10 Sales Trends and Predictions for the Future of Sales in 2020

It’s that time of the year again! Time for Hacker’s annual Top 10 Trends and for the Future of Sales in 2020.

This year also marks the 5th year of my predictions posts! Wow, time flies. It’s been a fun ride, and I still feel like we’re just getting started.

So, without further ado, here are my top 10 sales trends and predictions for the future of sales in 2020.

10 Trends and The Rise of Sales Tech

When I started Sales Hacker, sales technology was in its infant stages. There were very few sales-tech companies, and the sales stack (plus it’s associated budget) was non-existent! But I knew it was necessary.

I created Sales Hacker to be the rising tide that lifts all boats. I wanted it to be the driver of sales technology adoption across the world. With over 140,000 active and engaged subscribers globally, we have truly made a dent in the past (ok, recent past), present, and future of sales.

Because of all of this, you’ll notice that a lot of these predictions have to do with sales tech specifically. But don’t worry. These changes affect everyone.

Ok, enough with the color commentary. Let’s get into the predictions.

#1: The rise of the sub-community, and everyone knows something

I feel like I’m in a million different sales communities that take place across Slack instances, LinkedIn Groups, and even in my email with Google Groups. This will likely continue to ramp up as everyone has something to share, and these niche communities are a great place to do it.

There’s no better way to learn than from the people building the playbooks at companies similar to yours. The most interesting part of these groups is that they’re all different.

The way I look at it, professional communities all differentiate themselves with one of a few things:

  • Location – ie., Chicago, Salt Lake, etc.
  • Diversity and Inclusion – ie., Women in Revenue
  • Seniority/Leadership – CRO, VP Sales, etc.
  • Function or Task – ie., Sales Ops, Sales Dev, etc.
  • Career vs Company – ie., negotiating my own comp vs building my team
  • Industry – ie., Tech, FinServ, Security, etc.

In 2020, you’ll see even more of these pop up in the sales world. We’re a social group, so this makes a lot of sense.

Sales Hacker is also planning an exciting relaunch of the Sales Hacker Community that was originally running on LinkedIn Groups (sadly, they haven’t built this area of the product out so we need to move it).

It’ll be fun to watch as vendors try to build their own communities too.

#2: Tech stacks becoming a platform focused on seamless integrations

Mulesoft was acquired for $6.5bn. Zapier, Tray, and many other up-and-comers continue to raise money to tie SaaS products together so data and workflows work seamlessly across tech stacks.

As we get to the next evolution of the sales stack, we’ll start to see the products seamlessly tie together. This will be a high priority for vendors as they realize they need to play nice with the rest of the rep’s and manager’s workflow.

We already have a lot of tech for sales. Now, it’s time to tie it all together.

#3: LinkedIn goes mainstream

We’re starting to see LinkedIn become the place to be when it comes to business content. It used to be primarily marketers and influencers, and now I’m starting to see more and more junior level SDRs on there building their brands.

I’m loving what I’m seeing from our SDRs at Outreach. You are never too early or inexperienced to share your learnings.

I’m so excited to see where it goes from here.

Not sure where to start? Follow some people you really admire. See what and how they write. Think about the things you do on a daily basis. Where are there opportunities to share? What would someone in your shoes want to know? I wrote my first posts back in 2013 and I was just 2 years into the workforce. It was scary, but the best thing I ever did. Leaders, encourage your people to post and share.

#4: Content gets an overhaul

Sales content is a huge part of any engagement strategy, but I’ve rarely seen it get a dedicated effort.

Now, the leading companies are hiring sales content experts, internally and externally, as consultants to uplevel their outreach game. Consultancies are popping up left and right, and there’s a real business need here. Email isn’t going away, but it’s more than just email.

It’s about time content gets taken seriously too. I’m all about omnichannel outreach, but if the message isn’t any good, you’re wasting your chances.

This isn’t the end of an era. Nothing is dead. Cold contact still works. Just invest in doing it well.

#5: Machine learning becomes real, finally

Why do I say “becomes real”? Because AI and machine learning have been buzzwords for years now, but they’ve never quite lived up to the hype. In 2020, you will start to see it really live up to the expectations.

Why was it so slow to reach its potential? It takes time to build the engine, then another 2–3 years to let the engine learn. Well guess what? The engine has learned with neural networks, deep learning, and advanced learning algorithms and it’s changing the game.

In 2020, you’ll be able to clone your best reps…. Ok, not literally. But you’ll be able to clone their actions convincingly.

For example, some sales engagement tools can now use AI to read the text of an email and actually understand the sentiment behind it. That means that we no longer have to rely solely on open and reply rates to understand what’s working and what’s not.

You’ll begin to know what works in any situation your reps will encounter and what action to take. Even better, it can automatically take that action, allowing your reps to be focused solely on selling activities that need a human touch.

Today’s tech can already understand if a reply is positive or negative, or what your next best course of action should be during the sales process. It will only get more sophisticated throughout 2020 and beyond.

We’re truly entering a new era in sales technology. The goal is not to replace or automate reps but to empower and enable them in ways that get the deal across the line with as little friction as possible.

#6: Rise of the millennial buyer

Ah, the great generational divide. As if this isn’t played out enough on Twitter. Jokes aside, this could actually be the most important change occurring over the next few years. The gaps between generations is getting shorter as technology creation accelerates.

The faster tech advances, the shorter the generation gap. 58-year-olds and 28-year-olds are supposed to think differently. They came up 30 years apart in completely different worlds. Soon, 28-year-olds and 20-year-olds will have been brought up in completely different worlds.

Technology’s moving fast. Right now, Millennials are entering their early to late 30s. That means they are becoming decision makers, and this is changing how you need to sell whether you agree with it or not.

How are you going to adapt?

#7: Diversity and inclusion takes a big step forward

Speaking of Millennials becoming decision makers, they are also becoming leaders.

Unless you’ve been under a rock, you’ll know that the world has become a lot more inclusive over the past few years. This means there are more cultures represented on the sales side AND the buyer side than ever before.

This will obviously only progress, as history has shown it has gotten better over time.

This means real, measurable change and not because of optics or because you need to interview that one minority employee before you can make the hire.

No, it’s because diversity and inclusion is actually important to the people doing the hiring in 2020 and beyond.

#8: Adoption is the new ARR

I saw a CRO lose their job the other day, not because they missed their new business number but because their churn in the upper segments was too high. Today’s sales world isn’t about measuring seats sold, contacts sold, or however your pricing and packaging work. It’s about usage.

How are you measuring if and how a customer uses your product?

Do you have your finger on the pulse of that account?

Are you even selling to the right customers?

One year of ARR is rarely worth the sales process of getting that customer onboard if they then churn out.

More companies will start to focus on how they’re tracking this, how they’re reacting to it, and the way they currently focus on landing net new business.

#9: More and more sales development teams will roll up to marketing

This is typically an unpopular take with my audience, but I’m going to say it anyway. I’m starting to see more sales development teams roll up to marketing, and I like it.

To me, there are 3 main stages of the sales process: pipeline, closing, and success.

Sales Development and Demand Gen create pipeline. Account Executives and Solutions Consultants or Sales Engineers close deals. Customer Success and ProServ ensure success.

You can still do SDR/AE pods and pair them up, but the accountability stage should be centralized in one place and roll up to a number.

#10: One or two big exits

I think we’ll see the first 1 or 2 big exits (price tags of a billion, or close to it) in the modern sales-stack era (companies started after 2013).

Lately, we’ve seen a couple of these companies raise in the quarter – Only Infotechhalf-a-billion-dollar range, and Outreach is at $1.1bn. All of them are growing aggressively, and it’s only a matter of time before the bigger players start to scoop up some of the larger up-and-comers. By bigger players, I mean the Microsofts, Salesforces,and SAPs of the world.

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