Case Study: Growing Your Sales Organization Beyond The Deal

By David Mizne

Sales teams are the lifeblood of every company that has reached a certain stage in their growth trajectory. Whether sales are stagnant or growing, many leaders of sales teams face the same challenges – they need to understand why their methodologies worked or didn’t work, so that insights and learnings can be shared throughout.

In either of these scenarios, the sales organization needs a solution to navigate through underperformance or growing pains. Sales managers need to understand where things get stuck in the sales process, so that they can provide their teams with the skills and training necessary to close deals. In the following case study, you will learn how a high-growth company uses a software solution to respond to these challenges.

Growing Beyond the Deal

The ability to ask pointed questions, gather information, consolidate learnings, and coach individual sales reps is incredibly valuable; yet difficult. Unfortunately, for many growing teams with first-time managers, they are underprepared to coach and develop their sales reps. But when done right, talent development translates to more revenue, lower attrition, and a better culture that attracts more A-players.

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Most sales people measure their careers by how many deals they get done or how many quarters they made quota. But some employees eventually want to develop their careers by managing people. They may have been amazing sales reps, but they lack management training. Without development opportunities, many sales reps begin looking for work elsewhere.

Focusing on Talent Development

Turnover is a major issue for sales teams. A survey by The Bridge Group and For Entrepreneurs of 342 B2B SaaS companies, found the average turnover rate for sales reps is now 34%, the majority of which is involuntary.

The same research suggests that one in ten companies experiences turnover rates above 55%. And research by Glassdoor indicates that of 1,000 salespeople surveyed across industries, more than 68% plan to look for a new job in the next year, and 45% plan to look in the next three months.

Career advancement is an important factor to keep your best people. Successful companies will create frameworks so that employees can be promoted to management and leadership roles. To do this, it calls for better coaching from managers and a focus on talent development throughout the organization.

WePay is a rapidly growing company that has made the Inc. 500 List for the past two years. They are the leading payments provider focused solely on meeting the needs of online platforms that need to settle money between their users.

Founded in 2008, WePay provides everything an online marketplace or cloud software provider needs to provide integrated payments from within their app while maintaining trust and safety. This includes not just credit card processing, but also complete solutions for managing fraud risk, regulatory compliance, and customer support provided at no extra cost.

Common Sales Challenges

Kurt Bilafer, Chief Revenue Officer at WePay, sought a way to capture tribal knowledge stored in the minds of employees and convert it into institutional knowledge. WePay also had some issues around sales enablement and needed to understand where things were getting stuck in the sales process. Over the 20+ months since Kurt has been leading sales, the company grew from 65 to over 200 people.

Kurt has run sales teams for over two decades, and has used the 5-15 methodology since 2003 as a great way to check in with employees on what’s holding them back or going well instead of just focusing on the tactics of a particular deal.

Individual contributors use the 5-15 process to recap the good and the bad of each workweek. That information cascades up as managers summarize the feedback from individual contributors within minutes. For example, responses to “what are you hearing about our competition?” then get passed up to the CEO.

The old way of managing a sales team was to do a deal-review each week. After an hour of walking through all of the deals, managers would spend only several minutes actually coaching or guiding them. The questions asked outside of the deal-review were not standard or consistent across the team.

The Solution

Kurt now uses 15Five, an automated version of the 5-15 methodology to manage at the deal level also. Every week his sales-people provide details about what’s happening in their particular deals.

Additionally, he is provided detail on overall trends, obstacles, and cross functional wins, as well as highlighting the professional development of team members. With this feedback, Kurt can pinpoint where he needs to allocate more of his coaching time to efficiently influence specific deals.

Kurt sets consistent questions across the group and sees the common themes of what’s going on. For example, his SDRs are capturing all of the biggest objections that they receive early in the sales cycle. 15Five was able to help isolate several different themes that the marketing team then used to develop new sales materials.

One of the most impactful benefits of using 15Five is the ability to quickly see where people are off course and realign the team. With the channel of open and transparent communication the app provides, Kurt spends less time on status updates and more time focused on coaching and maximizing talent.

The deceivingly simple practice of asking questions allows employees to engage in much needed reflection. Managers can respond with support, essentially becoming coaches that bring out the best in their people. Sales managers in particular can quickly help individual reps improve, so that they can achieve their quotas while elevating their team culture. And all this translates to longer tenure at the company for top employees.

David Mizne is Content Manager at 15Five, a lightweight weekly check-in that delivers a full suite of integrated tools – including continuous employee feedback, OKRs, pulse surveys, and peer recognition. David interviews thought leaders & writes on trends in employee performance management. Follow him @davidmizne.

Image Credit: Duncan Hull 


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