r/salestechniques

I'm considering setting up a digital sales room for my sales team, but i'm not sure where to start. Right now, were using email chains and google drive, but it's getting messy. I need a solution that can centralize everything, documents, notes, communication, and updates, so were not constantly chasing after files or trying to track down information.

I'm looking for something simple to use that's also secure. Our deals are getting bigger, so i need a space where all stakeholders can collaborate without having to leave the platform.

Any platforms that you recommend and have used?

The older I get, the more I realise a huge percentage of professional networking is basically:

• finding people online
• studying their life for 20 minutes
• pretending the message is casual
• hoping they reply

Half of LinkedIn feels like:
“Hey man, loved your recent post”
followed immediately by:
“Would love 15 minutes of your time.”

Honestly respect people who admit they’re networking instead of pretending every interaction happened naturally.

Hey all! I recently launched my own small pentesting service geared towards people building apps with Al tools (think lovable/ cursor/bolt/claude, etc.). Im working with both founders that are technical and non technical. I've been at somewhat of a crossroads, as l've tried a handful of tactics to no real avail.

I tried a strategy before where i would source people from builder communities (such as the ones above), and with DMs ive had patchy results. Some replies, but had a few people call me out for being "too direct". Basically, came to find out that a security sales strategy leading with findings first comes off as threatening from just a cold message alone, and this seems to be the default outreach method for most people in the security consulting space.

I then resorted to just starting simple conversations, mapping out peoples stacks and giving pointers where needed. Good, since it gets them talking and builds trust, but pitching this way is a bit more difficult and the reply rates are notably lower.

Honestly, I've got the pentesting stuff down pat but the sales part of this journey is definitely not within my domain of strengths. Im not going to pretend i know what im doing in this domain, as i don't really have a clue.

Just curious from fellow tech sales people (cyber, all the better), what seems to work for you? Any suggestions for alternative strategies or avenues ?

Thanks in advance!

(EDIT: grammar, didn't proof read this originally)

This is my 2nd week cold calling for a tech company, its b2b and i have a call list im going through.

I only got 2 appointments booked today and i want to aim for 5 a day. It made me feel really bad because im on $20/hr and i get 10% if the sale booking leads to a sale. If i dont have any calls that leads to a sale for the month my salary is split in half. So i think i have a pretty good set up and feel lucky i get paid hourly.

I want to know if 2 booked calls over 6 hours is acceptable or if im doing something wrong and need more training, 2 is my lowest so far.

Hi, this one is for founders who have actually used something like this. Please do not promote your apps. I am specifically looking for people who have personally used something and can genuinely speak from experience.

We are building quantitative algorithmic products as a B2B SaaS startup. Very small team, just 5 people. We are bootstrapped, still running pilots and validating things, so there is basically no marketing budget right now.

None of us really come from marketing. We are trying to figure out everything from scratch.

What I am wondering is this:

Is there some AI driven marketing platform that acts almost like a copilot for startup marketing?

Not just content generation, but something that helps you systematically set up the whole motion.

For example:

• What forms should exist on the website?

• What email flows should be set up when someone signs up?

• What should onboarding look like?

• What can be automated?

• What early marketing infrastructure should exist even before serious growth?

Basically something that guides planning and execution while helping implement AI powered workflows.

I know this sounds vague because honestly I do not even know exactly what I am looking for. I just feel that in the AI era there has to be something beyond asking ChatGPT random questions.

Has any founder here actually used something like this and found it genuinely useful? Would appreciate hearing real experiences before we start building all of this from scratch.

There's a gap between what reps say they do before a discovery call and what actually happens when they have 10 minutes and a Zoom link.

Do you look up the company? The person? Their LinkedIn activity from the last month?

I'm in sales tech so I have obvious biases here. But I'm genuinely curious about the real answer, not the aspirational one.

What's actually in your prep stack before a first call?

How are you handling first line personalization at scale?
I’ve been doing cold outreach for my own SaaS and the part that kills me is writing personalized openers for each lead. Manually it takes forever, and the AI tools that scrape LinkedIn bios feel fake and prospects can tell instantly.
Curious what’s actually working for people here — are you writing them manually, using a tool, hiring a VA? What’s your actual workflow when you have 500+ leads to contact?

I want to use the LLMs for effective way to increase sales conversions and lead generation. My organization has given to our team both chatgpt and claude to use in our sales process. what can be best way to use it. I’m not aware much other than email writing or follow up writing. Can you share the use cases and prompts for work in better way?

I started doing freelance full stack web development this January while still being a student. Honestly I had no idea what I was doing in terms of freelancing itself. I knew how to build websites, but I had no network, no clients, no connections, nothing.

So I just started cold messaging businesses on social media and pretty much anywhere I could find people who might need a better website. Most people ignored me obviously, but eventually a few replied, then one project became another, and somehow over the past few months I managed to land 5+ pretty high paying clients including businesses outside my country.

Now I’m at this stage where I finally have proper projects to showcase, real client work, testimonials, some money saved up from the projects, and way more confidence than when I started. But almost every client still comes from me manually reaching out to people myself.

So now I’m wondering what the next step usually looks like for someone in this position. Once you finally have proof that you can actually deliver results, what’s the smarter way to grow from there? Would genuinely love to hear from people who crossed this stage already.

Throwaway account here. I also want to preface before getting into it that I am European, but I have lived in the US and in Asia. I am aware that different cultures have different ways of using utensils and etiquette when it comes to eating. I have eaten with a knife and fork, chopsticks and my hands and I actually love learning about how different cultures eat and treat food!

Here’s the situation: I work in sales in a big city in the USA. I travel a lot for work and go to many client dinners. A few weeks ago, I was at a client dinner with a junior salesperson on my team, and the way they were using their utensils and overall behavior at the table was incredibly rude. They would hold their fork in their hand like a fist and could not cut their steak properly using a knife. I understand that it comes from privilege to learn how to eat in a nice restaurant, but this person comes from a wealthy suburb and went to private school, as they like to talk about. I observed multiple people at the table, including our clients, looking at my colleague with strange looks and making slide glances. It was awkward.

The next day, I had coffee with this colleague before we were supposed to go a meeting at our clients’ office. At the coffee shop, I decided to bring up how my colleague was using their knife and fork at dinner. I said something along the lines of, “hey, I noticed that the way that you use utensils is a bit informal. I would be happy to show you the way that I use my knife and fork, or I could send you a YouTube video”. They were extremely embarrassed and offended by my comment. I dropped it. We went to the client meeting, and they didn’t really interact with me much after.

Now, last week, I got a message by someone in our HR group to speak to me. My colleague had reported me to HR for “discriminating” against them, and i feel like there has been just a huge misunderstanding.

I am the type of person that would want to know if I had food stuck in my teeth, or if I had sat in something that stained my pants. I told my colleague this feedback in a private setting, not in front of other people. I cannot believe this has created an issue at work now.

AITA for bringing this up, how should I solve this?

EDIT: I didn’t expect my post to get this much traction! Thank you for the feedback here. Some people have asked questions and I’ll add more context here:

Firstly, when my colleague told HR that I was being “discriminatory”, it was in a sense that they felt that I had embarrassed them about their behavior, not related to disability or mobility issue. If it was, I would never have posted this in a public forum on the internet. HR said to me that this person came to them because they felt that I had made an offensive comment to them. I think that if it was disability related, HR would have mentioned.

Second, I am not this persons boss. We are peers. We are on the same sales team but I am more senior to them. They joined the company 6 months ago and this is their first job out of university.

Based on the feedback here, I’m going to apologize to my colleague and explain my side of the story to HR. I absolutely meant my feedback as a way to guide a young person on my team as in my company, senior salespeople are expected to be mentoring to younger people.

In my profession, there is a lot of etiquette and expectations around working with clients. I have lived in the US for 10+ years and have found that corporate America also has specific standards, for better or for worse. I appreciate the people in this thread saying that I had good intentions but that it’s best not to make comments on people’s behavior, especially in American culture.

SECOND EDIT: I wanted to add a further comment here, as there has been a great deal of thoughtful discussion in this thread about invisible disabilities and how people may use utensils differently due to mobility difficulties. I have replied to various comments clarifying that my colleague does not have a disability or mobility issues, and that this was not the reason they reported me to HR for alleged “discrimination.”

My colleague comes from a privileged background and has never been told “no” in their life, having coasted along with poor manners going largely unchecked. At the dinner, they used their cutlery in a manner that was poor etiquette, alongside other behaviors such as speaking with their mouth full and gesticulating with their cutlery. I appreciate now that singling out the cutlery usage in my original post is what prompted so much commentary around disability.

I should also provide some more context: junior salespeople do not typically attend client dinners of this nature within their first few months. I arranged for this person to be invited specifically because they are shadowing me on this deal. As part of that arrangement, we have had debrief meetings and they have sat in on three external calls with this client prior to the dinner. I suspect this context was necessary to add, given that several people have suggested it was not my place to mentor them. Shadowing a senior salesperson is entirely standard practice in sales organisations.

I also understand that HR is legally prohibited from disclosing whether someone has a disability, and that there are workplace protections in place for people with disabilities. Had I been formally written up or reprimanded, I would have been entitled to know the grounds for that action, which would need to constitute discrimination. My colleague is, in my view, using “discrimination” as a means of weaponising HR and leveraging the system against me.

I think the conversation around disability is genuinely important, and I am grateful to those with disabilities who have shared their experiences in the comments, but that is simply not what is at play in my situation.

Courses/ Books recommendations?

TL;DR: Most reps act on "surface signals" (company raised funding, exec got hired). The real opportunity is in the detail nobody reads - the earnings transcript, the press release fine print, the job listing requirements.

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Everyone in sales reads the same headlines. Which means everyone sends the same message. "Saw you're hiring", "Congrats on the series B funding" is kind of noise these days.

The money is always one layer deeper. I've started thinking about this as "surface signals" vs "deep signals."

Surface signal: SaaS company raises Series B.

Deep signal: The press release says "funding will be used to expand into EMEA." They don't have a sales team, pipeline, or demand gen engine in Europe yet. Someone just got handed a target in a market where they're starting from zero.

Surface signal: Bank misses earnings.

Deep signal: The CFO says in the transcript "we're closing 200 branches and going digital-first." Every company that sold into their branch network just lost their buyer. Every company that sells digital transformation just found one.

Surface signal: Ecommerce brand starts selling on Amazon.

Deep signal: Their own checkout is broken - 12 fields, no Apple Pay, account creation required. They're not on Amazon because they're growing. They're there because nobody can finish buying on their own site.

All of this is public. You just need to actually read it, or find a way for an LLM to process it.

Surface signals tell you WHO. Deep signals tell you WHY and WHEN.

I've been in sales for 15 years. Started in retail, moved to SaaS, now I run a team. I've been the bottom rep, the top rep, and everything in between. Here's what actually moved the needle for me.

1. Shut up more.

This is the #1 skill. New reps talk too much because silence feels scary. But the person who's quiet usually wins. Ask a question, then close your mouth. Let them fill the space. They'll tell you exactly what they need if you let them.

2. Ask better questions, not more questions.

Most reps fire off questions like a checklist. "What's your budget? What's your timeline? Who's the decision maker?" Boring. Cold. The buyer feels like a form.

Better questions sound like: "What made you start looking now?" "What happens if this doesn't get fixed?" "What's been tried before that didn't work?"

These get you the real story. Real story = real deal.

If you want to get good at this fast, read SPIN Selling by Neil Rackham. It's old, it's dry, but it's the bible. Also Never Split the Difference by Chris Voss for the psychology side, the chapter on calibrated questions alone is worth the book.

3. Care more than the other reps.

Sounds soft. It's not. Most reps don't actually care about the customer's problem, they care about closing. Buyers can smell this from a mile away.

If you genuinely want to help, even when it means telling them your product isn't the right fit, you'll build a reputation that pays you back for years. I've gotten referrals from deals I LOST because I was honest.

The book that changed how I thought about this was To Sell Is Human by Daniel Pink. Also worth listening to The Advanced Selling Podcast and 30 Minutes to President's Club, both have full episodes on this. Bryan Burkhardt's stuff on LinkedIn is also genuinely good if you can ignore the algorithm-bait posts.

4. Confidence comes from reps, not affirmations.

I used to think confidence was a personality trait. It's not. It's just the result of doing something a thousand times. The 10th cold call is terrifying. The 1000th one is boring. Just do the reps.

If you want to speed up the learning curve in between reps, Fanatical Prospecting by Jeb Blount is the most underrated book in sales. Also The Psychology of Selling by Brian Tracy if you want the classic. For mindset stuff, Mindset by Carol Dweck isn't a sales book but every top rep I know has read it.

5. Learn how the buyer's business actually works.

If you're selling to CFOs, learn how CFOs think. Read their reports. Listen to their podcasts. Understand what their day looks like. The reps who can talk like a peer instead of a vendor get treated like one.

I do most of my learning on commutes now. Been using BeFreed for the last few months and it's been useful for this kind of cross-domain stuff. You input your current level, your goal, and how much time you have, it evaluates you, then builds a personalized learning path from the best sources, sales books, psychology research, expert talks, finance content, whatever fits your goal. You can pick the voice and length too, I have mine on the humorous style at 15 mins because dry finance content is brutal otherwise. Replaced most of my podcast listening at this point.

6. Stop pitching. Start diagnosing.

Doctors don't pitch surgery in the first 30 seconds. They ask where it hurts. Sales is the same. If you're pitching before you've diagnosed, you're guessing. And guessing loses to the rep who actually understood the problem.

7. Follow up more than feels reasonable.

Most deals don't die from a no. They die from silence. Follow up 3x more than you think is appropriate. Half my closed deals came from a follow up that felt awkward to send.

8. Take care of your body.

Sales is a physical job. You're talking all day, riding emotional waves, dealing with rejection. If you're tired, hungover, or stressed, your numbers will show it. Sleep, lift, walk. Boring advice. Works anyway.

TLDR: shut up, ask better questions, care, do the reps, learn your buyer's world, diagnose don't pitch, follow up more, take care of your body. That's the whole thing.

What would y'all add?

This is an expensive pattern startups follow.

Year one: founder does outreach manually, LinkedIn messages, cold emails, a spreadsheet of prospects. tells themselves they'll build a proper system when things pick up. things pick up but the system never gets built

Year two: the spreadsheet is a mess, follow ups are slipping, good leads are going cold because nobody caught them at the right moment. they hire an SDR to fix it

Year three: the SDR is busy but the pipeline quality is still inconsistent, some leads convert, most don't, nobody really knows why. so they hire a sales consultant or a head of sales to figure out what's broken

that person spends the first few months not doing what they were hired for. they're trying to understand why outreach isn't converting when the real problem was never the outreach itself

there's a difference between someone who is vaguely aware of your product and someone who is actively feeling the pain you solve right now, most founders are spending all their time and money on the first group and wondering why nothing is closing

the sequence matters

you need to know who has intent before you spend anything on reaching them. an SDR without intent signals is just sending volume into a void. a sales consultant without clean targeting data is just expensive opinions

most early stage founders don't need a bigger sales team, they need to know which people in their market are already raising their hand right now

so genuinely curious, what are people actually using to figure out who has real buying intent before they reach out

because the tool that changes everything isn't the impressive sounding one, it's the boring one that just makes sure you're talking to the right person at the right moment

Has no one figured out a tool for this?

Hi everyone,

This is a long story, but I hope it helps some of you. I have been reading some posts and it reminded me of my first sales call on the phones, so here's my story and some tips on how to crush sales!

I started my 15 year career on the phones cold calling people to upgrade their phone plans. My first call was very embarrassing. The prospect picked up and I remember immediately hanging up on them. I was so nervous I wanted to leave... But I didn't.

I called them back and I got the sale on my first call. My commission was $3 for that sale and I was making $13/hr. So in my eyes, If I sold 10 per hour, I could make $43/hr. At 18, that's real money. So I started grinding. I quickly became the leading sales rep and also became obsessed with trying to break my previous record (I think I got like 50 sales in one day). My quota was 2 sales per hour.

Throughout the next 24 months, I landed random jobs (weight loss cold calling - WORST job ever, pretty much a scam so I quit), financing sales roles, cold calling as a contractor for startups, and even a marketing gig. Learned a lot but nothing lasted more than 3 months.

Eventually I moved on and got a job at a paper scanning company which I worked at for 4 years. I was put into another acquisition patch because people thought I had good energy and I was OK hearing "no". This time my salary was $60K a year and the OTE was $100K. That was serious money for me. I smashed my quota again but felt like it was quite a mission to make $100K salary, and the organization didn't approve any forward-thinking ideas that I put forward so I started to feel like I was 'living in someone else's shoes'. Every $1M sale I landed, I felt like it could have been mine if I started my own company, since this company didn't seem to have much of a strong brand, it was purely relationship selling. (my quota was $4M)

Trying my luck, I decided to start a company myself focused on fintech. I managed to raise some capital and brought on some technical people while I focused on sales. This was truly a humbling experience as you literally are life-or-death. You have no brand. Your outcome/attendance at conferences is 100% your warm leads, there is no existing data, no fancy tools, no manager, nothing. It's just you, your motivation and the phone waiting to be dialed. I managed to land a few enterprise clients, and kept building the product further and further. The enterprise clients that we landed unfortunately didn't pay the bills, and so I started feeling like a failure.

I needed something to raise up my self-worth and feel like I've accomplished something, so I started applying at the big-3 tech firms, Microsoft, Google, and AWS.

After 100 rejections, I finally got in! Working at Microsoft was a dream of mine, and I was ready to devote the next decade of my life. I was making $250K a year with a bunch of benefits on top of that. I felt like I had bank finally. I was at the pinnacle of technology working alongside the brightest people, biggest companies and felt great telling people where I worked. I surpassed my quota but strangely felt like it was way less challenging than other sales organizations I've been at, definitely my easier than own company... and after a few years there, I decided to quit.

At Microsoft, I ended up in a role that didn't involve hunting... that didn't have a quota I could influence. I didn't feel challenged enough and I realized that I was born for real sales. I ended up starting a few projects focused on sales, AI, and consulting.

If you've lasted this long, let's talk about how I managed to become the #1 sales person in every organization I've worked at, and even land a job at Microsoft.

First: Get any narrative out of your head that you aren't good at sales. My first call was a disaster. I literally hung up on the client. If I accepted that I wasn't good at sales then I wouldn't have gotten here today. You don't need to be perfect, but you need to believe in yourself, even after failure! What you have right now is probably enough to impress someone!! Stop over building and over thinking, just talk about what you have!

Second: Have fun with it. What really helped me is having fun little competitions with myself or a peer I enjoy being around. Being competitive is underrated and I think it builds confidence and drive, despite how sensitive people have become!

Third: Spend time understanding your product. I've met quite a few sales people that have no idea what they are selling. This voids the entire #2 rule because you can't have fun if you feel stressed about technical questions. If you take the job and you don't have passion in what you're selling, then go to the store/online, and BECOME in love with the product. No excuses here. You need to love what you do or you'll never do great things in sales. Even if you are 18 - 24, this rule should apply (I started selling phone plans) because even selling phones, I remember spending my free time searching up phone comparisons! I became quite a nerd around mobility. you need the passion. Clients will buy from you much easier if they see you love what you do.

Fourth: Passion. Disclaimer: I understand there might be activity requirements but hear me out. I personally NEVER do cold/warm prospecting when I'm feeling tired/groggy. A lead is extremely valuable. Even if you're using AI to outreach, try to put your full passionate effort behind drafting the script, email, or even having the meeting itself. People buy from people. Unless you are Anthropic or OpenAI, you need people to like you. This is where I highly recommend you follow rule #1-2-3. If you come off as confident, passionate, knowledgeable and intentional, people nowadays respect less small talk, more transparency. The "Sales Guy" mentality is dead. Guess what? Your client knows they are in a position of power. They know you want to make the sale from them. So what? Show them you want the sale. Treat them like an Enterprise client. Ask good questions and build rapport with them by being yourself! Thats what people want nowadays!! Everyone is tired of the passion-lacking sales guy who is surface level and probably hates their life because they didn't do what they love.

Five: Use all the tools you want. Research all you want. These things help, they do. But PLEASE, just get on the phone. If you do not work at an established company, or if you have a startup, guess what!? NOBODY is going to do the shitty part for you (cold calling). Its YOU and only YOU! I will give tips on how to succeed cold prospecting below.

5.1: AI Agents. I didn't have these 10 years ago, but this will save you A LOT of time when prospecting. Use Claude or OpenAI to help you curate a list of potential ICPs. You can work with it to set up a great initial outreach email. I suggest spending 1hr+ drafting a solid email with your AI. Don't be lazy here. Read it out loud and make sure it sounds human and not AI slop.

5.2: Put yourself in their shoes. If you were in your ICP's shoes, and you got a random email, how would you feel? If your email doesn't stimulate some sort of emotional (or logical) response, then its a crappy email/outreach. This is where the greats stand out. Treat every outreach/lead like they are gold. A single client can make your entire business.

5.3: Start low. Despite what people say, aiming for VPs, CEOs, Directors, etc, almost never works. They get emails every single day. Your email domain might not even pass their email firewall or they'll flag you as spam and kill future opportunities. If you are serious about getting in touch with them, call the receptionist and show them your passion. Show them you really want to speak with that person because you have an amazing product that can (this is your explanation). You just need 10 minutes with them. Your passion will be contagious and people will want to help you. Which leads into my next point.

5.4: Trust. Trust by far is the most important thing you need to gain with any prospect. They need to believe in you, your product, your company's financial well-being, your security, your ability to deliver, everything. Trust is the magic 'X factor' in sales. But Trust doesn't always have to start with your target customer. Trust can start with the receptionist, who has Trust with your target. So you're leveraging trust between two parties which essentially gives you "temporary trust" because you've been referred into a trusted circle. You need to continuously maintain trust with your prospects and clients. We all know legal kills deals, well so does mistrust. The more someone digs into nitty-gritty details, it's likely they don't fully trust you and they'll find something (likely not harmful, but enough to kill a deal). Focus on listening to your client's needs, be yourself, be transparent, and sell your passion. That's how you maintain trust.

5.5 I like you, but I won't pay. In my startup days, this was a grim reality. I was able to get many clients booked in for meetings but people kept treating what we were offering as if it were just a "nice to have", not a "need to have". I quickly realized that I wasn't selling, I was being desperate. The Apple phone was never a "need to have". In fact, nothing in this world is a "need to have". No matter what any VC tells you, any advisor tells you, a coach, etc, nothing in this world is important, except for your passion and the customer's needs. Almost every single company I've worked at has the ability to create a custom product for their client's needs. For example, your product has 10 screws, but the client mentioned they have a hard requirement for 9 screws. You have three options here: End the call, mark as Lost. Convince them 10 screws are better than 9 screws. Or, the expert option, ask them why they need 9 screws. The WHY 9 screws might be your biggest opportunity you've ever landed. That single difference in screws may be a massive opportunity to develop something even larger and more custom for their enterprise. It might touch their call centers, it could touch their marketing, their infrastructure, etc. You need to genuinely be passionate enough that you WANT to learn why 9 screws is so important to them. They want to tell you. They know you want their business. They know you want the sale. Be curious and passionate!

6: Ask for their personal cell phones: I win deals by being available. Anyone who thinks they are too busy to pick up their clients calls are not great sales people. Consider sales like dating or friendships. A great sales person will always take initiative and make the other person feel like it's OK to call each other at any time. This single strategy has helped me close million dollar deals because nobody wants to be "corporate mode" all the time. We're tired of Zoom calls. Teams calls, emails. We just want to chat on the phone, even if its 5 minutes for a quick question. Make them feel comfortable and also, try call them out of the blue to ask a "question question". They'll appreciate your confidence.

Alright, my DMs are open if anyone wants additional help.

Believe in yourself!!