Overcoming the Biggest B2B Sales Challenges of 2019

January 7, 2019


Editor's Note: As 2020 approaches, we're looking back at some of 2019's most popular posts on the LinkedIn Sales Blog. This one ranked No. 7.

What are the biggest challenges and obstacles confronting B2B salespeople as we head into the new year?

Obviously, the answers will vary based on company, industry, and context. But, there are a number of common pain points faced by those in the profession. Recently, Venture Accelerator Partners asked several pros in the field about the greatest challenges they faced in 2018, with an eye toward offering up B2B sales tips to conquer them in 2019.

Today, we’ll touch on a few of their responses, while adding our own insights and pointing you toward content that specifically addresses some of these pervasive snags.

B2B Sales Tips to Overcome Key Challenges in 2019


Finding experienced sales pros that fit in your organization is a perpetual paradox for sales managers. Proven performers with relevant expertise are in high demand. Jonathan Jones, Business Development Manager for Bridget, says his approach has been to broaden scope and search outside of traditional talent pools, identifying strong candidates in industries like banking and insurance that may not have formal sales experience.

“I think it’s essential that organizations continue to partner and support sales academy programs,” Jones adds. At LinkedIn, we’ve been focused on beefing up our own Sales Academy resources, and will continue to offer up courses and workshops here in 2019.   

Getting Close to Customers

“Although it’s theoretically easier than ever to reach customers, it is harder to get meaningful interactions unless we are closer than ever to them,” says Carlos Hernandez, Regional VP for Sandvine. We couldn’t agree more. This is one of the core messages we’ve been reinforcing, because data continues to show that salespeople who understand and empathize with customers achieve far stronger results.

For inside tips on using LinkedIn to forge meaningful connections and conversations, check out our guides, Get Closer to Your Prospects and Get Closer to Your Customers.

Ops and Enablement

“Expectations continue to grow with prospects and customers. Getting reps up to speed across the whole system is a continuous challenge,” says entrepreneur Chad McCaffrey. Indeed, the operational elements of equipping the sales team with optimal tools and resources have grown so extensive that many companies are creating sales enablement departments and dedicated roles.

We put together a hefty article on the what, why, and how of sales enablement, and it was one of the most popular posts on our blog last year.  Check it out for tips on getting your sales department the help it needs.

Demonstrating ROI

When it comes to sales technology, one priority stands out above all others: showing results and proving value. If you can’t demonstrate ROI to top decision makers, you’ll have a hard time earning more budget.

“There are lots of new tools and technology that become available on a regular basis. Cutting through the noise and finding the right tools that provide ROI is very important,” says Mark Elliot, cofounder of VA Partners.

Recognizing this widespread directive, we recently published a new guide for Overcoming Barriers to ROI with Sales Navigator.

Pipeline Consistency

The ebbs and flows of a sales pipeline are realities that many businesses deal with. As competition grows, lulls and down spells can be especially problematic.

“We can reasonably predict how many opportunities we’ll generate from inbound, but due to seasonality and other factors there is so much variance,” says Shane Gamble, Head of Sales for Smile.io. He notes that his company is working to build an outbound development team in 2019, and relies on technology to stay constantly tuned into the marketplace and target audiences. In Sales Navigator, you can set up alerts to detect triggers events that may point toward opportunities.

Aligning Different Sales Units

“My biggest sales challenge at the moment is having three different business lines selling to the same clients with grossly different offerings and maintaining a consistent message about how our organization can support clients in the tech sector,” shares Ryan McCartney, Communitech Partner at BDC.

This is a common scenario in large companies and enterprises — one that can lead to a lot of confusion and frustration on the customer’s side. It’s a big reason we made pipeline visibility a central aspect of Sales Navigator Deals, which creates a unified dashboard for collaboration. With updated deal data and details that everyone can access and see, you’re less likely to have crossed wires when a prospect is approached by different business lines.

Bringing B2B Sales to New Heights in 2019

The top challenges in B2B sales tend to sustain and endure — you can argue that the six items mentioned above were all just as prominent in 2017 and earlier — but the structures and specifics are evolving. So, too, are the ways we tackle and triumph over these obstacles.  

Thanks again to Kayla Thomson and Venture Accelerator Partners for aggregating and sharing these insights. You can find full versions of the quotes, plus many more, in the original post.

You can also subscribe to the LinkedIn Sales Blog to stay plugged into helpful B2B sales tips all year long.