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August 30, 2021

Sales Leadership Tips From a Veteran


Here at Norwest, we are committed to providing our portfolio companies with the tools to grow and succeed. True to that commitment, we are always willing to share advice, lessons, and insights from our own experiences. Many of our founders have also become great resources. As a general partner here at Norwest, I can say that very few things are as valuable to the growth mission as sales excellence driven by committed and experienced sales leaders.

Recently, I had the pleasure of sitting down with the highly experienced Neil Hudspith to get his take on what outstanding sales leadership looks like. Neil is a titan when it comes to sales excellence and human capital management. He was Docusign’s president of worldwide field operations and currently serves as an advisor there. Neil was also president of human capital management for Oracle. Having led such complex yet highly effective sales organizations, Neil is an absolute goldmine of good advice.

I encourage you to watch our entire conversation by following the link at the end of this blog. In the meantime, here were some of the highlights.


Founders Can Only Manage Sales Reps in the Early Days

Excellent sales leadership, says Neil, has become more crucial than ever. Why? Because today’s markets have grown hyper-competitive. Markets have always been fierce, but the added pressures of ever-quickening globalization and the pandemic mean things are more fierce than ever.

There’s also the unusual volume of venture investments. This presses companies further to generate sales and secure cash flow as disruptors enter virtually every vertical. According to Crunchbase, $125 billion was invested in venture-backed companies in Q1 of 2021. That figure represents a massive 94% year-over-year growth from Q1 of 2020. Whether playing catch up or trying to stay ahead, capitalizing on this growth means constantly pursuing excellent sales leadership.

I asked Neil: When is the best time to get a sales leader? And then when is the perfect time to scale talent? He responded with,

“A founder should initially manage a couple of sales reps with proven startup credentials. These reps should be experts in the startup world rather than necessarily domain. Then, when getting a little bit bigger, you need to start thinking about a sales manager coming on board. I think when you start scaling beyond three, and you start looking at three to ten, three to twelve, then you start needing to look at a sales manager that can manage a department.”

Neil, however, warned against being too aggressive. Getting a senior sales leader should be a priority only when the scale of the business and responsibilities grow. Hiring a senior sales leader too early could be a recipe for misalignment.

Validate the Customer’s Voice

Here’s something you probably already know: Happy and satisfied customers are critical to increasing upsell. This is why companies invest so much in delivering positive experiences. But customer experience is not enough. According to research by Adweek and Accenture Interactive, approximately 80% of brands believe they offer a superior customer experience, yet only 8% of their customers agree. Neil believes that salespeople are really in the best position to capture the authentic voice of the customer. Their insights are helpful in validating products and services in addition to meeting customer needs and expectations.

“The salespeople coming on are valuable partly because they help you get the voice of the customer on the validity of the product, or what’s needed… If we’re amplifying voices, we’re finding out more of what the customer thinks of us, which enables us to meet more needs of the customer, which leads to revenue.”

Good sales leaders are aware that their sales team can act as a customer feedback arm. Salespeople help us fill the blanks and complete the sales picture. A good sales leader must always maximize this information channel.


Always Align with Marketing

Sales and marketing are two different things, but they are intertwined and equally important. We also know that companies can close more deals when sales and marketing strategies and goals are aligned. So, which comes first in terms of priority? Sales or marketing? Or should they be weighed equally?  Neil says, “If you can get a sales leader who’s also a marketing leader, go ahead. But if it comes down to a choice between the two, choose sales. Sales first is more pragmatic. Because before you do all of that, you get the knowledge that you get from the customer.” By bringing in salespeople first, you empower your business to know more about your customers. They acquire information that is crucial to driving sales for your business. Then, when it’s time to add marketing, you already have a wealth of insights and knowledge. You can reverse-engineer your tactics from there.


Sales Must Love Data

If you are looking for top-class sales leadership, Neil recommends candidates that love to work with data. A true sales leader, according to him, is someone who “truly loves and understands how to utilize the data.” There is no doubt about how powerful data is in driving sales. Neil is among those who have always relied on data to forecast business trends. He says, “When you’re in a corner, all you can do is execute. But the big thing for me was, could I reliably forecast one quarter out, then two quarters out, then three quarters out? If you’re using the data in the right way, you can.”


Red Flags When Hiring Sales Leaders

It’s common knowledge that hiring sales executives and leaders is not easy. There’s a lot of vetting, validating, and interviews before a hiring decision can be confidently made. So I asked Neil for pointers on what to look out for when hiring a sales executive or leader. “Company hoppers,” says Neil, raise a lot of red flags.  “I can take somebody giving me an explanation that the company just didn’t go anywhere. But when I’ve heard that 14 times from a candidate, you probably have a red flag there.” He also says “horn tooters” – candidates who only talk about how good they are questionable. “Anybody willing to be a little bit broader is a better bet than somebody that only wants to talk about how good they are.”


Success Should Be Rewarded

Its commonly accepted that employees perform better when they are fairly rewarded and recognized. Neil also makes it abundantly clear that the reward for salespeople should always be earned and commensurate with the results and whether they meet targets. But what if they go beyond target? Neil also believes in paying accelerators for people that overachieve targets. He says, “while you don’t want to pay below 80% attainment, it’s important to pay for overachievement.”

Watch the entire conversation here.

Thanks to Neil for sitting down with me to share his wisdom. In just one hour, he provided all our attendees with a wealth of valuable insights that can be used to achieve excellent sales leadership within any growing organization.