Sales is The Most Stagnant Profession in The World. Here’s Why—and Why That Has to Change

In 2020, every little advantage matters. It’s time to really look at how we’re approaching sales. It’s time to disrupt sales from the inside before it gets dismantled by outside forces. Here are the problems Proposify VP of Sales Daniel Hebert sees in the industry and how to start moving the profession forward—before it’s too late.

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10 min. read

Have you ever read the book ‘How I Raised Myself From Failure to Success in Selling’ by Frank Bettger?

It’s an amazing rags-to-riches true story from someone who became one of the top sales reps in America. After being fired from professional baseball, Bettger went into insurance sales. By trial and error, he figured out how to set appointments, run meetings, get prospects interested, and close deals.

There are great tips in the book about question-based selling, knowing your numbers, gaining confidence, and much more. The only problem with this book?

The book is about the height of Frank’s career—in the 1920s.

You’re probably wondering why I’m even bringing this up—what’s the problem with an old sales book? Well, most of the 100-year-old advice I read in the book I still see being used by sales teams today. Which leads me to question…

Is sales one of the most stagnant professions out there?

Yes, it is. Consumers have changed. Buying has changed. But sales remains stubbornly stuck in its ways. In fact, I experienced it recently myself in both expected and unexpected places.

I went car shopping last weekend. I know, the way we buy vehicles is notoriously outdated. It’s a cliché how much people hate it, and no wonder. The whole thing felt ancient.

After doing a test drive, I went into an office to discuss numbers. The salesperson punched in some digits on the computer, then proceeded to write down, on pen and paper, the monthly payments for the car.

I was confused. I didn’t even know what that number represented, what I was paying for. I asked to see a price breakdown for the car. Twenty or 30 minutes later, I still didn’t know what I’d be paying for, even though by this time the salesperson had brought in a senior salesperson and the sales manager.

Needless to say, I didn’t buy the car. I was shocked at how that kind of old-school sales approach still exists.

In the SaaS sales world, I thought, surely we’re better than this.

But then it got me thinking back on my career, spent exclusively in SaaS, and I wasn’t so sure.

  • When I first joined Proposify, we had invested heavily in a training system that came out in 1967. A fifty-year-old methodology was what our reps were using to run a 'modern' SaaS sales cycle. Ouch.
  • At a previous startup, the VP of Sales was very into the “let’s add more butts in seats to increase revenue” camp, instead of making the process better. We all know that sales is lead-driven, headcount-closed. Increasing the sales team size won’t magically make anything else better.
  • At another startup, when reps were having difficulty hitting quota and we were behind target, the CEO decided that instead of investing in better processes, more leads, and training, we should increase the quotas even higher. Because increasing quotas always increases revenue, right?

A few things are clear here:

For decades, we haven’t changed how we set targets for sales reps.

For decades, we haven’t changed how we compensate sales reps and build out our sales teams.

For decades, we haven’t really changed the methodologies we use to sell.

Sales hasn’t changed—but the rest of the world has

For years, buyers have been conditioned by sophisticated marketers to want things now.

Netflix gives you the ability to stream your favorite show, now.

Amazon allows you to buy pretty much anything, now.

Spotify allows you to listen to your favorite music, now.

This kind of conditioning trickles into everything we do, including how we are as employees or B2B buyers.

So, buyers have significantly changed their purchasing process over time. And marketing is pretty good, in general, at keeping up with how people buy. But we can’t say the same for sales.

The stagnation I see in our profession can’t really be found anywhere else. Engineers. Marketers. Doctors. Manufacturers. They’ve all had to drastically change how they do things as the human beings they serve evolve.

Although there are still underlying theories and principles that are decades or even centuries old in marketing, manufacturing, engineering, or medicine today, there are significant advancements in processes or how things work that happen at least once every decade, or sooner.

When was the last time there was a major disruption in how we sell a B2B product? If you look at a common B2B selling process from two different perspectives, it’s not hard to see why our profession lacks innovation.

1. The “paperwork process” from the sales leader’s perspective

This is typically what I see in the market for B2B sales processes:

  • Demo your product
  • Create a proposal or a quote
  • Send it to the customer for approval
  • Once approved, generate an order form and contract
  • Get that signed with e-signature.

Seems pretty logical on the surface, right? No need to mess with simplicity. Simplicity works. It’s just paperwork, after all.

Not so fast.

I once asked a CRO at a very well-known MarTech company why he didn’t pay more attention to his paperwork process. I shit you not, he answered:

“Dan, I got to $30M ARR without putting effort into it, so why change now?”

If that isn’t a stagnant mindset, I don’t know what is. The most frightening part of all this? He’s not an outlier. I’ve gotten the same answer from dozens of other sales leaders.

2. The “paperwork process” from the sales rep’s perspective

When you speak with a sales rep, however, this is usually what they have to go through to create the paperwork needed to close a deal:

  • Open up a blank Word doc.
  • Spend an hour trying to figure out what to write.
  • Give up and open up seven other Word docs they’ve used recently.
  • Furiously copy-paste from those other docs to get the ‘right’ info.
  • Realize, in their fury, they created a Franken-proposal that doesn't make sense.
  • Spend the next three hours rewriting 50% of it.
  • Spend an hour formatting an image that ruins the flow of their document every time they hit enter.
  • Get frustrated.
  • Ship it over to marketing, thinking they can do it faster.
  • Marketing doesn’t like the layout so they want to redo it, but it will take a week because they have other priority projects on the go.
  • Spend the week worrying that this is taking too long for the prospect.
  • Get it back from marketing.
  • Looks great, but marketing completely generalized the personalization, so they need to go through and edit it.
  • Realize marketing did the layout in InDesign, so they have to do all edits through them.
  • Get angry at marketing, because they don’t want to do this again.
  • Send edits back and forth.
  • This takes another week. The prospect has asked for the proposal twice already.
  • Get anxious that they might lose the deal to a competitor.
  • FINALLY send the prospect the PDF.
  • Crickets...
  • Call the prospect, only to realize the file size was too big so it got caught in the spam filter.
  • Prospect asks for edits on pages 3 and 7.
  • Send the edits to marketing.
  • Compress the file size on the updated doc so it doesn’t get caught in spam again.
  • Send updated PDF to prospect.
  • Realize they forgot to replace a previous customer's name.
  • Edit again, export PDF again, and resend.
  • Hope the prospect didn't notice.
  • Prospect likes it but with changes to pricing.
  • Send pricing edits back to marketing.
  • Get the PDF back, compress, send to client.
  • Then wait...
  • And wait...
  • Has the deal gone dark?
  • Wait some more.
  • Lose sleep knowing they need to do this eight more times this month for a shot at hitting quota.

Does that look like an “effortless” process to you? One that’s optimized for a modern buyer?

The underlying technology that enables this process today is Microsoft Word or PowerPoint, saved to PDF. The PDF came out in 1993. It’s no longer the best way to deliver a proposal. Yet, it’s still the anchor in most paperwork processes in sales today. And no, slapping an electronic signature on it won’t suddenly make it innovative.

So what would happen if you actually put a bit of effort into your paperwork process? You might meet (or even exceed) buyer expectations.

Why sales leaders should care (hint: buyers do)

Consumers have become accustomed to a certain experience, mostly driven by web and mobile. But the PDF experience in 2020 doesn’t live up to those high standards.

Here’s what today’s buyer expects:

Customers want to interact with what they buy.

If you have more than a couple pages, your PDF needs a table of contents. Who still uses those? Websites and apps have easy navigation, not static lists. Buyers want to be able to freely navigate through info and options. Explore choices. Click on stuff. Maybe get a video walkthrough.

You can’t do any of that with a PDF.

Buyers want things now.

Think about how common same-day shipping, instant downloads, and buy-now-pay-later apps are becoming. When you have to send six different versions of your PDF back and forth through email each time you make a change, you delay the purchase at the exact point where the prospect is most excited.

Buyers want convenience (for themselves, not you).

The paperwork process is typically something that gets ignored. It’s one of these things that “just has to happen.” And usually, it’s designed with sales ops, legal, and finance in mind—whatever is easiest for them.

The closing process is never approached with the lens of what’s best, or easiest, for the customer. But when sales organizations put in that extra effort into their paperwork process, they close deals at a higher rate and much faster.

For example, when we dug into our Proposify database of more than two million proposals we found that in an industry like SaaS:

  • Including video in proposals increases close rates by 41%.
  • Proposals with interactive pricing are 173% more likely to close.
  • Proposals with a payment integration, such as Stripe, are 44% more likely to close.

Can your PDF do all that?

In 2020, every little advantage matters. It’s time to really look at how we’re approaching sales. It’s time to disrupt sales from the inside before it gets dismantled by outside forces.

Are you in or are you out?

Are you part of the problem? Look at how you’re doing things now and take my four-step assessment:

1. Is your sales methodology decades old?

2. Do your processes remind you of the 1980s and 90s?

3. How are you compensating reps? How are you setting quotas? Is that still relevant with today’s generation? Is it best for the customer?

4. Does your closing process make it easier for your buyers to make decisions or does it just make your legal and finance team’s jobs easier?

There are plenty of areas of opportunity where you can innovate your go-to-market approach, but the closing process is the one I see neglected the most.

Don’t be one of those sales leaders that retires doing things the same way as you did when you first started. Let’s do what we can to make the sales profession better for the next generation.

What do we lose? Nothing.

What’s the price of not changing? Customers are not getting value speaking with salespeople anymore, eventually leading to the demise of the profession and getting replaced by self-serve technology.

This has already happened in other professions. Let’s not let this happen to us. It’s up to us to take action.

Sales is The Most Stagnant Profession in The World. Here’s Why—and Why That Has to Change

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