Post

The Evolution of the Modern Buyer’s Journey: Why Sales Needs to Care Now

Guest post by Jake Dunlap, Founder & CEO @ Skaled

When is a change first noticed? Where does evolution begin?

We often miss the subtle shifts in habits, and most changes don’t occur overnight. They occur in long stretches of tiny differences that build up and result in a massive revision.

For a long time, those of us in sales thought we were exempt from change. We had cracked the code. We had established repeatable processes that would work now through eternity. There was one problem: we weren’t looking beyond 2016.

The buyer’s journey has experienced a massive shift over the last three years. As a result, we’re all scrambling to understand why our pipelines are low, competition is high, and forecasts are neutral.

A Look Back at the Last Decade

The last ten years have been transformative to the sales community. Coming off of the financial meltdown in 2009, we created a culture of distrust. Buyers became cautious, and more people were looped into the process. In the years before, I would sell massive deals to one decision-maker and then connect with the others. Once that level of trust disappeared, I suddenly had to talk to five to seven people to get a proposal on the table.

Email marketing was a regular part of sales communications over the next few years, but cold calling still took the lead on favored outreach. You didn’t have as much information on the front end. You had to get your prospect on the line to understand what they were seeking.

In 2013, the year I started Skaled, I was introduced to email tracking software. I could create basic cadences, and it became obvious to me that this was going to be big. I remember thinking, “This is it. This is going to be the biggest shift in sales we’ve seen so far.”

And I was right. Email marketing took the world by storm.

% of AEs personalizing emails
Learn more about email personalization in our eBook, Everything You Need to Know About Sales Email Personalization.

The next three years accelerated everything. Outbound lead generation blew up. Almost every marketing organization across the country adopted Hubspot’s Inbound Marketing play. Customized emails were working, and SDR teams were going all in. Sales and marketing automation was the saving grace of B2B. We were winning.

In 2016, everyone was scaling their SDR teams. But it still felt like sales. It didn’t feel much different than what we were doing in 2009 or even in 2003. We were just doing more of and getting better at it. Sales technology continued to emerge at a rapid rate.

I remember attending a few conferences around this time and thinking about how special this all was going to be in the years to come. This space would be huge. I realized we needed to go all-in on sales technology. We needed to embrace technology for what it was worth and not fear its power.

LinkedIn entered the arena around this time. Between 2016 and 2018, we started to see the downward crawl of the effectiveness of email marketing. Companies like SalesLoft are now in full swing to help us diversify our cadences, but also help us make our emails better… because they weren’t working the way they used to.

By 2017, a lot of sales teams started to struggle. Salespeople were hesitant to pick up the phone. SDR teams began underperforming. Buyers were becoming annoyed with the process. Companies cared more about qualifying than adding value. But small nuggets of hope continued to emerge.

G2 Crowd began gaining popularity. Buyer’s now had a place they could not only find value and answer lingering questions about products and services, but a place where they could engage with the quality of service other buyer’s had experienced. Salespeople were still inherently distrustful, but buyers could settle their fear of buyer’s remorse in other places. LinkedIn and other social selling sights also gained increasing popularity, creating a sense of community within these otherwise niche places, and giving salespeople a place to engage.

By 2018, it suddenly became obvious to me that we had just experienced micro-moments of change, leading to this massive shift. More executives and VPs than ever were reaching out to me, looking for advice on how to reach quota, or fill their pipeline, or reach their buyers.

More information is available than ever before due to the unanimous adoption of content marketing by all B2B marketing teams. Yet salespeople are struggling to add value that goes beyond what the eBook offers.

LinkedIn became a force in prospecting, but grade A players are sparse. Salespeople are treating InMail like email and not dedicating the delicacy a social network requires. Buyers prefer speed over cost. Buyers are already in the intent phase the first time they reached out. We had to figure out a way to reach them where they are.

A Pendulum Shift

In 2018, Skaled realized this shift and had a change in the sales process was required. We had to take a good hard look at what was working and what wasn’t to not only compete in the space but also offer the best strategy to our clients that we could.

I remember sitting down with my team and saying, “We’re on the verge of something spectacular, but it’s not going to be an even road to get there.”

We knew there was a new buyer who had entered the arena. Now we had to figure out how to work with this modern buyer.

The Modern Buyer

After extensive research, we realized the buzzword of the century might be the golden ticket of understanding today’s buying landscape. Millennials had entered the space and become a force to be reckoned with.

In most industries, millennials make up a large share of the decision making power. According to Trust Radius, over 45% of B2B technology buyers are 25-34 years old, making them the single largest demographic. They are followed by 30% in the 35-44-year-old age group.

selling to millennials

We have to drop the notion that millennials are just junior professionals, struggling to buy houses and “canceling” plastic straws. Millennials are our buyers.

What makes Millennials interesting is their stark difference in buying behavior compared to generations prior. Millennials don’t even engage with your sales team until they are 57% of the way through their journey. They don’t want to hear more information from your sales team; they want inspiration. They don’t care if your product is the most (or least) expensive; they care about what it’s doing for the greater good, how it will solve their problems, and how their money spent will impact the world.

Millennials are acting like consumers along the path. They will buy your product the same way they buy their shoes. They will research your company the same way they research the ingredients in the food they order online. Millennials are consumers, not businesses. They want to be treated as such.

Millennial expectations are high. Only 32% believe that sales reps are exceeding their expectations. Millennials expect a sophisticated process. They want to be reached in more way than one. They are in constant conversation all day long and want to communicate with you similarly.

There are plenty of reports out there that go into the granular differences between Millennials and generations prior. I’ll let you research that yourself. What I’ll leave you with are three ways that you can start reaching your Millennial buyers immediately.

1. Engage with Millennials on the social media platform where they are most active.

Are you selling a product or service that makes sense on Instagram? Great! Slide into their DMs.

Do you follow your buyers on LinkedIn and engage with every single one of their posts? You need to create a level of affinity with your buyer in order to cut through the noise. You aren’t annoying – you’re engaging them.

2. The job is sales, not information giving.

If you’re talking to a millennial, remember that they’ve already completed more than half of their decision-making process. They have intent; they’re interested. Your job is to take them over the finish line by showing the value, increasing their inspiration in your product, and leveraging yourself as an expert that will continue to be an advisor post-sale.

3. Relationships don’t end after the contract is sent.

Your marketing team should be thinking about ways to delight and re-engage your customers, but don’t leave it up to them. Re-engaging current customers into upsells or resells is easier than acquiring new business.

Millennials are evangelists at heart. Let them be an advocate for your product. Word of mouth continues to be one of the most effective sales and marketing strategies. By engaging your customers post-sale you’ll create lasting business relationships and increase your chance at add-on sales.

Where to Go From Here

Millennials are here to stay. We have to figure out how to reach this pool of buyers, but the evolution of the modern buyer doesn’t end here.

As new behaviors are adopted and evolved, our efforts will have to shift with them. In order to compete, we must seek a balance between new and old and remain at the forefront of innovation for sales and marketing strategy.

To learn more about the Millennial Buyer, check out my Weekly Recap here and connect with me on LinkedIn where I put out daily content on how to cut through the noise and remain resilient in a developing landscape.


Sales engagement with SalesLoft helps the world’s best sales organizations deliver value and create trust by connecting with their customers in an authentic, human way, at scale. Learn more about how we do this in our Sales Engagement Buyer’s Guide.

Sales Engagement Buyer's Guide

Get the latest in your inbox.