[17] Selling with Style: Your Style Is Your Strategy
Dear Diary: Sales, Sass, and the Power of Not Blending In
Let’s be real—being a woman in sales is hard. Actually, being anyone in sales is hard, unless you’re a LinkedIn influencer who wakes up every morning with a fresh President’s Club trophy and an inbox full of cold email replies (and probably, let’s be honest, a puppy). The rest of us? We’re out here refreshing Salesforce like it’s a slot machine, wondering if our “champion” actually likes us or just has a thing for saying, “Let me circle back.”
The Social Media Mirage (or, Why Everyone Else Looks Like They’re Crushing It)
Thanks to social media, it feels like there’s this never-ending highlight reel of reps who are always selling more, smiling wider, and somehow landing meetings with people who reply within seconds (and probably send muffins). Meanwhile, you’re just hoping your sequence gets opened by a real human and not just another spam filter.
But it’s not just Instagram that’s out here gaslighting us. Sales methodologies do it too—turning your instincts into checklists, your charm into acronyms, and your gut into a series of “value-based” questions that sound like you’re interviewing someone for a job they didn’t apply for. “What’s the impact of doing nothing?” I don’t know, Bob, maybe they drown in their own workflow? Can we just offer the life raft already?
Standing Out (When You’re Literally 6 Feet Tall in Heels)
Now, as someone who is six feet tall (6’4 in heels, and yes, I still wear them), I’ve never exactly blended in. I used to try, though. I’d soften my voice, shrink my presence, and play by the “likeable rep” rulebook. Spoiler alert: I was never meant to fade into the background. The real magic happened when I leaned into my “giraffe in a blazer” energy instead of hiding it.
The moment I stopped trying to disappear and started owning the fact that I stand out? That’s when everything changed. That’s when I found my power (and also, ironically, my best pipeline quarter).
When I Ditched the Script and Found the Close
Take one of my favorite deals: I showed up to a call in a Longhorns cap. Not because I was trying to make a statement, but because it was Friday, I hadn’t washed my hair, and the hat just matched the vibe. The CTO logs on, sees me, and says, “You already don’t look like the last five vendors I talked to this week.” Without missing a beat, I grinned: “Well, lucky for you, I also don’t sell like them.”
We closed two weeks later. Not because I had the slickest pitch deck or used AI to write the perfect follow-up, but because I was just being myself—awkward, confident, and real.
How You Can Start Bringing Your Own Flavor (No Leopard Print Required)
You don’t need animal print or a college hat to stand out (though, highly recommend). What do you need? Tiny, honest cues that say, “Hey, I’m a human. Not just another sales bot.”
Wear Something That Sparks Conversation: Concert tee under a blazer, a beanie, or a mug with a meme. Let your personality walk in the door before you do.
Open With Honesty, Not Polished Platitudes: “I’m on my 7th meeting today, haven’t had lunch, but I’m genuinely excited for this one.” Watch how fast people’s shoulders drop.
Use Your Background: Got a bookshelf? Stick a Golden Girls bobblehead on it. A plant named Kevin. An aggressively large mug. Let people see a slice of your reality.
Let Go of the “Perfect Pitch” Voice: Talk like you’re at happy hour with a smart friend. Curious, candid, and not reading from an outdated script.
Call Out the Awkward: “This feels like one of those Zooms where everyone’s waiting for someone else to blink first—let’s break that.” Humor = trust.
Tactical Ways to Be Yourself (and Still Hit Your Number)
This isn’t about being “the funny sales rep.” It’s about consistency—in tone, style, and in owning how you show up.
Rewrite the Rules (and Your Sequences)
Add Human Texture to Your Pitch
Don’t Tone It Down—Tune It In
Follow-Up Like a Human
Why Your Style Closes Deals (And Makes Life a Lot More Fun)
People buy from people—period. No one ever signed a contract because your “touching base” email sounded exactly like the last five in their inbox. Authenticity breaks down resistance. Being genuine is rare these days, which means it’s instantly memorable—like spotting a dog in a Zoom background or a pineapple on a pizza (controversial, but unforgettable).
Here’s the thing: we all secretly want to be the smartest, most impressive person in the room. But sometimes, the smartest move is to be the most relatable. That’s true in sales, but also true everywhere else—in the elevator, at happy hour, chatting with your neighbor about why their dog won’t stop barking at 2 a.m.
And if being yourself feels awkward at first? Fake it till you make it. Try out being a little more “you” one day at a time—inside and outside of work. Start with a quirky mug in your team meeting, or crack a joke in your group chat that actually sounds like you. The more you practice, the less you’ll cringe, and the more refreshing—and powerful—it will feel. Eventually, showing up as your real self won’t be a risk. It’ll be your superpower.
Final Thought (With Extra Zest and Zero Apologies)
So here’s to the reps—and the humans—who show up with confidence and quirks, who get told, “You’re a breath of fresh air” both after demos and at brunch. To the ones who win deals because they made someone laugh, who make team meetings less of a snooze-fest, and who turn awkward small talk into actual connection.
Here’s to the heels, the sarcasm, the killer follow-up lines, and all the perfectly imperfect things that make you unforgettable—not just in your pipeline, but everywhere you go. Because the more you practice being yourself, the more natural it becomes. One day, what felt awkward will feel like a relief—not just to you, but to everyone who gets to experience the real, unfiltered, unapologetically awesome you.
This isn’t just your personality. It’s your strategy. On calls, on coffee dates, on Mondays when you wish you could work in pajamas.
So go ahead—use it. Everywhere.