So you're considering becoming an Outside Sales Representative? That's gutsy! You must love a challenge. Perhaps you're an adrenaline addict. Perhaps you simply prefer a career where you don't have to pretend to be busy sitting at a desk for eight hours a day. Either way, congratulations—you're about to leap into one of the most unpredictable, untamed, and rewarding careers on the planet!
Individuals think outside sales is a schmooze for the customer, so close the deal and swim in a commission cash game. Reality? It's a never-ending cycle of being ignored, lost, caffeinated, and sometimes winning. One day, you win. The next, you're in an empty parking lot, wondering about life decisions because your GPS double-crossed you again.
This isn't a job for the faint of heart. But if you've got toughness, a sense of humor, and the capacity not to cry over rejection every afternoon in your car, you're going to do just fine. So, here's the skinny—the honest, no-nonsense, sometimes agonizing, but mostly funny stuff about being an Outside Sales Rep.
1. Survive Rejection or Perish Like a Bad Cold Call
If rejection hurts your feelings, you’re in the wrong business. Clients will ghost you so hard you’ll start to wonder if you imagined the entire conversation. They will make empty promises, cancel last-minute, and “forget” about meetings they personally scheduled. Some will even lie to your face, telling you they’re just not making any changes right now—only for you to see their competitor’s logo on their office wall next week.
At first, this will sting. But over time, you develop a special kind of sales immunity. Suddenly, a “no” doesn’t mean failure. It just means, Not today. Try again later. Maybe after they realize their current solution is a dumpster fire.
Rejection is part of the game. The key is keeping your numbers up. The more doors you knock on, the more deals you’ll close. The best sales reps don’t take it personally—they take it as a sign to move on to the next prospect who actually deserves their time.
2. Your GPS Will Betray You Like a Reality TV Villain
Your car is your second home now. And your GPS? It’s your toxic best friend—helpful one moment, completely unhinged the next.
One day, it’ll take you directly to your prospect’s office with military precision. The next, it’ll dump you in a random back alley next to a dumpster, claiming you’ve arrived. It will reroute you for no reason. It will fail to recognize road closures. And on at least one occasion, it will lead you into what looks like a horror movie setting instead of an office park.
Nothing builds character like explaining to your boss why you were 30 minutes late because your GPS decided roads are a suggestion. Pro tip? Double-check every address before you leave. Because nothing is more awkward than confidently walking into the wrong office and pitching to someone who just wanted to eat their lunch in peace.
3. Talk Like a Jedi, Sell Like a Mafia Boss
Great Outside Sales Reps don’t just pitch. They persuade. They hypnotize. They make clients feel like not buying would be the single worst decision of their professional lives.
The secret? Stop selling products. Sell outcomes.
Nobody wakes up thinking, Wow, I really want to buy a software subscription today! No. They want more time, fewer headaches, and an easier life. Your job is to show them how your product does exactly that —be their sales accelerator, not just another salesperson pushing a product.
You’re not selling cybersecurity software. You’re selling "a world where hackers don’t ruin your day."
You’re not selling fleet tracking services. You’re selling "peace of mind that your drivers aren’t napping in parking lots on company time."
You’re not selling office coffee machines. You’re selling "a workplace where nobody wants to commit caffeine-deprived violence before 10 AM."
And if all else fails? Just shut up. After you drop the price, say nothing. Silence is power. The first one to talk usually loses.
4. Follow-Up or Watch Your Deals Die a Slow Death
You think the sale happens in the first meeting? Adorable. No. The sale happens in the follow-up.
Clients are busy. They get distracted. They tell themselves they’ll “think about it,” but what they really mean is, I’ll forget about this the second you walk out the door.
Your job? Make sure they don’t forget.
Send a quick thank-you email within 24 hours. A few days later, check in with something useful—an industry article, a relevant statistic, even just a “Hey, wanted to see where you’re at with this.” If they start ghosting? Get creative. Send a meme, a personalized video, something that reminds them you exist.
If after four follow-ups they’re still dodging you? Move on. Some leads aren’t worth the chase.
5. Lunch Meetings Are a Scam—And You’re the Victim
Everybody loves a free meal—especially clients who have zero intention of buying from you but are more than happy to enjoy your company-funded lunch.
At first, you’ll feel like a big shot. You’ll take people out, make small talk over sandwiches, and feel like a networking genius. Then you’ll check your bank account and realize you’ve spent half your commission on people who just wanted a free steak.
Be strategic. Coffee meetings are cheaper and just as effective. Happy hours work great too—plus, drinks make people more honest. And if you do end up paying for a meal, make sure it’s for someone actually considering your offer, not just "thinking about it."
6. Your Day Will Be 90% Chaos, 10% Pure Adrenaline
Every morning, you’ll start with a plan. By noon, that plan will be a distant memory.
Your best lead will cancel a meeting as you pull into the parking lot. Your backup client will “step out for an emergency” right before your scheduled demo. Traffic will sabotage your afternoon, and just when you think the day is a lost cause—boom, you’ll close a deal out of nowhere.
That’s Outside Sales. A never-ending, unpredictable whirlwind of frustration, excitement, exhaustion, and euphoria.
And somehow? You’ll get addicted to it.
7. Sales Is a Bloodsport, But the Rewards Are Insane
This job isn’t easy. It’s not glamorous. You will question your sanity at least once a week.
But here’s why it’s worth it:
- You control your paycheck. No salary cap, no waiting for promotions. Just hustle, skill, and the thrill of knowing your effort translates directly into money.
- You get freedom. No sitting at a desk all day pretending to work. You’re out in the world, making things happen, running your own show.
- You experience wins that feel better than finding an empty Costco checkout line on a Saturday.
So, if you’re ready for a job that’s chaotic, hilarious, frustrating, and ridiculously rewarding—welcome to Outside Sales Representative position.
Now go close some deals.
