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Sales VPs are having trouble sleeping.

Throughout the year, many sales leaders found themselves tossing and turning at all hours of the night. And it wasn’t because their companies were struggling. No, most of the sales leaders we talked to head up companies that had successful 2014’s by almost any measure. One of them even filed to go public this year, with a $100 million IPO!

So what was the cause of their insomnia?

On the one hand, this is just how sales leaders have to be wired – they’re always looking back and looking forward, thinking holistically while operating granularly, and never resting on their laurels.

Digging deeper, we wanted to find out what some of the most prevalent top-of-mind issues were that prevented these sales leaders from getting a good night’s sleep. And we didn’t just mean, “Hitting our number” – of course every sales leader worries about that! But we wanted to really pinpoint some of the most common concerns.

Without further ado, here’s what kept these 10 Sales VPs and leaders up at night in 2014!

The Most Common Thread – People

As a Sales VP, you’re working for your people – it’s my job to put the salesperson first.”

- Nick Frank, Mojo Motors

While Sales VPs might not sleep very well, the sales reps they oversee undoubtedly sleep much better. That is the Burden of the Leader, to suffer so that their reps don’t have to. Unsurprisingly, the most common thread keeping these 10 sales leaders up at night was worrying about the people they manage.

This covered several different areas. For starters, even bringing in the best sales talent proved to be a great challenge, as Glenn Gaudet, the President & Founder at GaggleAMP, found out.

“One of the hardest things is just finding great talent, not just with us but with almost every emerging tech company,” Gaudet lamented. “If you look at what colleges are putting out for people, how many people actually get a degree in sales? A lot of times, the quality isn’t there [for inexperienced sales recruits] and you have to backfill with a lot of training.”

Mark Roberge, the Chief Revenue Officer at HubSpot agreed on the challenge of hiring. “The hiring we do today will accelerate revenue growth in a few months,” said Roberge. “Are we keeping the quality bar high on these hires? The people we are developing today will be our future managers.”

But it’s not just about hiring, bringing in fully-developed sales reps who are ready to hit the ground running from day 1 – if that were the case, the role of the Sales VP would be much easier. No, as we found out from talking to these leaders, another top challenge centered around one of the buzziest sales catchphrases in 2014:

The Emergence of Sales Enablement

As Anthony Zhang, the Director of Sales at SalesLoft, posited, sales leaders are always asking themselves, “How do I arm my sales reps with the intel, talking points and resources they need to be successful? What type of arsenal do they need?”

No sales rep comes into your organization as a fully formed selling machine. They need training, coaching, and access to the right resources in order to be successful at their jobs. That is all on the sales leader to provide. And the faster they provide this, the quicker both the individual rep and your organization will see true value.

“It’s all about time-to-productivity [for new sales reps] and, indeed, productivity,” said Steve McKenzie, VP of Sales at InsightSquared. “In this hyper-growth phase of our business, it’s critical to get the right people in the right roles and empowering them to be the best versions of themselves they can be, as soon as possible. If we can make time-to-productivity quicker, we’ll smash it out of the park.”

“As a Sales VP, you’re working for your people – it’s my job to put my salespeople first,” Nick Frank, the VP of Sales at Mojo Motors, agreed. “The role of the leadership team is to put salespeople in a position to be successful. You don’t necessarily hit your goal every single month, but you want to put guys into a position to hit their goals.”

Am I sufficiently connected to the frontline salespeople? I am paranoid about missing signals for optimization and development.”

- Matt Cameron, Scripted

Sales enablement can cover a wide swathe of different tools and processes. At the very basic level, you want to make sure reps have the skills to handle the demands of their position, be it prospecting, qualifying or closing. They need the right tools for the job. They need talk tracks that have proven to be effective. They need access to leads and a robust pipeline of opportunities. If any of these aforementioned requirements are missing, it’s on Sales VPs like Jim McDonough of Attend.com to get to work and provide the necessary enablement tools.

“When you are building a sales organization at a startup, there are many things that keep you up at night – most recently [for us] it has been sales enablement,” said McDonough. “How do we produce enough quality content that my team can provide to our prospects at the right time during their buyer journey? I am currently building a buyer’s map with our buyer personas to help us with this process.”

Learn More About Sales Enablement»

That type of in-the-trenches granularity is absolutely key for Sales VPs – if you see a problem, it’s on you to find the solution, even if you have to build it out with your bare hands. The problem, of course, is that it’s not always so easy to see the problem, especially as a Sales VP who isn’t selling alongside their reps, a concern that Matt Cameron, VP of Sales at Scripted.com, shares.

“Aside from hiring velocity, one of my primary concerns is whether I am sufficiently connected to the frontline salespeople to ensure they are maximizing the opportunity for the company and for themselves,” said Cameron. “I think about my organization as a sales academy that develops world-class professionals – I am paranoid about missing signals for optimization and development.”

The Power to Look Ahead

Beyond worrying about the present, and all the issues that today brings, sales leaders also have to keep a worried eye on the future at all times. Even when dealing with the development of the people they have in their organizations today, Sales VPs like Bridget Gleason of Yesware are still looking forward.

“I want to make sure people on my team are continually learning, being challenged and getting promotions within the company so that they stay with Yesware for a long time,” said Gleason.

In the VP seat, it’s really important to be looking ahead 6 months. Oftentimes, by the time issues surface, it is usually too late to recover.”

- Mark Roberge, HubSpot

Unfortunately, not all forward-looking concerns have to do with the happy outcome of promoting and keeping your team together. In fact, most glimpses into the future for Sales VPs are concerning ones – how can we be as successful, if not more, in the upcoming years as we are today?

“Ultimately, sales management is a balance of short-term and long-term goals,” said Shane Cough, VP of Worldwide Sales at OpFocus, Inc. “Are we set up to succeed now and over time? Are our organization structure, sales process, resources and packaging built to scale to meet longer-term company goals?”

Unfortunately, sales leaders don’t have the power to really look into the future (yet). At the highest level of sales management, there is an overriding concern that everything you do might be too late, that you’re ultimately reacting to situations and acting accordingly, rather than being proactive. That strive to get ahead of your problems is ultimately what drives sales leaders like Randy Frisch, the Chief Operating Officer at Uberflip.

“My scariest night-time fear is waiting for an email to come in from a customer that is not happy,” said Frisch. When that email comes, it typically means we’re too late. When we welcome a new customer or see a great case study, we all high-five, but when we hear about a customer not succeeding and considering churn, it’s often too late.”

This is a terrifying concern that Roberge has experienced himself, and certainly agrees with.

“What keeps me up at night is not seeing an issue early enough,” said Roberge. “In the VP seat, it is really important to be looking ahead 6 months. Often times, by the time issues surface, it is usually too late to recover.”

“It is hard to look that far ahead. But it is necessary and absolutely critical to get it right.”

None of these concerns – finding the right people in the right roles, enabling your direct reports to succeed and always be looking ahead to anticipate potential pitfalls – are likely to vanish in 2015, meaning these 10 sales leaders are likely in for another year of restless sleep. However, if all that restlessness and worrying leads to them acting proactively, putting in the right measures and helping their reps and teams succeed, these 10 sales leaders would gladly take that insomnia every single night.

Welcome to the sleepless life of a sales leader.

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