Ever feel like an alien on your own sales calls? You’re not alone. This week, we’re diving into discovery done right — how to stop pitching, start asking, and use Sandler’s questioning techniques to turn awkward conversations into authentic connections.

Because great discovery isn’t about having all the answers — it’s about curiosity, empathy, and the confidence to admit when you’re out of orbit. Whether you’re new to your industry, learning the lingo, or just trying to keep your foot out of your sales mouth, this one’s for you.

Read on to learn how to make your discovery calls feel less like an interrogation and more like therapy (with a few Halloween tricks and treats along the way).

Command of the Message: How to Sell Like You Mean It

Ever catch yourself mid-pitch thinking, “Wait… even I wouldn’t buy this”? We’ve all been there.

Whether you’re new to sales, stepping into a more technical industry, or just trying to tighten up your value message — this post is your confidence reboot. We’re diving into Command of the Message, breaking down how to stop sounding like a walking brochure and start selling with clarity and conviction.

You don’t need to memorize a script or master every buzzword. You just need to own your story, know your value, and communicate it like you mean it (preferably in heels).

Let’s get real about what it takes to sound — and feel — like the pro you already are.

Let’s be honest: blending in is overrated—especially in sales (and honestly, life). The real magic happens when you ditch the “perfect pitch” voice and show up as your unfiltered, quirky self. It’s awkward at first (trust me, I’ve been there), but the more you lean in, the more refreshing—and effective—it becomes.

Whether you’re sending a cold email, running a demo, or just surviving another Monday, authenticity will always set you apart. People buy from people, not personas. And one day, the things that once made you feel awkward will be the very things that make you unforgettable.

Check out my latest article for real talk, practical tips, and a few laughs on why being yourself isn’t just good for your pipeline—it’s good for your soul. 🚀

🚨 Most deals don’t get killed. They just… die quietly.
No breakup email.
No "we went in another direction."

Just a promising demo that fades into the CRM abyss.

You thought they were the one — and they ghosted you like a bad date.

In Part 3 of my Selling Smart, Not Hard series, I’m diving into:
✅ Why ghosting happens (hint: it's usually our fault)
✅ How to spot a dying deal before it flatlines
✅ And exactly what to say to revive a cold thread without sounding like a desperate situationship

MEDDIC, Sandler, and a few spicy tactics included.

It’s the post I needed when I was 70% to quota and chasing pipeline that had no pulse.

Sales systems don’t have to feel like a bad relationship — chaotic, exhausting, and full of unanswered emails. 💌✨

Let’s trade the grind for smart workflows that actually work for you (and leave you time to ugly cry over Salesforce reports in peace). 🫠

💅 Ready to build a system that closes deals and lets you breathe? Check out my latest blog on Deals-In-Heels: ‘Building a System That Works While You Sleep (Kind Of).’

Because consistency — not chaos — is what actually pays the bills. 💸

[14] Stop Chasing. Start Closing.

Think every lead deserves a follow-up? Think again.

In Part 1 of Selling Smart, Not Hard, we’re talking about one of the most overlooked skills in sales: qualifying like a pro — without losing your personality in the process.

Inside this post, I break down:

• Why chasing every “maybe” is killing your close rate

• The sales frameworks you actually need (BANT? MEDDIC? Let’s simplify it)

• My personal qualification workflow (built with intuition and strategy)

• How owning your full personality makes you a more trustworthy, memorable seller

Whether you’re just starting your sales career or reigniting your spark, this one’s for you.

Click in and let’s rework your pipeline — with heels on.

I open up about navigating unexpected changes in both life and work — from personal transitions and looming apartment hunts to the chaotic beauty of startup life. I’m sharing real talk, fresh energy, and four practical tips to stay grounded professionally (while keeping your heels on and your pipeline hot). Plus, I break down how I’m keeping my Q2 sales game strong with calendar blocks, creative follow-ups, and a little flair. Because when life gets unpredictable, we don’t panic — we pivot.

We’ve all been there—the deal felt perfect. You nailed the discovery call, they were vibing with your demo, and then... total silence.

In this Deals in Heels breakdown, I turn the ghosting struggle into a glamorized science, walking you through my proven 5-step follow-up formula to turn cold leads into contract signers.

✨ Inside you'll get:

• Timing rules that make your messages land

• Real-world email templates for every stage of the sales cycle

• My sassiest subject lines and softest nudges

• A little dating wisdom (and a lot of pipeline power)

You’ll leave with a follow-up toolkit that works harder than your espresso machine during QBR week. Ready to turn “let’s circle back” into “let’s get started?”

Forget feature dumps and slide decks. If you want to win more deals, you need to know how to tell a damn good story.
In this post, I’m breaking down the art of storyselling — including the 3 types of stories every rep needs, where to find them, and how to use them without sounding like a cheesy sales robot.
Plus, I share a real story that helped me close a major deal.
Spoiler: it starts with a Longhorn hat and ends with a signed contract.

What do SaaS deals, closet space, and brunch reservations have in common? You’re negotiating your way through all of them — whether you realize it or not.

In this spicy, heels-on-the-ground guide to closing without compromising, I dive into the emotional chaos of deal-making, the unspoken power of silence, and why “every give needs a get.” Learn how to set your floor (and stick to it), turn every discount request into a power play, and finally stop treating yourself like a clearance rack item.

Spoiler alert: You are full price. Always.

💋 Grab your coffee (or cocktail), and click through for my take on negotiating like a pro — without losing your sparkle

80% to quota. Leading the leaderboard. Living alone on WFH Island with a fridge full of meal-prepped protein and an inbox full of "Can we revisit this in Q2?"

This article is my personal survival guide to the end-of-quarter chaos — a little sales therapy for anyone chasing numbers, juggling real life, and trying to keep their head on straight while working from home. It’s real, raw, a little ridiculous, and packed with stories about prospect ghosting, creative urgency plays, and how I manage stress (spoiler: there’s cookies involved).

If you’re feeling the pressure and need a pep talk from someone who gets it, read on. And if you want to talk 1x1 about deals, burnout, goals, or baked goods — my inbox is always open. 💌

First impressions aren’t just about looking the part—they’re about bringing the full package. Whether you’re crushing sales calls, battling Salesforce updates (the struggle is real), or staying consistent in the gym, confidence comes from showing up, preparing, and following through.

🔥 Bring the energy—your presence sets the tone.
📚 Confidence = Preparation. Know your product, your prospect, and your goals.
💪 Consistency wins—because motivation won’t always show up for you.

Accountability is key—time block your day, grab a work buddy for focus sessions, and don’t let yourself turn on Netflix until your tasks are done. Need more personalized strategies? I offer 1:1 coaching—you can book a 30-minute session via my website to level up your sales game. Also, if you need quick, healthy meal ideas to stay fueled, I’ve got you covered!

What do sales and raising a 120-pound Great Dane have in common? More than you’d think. From persistence (hello, endless follow-ups) to building confidence (one awkward cold call at a time), my late work-from-home sidekick, Ronin, taught me everything I needed to know about selling—and life.

This post is part heartfelt tribute, part career advice, and 100% proof that even a drooly, oversized lapdog can teach you how to close deals. Plus, I’ve included my ultimate road trip playlist and go-to travel snack—because no great sales journey (or puppy pickup trip) is complete without good tunes and snacks.

🐾 Read now, and bring a little Great Dane energy to your sales game.

Prospecting without structure is like playing volleyball without a game plan—you’re just hoping for the best and getting blocked every time. That’s why I stick to the 4 Rs of Prospecting:

🏐 Research – Know your prospects inside and out (yes, even digging through SEC filings and deep-dive LinkedIn sleuthing).
🤝 Relationships – Build trust before you pitch. No one likes feeling like just another lead in your CRM.
🎯 Relevance – Tailor your message so it actually matters to them—no cookie-cutter outreach here.
📊 Results – Track, tweak, and improve. If it’s not converting, it’s just noise.

Sales isn’t just about numbers—it’s about strategy, execution, and constantly leveling up. And if all else fails? I take a break, watch The Great British Baking Show, and remind myself that even the best bakers burn a few cakes. 🍰

Need a little extra motivation while prospecting? I just dropped a February work playlist —because cold outreach is better with good music. 🎶

Success in sales isn’t about luck—it’s about preparation, execution, and the relentless pursuit of improvement. Learn to bring the mindset of a competitive athlete to the sales floor, focusing on the strategies that separate the good from the great. Just like in three-day eventing, where every jump, stride, and decision determines the outcome, top sales reps don’t just show up—they prepare with precision, anticipate challenges, and adjust on the fly. Whether it’s understanding your prospect like you’d understand your horse, mapping out a sales call like walking a competition course, or handling objections with the same confidence as navigating an unexpected hurdle, sales is about strategy, control, and execution. And just like in competition, the best never settle. If you're looking to refine your approach, improve your pipeline strategy, and close deals with confidence, let’s connect—because winning doesn’t happen by chance. It happens by design.

January in sales can feel like a ghost town—prospects that were eager in December suddenly vanish. Instead of stressing over stalled deals, I’ve been testing creative ways to pivot and keep momentum alive. From time-sensitive incentives (like free migration services) to shifting the conversation toward ROI pain points, small tweaks can make a big difference. The key? Approaching stalled deals with empathy and fresh value. Want more ideas?

2024 was a tightrope year—a new role, a hyper-competitive market, and a humbling Q2 where I missed quota for the first time in years. The lesson? Balancing confidence with humility is the key to staying steady and successful. In my latest Deals in Heels post, I’m sharing how I leaned on the basics like MEDDIC, Sandler, and active listening to rebuild momentum—plus, how walking in heels on cobblestones inspired this whole perspective. Ready to level up your sales game?

January means one thing in sales: prospecting season is in full swing. But let’s be real—endless “just circling back” emails aren’t exactly thrilling. In my latest Deals in Heels post, I’m breaking down fresh, budget-friendly ways to make your outreach stand out—think custom flyers, cheeky video messages, and creative follow-ups that actually get replies. Plus, I’m sharing why humor, personality, and a little flair can make your message impossible to ignore. Ready to make your January outreach the talk of 2025?

You already know the drill—the stretch between Thanksgiving and the New Year is a whirlwind of closing deals, holiday potlucks, and trying to keep it all together. If you’re feeling the year-end crunch, you’re not alone!

I’m sharing my approach to surviving (and maybe even thriving) during this festive chaos—from wrapping up contracts without losing holiday spirit to baking cookies that would make The Great British Baking Show proud.

This one’s packed with:
🎁 Quick work-life balance tips to stay productive and enjoy the season
🍪 Go-to potluck recipes that won’t let you down
🎶 The best holiday albums to work or bake to (Kaskade’s Christmas Deluxe and A Very Teddy Christmas by Teddy Swims are on repeat!)

Welcome to Deals in Heels, where I share the real, unfiltered world of tech sales: the highs, the lows, and the hilariously relatable moments in between. I’m Jeniffer—an animal lover, puzzle enthusiast, wake surfer, and UT football fan who thrives on competition and creative problem-solving (and yes, I like to win).

If you’re looking for sales tips, funny quips, or just a fresh perspective on the hustle, you’re in the right place. Click below to join the ride—heels optional. 🖤