3 Emerging Priorities of Successful Sales Leadership

WalkMe Team
By WalkMe Team
Updated July 13, 2022

The times they are a-changin’. As the millennial generation continues to fill the workforce, sales leaders are facing a new breed of employees with entirely different expectations and goals.

Although sales organizations traditionally maintained a formal separation between leaders and team members, the younger workforce desires a closer working relationship, greater transparency, and open communication.

They want to do meaningful work and see the results of their efforts.

Today, successful sales leadership requires striking the right balance between solid mentorship and coaching while maintaining a laser focus on fulfilling business goals and meeting quotas.

Sales leadership has a direct impact on performance

Research continues to demonstrate how leadership is essential to the performance of the employees that they oversee. In a study cited by the Harvard Business Review, sales team members were asked to rate their managers and these ratings were studied in relation to their own performance.

“69% of salespeople who exceeded their annual quota rated their sales manager as excellent or above average.”

This finding shows us that the quality of sales leadership is a critical factor in determining how successful a sales rep will be. Even the most talented and driven individual is prone to failure under poor leadership.

Dive Deeper: 7 Sales Management Mistakes to Avoid

Technology has become instrumental to effective leadership

Excellent sales leadership motivates team members to grow, increase productivity, and achieve new levels of success. Technology plays a primary role in the management of this “information generation.”

Combined with a more hands-on coaching style, a wide range of sales technologies can help leaders provide the level of transparency and data that their teams desire and accommodate rising standards.

These three sales leadership priorities are essential for success in today’s distinctly “millennial” corporate culture.

Priority #1: Embrace transparency

sales leadershipThe old corporate model lauded authoritative leaders that made unilateral plans and shared very little with their team. But studies have revealed that salespeople are more motivated by their leaders when they are included in the decision-making process.

Collin Cadmus, VP of Sales at Aircall, shared his experience as a young sales executive in a high-tech company on an episode of The Sales Hacker Podcast.

Cadmus consistently receives skeptical feedback from his more traditional contemporaries who tell him that he is way too open with his team. His response? “I know. And that’s why we’re crushing it.”

His decision to share information with his team about the challenges and obstacles he faces as a sales director is definitely not the norm, and yet his team’s success speaks for itself.

Visionary sales leaders that clarify the purpose of the sales strategy and even solicit input from their team glean the benefits of more brainpower, different perspectives, and most importantly, higher engagement from their sales reps.

A team that is entrusted to collaborate, participate, and brainstorm with their manager, will be more motivated to excel and reach their goals.

A leader who isn’t afraid of transparency is also modeling openness to feedback and is leading by example. Modeling an attitude of self-reflection and openness demonstrates that there is no shame in receiving help from the team, and ultimately cultivates a culture of collaboration, shared success, and trust.


  • Create a culture that values collaboration and sharing ideas. Consider your team’s ideas and perspectives when crafting your strategy.
  • Make sure that you designate time during your team meetings to gather feedback from your sales reps.
  • Make an effort to “be yourself” with your team instead of staying strictly business. Millennials want to see that you’re not just their boss, but also a regular person.
  • Make data accessible to the team. Invite your sales reps to share their performance metrics for both successes and failures. For example, your team can review calls that led to a closed deal and a lost lead, and compare what sales techniques were at play in each.

Priority #2: Empower each team member with growth and development opportunities

sales leadershipBeyond the short-term goal of reaching quotas, today’s sales workforce places greater emphasis on continual development and growth.

Employees want to be empowered and feel that they are really a part of something important and meaningful.

Avner Baruch, Head of International Sales Enablement at WalkMe, says the shifting expectations of millennials are causing sales leaders to transform their mindset on sales leadership.

The younger generation expects a higher level of personal satisfaction from their work. For managers and executives, this means entrusting employees to take risks, giving them meaningful work, and investing in their growth. That’s why Avner is always looking for engaging ways to provide effective training, create interactive presentations, and deliver personalized feedback.

According to a Gallup study titled “How Millennials Want to Work and Live,” millennials are the “least engaged generation” at work.

“Only 29% of millennials are emotionally and behaviorally invested in their job,” the study found. In order to increase engagement and loyalty, sales leadership has to seriously up their game with ongoing training, coaching, and incentives.

Generic training and once-a-year career development are no longer enough. Your sales team wants personalized support that is tailored to their goals throughout their work experience.

The biggest incentive for sticking around is seeing that there’s room to grow. When employees are encouraged to take on more responsibilities and climb the ranks, their trust and commitment to the organization grows.


  • Invest in fostering personal relationships with each salesperson. Set regular time with each team member to go over their performance, give feedback, and answer their questions.
  • Workshops and team activities are extremely important for cultivating comradery and a culture of teamwork. Make sure your team has fun together regularly, both at work and also through non-work-related events.
  • Give your team members room to grow. Encourage employees to take on challenges and show them how they can move up in the company. Empower them to exceed expectations and reach their full potential.

Priority #3: Take advantage of innovative sales technologies

sales leadershipSales technologies create endless opportunities to boost productivity and improve performance on both the team and individual level.

Yet essential sales technologies, such as Salesforce, ServiceNow, and other CRMs, are often poorly utilized by the sales team. Limited usability means your team is missing out on the full benefits of the system.

Overcoming this usability challenge requires a strategic and robust approach to software onboarding and continual retraining.

Traditional methods of training, such as in-person classroom sessions or webinars, don’t promote long-term knowledge retention and they’re ill-equipped to support users in the face of automatic updates and new feature releases.

With a digital adoption solution, you can be confident your sales team members receive tailored, real-time guidance whenever they need it so they can complete any process with ease and efficiency. Your CRM has the potential to raise your entire department’s performance — but without a solid approach to digital adoption, it can easily become a bottleneck to efficiency instead of an enabler.

Beyond the CRM, other sales platforms provide invaluable insights and capabilities.

Gong, for example, a tool that records, categorizes, and analyzes every sales conversation, allows sales leaders and reps alike to access all of their team members’ interactions with leads. The conversations are indexed, organized, and customized for easy access. This data provides important insights that sales leaders can use to deliver specific feedback and analytics on sales reps’ performance.

Beyond expediting team efficiency and monitoring sales efficiency, sales tools can also provide clear data on individual sales rep performances. Such insights eliminate some of the subjectivity of feedback and allow for in-depth communication between management and salespeople.


  • Create a robust software onboarding strategy to ensure your sales team can maximize the full range of features and value of key software, and has adequate support for ongoing learning and process optimization.
  • Look for other sales technologies that can support important functions within the team and provide meaningful data
  • Get feedback from your team about the software they use. Some good questions to ask are: Is the platform helpful? Is it easy to use and understand? Is there a need for a new tool that could improve the sales process?

Just roll with it

Sales leadership that motivates and inspires will continue to change. An agile mindset is essential for rolling with the punches of an evolving corporate culture.

As employees’ demands for more frequent and individual feedback, transparency, and support using digital tools rises, sales leadership must determine how to balance employee development with achieving key business objectives.

In order to maintain a high level of trust, engagement, and motivation, sales leadership must lead by example, cultivate a culture of transparency, and above all, value and respect their team members as individuals. Sales reps don’t just want a quota, they want a purpose.

Successful sales leadership in the digital era embraces change and utilizes the tools to enable it.

WalkMe Team
By WalkMe Team
WalkMe pioneered the Digital Adoption Platform (DAP) for organizations to utilize the full potential of their digital assets. Using artificial intelligence, machine learning and contextual guidance, WalkMe adds a dynamic user interface layer to raise the digital literacy of all users.