3 Surprising Operational Lessons from High-Growth Sales Leaders

One of the things I love doing is hosting sales leadership meetups. It’s a chance to connect with peers, trade stories about the challenges and opportunities we’re seeing in our sales operations, and bounce ideas and perspectives off each other in an effort to improve.

During a dinner with 20 such leaders, three amazingly consistent themes emerged when it came to operational metrics, recruiting, and key factors influencing their technology purchasing decisions.

1. Optimize sales cycle efficiency for both wins AND losses

Many sales leaders are focused on improving the efficiency of their operation in terms of securing new business. That is, analyzing each stage of the sales and customer buying process to determine which steps are generating the most friction so that that friction can be reduced. But some leaders are taking a counterintuitive but highly insightful approach to analyze their “losing” efficiently as well. TTL or “Time to Lose” was a metric describing the efficiency with which our team loses deals. In other words, we can sell more by losing faster.

Interestingly, in my last two VP Sales roles, I uncovered a data trend that was both scary and fascinating. When I measured the amount of time we were spending in the discovery phases of our sales cycles I found we were spending three times longer doing discovery for deals that we ended up losing compared to deals we won! I also found that sales reps who were able to keep their pipeline “fresh” by moving their deals through the sales funnel faster and deading-out poor fit deals sooner had higher levels of quota attainment.

These trends are consistent with a story one of my clients shared with me after working with his company on their discovery approach. He said that during the first month after implementing the focusing strategy we covered, he deaded-out 75% of his pipeline and focused his energy on the remaining 25%. In that month he hit a whopping 304% of his quota and the trend continued into subsequent months as he maintained his focus on high potential opportunities.  The take-home message; make sure you’re losing fast, staying focused, and ensure you’re spending time on the RIGHT customers.

2. Always be recruiting but know your ideal seller profile will change over time

When I was at Salesforce our leadership team would often joke (with a strongly serious undertone) that missing your hiring target was just as bad as missing your revenue target. And with good reason. According to research from Bridge Group, typical sales rep turnover within sales organizations is about 33% annually (with 2/3 of that being involuntary) and on average a rep takes 3-6 months to ramp. In fact, the same research suggests that one in ten companies experience turnover rates above 55% and one in six reps will take over seven months to fully ramp. Of course, that means you should always be cultivating a bench of top-shelf sales reps you can call when needed, but our group identified a hidden nuance to this strategy. 

But the type of rep and skill set required to effectively drive your business forward might be different based on the stage of your company or the evolution of your product. For example, in my start-ups I would often interview sales reps with a solid foundation of skills and experience, but who lacked the entrepreneurial toolset needed to be effective in the early days of operation. In short, they would be great as the 20th sales rep on my team but not the second.

Keep in mind though, that the ideal customer profile for your business will likely change over time. For example, many B2B technology companies start out selling their solution to SMBs but later decide to pivot to large companies due to a rising cost of sale relative to the price point of their solution. While some of these less experienced SMB reps may be able to make the shift to longer, more complex sales cycles, chances are most won’t. In order to keep up with the pace of your business, you must always build a broad bench of talent for when a new skill set is required.


3. HOW You Sell Is More Important Than WHAT You Sell

As you can imagine the sales leaders in our group are also BIG purchasers of sales and marketing technologies. So you might expect that as solution-oriented sellers, the business and operational value of the solutions they purchase would be the dominant factor in their purchasing decisions. But you would be wrong! 

Almost all the sales leaders remarked that the value and fit of the technology they invest in were NOT as impactful to their own purchasing decisions as the experience with the vendor’s sales team. Yet, this isn’t surprising when you consider that Salesforce’s State of the Connected Customer report shows that 80% of customers say the buying experience a company provides is as important as its products and services. And in the complementary State of Sales report, when salespeople were asked to list factors which they felt had an extreme or substantial impact on converting a prospect to a customer, listening topped the list. Demonstrating ROI was a distant tenth.

And when it comes to buying experience, news travels fast within the community. More than one leader referenced a specific rep at a technology provider whose demeanor and approach completed turned them off and caused them to lose their business! This means that when it comes to the execution of our own sales teams, focusing on buyer experience and HOW you sell is more critical than ever (even when selling to savvy buyers).


In high-growth sales operations, sometimes the most impactful advice we get comes from peers outside of our organization. So if you’re struggling to make that next big breakthrough, consider connecting with a group of like-minded sales leaders in your local community. You may be surprised by the counterintuitive, insightful, and consistent themes you hear!

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