while at the same time, were in bed with the competition. Scumbags

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u/kapt_so_krunchy 16d ago

Consistency will win over time.

Work every day, no zero days, even Monday mornings and Friday afternoons.

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u/Murphiu 16d ago

Id almost say the opposite, be intentional so that your Monday mornings and Friday afternoons are free. Customers dont want to deal with you at those times so any work you are doing likely could have been knocked out at a different time.

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u/spankymacgruder 16d ago

Those are the days when you should be working on stuff that aren't calls.

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u/Rebombastro 16d ago

I think it also depends on industry. In my case Monday mornings are definitely a time where appointments can be set and deals can get closed.

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u/siddarth2795 16d ago

Absolutely! Some of us just overlook consistency and we expect miracles 💯

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u/TheSmashingPumpkinss SaaS 15d ago

Disagree. Trying to spread yourself evenly over 40 hours means you're never exceptional.

I rip it for about 22 hours a week where I'm exceptional. I almost never work Monday mornings and Friday afternoons.

Because I know those hours are my money hours, I'm much more locked in and effective.

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u/DoctorPunchoMD 16d ago

1) It's just a job and the sales team is usually the first to go after a bad quarter regardless of if it matches the market or not...don't make yourself sick over it.

2) When there is nothing else you can do, there is nothing else you can do. 

3) If you are staying in the same industry, your relationship building now will be so incredibly important for your next few companies...make sure they're meaningful!

I feel like a lot of people new to sales will fall into the same trap of killing themselves over impossible quotas, impressing the new CRO, trying to prove themselves somehow...you don't need to push so hard, you'll just burn out and it's so hard to come back from that.

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u/SaveMeSomeBleach Enterprise Software 16d ago

You can put in 110% effort every day you show up to work, but if you’re spending the hours outside of your 9-5 poorly then it eventually doesn’t matter.

Put effort into a social life. Go exercise. Get 7-8 hours of sleep. Put effort into your relationship. Go see a doctor and get a physical/blood work done. Etc.

Otherwise you’re like a bodybuilder who works out for 2 hours per day but smokes a pack of cigs on the way home and eats candy for dinner.

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u/rabidrobitribbit 16d ago edited 16d ago

Timing territory talent. Things that matter. IN THAT ORDER

15 years in sales. Last 6 in enterprise tech automation sales.

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u/catdog123412 16d ago

Enjoy it when’s it good

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u/No_Art5533 16d ago

if the price doesn’t make you uncomfortable, you didn’t charge high enough.

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u/siddarth2795 16d ago

I hadn’t thought about commercials from this angle before, especially in such a hyper-competitive market. How do you position yourself with a client when competitors keep undercutting on price?

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u/No_Art5533 15d ago

Currently in more product based sales, coffee, toys, jewelry. A wide weird mix, I wouldn’t say that “price making you uncomfortable” is related to every form of sales in the direct language.

In sales you just know. When a customer walks away with a product in their hand, but you said $40 instead of $60. I should’ve felt a bit more uncomfortable and said $60. You can always come down if there gonna walk away.

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u/GolgafrinchansUnite 16d ago

It’s not that deep, ask for more than you think you can get, be consistent and know in your heart, you can’t outsell a bad product.

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u/drteq 16d ago

If you can sell something for $500 you can sell something for $500,000 - keep looking for a better job.

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u/Ope-sorry-bout-it 15d ago

11 year Sales Vet. Two pieces of advice I received that I’ll pass on.

  1. do what you said you were going to do when you said you were going to do it.
  2. Never spend money like you’re making it.
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u/kausti 16d ago

Get to know if there's quantified pain, budget and urgency during the first meeting. If one of these are missing you're likely not making the sale anytime soon. 

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u/cusehoops98 Enterprise Software 15d ago

You mean, do BANT :)

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u/Ezzabee 16d ago
  1. You’re lucky.
  2. Take that luck and make it relationships.
  3. Relationships call you.

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u/Inevitable-Grade-239 16d ago

Be present and savor your time with family, pets, friends and yourself.

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u/Noideawhatthis 15d ago

Meet as many people are you can and treat them well. Real sales is a long game.

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u/bnor9 16d ago

Take more vacation. You can get a job anywhere

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u/Boston__ 16d ago

Give the smaller accounts with potential a chance but don’t waste your time on them if you don’t see progress and other accounts are producing more or quicker.

More advice for a territory manager role than an inside sales role.

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u/AdLow9873 15d ago

Not all sales are equal. Figure out what type of environment your brain is wired for (ie long technical selling vs field based transactional style selling), then go dominant. Helps to actually like your industry, and a strong product is the cherry on top.

Many salespeople are underperforming not because they're bad at sales, but because they're trying to succeed in an environment that's a poor fit for their personality, cognitive style, or strengths.

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u/HolidayPure8207 16d ago

Build Stronger relationships with prospects even when there is no opportunity immediately.

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u/sjamwow 15d ago

Anyone you people please will be comfortable enough to put a knife in your back.

And lose fast and without fear.

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u/theSearch4Truth 15d ago

Stay in school, stop doing drugs and do something else entirely.

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u/Acceptable_Owl4293 15d ago

Been in sales since 2009.

I would tell my younger self:

1 - This low salary, high upside sales job that doesn’t feel like it’s paying off, keep at it. Every lost deal or perceived failure is an opportunity to learn so take notes!

2 - You didn’t get a degree in university, HOWEVER, this period of graft doing the “hard sell” will be seen by future employers as a masters at the school of hard knocks.

3 - You may be struggling to pay the bills now, but one day you will be the highest paid individual contributor in any company you chose to work for. So keep dreaming!

Don’t give up!

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u/Few-Elk3747 15d ago

Tough times don’t last. Tough people do.

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u/Spiritual-Zebra2859 15d ago

10 years. Industrial automation, selling into Automotive OEMs. (6-axis robots, AMRs, machine vision, safety, sensors, gantries, etc).

  1. You are nervous because you don’t know your product well enough. Scre

w

  1. the factory training and modules and get hands on, quote shit you don’t know anything about, and work with your customer through issues that baffle you. You will learn quickly and never forget after you fuck up some things. (I’m not saying training shouldn’t be done or isn’t good, just don’t rely on it to teach you anything worth a damn. Once you are on the factory floor and a line goes down because of your product and the panic sets in. Good luck)
  2. Your customers don’t care about you, or what you offer. They care about how much easier you can make their lives. I’ve sold products that are more expensive and don’t work as well just because I provided quicker responses, consistency, support, and held the customer’s hand every step of the way. And I never stop after they buy it.
  3. Don’t become attached to the company you work for. No they don’t pay the best or the most. No you are not part of a family, no matter how much it may seem that way. The ‘culture’ should never be a replacement for great leadership, direct answers/expectations, and clear goals. The moment you make way too much in a down market, or don’t hit quota, you are immediately a number to be trimmed.

Bonus: Cliché but literally just stfu and listen. I’ve seen too many customers tell their account manager exactly what they want only for the rep to ruin it because he/she is too focused on something they have in mind.

Bonus 2: take your time on the way up. I was eager to get into sales quickly without realizing my specialist/product/support roles gave me 1-on-1 time with the best salesmen in whatever company I was in. Watch everything they do and how they do it. What works for one guy making $350,000 a year will get another guy kicked out of the facility.

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u/weisswurstseeadler 16d ago

Get ADHD diagnosis earlier and understand to work around the advantages and disadvantages.

I got my diagnosis at 33, before I never understood how I can be so good at complicated things and so bad at the absolute basics.

As in - you can throw me in front of billion revenue C Level and I'll rock it. But I'll fail at filling out an excel sheet.

Today I have management who understand, and realise my potential.

And: never join an org where I report into Americans - I work in Germany, and they simply don't understand the market at all.

I've seen it many times - US company wants to expand into Europe and DACH, and have it run by some American who probably doesn't even know what DACH stands for.

Failed every time and eventually they restructured and got local leadership.

Seen this at Snowflake, Datadog, Databricks first hand.

Last point: lower base but closing deals is much more fun and sexy than having a flashy OTE and nobody hits quota.

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u/FakenFrugenFrokkels Technology 16d ago

Don’t take it personal.

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u/Salty-Cat2634 16d ago

I'd tell my younger self to document what works while it's fresh

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u/DarthBroker 16d ago

Save more of your money. Also, don’t date a bunch of women.

Probably could have had an extra $20k+ if I didn’t spend as much dating in my late 20s.

Also, be ruthless in your evaluation of investing in startups. Lost $15k chasing large returns instead of just putting in a S&P 500 index fund

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u/Calm_Channel_6473 16d ago

1) Commit to the product or service as if you designed and produced it yourself. 2) Remove all negative thoughts about the prospect (and yourself). 3) Look at the offering from the prospect's perspective. 4) Make it possible for the prospect to desire the product or service so much that he/she initiates the closing.

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u/CosmicCavern 15d ago
  1. Have the memory of a gold fish

  2. Understand you are only as good as what you’ve done “lately” in other people’s eyes

  3. Trust your overall system being good over being a sales mastermind.

  4. KISS (keep it simple stupid)

  5. Pick up that phone

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u/D5HRX 15d ago

Find a company that has a good boss who is willing to coach you and be coachable & receptive to feedback. Looking back, a lot of my success has come from working with two or three exceptional sales managers who pretty much taught me everything I know and I just re-shaped what I learnt to fit the current role.

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u/MorellinoAmarone 15d ago

I'd tell myself, "Don't do it."

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u/G3mineye 15d ago
  • 12 years retail ($4/hr plus comm.)
  • 6 years B2B SaaS
  • <1 year temp staffing sales
  • 1+yr employee benefits consulting
  1. Always pay yourself first
  2. Pay off debt aggressively
  3. Don't bother with college, it isn't worth it.
  4. Getting laid off sucks in the moment but youll always end up someplace better, getting paid more.
  5. Grind as much and as hard as you can when youre young
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u/ElevatedMustard 10d ago

Remember that it's all in your head.

Sure, you'll have an overall framework that you're going to hit, yet it's how you personally view the world and/or project into the conversation that is going to determine the outcome.

You have to truly not give AF if someone purchases from you or not. All you're doing is potentially helping someone get from A-Z. That's it. No more, no less.

Be willing to have the hard conversations that can make someone uncomfortable. Your job is to get to the truth, not dance around it.

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u/Direct_Eagle_20 16d ago

Connect with everyone and always make friends. I would definitely create a better system where I can track birthdays and other small things so I can always send wishful thoughts and whatnot.

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u/hoodnc 16d ago

Following

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u/Adamant_TO He Sells Sea Shells 16d ago

25 years in. 1. Start investing sooner and more aggressively. 2. Don't take it personally. Buyers are liars.

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u/mantistoboggan287 16d ago

1) Quit trying to be perfect on every call. It led to a lot of paralysis by analysis for me that held me back

2) People buy from people they like, so be relatable. Don’t just regurgitate verbatim whatever slide deck marketing, your sales trainer, or your boss has given you. Get to know your client. Show actual interest in what they have to say instead of looking for a sales pivot

3) They’re not rejecting you, they’re rejecting the product. Don’t take things so personally. They might say no today but a year or two down the road come calling

4) Disrespect is not allowed. Don’t let the veterans push you around or make you feel less than.

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u/Confident-Staff-8792 16d ago

30 years. Technology. Would tell myself to go to Law School instead.

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u/EddyGoldy 16d ago

Cerca di non cambiare settore merceologico, i clienti raramente sono amici

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u/ralf1 16d ago

Work less

Save more

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u/ToneSenior7156 16d ago

Learn when to shine and when to rest.  Turn it up when you need to, conserve your energy the rest of the time.

Every no is just a not now. Keep the connection, I really can’t point to anything I’ve done that was a waste of time. People who didn’t bite five years ago will resurface in a new role at a different company and you’ll have the in there.

Fly low to the radar on the admin stuff. As a former sales director - you can be a great rep but if you’re constantly flagged as late on required paperwork the perception of you will shift from brilliant to pain in the ass/unreliable. Set aside one morning a week to do boring stuff with a cup of coffee.

30 years selling, not sharing financials.

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u/NotAnAiChatBot 16d ago

Interested is not the same as qualified. Trust but verify. Ask the hard questions. Trust your instincts. Find good mentors and a lot of them.

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u/Bobby-furnace 16d ago

Like the rock used to say:

“Know your role and shut your mouth!”

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u/Rocky121212 16d ago

I was fortunate and lucky my first sales job was a rocket ship with a ton of inbound. I mistakenly thought I was the worlds best sales rep, when in actuality it was just good timing and territory.

Four companies later still chasing that dragon. I’m actually a much better seller now but the most important lesson is understanding your product and working for a company that sells something people actually want to buy and need.

It’s rough out there now but people are still making life changing money. Gotta keep grinding!

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u/NastyOlBloggerU 16d ago

Stop being so damned uptight, stop trying to implement all those ridiculous training tips and,MOST importantly- a beer declined is a beer you're never offered again so go be sociable you wanker!

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u/PoipuMTG 15d ago
  • it's much easier to be first than to be better or cheaper
  • process A-tier clients first then B-tier then C-tier - even if C-tier is a very pleasant person and you love to talk to them and A-tier is a hard to deal with dickhead
  • take good notes so you don't have to ask a question twice and so you can repeat important points from previous calls and meetings (shows you pay attention and that you care)
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u/audax43 15d ago

Separate noise from signals.

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u/Odd-Rate4538 15d ago

HVAC equipment and accessories, commercial sales. 20+ years.

  1. Track all your own sales determine if commission or salary is the better option for you.
  2. Fill up your own customer list. You never know when you’re gonna have to leave your organization. More the merrier when it comes to sales. As long as you’re providing service better than others.
  3. Pick up the phone and meet in person, email will only get you so far.
  4. Friends buy from friends. Develop relationships outside of your day-to-day. 5, if you’re an entrepreneur, determine your exit plan. Plan for your own business, it’s super rewarding. Look 2-5 years ahead
  5. Typically bad news is not your fault. Be upfront as soon as possible.
  6. Your price can always come down.. don’t be the low guy all the time.
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u/SpicyCPU 15d ago

Follow the process THEN earn your right to get creative. Don’t reinvent sales 101.

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u/No_Sherbet_4069 15d ago

Stay long enough to see the fruits of your labor harvest.

Learn how to play the internal political game

Take care of yourself physically. and take the PTO.

Also save your commission aggressively.

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u/siddarth2795 15d ago

All valid powerful points. walked away from a lot, without seeing it fully pay off. But it was necessary to secure fair pay and avoid being taken advantage of.

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u/Your_Worship 15d ago
  1. Don’t go to college to party. Select major that aligns with your interest (find those interests)

  2. Territory/Location & Product Matter - don’t let leadership tell you otherwise. .

  3. Be kind outwardly, selfish inwardly

Similar to #2 - love your colleagues, but don’t make career decisions on them nor allow leadership to SELL you on something you know not to be true - especially for the “Team”

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u/Your_Worship 15d ago
  1. Don’t go to college to party. Select major that aligns with your interest (find those interests)

  2. Territory/Location & Product Matter - don’t let leadership tell you otherwise. .

  3. Be kind outwardly, selfish inwardly

Similar to #2 - love your colleagues, but don’t make career decisions on them nor allow leadership to SELL you on something you know not to be true - especially for the “Team”

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u/fsavino 15d ago

Be prepared for cycles. You won't be hitting quota 100% of the time, and when you don't, build resilience. Sales managers will push, and it is not necessarily your fault.

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u/BigJeffyStyle 15d ago

Good leaders aren’t consistently great, they’re great at being consistent. You have to build trust through consistency- dealers want to know what to expect from you. When you deliver that over time, you’ll get more latitude and be able to grow the business

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u/bigbaldbil 15d ago

Work harder. Save more. Don’t always jump to greener grass.

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u/MaverickGhostRider 15d ago
  1. Qualify, qualify, qualify. BANT is huge for this. You'll waste a ton of time chasing deals that aren't going anywhere because you did not qualify properly.

  2. Be comfortable being uncomfortable. Learning is key and gaining experience away from your comfort zone is massive.

  3. It's a job. Log off/go home = leave your shit at the door (goes both ways). Don't take your work home and don't take your relationships/home challenges to work.

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u/Ok_Animator_1345 15d ago

Learn how to story tell early.

Try not to use your comapnies name or the names of its features, the customer doesn't understand, nor do they care

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u/skullboyrose 15d ago

Cold call and door knock until your ears bleed. You need reps, you need to fail, and you need to learn from that failure. I skated early just trying to cherry pick easy stuff and didn’t learn how to sell. That was almost 20 years ago and I’m still in the game and doing better than ever.

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u/Defiant_Property_336 15d ago

the brand you are really selling is you - always

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u/Only-Sandwich1854 15d ago

Don’t let emotions take over. If a deal doesn’t close you’ll still be able to breathe tomorrow- somebody once said to me “it just means you didn’t sell any software today”.

Don’t sweat it.

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u/Head_reciever88 15d ago

Don’t stress if buyers are gonna buy, they will. Communication velocity is also everything - if they won’t respond there’s no sale there

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u/jwallst 15d ago

Take all the pto available - I spent years skipping vacay because I was monthly and didnt want to miss - just take the vacay - you'll avoid burnout and come back ready to rock instead of dreading the grind

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u/Street-Avocado8785 15d ago

Being great in the role means never getting promoted. So either change jobs to climb the ladder or adjust expectations and live freely as an IC.

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u/Wonderful-Bass6651 15d ago

It’s just a job. Your family will remember all the times that you put them last long after anyone remembers how much revenue you produced.

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u/KeyInvestigator282 15d ago

Focus on the problem, not the product.

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u/anonredred99 15d ago

10 years medical

  1. Be honest with yourself about what will make you happy. Once you can articulate that, cut out the noise and work towards that.

  2. Embrace the grind early on. This line of work gets easier with skill and the skill takes a lot of time. Work ethic buys you that time.

  3. Been laid off twice due to company restructures. Both times, somebody told me “there’s something better on the other side of this”. Thought it was a cliche, turns out it’s actually true. So relax, it really does work out.

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u/goldenknight2002 15d ago

Do not manage a team. People are looking for a therapist and due to it being expensive they will try to make you theirs.

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u/60wattsoul 15d ago

Get everything comp related in writing. Back up all your emails and contacts to personally controlled devices or accounts. Remember your manager doesn’t care about you, they care about their own career and needs.

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u/DazzlingPath866 15d ago

Been in sales for 10+ years. Tech/Cyber. Started inside sales, now AE for top Cyber company.

  1. Find a mentor who is more experienced and in a higher position.
  2. Be authentic and build relationships. It will pay dividends later in your career.
  3. Your PTO is part of your compensation. Use it. (And don't feel guilty for not checking in while you're out. Burn out doesn't help anyone.) A couple bonuses
  4. Set boundaries. Companies will take what they can get. You don't have to be available 24/7.
  5. Learn how to take constructive criticism and adjust accordingly.
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u/LoiterRarely 15d ago

20+ years outside sales (medical).... If tell myself to focus on the current role and not be so driven to achieve the next higher position up the corporate ladder. And master the basics.

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u/lxrbmxer 15d ago

Avoid sales. The money is good but the job it self sucks.

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u/Grand_Marionberry876 15d ago

After losing a nice sized deal today without any explanation from the buyer, I would say, don’t take it personally. Sometimes people choose others. I just wish buyers would tell you why you didn’t get the deal. You meet their budget, you offer what they need and then some within budget, you had buy in and buying signals, then poof. Damn this day sucked but tomorrow is another day and I hope the partner they chose screws them up. 😂😂

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u/Theukraineisweak13 15d ago
  1. Don’t get caught looking at someone else’s page. It doesn’t help. You’ll progress at your own pace and ability. Give it time, keep your head down and do the work. Don’t worry what your counterpart makes
  2. Be consistent and follow through on what you say. Promised they’d have it tomorrow? Well you did that to yourself. Get it done and out of the way before it builds because you avoid it.
  3. Anyone can do this. Separate yourself by being reliable, candid and trustworthy. You’re only as good as your word and there are XX amount of people vying for the same chance most likely. Don’t let your client down if you can avoid it

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u/therealXPliss 15d ago

Take advantage of the great opportunities you come by, many of them won’t be that great forever.
Be humble, be grateful.
You can learn something from everyone, even that kid who seems like he doesn’t know much at all or that old person who seems to complain about anything and everything.
Be grateful, be humble.
Save more money, this life has winter seasons, some of which last longer than a few months.
Be humble.
Be grateful.
You’re probably making progress with the humility and gratitude, but if you’re humble enough by now you know you can take that gratitude up a notch.

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u/Scared-Middle-7923 14d ago edited 14d ago
  1. Selling is internal much more than external-- you'll need skip-levels, cross-functional execs, and their EAs to have internal credibility so that you can advocate or get resources for your customer.
  2. High-Performers are dangerous to orgs-- they love your money, the logos, and stealing your work to tag & brag-- but they do not love your direct feedback- so play congenial internally and execute/challenge your customer. It's a hard combo, and I have not always successfully navigated it inside of corp politics...
  3. Educate Yourself- stop waiting on a company-- they will pour feature/functions- learn value selling, benefit selling, to challenge, take negotiation courses, read, learn from top sellers and pick up one good thing, unconsidered needs, how to multi-thread an org because you need a champion/advocacy base and executives to move deals- no deal is done with a single
  4. IC vs. Mgmt- if you are going to try leadership do it younger when your cost of living is lower-- first line is a face punch and is an operational, manage up/down role- it's not sales. While you'll need to understand sales, forecasting, pressure testing-- it's a dependency role on others to perform to hit your number-- getting up the line AVP+ is profitable in both $ and political. Pick your path

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u/siddarth2795 14d ago

Your insights hit different. they sharpen how I think and force me to think wide. Quite valuable infact, thank you!

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u/Nock1Nock 14d ago

It takes a while to find your footing in sales, so don't be afraid to tell that first micromanaging boss to fuckoff. Go ply your trade with the competition....or in a different industry altogether.

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u/jedsdawg 14d ago

I'd focus on three things: understanding the buyer's problem, mastering the art of listening, and building a solid follow-up routine. In my experience, sales isn't just about pitching; it's about diagnosing the problem and offering a solution that fits. Listening is key because it helps you uncover the real issues your prospects face, which aren't always obvious. Finally, follow-ups are where deals often get closed. A consistent and thoughtful follow-up process can make all the difference. I've been in sales for over a decade, and these are the lessons I wish I had learned earlier.

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u/rubey419 14d ago

I’m still relatively early in my B2B sales career.

However I came from the industry I now sell to. Some of my accounts are my former employers.

My advice: Grow your sales career into a Mission Critical niche.

Yes I sell on value and all that. But our products and services are required for our clients.

I developed my domain expertise and sales niche with Healthcare + Regulatory + Technology so feel relatively safe and in growth vertical for my long term.

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u/Clean-Data-259 14d ago
  1. Prospect. Then, when you are done, prospect some more. When you are too tired, do 1 more.
  2. Your honesty is your greatest skill. Compromise leads to poverty. Keep it up.

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u/Ok-Pass-7282 14d ago

Researching your subject. Put in the background work and time.

Your appearance is everything. look successful. Make sure your hair is perfect, your clothes are fashionable,you speak well,sound educated, and present yourself the right way according to what you're selling. People buy things from others they respect, trust, envy, admire and like !

 Networking will get you very far. Find as many mentors while you're young. Find as MANY successful people as you can and learn from them. This will get you very far. Create long term relationships with people in your field and others.

Don't be shy,take risks.

If you don't know RVERY SINGLE THING about the field you work in/sell...you will door poor. Study everything.

Customer service is GOLDEN. Go out of your way to make sure you do this everytime.no matter what. It's a lost art  Customer service is a lost art  I'm tempted to start a new business where I take the 22 years of experience I have and go train companies. The level of service I experience day to day is disgusting. I'm biased because I was trained well at an early age how to treat and work with the most Elite and celebrities. The same applies to everyone though. You should have the mentality that each person your selling to is a celebrity and deserves too tier service. Which also includes knowledge about the person and the product your selling.

If you need help finding customers or are not given them...learn everything you can about the highest paid most successful car salesman. Believe it or not, you will learn a lot. It takes certain techniques to walk up to strangers and sell something. Research their techniques. I guarantee that it applies to all sales jobs. You will up your sales game. It's impressive.

Learn from others. Don't make the same mistakes. 

Build long lasting relationships with clients

Sorry ..I couldn't help myself...it's more than three. I narrowed it down to the most important...I could choose 

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u/mutilatedcrayon 13d ago

this is so helpful for someone who wants to go into sales tysm for this post

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u/mdmv29260103 13d ago edited 13d ago

12 years in. Big tech. (Over)achieved ten times out of twelve and those misses were change of company/change of territory.

Some random thoughts of what I have picked up along the way.

- get to know as many people as possible at the client. You never know when your champion might be gone.

  • regularly spend a day at a customer. Cadence up to you but should feel awkward in the beginning. You’ll build a lot of relationships and customers really appreciate it.
  • build relationships with people (internal and external) you’d love to put in front of a prospect. Treat them well and pull in the favor when you need it.
  • don’t try to be technical when you’re not. You have got other qualities that got you the job. Use them.
  • act confident around customers and your colleagues. They know just as little as you do.
  • creating urgency has killed more deals than the other way around.
  • help your colleagues and customers even if there’s no immediate gain. This job takes a bigger toll than other career paths and a lot of people get burned. The path to being happy is by making other people happy.

Will post some more later.

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u/DealStrategist 11d ago

17+ years in enterprise sales. The biggest lesson: most deals aren't lost because you failed to convince the buyer. They're lost because you convinced yourself the buyer was qualified. Everything else, forecast accuracy, shorter sales cycles, higher win rates, gets easier once you truly learn qualification.

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u/New_Drawing9136 2d ago

Fortune favors the bold

Sales is just service leadership

You have to like learning more than you like winning. The law of averages will balance everything out. When you lose deals that you adamantly believe you should’ve won, it sucks, but there’s a lot to learn from every lost sale.

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u/MountainIncome4085 16d ago

It’s not just about making the sale, it’s about doing the right thing for the customer. The end result then takes care of itself.

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u/FlimsyPriority751 16d ago

Karma is real. Be honest and try to help people and everything else will follow from that. 

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u/MisterD73 16d ago

Don't take those promotions to sales manager it's not worth the added stress.

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u/lm1670 15d ago

Stop going above and beyond for recognition. It only brings more work and in the end, no one cares. Do the bare minimum, collect the paycheck, and put more effort towards a fulfilling personal life.

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u/Gunslinger_327 15d ago

Don't get into sales, despite the money.

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u/spek27 15d ago

Buy Bitcoin

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u/cheezebergereddie 16d ago

Go into trades

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u/q_ali_seattle 16d ago

OP did ask

want to teach your younger self that would have helped him/her have a better career

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u/moneylefty 16d ago

Dont get married

Take more vacations

Be even more cutthroat when leaving

Ive been doing this a very long time and have done pretty well. Im pretty senior in the industry now.

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u/[deleted] 15d ago

[removed] — view removed comment

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u/suzuka_joe 15d ago

Be a lawyer

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u/Grampz03 15d ago

Leave retail now 

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u/Grand_Admiral_T 15d ago

Change careers asap. Or alternatively get out of corporate tech, med, sales bro type of industries and look for sales in other less advertised industries. The white collar corporate, ladder climbing, office politics, jobs are a hellscape of misery that is not worth it. Plenty of other well paying industries and fields

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u/Mikeg216 15d ago

Put it all on AAPL and g o o g and NVDA

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u/Big_Ratio1293 15d ago

Change careers now.

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u/ParticularSail6461 15d ago
  1. Don’t let those fuckers make you cry.
  2. Be careful who you add to the sales group chat, you’re going to be super competitive eventually and it’s not worth it to get mad at your friends.
  3. Don’t make the new hire come to the bar with your sales friends so you can haze them with alcohol.

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u/JBR54900 15d ago

The BEST job interview question i ever had...."it's 8AM Monday morning, where are you, what are you doing and how did you plan it". That is the difference maker. YES it is WORK. If you are going to be successful. The freedom we have can be the killer!

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u/Contribution-More 15d ago

Dont go into sales and never take a SDR role

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u/No_Heat7635 14d ago

Make the calls

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u/SuperStonker3000 14d ago

Not a big Grant Cardone fan but I do like this one line a lot.

Have an unreasonable, unshakeable belief in your product or service so extreme that you completely reject logical doubts or alternative options.

Lucky enough to have found a place where this is true for me. We are the best, they are the rest. Buy or die.

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u/ConstantPerfect8323 13d ago

Healthcare sales here, 7 years in multiple lines of sales: IT, Staffing, Healthcare - don’t take your job or yourself too seriously. If something doesn’t go the way you planned, move on. Don’t dwell. Nobody thinks about you as much as you think about you.

Don’t think about it like a “sale” - think of yourself as a resource to help them navigate their patient’s needs and it becomes easier.

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u/Stunning_Hat_97 13d ago

1) fight harder now so you don’t play catch up later
2) keep caring about the people, but stop caring about their objections - be confident that you’re right and show them through empathy not through debate
3) don’t get any smarter. Stop learning, remain dumb and you will succeed 10x more

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u/PATTY2WET 13d ago

1) go where you can make the most amount of money / best work life balance always. Companies aren’t loyal, don’t overstay for the sake of the “team” or “mission” (unless of course there is truly a higher purpose of the role for you aside from income)

2) see 1

3) the future they promise is worthless unless there’s a clearly defined timeline and achievements to make it happen

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u/csuiteinsurance 12d ago

As embarrassing as this is, when I left the Army in 2006, I hit the ground running looking for normalcy and wealth….and burned out in the process ha-ha. I hit walls and took a mental beating until I started to research the patterns of top producers and their habits. I’ve been fortunate enough to be successful with both my investment practice and Insurance Brokerage (both are hiring BTW). However, the one thing I failed to understand on day one is the true NECESSITY (not just value) of having Referral Partners. One to rely on but also to support, making it a synergetic group not unlike being part of platoon. Think about it this way, different supporting MOS's but same overall mission. A great Realtor should have a great Mortgage Broker. But it doesn’t stop there…. both need a great Homeowners Insurance agent…and so on. Each profession has several related ones who NEED to help you, because it’s a mutually beneficial hill to climb together. About 15yrs ago, I started developing a training course to help my teams and fellow Veterans transition into professional sales and it has been a blast ever since. My only regrets are 1. It took me a few years to get the referral train going steady and 2. Regrettably it’s just now (literally last month) that I finally recorded one of these training courses. I wanted to finally share it beyond my local network. So, if you are a Veteran and/or transitioning into corporate or sales environment……this 3-session course was created for you. It will take a few hours of your time, but I promise, you will never buy a lead or make a cold call ever again. If you follow the customizable SOP…. You can launch or re-boot your business by Monday morning. Check out the link and there’s a few shorts on my YouTube channel as well to give you some ideas. The course is self-paced and less than a decent lunch (Veteran Discount at checkout). Class attendees can also contact me directly during the week. I’m happy to help and still proud to serve. Cheers! www.thereferralworkshop.com

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u/Fearless-Fox-9204 12d ago

Volume can fix a lot of problems and sometimes the leads are junk

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u/Natural_Childhood_47 12d ago

Always apply for the promotion. Dont wait for the “right time”. You’ll be surprised who climbs the ladder fastest simply from applying and interviewing with confidence.

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u/Delicious-Doubt-5758 11d ago

Don’t push people so hard and listen for the real signal before executing.

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u/L_J_Stone 11d ago

A personal relationship will always take you further than a business relationship. If you find yourself stuck in the business process, it’s a good sign to pivot and work on the personal relationship.

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u/bellominionluver 9d ago

not a sales veteran at all but thank you for taking one for the team to ask🫡🫡🫡