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Lou Shipley: How to Build a Culture of Enablement

How can the “plane” model help you develop your sales force?

What’s Sales Enablement’s role in delivering sales excellence?

What are the key traits of a great Sales Enablement manager?

On a recent episode of the Reveal podcast, we connected with investor, lecturer, and previous CEO of Black Duck Security, Lou Shipley, for answers to these and other questions that are top of mind for revenue leaders.

Here are the key takeaways and highlights from that episode.

Master Both the Product and Selling the Product

In a small company, you’ve really got to know how to do two things well. You’ve got to build the product and you’ve got to sell the product. The best companies are good at doing both of those really well. 

There are companies that are successful that may be better at product than at sales, or at sales than at developing product. But the best companies are really good at both. And take both really seriously. And take them as areas where you can continuously learn. 

And so what I did, was I went from Sales to CEO, and then I sold my company to Citrix, and then I became a product group general manager at Citrix, and got a whole different group of products to run. And that’s where I think I really learned product development, because it was a multi-product, larger company. 

So when I went back to Turbo and when I went to Black Duck, more single-product companies, I had a much better sense of how you had to build it. And then I focused on how to sell it and make it more efficient as you grow the sales team.

Sales Planes

We built what was called a plane. It had a pilot, a copilot, a gunner who was doing outbound prospecting, and a navigator who was dealing with inbound leads that marketing generated. And the way you scale that plane in a sales capacity is when it has covered its costs, covered their quota and their expenses, you launch a new plane. You take the copilot and you make him or her the new pilot. 

And we started with one and we ended up with 20. But we knew exactly where we were on our cost structure when you launched a new unit of sales capacity, a new plane.

The basic idea was the copilot, the gunner, and the navigator owned the sales-qualified lead quota. So they had a quota for leads. And the pilot was the one that was closing the larger deals. And we were doing 20, 30, 40K deals. And then if that copilot could start to close little deals, we thought he or she was good, we could launch the new plane with them running it. And then add on a gunner and a navigator, and another copilot.

Really good enablement is not just quarterly or monthly, it’s daily and weekly. And if someone’s embedded in the team, they can listen to the calls, and then do the instant training, and give the reps feedback on what’s going well, or what’s not going well, to solve their problems.

Data Breakout—Sales Enablement

There are multiple benefits to having a standardized onboarding process, but here are the three that really jumped out:

  1. Just having a standardized onboarding process leads to 54% higher productivity of new hires. 
  2. 77% of new hires who hit their first performance milestone experienced a formal onboarding process. This is especially interesting for organizations looking to shorten their time to value, or time to first deal, for sales reps.
  3. Going through an onboarding program makes an employee 69% more likely to stay with an organization for three years.

So productivity, time to value, and employee retention all start with how you onboard your new employees.

What’s the cost if you don’t onboard successfully? 2018 stats show that the average cost to replace a new hire is $3,000 to $18,000, depending on seniority.

The Value of Sales Enablement

When you think about the term sales enablement for an old-timer like me, when I went into tech back in 1990, I would have been like, “What are you talking about? What is sales enablement?” 

But you realize the power of it. What it did is it enabled us to grow our sales team but shorten the ramp time. And we actually paid for it by knowing we could take someone from six months to four months in terms of ramp time. Those are hard dollars.

Sales Enablement Metrics

The other piece of what we did at Black Dog which I think was special, was the intersection between Sales Enablement and Sales Operations. I had Sales Ops at Black Dog report to me as the CEO. I didn’t have it report to Sales. Because what I wanted was a single version of truth. I didn’t want Sales’ truth and then Marketing’s truth, and I was the referee in the middle. I needed somebody to just say, “This is the truth. These are the real conversion rates. This is really what’s happening.”

And so, when that person could identify the problems, it would just create a list of things for the Sales Enablement team to do. One of the things they would do is A/B testing on email cadences. A/B testing on, “Would this open work on a cold call? And would it work on this message that you leave?”

The culture was, “Let’s identify all the problems and solve them. And the minute you solve that one, you’re going to find 10 new ones. Let’s solve those.” And then you’re just getting more efficient. 

And it ended up, in terms of me as CEO, being able to improve my sales forecast predictability. And that’s a nice way to live. It’s no fun to make a quarter, miss a quarter, make a quarter, miss a quarter.

If you build a culture of continuous learning and celebrating failures, then I think you’re building enablement into the culture to begin with.

Key Traits of a Sales Enablement Manager

First, a natural affiliation with sales. They don’t look down their nose at it. They recognize that it’s a hard domain. You have to learn it and respect it. 

Secondly, that you’re pretty technical about the product, so that you could help diagnose a problem that a sales rep who maybe isn’t very technical could be having. So a little bit of product background, product marketing, product management. Maybe even engineering, but more likely someone who’s already been one of those pieces of the organization who does both—talks to engineering and talks to the salespeople. 

You won’t find many that have had a quota. But if they’ve earned the respect of the salespeople and understand how tough the job is, I think then it could work.

[Sales] is an area of expertise you can explore and get better at. Most people think the best salespeople are the born salespeople. What we’re talking about here with enablement is you can teach it, and get better at it through practice.

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