Sales Veteran - Sales Advice (long story, but good advice)
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!!