How Sales Got So Complicated (And What to Do About It)

Dave Koslow
COO, DocSend



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[Editor's note: Thanks to DocSend for being a silver sponsor and supporting this year's EXCEED! Please enjoy this insightful guest blog post by DocSend's Co-Founder and COO.]

Sales isn't just about closing deals.

If you're a sales leader, it's about making the most of your resources and thinking long-term about strategic growth.

If you're a rep, it's about tuning out distractions and following up with the right accounts at the right time.

And if you're a sales operations professional, it's about making it easier for everyone to do their jobs more efficiently. But as I've learned first-hand while scaling the sales organization at the company I co-founded, DocSend, that process is a significant undertaking.


Because sales has grown incredibly complex. And not just because the products we're selling have changed, but because there are so many new demands on a seller's time. So many new sources of data and information they're required to make sense of and act on in order to be successful.

To put it simply, sellers have so much information coming in at all times that it's difficult to do the very thing they're hired to do: sell.

Driven to Distraction

The growing complexity of the sales process should force sales leaders and operations professionals to train a critical eye on selling activities. With new requirements for success and increasing demands on their time and attention span, sellers may have less time carved out to sell than one might think. According to David Brock, CEO of Partners in EXCELLENCE and author of Sales Manager Survival Guide: Lessons from Sales' Front Lines, selling may only take up as little as 12-22% of their day. In an examination of the root causes of this inefficiency, Brock acknowledges the usual culprits like mobile devices and endless app notifications. But as he pointed out at a recent talk given at Clari's EXCEED conference, there's something else that's stealing the seller's productivity, but it's far more subtle: organizational complexity.

What exactly is "organizational complexity?"

Put simply, it's the degree to which your people, programs, and processes help your sales team succeed. If your organization grows too complex in any of these three areas, you might find your team gazing inward, focusing on processes instead of keeping prospects and customers front and center. The result: overall sales team slowdown and dramatically stunted revenue growth.

So, what's a sales leader or operations professional to do?

Getting Your Sales Team (Re)Focused

Sales operations professionals are in the best position to simplify the everyday activities involved in the sales process. However, it shouldn't be the responsibility of sales ops alone. Your entire organization should make a commitment to enabling sales and reducing organizational complexity across the board. Based off of Brock's talk at EXCEED, here's what it takes to turn the ship around:

Measure how much time your reps have for selling.

You might think you know how your sales reps spend their day, but if they're underperforming, it's absolutely worth a second look. Brock recommends following people around with a stop watch or asking them to voluntarily track their time. As he points out, you don't need decimal-point accuracy—just order of magnitude.

Simplify workflows, communication, and processes.

Sales operations professionals need to make it easy for sales reps to complete routine, daily tasks. For example, if sellers are spending 10-20 minutes every day searching for the right information or content to send to prospects, that adds up each week. Anytime you're asking them to jump out of their workflow and into a related task, they risk losing momentum on the objective at hand. As a result, it's crucial to help your sellers get what they need right away, whether it's the right content to send out or more competitive info about a target. Similarly, if there's a broken feedback loop in place between sales and marketing that requires marketing to routinely waltz onto the sales floor for feedback drive-bys, it's worth exploring other ways to close that feedback loop that don't involve golden hour interruptions. The more you can do to keep them in their primary workflow, the more productive they'll be.

"De-layer" your sales process.

As Brock points out, most organizations simply layer on new programs and initiatives before they evaluate the performance of the last one. And that's an efficiency-killing error. Instead, Brock urges sales ops leaders to identify which program you'll eliminate before adding another layer on top.

It's Not "Always Be Closing"—It's "Always Be Learning"

One of the key pieces of advice Brock had at EXCEED centered on the importance of learning. Far too often in sales organizations, we're moving so fast that we forget to take a step back and evaluate how well our current systems align with our future goals. We need to ask ourselves if the status quo is working for our sellers and our organization and if there are ways to simplify organizational complexity. As a former software engineer and as a co-founder of a growing startup, embracing Brock's iterative approach to sales was a huge takeaway during the EXCEED conference and one that has already informed the way I'm leading sellers at DocSend. To put it simply, it's not just about closing, but about making it as easy as possible for sellers to put prospects and customers first.

Note About the Author

Dave Koslow is Co-Founder and COO of DocSend, a content management and tracking solution that helps sales teams find and send the documents that drive sales processes forward.