Sales technologies: the most important digital transformation investment this decade

Posted September 17, 2020

headshot of lady smiling

By Cari Murray

Senior Editor at Outreach

Paving a Path to the New Modern Sales Organization

Companies in every sector of the U.S. economy are racing to capitalize on the promise of “digital transformation.” IDC estimates more than $7 trillion will be spent globally on digital tech initiatives in the next three years — even in the midst of a pandemic and economic uncertainty.

One area where companies are investing significantly? Sales transformation.

To some in the industry, this isn’t surprising. According to a recent Forrester report, “2020 will be remembered as a watershed moment when B2B buying and selling changed forever.”

It’s clear: Sales leaders need to purchase advanced technology to meet buyer needs and expectations in today’s digital environment.

“Even when sales teams shrink, companies continue to spend on increasing the productivity of the salespeople they still have,” says Manny Medina, CEO of Outreach. “They’re feeling the pressure of a demanding market that rewards both growth and efficiency, and they’re rushing toward advanced sales technologies that will help them land new customers, faster customer growth, and increased revenue.”

Customer journeys are getting more and more complex as B2B buyers expect B2C experiences. To close this gap in expectations, many sales organizations have poured millions of dollars into tools and analytics that promise to give them an edge in digital selling.

But if they invest in the wrong technology, they’ll get left behind.

So, how can they accelerate digital transformation to drive better customer experiences? We interviewed a handful of longtime sales practitioners and experts to get their insights about reinventing go-to-market strategies for 2020 and beyond.

4 steps to digital transformation

Pivoting to the New Modern Sales Org

It’s tempting to imagine that chief revenue officers (CROs) can buy their way into the future — and that implementing sales tools is all that stands in the way between revenue forecasts and market dominance.

The reality is that succeeding at “the digital transformation of sales” requires a deep understanding of the areas that create friction within the customer journey.

“The pandemic was just an accelerant,” says Craig Rosenberg, chief analyst at TOPO Research. “People were already talking about the many ways they needed to change. The crisis is forcing them to do it.”

The typical sales organization used to be made up of direct sales reps making introductory sales calls, taking clients to lunch, and logging thousands of frequent flyer miles to follow up on potential deals in target markets. Today, this model seems like something we’d see in an episode of Mad Men.

Graphic explaining the evolving sales toolkit, what buyers used to expect and what they expect now

Driven by the explosion of cloud services, mobile technology, and artificial intelligence, the sales function has shifted. Buyers have price quotes, live demos, digital content, and free trials at their fingertips 24/7. They’re much more informed than B2B buyers of the past, and they expect the same seamless consumer experience B2C companies like Amazon provide.

This consumerization of B2B buying behaviors is shifting the way teams go to market. Sales teams need to consistently reach buyers with powerful content that breaks through the noise and helps decision-makers make sense of their options. It’s a model that CROs should embrace, not resist.

Invest in Smoothing Out the Friction Points

It's a buyer's market — but it's also a crowded, confusing market filled with noise and lofty expectations.

“They have so many choices these days and can access reviews in an instant, so one of the only ways you can compete and win is by building a reputation for being the most customer-centric business in your space,” said Brittany Hodak, a Shark Tank veteran and a sales and marketing consultant. “Customer experience is the only thing your competitors can't copy.”

The challenge then is clear: How do you integrate an incredible customer experience into the sales process?

In today’s marketplace, friction in the customer journey comes from a wide range of sources — onerous registration processes, opaque pricing, cluttered web design, and hard-to-find product information to name a few. Even too much information can lead to negative experiences. Compounding the problem, a 2019 Brevit survey showed that the majority of customers did not feel that the salespeople covering their account had a solid grasp on their product or buyer. All of this adds to lost sales opportunities.

A graphic with a dark blue background featuring a large quotation mark symbol in blue at the top. Below the symbol, there is a quote in white text that reads, "Customer experience is the only thing your competitors can't copy."

“Sales professionals must never forget that their buyer's experience while working with them is a more consistent predictor of outcome than any other variable,” says Jeb Blount, a sales and leadership trainer and the author of Virtual Selling.

TOPO senior analyst Dan Gottlieb agrees: “Selling is now about reducing friction for buyers, and sellers need to be in a position to succeed in every channel, exceeding expectations at every step of the process,” he says “This used to be a ‘nice to have,’ but now it’s a ‘must have’.”

Another challenge is the fact that the global pandemic has driven buyers’ budgets down; selling in 2020 is harder, and that challenge likely won’t get easier.

“Post-COVID, many buyers will have less to spend,” says Beth Rogers, a visiting fellow at the Cranfield School of Management and author of Rethinking Sales Management: A Strategic Guide for Practitioners. “They are more likely to spend that money online, more likely to seek information about a variety of potential products or services before buying.”

Now, more than ever, sales organizations need to lead with empathy, understanding the pain their buyers are feeling. Focus less on selling and more on solving a pain the customer feels, so they can reach their business outcomes faster. Savvy sales orgs are leaning on a combination of technology and process to help their teams achieve these outcomes and transform the customer experience.

TikTok? The Clock is Running on Great Content

At a time when it’s nearly impossible to meet with a prospect in person, how can sales leaders get key messages across at the right moments? By creating high-quality, informational content that serves critical needs of top prospects.

“Customers genuinely want to be led and to learn something new,” says Kelly Breslin Wright, a director for various tech companies and former EVP Sales for Tableau. “A content strategy needs to be about thought leadership and teaching customers where they need to be.”

White papers, blog posts, and how-to material are effective strategies to keep customers in all stages of the funnel, while social media tools are growing in importance. And it’s especially important to remember that content strategy means more than content marketing. Reps need to be armed with effective sales decks, talk tracks, emails, and other materials that enable them to better sell your solution.

“Content has never been more important,” says John Hall, president of Calendar and a prolific speaker on sales management.

Salespeople, he says, need to communicate to content teams so they can continually identify customers’ precise pain points.

Distributing content at scale to the right persona through the right channel is also critical. How do you break through the noise to get your content noticed? Modern technology helps leaders experiment and test different communication methods to achieve the outcomes they need.

types of content to keep customers engaged

Personalize to be More Productive

Looking forward, sales organizations need to be more agile, adopting the most effective selling techniques and adapting to the needs of every customer.

“Sellers must choose the communication channel with the highest probability of achieving the desired outcome at each step of the sales process, at the lowest cost of time, energy, and money,” Blount says.

Maximizing a sales team’s productivity also means leveraging tools that can easily automate high-impact activities, such as triggering follow-up actions for reps and sending basic service and support messages.

Taking away easy, mundane work means the new modern sales org can rely on personalized, multichannel communication to ensure their messaging, content, and timing are effective. If you don’t have the technology to automate the easy activities, your reps won’t have time to focus on the deeper work, such as building and strengthening customer relationships.

Leaders have real-time data at their fingertips to understand what’s resonating with the buyer — and perhaps more importantly, what’s not. They have the visibility to pivot quickly and reach buyers the way they want to be reached.

Technology Always Changes, But People Won’t

One message from our experts is clear: It’s essential to focus on what strategies leaders can control right now, especially as the future seems so uncertain. Digital transformation is an unstoppable force across the enterprise, but it’s also subject to misinterpretation and highly complex. We can’t predict what will come next.

The role of the buyer has radically changed, which requires a new way of thinking about how leaders manage sales rep performance.

“One of the root causes of organizations' missteps is misalignment on the go-to-market strategy,” Wright says. “Short-term operational focus without an overarching holistic strategy has become a huge problem in the enterprise. Departmental silos, an unclear unifying purpose, and an inability to explain the company’s value all negatively impact sales teams.”

Sales strategy must be better aligned with business outcomes and explained more clearly at every level, so reps understand how their roles and responsibilities align to immediate and long-term business outcomes.

To evolve to a digitally transformed sales team, companies must invest in sales technologies that drive proven business outcomes. They must also reduce buying friction during the customer journey, personalize the experience, and create compelling and timely content. CROs can then quickly position their teams for success, no matter what challenge — or crisis — comes next.


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