Sales

Guide to a Career Path in Sales [+ 6 Options for Growth]

Your career path in sales can follow a common trajectory…or take you on a wild adventure. It's all up to you.

Will you specialize in selling technical products? Train a team of 50 reps? Or maybe become a Chief Revenue Officer someday?

Starting your career in sales opens up a world of potential for new life experiences and high earnings. (And all of this potential makes the downsides of cold calling and cold emailing people totally worth it.)

But with so many different industries and roles at your fingertips, it can be hard to know which way to turn.

If you want to take your sales career into your own hands, then keep on reading.

We've got a list of common sales positions, the main options for career growth, and tips to help you advance your career at any stage.

30 Smart Sales Discovery Questions [+ The Ideal Call Structure]

The goal of a discovery call isn't to get the person on the other end of the line to say “yes” to working with you.

The goal is to accurately diagnose their problem and present the next best step for them to take.

To do that, you need to ask the right sales discovery questions.

But what do you ask? And when?

We’ve got all of the questions you need, plus tips on how to structure your discovery sessions.

Cold Calling Advice From a 16-Year Sales Vet

Talking to people on the phone is easy, right?

In a world enamored by text, phone calls aren't as common as they used to be, making it all the more awkward when you have to run outbound calls as part of your job. Add in prospect resistance, and you've got a recipe for a very difficult day.

But cold calling still offers an amazing opportunity to drive leads, which is why most B2B businesses still practice it regularly.

So, how do you succeed?

To get expert cold calling advice, our VP of marketing Nadia Milani sat down with Tom Slocum, a 16-year sales veteran and GTM consultant at The SD Lab. He shared some smart tips to guide you no matter your experience or comfort level.

Keep reading for the top highlights from our recent installment of The Closing Show Live or watch the full video.

(Or, skip to minute 24:02 to hear playbacks and reviews of real cold calls.)

How to Create a Killer Sell Sheet [+ 5 Great Examples]

Sell sheets are a great way to ace that first impression. Short, sweet, and designed to promote the best of your business in a concise one-page package, a killer sell sheet goes a long way in nailing those all-important early interactions with a prospective customer.

The days of six-panel brochures are long gone; here’s how to create and send winning sell sheets using Proposify.

How to Align Your B2B Sales and Marketing Teams

With more metrics, more channels, and more trends, B2B marketing and sales alignment isn’t going to get any easier in 2023.

So, we chatted with Jessie Lizak, CMO at BDEX, and Eddy Bahnam, Founder and Sales Consultant at EB3.

This dynamic duo cohosts Whiskey Wednesday, a weekly evening podcast that brings sales and marketing together like never before.

Jessie and Eddy work on improving sales and marketing alignment within their in-house roles. PLUS they collaborate together to grow Whiskey Wednesday (with Jessie bringing the marketing expertise and Eddy bringing the sales swagger), regularly chatting with experts in both fields on their podcast.

Needless to say, they’re really in the trenches.

Keep reading for their hot takes or catch the full episode here:

9 Social Selling Tips from a Pioneer of the Strategy

We sat down with social selling expert and coach Evan Patterson to get his piping-hot takes on the strategy. He’s been social selling since back when it was all manual, without fancy intent tools to help.

If you’ve been asking these questions, you’re in the right place…

How do we find the right people to sell to on social media?

How can we get our company on board?

What should and shouldn’t we measure?

The answers await. So keep reading for Evan’s very best social selling tips.

Or catch the full episode here:

Tough Year? Here's How Pro Sellers are Prepping for 2023

Sometimes ho ho ho feels more like whoa whoa whoa. As in…How can I close a couple more deals before everyone disappears? And how can I make our solution a priority for my leads come January?

Maybe you’ve had a tough year and gotten a lot more “Nos” than you’re used to. Or maybe your year was okay, but with the slowness of the holiday season settling in, you’re starting to worry about further economic downturns.

When the sales environment is tough, it can be challenging to stay upbeat and confident. But stay upbeat and confident you must.

During our holiday episode of the Closing Show Live, called Sleigh Your Targets, we chatted with four sales experts to help us buck up for the final push of Q4 and the year ahead: Tyler Lessard from Vidyard, Amy Volas from Avenue Talent Partners, sales trainer James Buckley, and sales development director Jesse Gittler.

Watch the full live event for their best tactics or keep reading for our favorite takeaways.

Sell Like You: Own Your Unique Sales Style to Unlock Growth

Do you put more trust in “the experts” than yourself?

Are you always searching for the next best framework?

These are signs that you’re struggling with mediocrity. Not because you are mediocre, but because you haven’t yet tapped into your unique style and personality as a salesperson.

When you’re out of alignment, your results will be so-so.

Jeff Bajorek, the creator of the #SellLikeYou movement, says that helping sellers believe in themselves is worth more than skill training. He laid down some piping-hot motivation on our recent episode of the Closing Show Live. And in this case, a video is worth a million words.

Catch the full episode here for his walkthrough of how to get yourself aligned with who you truly are. Or, keep reading for his step-by-step process to hone your unique selling style and transform your potential.

“You’re the secret ingredient to your own success.” - Jeff Bajorek, Sales Trainer

How to Write a Sales Proposal Designed to Close [+ Templates]

If you’re working on a sales proposal, there are probably two things you care about:

1. That the proposal will close.

2. That you won’t have to spend hours creating it.

You shouldn’t have to guess what to write, wrangle obnoxious software, or pretend to be a graphic designer.

Our actionable guide to creating a sales proposal will help you cover all the necessary details to win over your prospect—all while saving hours of time.

Plus, we’ve got examples and templates from a variety of industries, from consulting to construction.

8 Pro Tips for Asking Better Sales Discovery Questions

You can ask discovery questions that impress your buyer and show them that you’re the right person to help them. Or…you could totally blow it and bore them with the same basic questions they’ve heard on every other sales call throughout their entire career.

So, how do you make sure your discovery questions set you up for success?

We chatted with Hannah Ajikawo, CTM consultant for Skaled and a top voice in sales on LinkedIn, to learn how we ask better questions and improve the buying experience.

Click here to watch the full interview, or keep reading for Hannah’s best advice.