Key Takeaways from Building Winning Sales Teams Podcast

In our final episode of Talk of the Trade of 2021, we sat down with Challenger’s Jennifer Allen and Michael Randazzo to discuss hiring and retaining sales talent in 2022. The supersized episode covers a lot of ground, including why hiring is tough, what to look for when building a sales team, and ideas for keeping your sales people at your organization. Here are a few of the key takeaways:

Hiring for Sales Will Only Get More Difficult

Since Allen and Randazzo are sales practitioners as well as hosts of the Winning the Challenger Sale podcast, they have unique vantage points on the state of the industry. In his role, Randazzo keeps his pulse on sales research, which is how he knows that hiring for sales people – any sales role – is harder than it has been in a long time, and it is only getting worse.

For example, a recent study from Xactly revealed that 44% of sales reps plan on leaving their jobs in the next 24 months. Compounded with the cost of hiring someone new, the average time it takes to hire someone, and the average six months it takes to ramp a salesperson to full performance, it is clear that sales labor is going to be in short supply and that it will cost businesses real money.

What Sales Reps Want from Employers

With salespeople in such short supply, they have more power than ever to choose where they work. Allen sees this as an opportunity for the entire sales function to reprioritize and become more efficient. In particular, she and Randazzo see sales reps valuing new criteria over compensation:

Hybrid Work Environments

2020 proved to the corporate world that remote work is possible, and many reps discovered they work better from home. That said, Allen and Randazzo were fresh off an in-person team sales training that left them newly energized and inspired. They recommend employers find a way to offer a flexible balance: let the sales rep choose the day-to-day environment that works for them, but also plan for regular in-person summits that remind everyone they are part of a team larger than themselves.

More Respect

Too often, sales management devolves into measuring performance based on activities, rather than results. Allen says sales reps are likely to go to employers who treat them like valued adults who are trusted to get their jobs done. Even for entry-level sales development roles, Allen sees individuals as more successful when they are given the latitude to learn how to sell without being “mandated” to make a certain number of dials. 

Career Development and Support

Ultimately, the current generation of sales reps yearn for career development and support just as much as they value compensation. They want to join companies who are invested in developing their skills, who proactively support growth, and who make it clear the current sales role is not the final destination. That includes investing in sales technology so that each seller can spend their time selling, offering training opportunities, and allowing reps to get their feet wet in new roles when they express interest. 

Why Sales People Stay

Almost as difficult as hiring new sales people is retaining the reps currently on your team – especially the high performers. As Randazzo pointed out, it simply isn’t human nature for an employee to tell you they are thinking of leaving with enough time for you to course-correct, which means you need to start strategizing to keep your talent now, before they hand in their two-weeks’ notice. Randazzo and Allen have a few ideas on how you can do that:

Commit to Your Sales Team’s Development

Since sales reps desire career development, the more resources you can offer them, the better. On an individual level, make sure their managers are coaching them regularly on building skills. Offer mentorship opportunities across the organization. Invest in training, too, especially training that is personalized to each rep’s strengths and weaknesses. 

Offer Flexibility 

More than ever, sales practitioners desire flexibility in their day-to-days and in their careers. Allow them to select the work environment that works best for them, whether that is in your corporate headquarters or their basement. Give them opportunities to try out new roles, too, so that they can envision a future with your organization, whether it is part of the traditional sales career path or charting a new route. The more flexibility you can offer, the more likely it is you can keep talent on your team.

Give a Clear Line of Sight for Career Paths

Your sales team members want to know that their current role is not their final career destination. While they need to succeed in the job they were hired for, it is important that you give them a line of sight on where they can go from here. That could include exposing them to different parts of the business and discussing the skills needed to work on each team. Randazzo also suggests allowing reps to try out parts of a new role, so that the rep can recognize what the potential new job would entail. For example, allowing an SDR to lead a demo call will demonstrate that you are committed to helping them step into an Account Executive role, while at the same time illuminating for the rep what skills they might still need to develop in order to be successful.