Sales Best Practices

Top B2B Sales Challenges in 2019

Audrey Weber's Avatar

Audrey Weber

Associate Content Editor

"Sales is easy," said nobody ever.

There are pipelines to fill, metrics to exceed, and quotas to beat. And that’s just at home. Out in the field, bigger and more agile players are competing against you to chase down the same leads.

Nope, B2B sales is not for the faint of heart. But if you have the grit, the mad audacity, and the insane desire to charge head-on, then know that you're going to need to overcome a lot of obstacles. The field gets progressively more challenging every year, so if you want to win you've got to study your plays and bring your A-game.

So here are the top B2B Sales Challenges in 2019, plus some tips on how to beat any challenge and end the year as MVS (Most Valuable Salesperson).

Challenge #1:

Much of the buyer journey happens without you

Empowered by technology (hello, Internet), potential customers know more about you and your product than ever before. According to Gartner, B2B buyers spend 66% of the buying journey finding and processing information without any help from a sales rep.

Moreover, B2B buying involves more decision-makers than B2C sales (about 6-10), making the task of engaging each stakeholder and building consensus more difficult.

Takeaway: Provide high-quality sales and marketing content — including case studies — on the website and to your sales reps. This content should clearly articulate differentiation and value, and establish a compelling value proposition for your product. This ensures that customers interact only with the most impactful content at each stage of their buying journey — even when no sales rep is present to give a walkthrough.

Well-informed customers want trusted advisors who will help them build tailored solutions for their unique problems. To gain their trust, B2B sales practitioners need to perfect their listening skills and practice genuine empathy. They need to achieve product mastery and play the role of domain experts who can engineer solutions that work.

Sellers might also need to adopt different messaging and approaches (based on role/function, geography, and other criteria) to effectively and efficiently engage each decision maker in the buying hierarchy.

Challenge #2:

Caught between buyers’ demand for personalization and the company’s need to scale

B2B customers now seek what their B2C counterparts crave: personalized experiences. They want to be engaged by B2B vendors in the manner they prefer. As a result, it requires multiple touch points over different channels (email, phone call, social media, events, etc.) to engage each individual prospect and get them to agree to a meeting.

Takeaway: Orchestrating personalized prospect experiences at scale is among the toughest challenges in B2B sales. And only one solution stands out: advanced technology.

Simple marketing automation and sales enablement tools are the absolute minimum. To scale up sales operations, B2B sellers need precise applications of artificial intelligence and machine learning such as those used in advanced sales engagement platforms. These tools help optimize multi-channel playbooks and email/call sequences through A/B testing, intent recognition, and data-backed recommendations.

Challenge #3:

Leaks in the sales pipeline (and other parts of the B2B sales cycle)

The B2B sales process has become so convoluted that 57% of sales reps expect to miss quota, according to a Salesforce study. Because B2B sellers spend much of their time on administrative and non-core tasks, they have far less opportunities to directly engage customers and actually do some selling.

In a HubSpot study, salespeople spend most of their time writing emails (21%), updating data (17%), doing research (17%), scheduling client calls (12%), and attending meetings (12%). That leaves salespeople only 34% of the time for actual selling.

Meanwhile, B2B sellers cited gaining appointments (14%) and connecting with the right stakeholder (12%) among the top challenges in prospecting, according to a Richardson report.

Takeaway: Nobody said B2B sales teams need to stick with the same sales process and playbook all the time. Customers change and so do their buying journeys, so as salespeople we must change and adjust our sales processes accordingly.

If leaks in the pipeline persist, revisit your ICP (ideal customer profile) to fix the lead generation and qualification process. If quotas for the number of meetings set remain unmet, then try introducing new sequences and training reps with new customer engagement skills.

If either of these entail a major change in the company’s B2B sales strategy, then so be it. Growth pains are a small price to pay compared to being mediocre forever.

How should you update your sequences? And how often?

Find out

Challenge #4:

New data protection regimes

There’s no question that data can drive process efficiencies and spur revenue growth. However, it can also bring your company to its knees if you fail to protect your customers’ data or respect your prospects' privacy.

Growing concern over consumer privacy and the weaponization of user data prompted the enactment of sweeping regulations such as GDPR (General Data Protection Regulation), which affects businesses who sell in Europe, and CCPA (California Consumer Privacy Act), which affects those who sell in California. Non-compliance to either can lead to multimillion dollar lawsuits.

Takeaway: There’s no going around this challenge. Strident privacy and data protection is the new normal and your company must comply with the new standards. The smart approach is to implement a full compliance policy and view the new regulatory environment as an opportunity to improve your data infrastructure and show your customers that you practice diligent stewardship of their data.

If you sell to Europe and/or California, make sure you read up on GDPR and CCPA and adjust your sales practices accordingly.

Challenge #5:

Hiring, training, and talent development

With some of the highest turnover rates among executives and staff alike, a career in sales can be very stressful. No wonder less than 20% of salespeople love their jobs (re: 17.6% rate their job satisfaction as outstanding while 47.1% rate their jobs as “just good”).

Amid this climate, the challenge for B2B sales organizations is to find, hire, and train qualified and diverse professionals who will not only thrive in the field of sales but also derive fulfillment in their jobs. Inclusion and diversity still remains a concern especially in our world of software and technology sales.

Asked about the skills they need to address current challenges, salespeople cited delivering a compelling value proposition (15%) and asking the right questions (11%) as the most important.

Takeaway: Even when AI and automation can perform a long list of tasks, the human element remains a crucial part of B2B selling. Organizations need competent and empathetic salespeople to orchestrate key touch points in the B2B sales cycle such as needs assessment, negotiation, and closing.

Recruiters have no choice but to broaden their talent pool and implement ongoing training programs to address the skills gap in professional selling. To date, most higher education has yet to offer formal sales training curricula.

Organizations also need to build an environment (compensation strategy, sales ops, support infrastructure) that will motivate and enable sellers to deliver high performance, as well as a corporate culture that makes them feel happy doing so. If you're curious, learn more about our culture and values at Outreach that make our employees proud to work here.


B2B customers have become more informed, sophisticated, and discriminating. They won’t fall for cheap selling tactics and will remember the brands that dare adopt such practices.

B2B vendors and sales reps can only match their customers’ level of maturity with greater agility, competence, and empathy. That might sound like a tall order, recognizing the need for change and making measured, incremental changes are small steps towards beating the challenges B2B organizations face in the shifting business landscape.

B2B buyers have changed. Sellers simply must do the same.

Learn more about B2B Sales

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