Humans of Sales

After 5 years and 4 internships, I still hadn’t found something that felt like me. I’d dabbled in research, tech, and even analytics. Nothing stuck. Then one day, I read a line in a job description that hit different: ‘If you can build a rapport with people, apply.’ That’s when it clicked. I’d always been that kid—extroverted, curious, go-getter type. My parents are both professors. So, changing cities, switching schools, packing up, and starting over—it wasn’t strange to me. It was just life. College was trickier. I was away from home and my parents. Eventually I figured it out. I joined sports teams, signed up for clubs, and found my people. I’ve always been that kid, you know. The one who sees a group playing outside and thinks: “If they’re playing, I want to play with them.” So be it—striking conversations, making new friends, or knowing exactly what to say, it was always a part of me. That sowed the seeds for sales in my mind. Not intentionally. I just… ended up there. I still remember—after trying my hand at everything from research to tech, none of it felt like me. I wanted to do something people-focused. So, when I saw that JD, I applied without a second thought. I took up every task that came my way, went all in for the application process without any experience, and after 5 rounds, I got selected! That’s how I landed my first job in sales. That was six years ago. Ever since, I have seen it all—the last-minute budget cuts, clients backing out, and even being ghosted after an almost final conversation. Sales can be unpredictable. If you don’t provide value in the first few minutes, the deal slips away. It’s chaotic, but now I’ve learned to champion the chaos by trusting my gut. Much like cycling, yes really. I’ve cycled over 5000 km in the past 3 years across India—traveling, exploring, and meeting people from all parts of the country. All that mileage leads to perseverance, patience, and skills to navigate difficult terrains, just like in sales. That is what keeps me going—being like a kid who just won’t give up. After all these years, when I make a successful pitch, it feels like knocking on a stranger’s door, and they let you in. They trust you before they even know you. That’s the win for me. And no matter how far I go, I hope I never lose that kid inside - Akshat Mishra Sybill Humans of Sales #stories #sales

Some people choose sales. Others stumble upon it. Some learn sales in school; others get here after a failed startup, the pandemic, or a friend saying, “You’re good at talking—try sales.” At Humans of Sales, I’ve spoken to people from both sides. And I have learned that, just as with Roger Federer, the detour often leads to the real destination. The best salespeople didn’t always plan this career. They learned to build trust without a script, to fail forward, and to show up even when they were scared. One person told me: “Sales was really different from what I’d expected. Now it’s where I found the best version of myself.” This is why we’re building Humans of Sales. 1️⃣ To tell the stories behind the title. 2️⃣ To share how to navigate the non-linear paths. 3️⃣ To share insights from those who figured it all out from the scratch. So, did you choose sales, or did sales choose you? I’d love to hear your story. Sybill Humans of Sales #stories #sales

I frequently slept 3 hours/day and juggled multiple jobs before I found tech sales. Growing up, I loved to be surrounded by energy. Large crowds, fitness, events. Such a big part of me as a kid came from performing in front of others. When I was on stage, I always wanted to share a little spark with the crowd. To inspire the audience to connect with whatever they were passionate about. Off-stage, I’ve always wanted people to feel welcome - like a guest in my home. It shaped my years bartending, how I taught fitness and my approach to sales. Thanks to those client-facing jobs, I learned to read people and match their energy. I started showing up in a way that was compatible and effective considering the person in front me. I love movement, I loved that energy but It got pretty crazy sometimes. “Working at a bar from 10am until 5pm, teaching a Zumba class, then working at another bar into the night only to get up at 7am to train clients at the gym.“ The first time I started thinking about Sales was back in 2020 when Covid hit. I was in fitness full time,and between classes and private clients I just pushed myself to “go go go go”. I used to work with a fitness trainer who transitioned to the tech space. He got started as an SDR and now is a phenomenal AE. I reached out to him back then and I never forgot his words to this day: “Moving from fitness to tech was one of the best decisions of my life”. I decided to commit. Did some research on how to break into tech sales from non-traditional backgrounds, and came across AspireShip. Their Sales Foundation course was amazing. I finished it and got placed in less than 30 days. I couldn’t believe it. Started as an SDR and worked my way up. I feel like the most important trait that allows me to be good at sales is authenticity. People want real interactions, they’re tired of scripts. One strategy that helps me stay grounded is something I call “Notice and Name.” It’s about pausing to recognize emotional triggers in the moment, naming what you’re feeling, and understanding how it might be influencing your decisions. Self-awareness is a superpower in sales - especially when the pressure’s on. In this line of work, no matter how good the product is, you’re at the mercy of people’s timelines. Their priorities shift. One day you think you’re closing a deal, the next day they ghost you and you’re worried about hitting quota. Acknowledge the feeling, accept it and let it go. You’ll bounce back faster and get better at detaching from the outcomes. - Nikki Gagnon #sales #inspiration #entrepreneurship Sybill Humans of Sales

I want everyone to have first row seats to the world's best sales talent. A peek behind the curtain. If you've always wanted to know how great sales people think, feel and act, this is for you. In the past 5 years, I’ve talked to 3500+ sales reps. I’ve seen the constant hustle - making cold calls, emailing with a high chance of getting ghosted, and deals breaking at the last moment. Everyone talks about storytelling. But not everyone gets their story told - especially in sales. The anxiety before a big pitch. The high of closing a dream deal. The burnout that creeps in when you're chasing monthly targets that feel just out of reach. The quiet pride of helping a client solve a real problem - something that rarely makes it to a leaderboard. At Sybill AI, We understood that silence and that’s how Humans of Sales was born. We want HoS to represent: 1. A space for honest, unfiltered stories from the people who live and breathe sales. 2. Actionable sales tips. 3. Fresh industry trends 4. And career-defining wins & losses. Because before someone hits quota, they go through self-doubt, failed demos, and missed callbacks - and somehow, still show up the next day. That kind of resilience deserves to be heard. If you’ve been through a crazy sales journey, or know someone who did, I’d love to hear from you! Sybill Humans of Sales #sales #stories

Like all good things, it started with food! But not in the way you’d expect. I loved everything – food and health, so a food science degree seemed like the natural choice. But by my third year, I started having this sinking feeling. What now? I didn’t want to spend my life in a lab coat, running experiments on yogurt cultures. For my internship, I needed to find something connected to food science, so I joined a small startup in Dublin that made calorie-conscious meals for older people. It was a tiny team, which meant I had to do a bit of everything. One day, they asked me to make cold calls. I decided to give it a shot. Turns out – I was actually good at it! I had a sudden revelation – this could actually be something I could enjoy doing. Around the same time, some of my friends were getting into tech. Dublin’s startup scene was booming and I wanted in, but my degree didn’t exactly scream “tech”. SurveyMonkey was opening their office in Europe. I reached out to the team, and they asked me to come back and do a pitch for an Account Executive position. The catch? I had zero sales or business development experience whatsoever. So I stayed up late nights prepping everything I could possibly learn about being an AE; how to pitch, how to structure a sales conversation, how to close a deal. I walked into that room with full confidence, even though I had no real experience. They said, “You don’t have the experience, but all right, we’re going to give you a go as an AE.” And the rest was history. I ended up staying there for five years and loved the job. I was employee number three on the sales team, and we went from just a handful of us to over a hundred AEs across Europe. But it wasn’t always easy. There was this one deal I had spent eighteen months working on. And just when we were about to close, they pulled out. I was completely shattered. Eighteen months of calls, meetings, negotiations and hardwork, all of it had reduced to nothing. That moment changed everything for me. I realized rejection isn’t the end of a conversation; it’s just a pause. Sometimes things just don’t go the way you planned. And that’s okay. The important thing to do is to keep showing up. The next day, I reached out to them again, just to understand what went wrong. Two days later, they came back. Turns out, the alternative they had chosen wasn’t working out. It became one of the biggest deals of my career. Now, I get to work with companies from across the world with products solving problems I never even knew existed! The journey has been full of twists and turns, but every step has been worth it. I’ve learned that if you’re open to new experiences, you can end up exactly where you’re meant to be. And you might even surprise yourself along the way! -Laura McAnena

I learned sales by accident. At 15 years old, I was pitching a startup that Apple shut down. My brother and I were broke and bored. So we started crashing hackathons across LA - show up Friday, grind through Saturday, pray for prize money, repeat. At one of those events, we built a speech encryptor. It could anonymize your voice by turning it into encrypted text, sending it across a secure server, and re-rendering it as speech on the other end. An investor approached us and said, “I like this. And you - you’re the sales guy, right?” Technically, I wasn’t. I just did the demo because my brother didn’t want to. But I went with it. “Sure!” That’s how it started - my journey into sales, but with a twist. We thought we were building for privacy. Turns out, we’d accidentally built the perfect tool for black-market deals and ransom calls. We learned this only when we tried to release the speech encryptor on the App Store. Apple shut it down - no surprises there. And with that, we lost the $100,000 check our investor had promised. “We didn’t pivot from there. We shut it down. Because sometimes the lesson isn’t how to sell harder - it’s what not to sell.” But the bug had already bitten. I spent the next few years launching more products, pitching random ideas, trying to build something that stuck. Nothing really did. But all this time, I was learning to sell. Through rejection. Through cold calls. Through chaos. Eventually, I landed my first formal sales role at a YC startup, while still finishing my econ degree at Berkeley. I was an SDR by day, student by night. Later, I joined another startup as a founding AE - but it wasn’t the right fit. “Those were my early years in sales, and being micromanaged even then just didn’t sit well with me. I didn’t stick around for too long.” My real sales break - and one that made me truly enjoy this profession - came at the fintech startup where I now work. A real company with real traction. Real product-market fit. And finally, real trust in the product I was selling. “I’ve sold products that shouldn’t exist. Ones with no customers. Ones with no use case. Now I sell fintech that moves $30 billion a year.” I run a fintech podcast on the side - to explore strange corners of the payment space. Zelle, money rails, obscure banking partnerships. I do it to learn. To stay curious. And I still approach every deal the same way I did when I was 15: test, iterate, figure out what people actually want. And build the pitch from there. “Good founders test and iterate. So do great salespeople. I learned it at 15 and never forgot it.” I don’t see my career as a ladder. I see it as a product in beta - always getting better. “But the real dream? It’s to retire early. Volunteer more. Travel more. Drink better wine. We’ll get there - one deal, one podcast, one substack at a time.” -Konstantin Dubovitskiy Humans of Sales Sybill #sales #stories

Some people ease into sales. I jumped. Without a parachute, straight into the deep end. It was scary. It was exhilarating. It was everything I had hoped for. I was in Kentucky, working at a cable company. A stable life, home, friends. That’s when I felt it. A deep, relentless pull toward something bigger. Something told me I wasn’t meant to stay. So, I didn’t. I packed up my son, my entire life, and moved to Florida. No job. No backup plans. Just an instinct. That was the first time I saw fortune favouring the brave. Within weeks, I landed my first SaaS job. They flew me out to Germany for training. I walked into a new world - where deals moved fast, numbers were bigger, the stakes were higher. "Once you taste software sales, there’s no going back. It changes the way you think about selling. The scale is incredible. The challenges are different. The opportunity is unmatched. And for someone like me - wired to compete, to win - that was all the invitation I needed." And then came my first big break. I still remember the moment. The name flashed on my screen. At the time, the #1 company on the Fortune 10 list. My pulse kicked up. A lead like this didn’t come around often. In my excitement, I didn’t realize that the deal wasn’t mine to close. I took action. I researched. I built the relationship. I uncovered their pain points. I made my case. And I closed it. That one win changed my trajectory. It proved that I belonged. Looking back, my entire career has been built on taking the leap before I felt ready. I moved states without a plan. I took a SaaS job with no software experience. I was always biased for action. And at every step, those actions turned into opportunities I never would have had if I had waited too long. "Sales, like fortune, favours the brave. The biggest deals don’t go to the smartest person in the room. They go to the one who sees the opening and takes it first." Because in this game, waiting isn’t playing. It’s losing.

No one hands you a promotion. No one hands you a comeback. You take it. I was 23 when my life collapsed. 4 years in and out of hospitals, hooked to machines, my body failing me. Nine surgeries. Then came the addiction. At first, painkillers numbed the recovery. Then, they took over. The world moved on without me. When I finally walked out of the hospital, I had no confidence, no direction, no job. When I stepped into my first sales role, I wasn’t looking for a paycheck. I was rebuilding myself. Some people start sales for the commission. I started because I needed to prove I could claw my way forward. That I could bet on myself and win. And I did. I picked a small startup because I wouldn’t have to wait years for a bigger shot. I didn’t just hit quota in those early years. I crushed it. I started closing my own deals, then helping my teammates close theirs. I got addicted to the rush - not just of selling, but seeing others win. I learned that coaching - or even selling - was not about telling people they have a problem. It’s about getting them to recognize it for themselves - and they have to care enough to take action. I wanted more of that thrill of making people better at what they did for a living. I had to bet on myself to get the role where I could do it everyday. “So I walked into the CEO’s office, unannounced, uninvited. ‘Your sales managers don’t actually do anything,’ I said. ‘Give me a shot. I’ll do better.’” He could’ve fired me on the spot. Instead, he challenged me. "You’ve got talent, but you need to prove it beyond yourself. Help others hit their numbers. Show me you can lead. And change your attitude while you’re at it." Within months, I was running teams, coaching reps, and making people better. I was on my way up. I was a sales manager just 7 months into my first entry level sales role. But then, I hit a ceiling. "You’ll never be a VP," they said. "You don’t have enough experience." So I quit. On the spot. No backup plan. No safety net. I knew by then that no one was coming to save me. Not my boss. Not my company. Not my connections. No one will hand me a promotion or a second chance. If I wanted more, I had to take it. I had to bet on myself. So, I did. The first few weeks after quitting were brutal. No calls, no offers. Just silence. I second-guessed everything. Had I just burned my career? But then, the phone rang…“Hey, we’re starting a new company. Want to be our VP of Sales?” That was my first VP job - less than three years after my role as an AE. Since then, I’ve helped build 12 unicorns, written two bestselling books, started my own businesses, and mentored founders and sales teams across the world. And at every step, I’ve stuck to the same principle: bet on yourself. No one will hand you an opportunity. No one will push you to get better. That’s on you. You can’t wait for permission to be great. You have to decide to be. When you do it right, the world will have no choice but to bet on you too.

From hearing a big fat ‘NO’ nine out of ten times on a call to hitting 350% of my quota in a single quarter. It wasn’t luck. It wasn’t magic. It was years of trial and error, learning the hard way how to sell—not just a product, but a real solution. Now, at Deel, I’m focused on something different: sustained success. Sales isn’t just about chasing big quarters—it’s about consistency, about understanding timing, talent, and territory. Master two, and you’ll do well. Master all three, and you’ll consistently exceed your targets. But I never planned to be in sales. I started my career working with sports agencies, negotiating sponsorship deals for athletes and teams. It was a grind—cold calls, endless pitches, convincing brands to put their names on jerseys and stadiums. I didn’t realize it at the time, but I was learning the fundamentals: how to read people, handle rejection, and turn a maybe into a yes. My first real sales job was in conference and exhibition sales—the kind where you’re on the phone 60 times a day, constantly refining your pitch. Sometimes, they didn’t even let me finish my pitch before hanging up. I’d exhale, force a smile, and dial again. You learn to take rejection like a reflex. It was exhausting. But I liked the challenge. The highs of closing a deal, the lows of losing one, the push to improve—it kept me going. For a long time, I thought I was failing. This wasn’t what I signed up for. But over time, I started seeing patterns. How to keep someone on the phone a little longer. How to turn hesitation into curiosity. Then came 2022, some deals had been in the pipeline for months, caught in slow negotiations. Then, almost all at once, they closed. Three multi-year contracts, each worth six figures. I remember seeing the numbers climb, watching my name move up the leaderboard. But the real turning point wasn’t the deals themselves—it was what led to them. I had learned to hold my ground on pricing. To stop thinking about just closing and start thinking about helping buyers solve real problems. That’s when everything changed. I never expected to end up in sales, but looking back, I wouldn’t change a thing. Big wins are great, but they don’t define you. What defines you is how you show up when things aren’t going your way.

Real stories, real people. At Humans of Sales, our mission is simple: To amplify the voices of sales reps by sharing their authentic stories—the wins, the losses, and the lessons that define their journeys. We’ll be sharing inspiring stories from: - A rookie rep who overcame rejection to close their first deal. - A seasoned AE reflecting on how failure taught them resilience. - A manager who helped their team navigate a tough quarter. - A top performer who shares why empathy is their secret weapon. These are real stories, from real people. And they’re just the beginning. Got a story to share? Link in the comment to share your story! Let’s celebrate the humanity in sales together!!!