Mainsail's Best Practices Webinar Series

Tips for Launching an Innovative Sales Organization

Matt Buckley By: Matt Buckley  |  February 25, 2019

From Mainsail's Sales Leadership Webinar

In a recent webinar, Mainsail Partners welcomed Lou Shipley, CEO of Black Duck Software, to discuss innovation in sales. Drawing from lessons learned in his own career, Lou talked about how building a technology stack, reorganizing a sales team, and investing in sales enablement can help drive sales.

Here are Mainsail’s primary take-aways from Lou’s webinar:

Ditch the Old Sales Model—Launch a Plane

Of all of Lou’s suggestions, the one that really turned heads was his concept for a new sales organization framework called the “Plane Model.” The concept is that every “Plane” is a unit of four individuals, each with a unique role, working together toward a quota. Planes can be organized by territory or by target-market.

On board each Plane there is a:

Pilot:            Closes larger deals; manages the team
Co-pilot:      Closes smaller deals; works closely with the Gunner
Gunner:       Outbound BDR
Navigator:   Inbound BDR

One benefit of the Plane model is that it creates a natural promotion path for your employees. You can hire someone right out of college, put them into “Flight School,” (what Black Duck calls their sales training program) and move them up the system. If they don’t move up, move them out. And if they move all the way up, they can be promoted to a “Wing Commander,” overseeing multiple Planes.

Furthermore, the Plane Model makes it easier to scale your company. Your Co-Pilots are already on a path to become Pilots and your single plane can easily expand into a fleet. Because everyone on your team went through the same training program and uses the same process, your company has a unique vernacular that will allow you to communicate efficiently as you grow.

Not Everyone Can Go to Flight School — Vet Carefully

The Plane Model will help you scale quickly, so you will need to be equipped to hire quickly. Look to support your hiring process with behavioral assessment tools, such as the Predictive Index to vet applicants for the core competencies they’ll need to succeed in your organization. When making sales hires, find people with a growth mindset who aren’t too stuck in their ways and who are excited to adopt your company’s systems and processes.

Focus on attracting the right people to your entry-level positions so you can train them in your company’s language. By starting early, you will build company loyalty, avoid recruiting fees and generate a constantly refreshed field of up-and-coming leaders.

By starting early, you will build company loyalty, avoid recruiting fees and generate a constantly refreshed field of up-and-coming leaders.

Beyond Sales Training — Invest in Sales Enablement

Another important concept that Lou discussed was the role of the Sales Enablement function. This individual or team serves as a conduit between Sales, Marketing, Product/Engineering and senior leadership. They own Sales training and onboarding and are also expected to be highly conversant in the product and its correlating marketing efforts.

On a day-to-day basis, the Sales Enablement team should sit on the same floor as your sales reps so they can be deeply embedded in the Sales team and culture.

Sales Enablement is the great connector in a business and capable of delivering unique value. Because they sit on the Sales floor, Sales Enablement should be able to close deals. And because they’re closing deals, they will be able to generate battle-tested Sales training content.

It won’t take long for this position to pay for itself, but to measure progress and success, hold the sales enablement function directly responsible for ramp time and the number of reps on your team that are achieving or exceeding quota.

Define Your Opportunity Funnel & Align your Sales & Marketing Teams

One of the most common downfalls in a sales organization is a lack of clarity when it comes to defining and measuring the sales funnel. To avoid this, work on tightly defining your sales funnel and closely measure the conversion rate between each stage. Enforce strict criterion for every stage and work aggressively to move deals through the funnel, or out. (Remember, it’s just as important to move a deal forward as it is to recognize it’s going nowhere).

One of the most common downfalls in a sales organization is a lack of clarity when it comes to defining and measuring the sales funnel.

You can also strengthen your opportunity funnel by better aligning your Sales and Marketing teams. Rather than compensating Marketing based on Marketing-Qualified Leads, compensate them based on Sales closing deals.

By tightly defining your funnel and aligning your Sales and Marketing, you can discover improved forecast accuracy and sales velocity.

Invest in Sales Operations & a Sales Technology Stack

On the path from $10M to $50M+ in revenue, CRM and marketing automation platforms alone aren’t enough to support your team. Avoid falling into this trap by carefully investing in sales technology that will set your team up for success. This can include sales acceleration tools, sales training and gamification, proposal and quote management, marketing attribution and quota and compensation plan management solutions.

Building this stack might seem like a large investment up front, but over time, these tools will help your team close sales by equipping them with accurate data and measurable milestones. Most importantly, support this investment in technology with a strong sales operations function that can own the implementation, training and ongoing management and utilization of these tools.

Innovate and Iterate—Make it Work for You

Lou’s concepts of building a sophisticated technology stack, organizing your sales team into Planes and building out a Sales Enablement team are by no means one-size-fits-all. After all, we recognize that no two sales expansion journeys are the same. The important take-away here is to invest in your sales team and push for innovation. Then, iterate. Build strong processes and be rigid in your evaluation. Create the sales organization that works for you.


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Matt Buckley
Matt is a Marketing Director at Mainsail Partners. He works with Mainsail’s portfolio companies to implement marketing and sales technology to fuel growth.
More by Matt Buckley
Lou Shipley
Lou is an enterprise software executive with more than 25 years of experience. He is an entrepreneur, sales innovator, technology business writer and commentator.
More about Lou Shipley
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