5 Ways to Win the War for Talent in Enterprise Sales

Kassidy Bird

In a recent roundtable discussion, we asked sales execs from leading global companies about their biggest obstacles in securing and retaining top enterprise sales talent. Here’s what we learned.

  • Salary expectations are higher than ever.
    Thanks to the pandemic, today’s workers are rethinking the value of their time and effort. Even college grads with minimal experience are asking for large increases in base pay.
  • Bottlenecks in the hiring process can be costly.
    Competition for enterprise sales talent is fierce in the wake of the Great Resignation. If your hiring process is too slow or complex, applicants will likely accept other offers.
  • Strong candidates are in short supply.
    As value selling becomes a vital approach to enterprise sales, qualified candidates are harder to come by—not just because of competition, but because traditional skill sets for sales reps have shifted. This is particularly true in industries that demand complex technical expertise.
  • Business acumen is imperative.
    Sales organizations are eager to get their teams reacquainted with the human experience in sales, as opposed to virtual. But many reps don’t feel prepared to speak fluently about specific use cases, metrics, and value—especially at the executive level.
  • It’s not “just a job” anymore.
    Candidates and employees alike are craving more meaningful purpose in their day-to-day work lives. Workers want employers who will support their development both personally and professionally.

How can you reshape hiring and retention strategies for enterprise sales talent?

1) Focus on building a team of value sellers.

  • Look for the right characteristics when hiring. Sales leaders in our roundtable said some innate qualities of top value sellers just can’t be taught—things like confidence, curiosity, resilience, and grace under pressure.
  • Shift to a customer mindset, so reps are prepared to tell a story that resonates with business value—not just talk about features and functions.
  • Be sure reps are fluent in the specific pain points and requirements of their target industries. You can’t deliver value if you can’t speak the language.

2) When candidates are in short supply, look inside the box.

  • Not all great enterprise sales talent is recruited externally. In fact, relying solely on external hires can waste valuable time and money. Instead, try asking your top performers for referrals. They’ll know what it takes to do the job well.
  • Don’t be shy about hiring and promoting internally. If the built-in qualities are there, almost everything else can be taught. Some sales leaders told us they’re training telemarketers into sales reps!
  • You can even consider hiring from your customer evangelists; after all, they’re familiar with your offerings, and they can speak to the value from a professional level.

3) Compensate in a way that’s both financially and personally rewarding.

  • High salary requests don’t have to be answered in cash alone. Create compensation packages that align to employee goals, so employees have a stake in succeeding.
  • Think beyond the basics. President’s Club is nice, but consider adding long-term incentives that increase retention—like equity, growth opportunities, advanced learning, profit sharing, and personal autonomy.
  • Nonprofit and community commitments matter tremendously to the younger generations. Include opportunities for employees to share their successes through corporate donations to charities of their choice.

4) Show candidates you set them up for success from day one.

  • We can’t stress this enough: Set realistic quotas. Sales leaders told us repeatedly that stress over demanding quota expectations scares workers away. No one wants a job, or will stay at a job, where success seems unreachable.
  • Ongoing, elite-level training is a must for today's enterprise sales talent. Candidates and employees want to learn the skills that position them for the hard, often uncomfortable, work of value selling. Offer courses that boost knowledge in business financials, technical platforms, industry requirements, and more.
  • Tailor sales training to the needs of sales people. Try engaging approaches like gamification, and be sure it’s so ingrained in the company culture that even the C-suite participates.

"People in sales organizations don't like to be trained. That's a fact. So we have to find a way to make that either quicker or more pleasant for them."

Director of Global Sales Operations, Global Medical Technology Company

5) Remember work/life balance.

  • Talk to candidates and employees about their “why” factors. Why do they want to work for you? Why are they in sales? Make the workplace an integrated part of an employee’s life journey.
  • Make sure your exec team walks the walk. When CEOs practice the same values they preach, it resonates deeply and strengthens employee satisfaction.
  • Of course, Paid Time Off (PTO) is vital to a fresh mind. Make sure your sales team has ample time to rest. Some companies are trying cool new approaches to increasing PTO, like offering Fridays off all summer.

Catching—and keeping—the best enterprise sales talent can definitely be a tricky endeavor, particularly given today’s tight candidate pool. With the right tactics and solutions in place, you can improve your hiring leverage while positioning your team for maximum performance day after day. Keep your finger on the pulse with what the most talented salespeople want by joining the Strategic Sales Network, the exclusive community for enterprise sellers.

About the Author
  • Kassidy Bird

    Kassidy is Vice President of Marketing at Databook, with over a decade of experience successfully scaling enterprise SaaS businesses across retail, supply chain, and digital experience. She is passionate about helping the world’s largest brands improve their customer experiences. Kassidy holds a Bachelor’s Degree in Business from the University of Southern California.

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