Why Outbound Sales Is Lagging Behind In Digital Transformation

Mar 29, 2022
Collin Stewart

Technology is an inescapable part of the modern B2B sales landscape, but certain arms of the revenue-generating organization have been more resistant to change than others. Art Harding joined the Predictable Revenue podcast to discuss why outbound sales are lagging behind in digital transformation and how to fix it.

Art is a global speaker, sales leader, and Chief Operating Officer at People.ai, where he helps build high-performing sales, services, and operations teams. Despite years of experience in B2B sales, it wasn’t until Art experienced the buyer’s journey from a customer perspective that he began to realize just how far behind the industry had fallen.

With more and more companies relying on remote operations, it’s time for B2B sales to catch up with digital transformation. 

Why outbound sales have been slower to adopt new technologies

While marketing and customer success are led by data-driven operations, outbound sales remain stuck in the past. Art credits this to the massive explosion of SaaS and tech companies, many of which invested heavily in top-of-funnel marketing to grow. 

Meanwhile, outbound sales leaders have been much slower to adopt new technology. There’s a common fear that these tools will eventually replace their human counterparts–when in fact, as Art argues, technology will only augment the outbound sales process. As technology continues to take off, human relationships are more important than ever. 

Outbound sales in the digital age

Part of the reason marketing has been at the forefront of this digital transformation is because it’s an inherently team-driven environment. Outbound sales can be isolating since most of a salesperson’s daily tasks are performed solo. 

But in contrast to traditional methods, the best sellers operate from a team-oriented mindset; they work with marketing and customer success and are curious about different disciplines. Where in the past these departments were isolated from one another, today they’re more connected than ever. One of the most fatal mistakes a sales leader can make is to try to do everything alone.

Instead, it’s important to recognize that your customers are being served by teams–they will interact with other disciplines in the organization, which means sales need to be connected to those disciplines as well.


How to audit your strategy as an outbound sales leader

Aside from working with marketing and customer success, it’s also important to look within your sales function at operations and enablement. These two areas are often neglected in favour of new outbound sales hires but are the key to integrating new technology. 

An effective sales strategy requires a leader who respects operations and enablement and advocates for investment on their behalf. Consider how well you know your operations team, and how well you communicate with one another. Have you set a culture of integration and learning in your organization? If not, it may be time to work on opening that communication line.

If you need clarity on what initiatives to prioritize in order to generate outbound success, book a free assessment call with us!

Advice for outbound sales managers 

For sales managers, Art recommends taking an inventory of all meetings and cadences and then classifying each as focused on leading or lagging indicators. If the majority of your meetings are focused on lagging indicators or retrospective reviews, the outcome has already occurred. There’s no way to alter it.

Instead, focus on coaching in real-time, while there’s still a chance to affect the outcome. Give your team insight on their performance that they can implement right away. Be ready to give meaningful, actionable instructions and coach them through it. And if you’re not ready to coach them on that subject, eliminate the meeting completely.

Streamlining the outbound sales process with technology

The best way to identify holes in your process is to evaluate the buyer’s journey as a customer moves through the organization. How do they move through each stage, who is engaging with them when, and how many tools are you asking them to move across?

Think about the tools your salespeople work out of (ie. Salesforce, CRMs), and how you could simplify that process. The next time you feel the urge to ask for new tools, instead speak to your operations team in terms of capabilities; explain what functional gap you need to fill, and let the operations team find the best tool.

Revenue and operations leaders need to set clear responsibilities and communication expectations to avoid any potential misunderstandings. The key to integrating new technology is to operate as a team, even across several different disciplines. 

Overcoming hesitations around new technology

Many outbound sales leaders may believe that because they didn’t need a certain tool in the past, they won’t need it in the future. Art argues that technology only improves the sales process. 

If you’re asking your outbound sales team to perform repetitive tasks like data entry, you’re robbing them of time to perform revenue-generating tasks. Adding technology to the sales process gets reps out of the busy work and lets them focus on selling. 

And while enablement tools can’t make a sales call, they can help reps better prioritize; for example, by flagging opportunities, the rep may have missed or creating a list of accounts to target next quarter.

For those that are still resistant to new tools, consider how it would look if a marketing leader refused to adopt data-driven practices. That person likely wouldn’t be hired, because technology has become so intrinsic to success. We’ve set a much higher bar for marketers, and it’s time outbound sales did the same.

The future of outbound sales

Relationships and customer experience have become the core of business success. Outbound sales, marketing, and customer success all need to work together because ultimately the entire company exists to serve the customer.

This is why both Art and another recent podcast guest, Leah Chaney, predict that customer success will soon take the lead in revenue generation. To succeed in this new era, outbound sales leaders need to think holistically about the customer journey and keep pace with the digital transformation around them.

If you want to connect with Art to learn more about digital transformation, reach out via email art@people.ai or visit people.ai.



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The tips in this book will help you navigate a better outbound process, one that focuses on human connection over quotas. Because ironically, focusing on your prospect instead of the sale will make you a more successful sales rep.

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