Redefining Sales Leadership In A Disrupted World


15 minutes


Luca D’Urbino

Sixteen years ago, as a newly minted general manager, I was responsible for accelerating growth in the Americas and leading an 85-person sales team. A Harvard Business Review article, “The Ultimately Accountable Job: Leading Today’s Sales Organization,” caught my attention. The piece highlighted some of the developing complexities of the role from communication to compensation to the emergence of new channels. The article inspired me then and I returned to it many times over the years as I took on greater commercial and operational responsibilities.

Since that time, the global pandemic forced sales leaders to accelerate their digital transformation. Building and managing a diverse virtual salesforce, creating and nurturing relationships with customers over video meetings, and responding to demands for more accurate forecasting all require sales leaders to cultivate new skills.

In my current role as VP and Global Innovation Evangelist at Outreach, a leading sales execution platform provider, I had the opportunity to work with Forrester Research on a sales leadership study we commissioned.[1] In a survey of 212 U.S.-, Canada- and U.K.- based sales leaders, fresh insights emerged on what is required of today’s sales executives. The research re-frames the way the job description of the top sales leader is evolving and describes six attributes leaders must increasingly have in order for their organizations to thrive. The themes presented here can be used as a guide for Chief Sales Officers (CSOs), Chief Revenue Officers (CROs), and other sales organization leaders looking to excel in their positions, and by CEOs and boards responsible for hiring the best people to fill these positions.

Twenty-First Century Leadership Attributes

Disruption and transformation are here to stay. Consider the following:

  • Businesses are reinventing themselves for the digital age.
  • Global enterprises are successfully adopting “work from anywhere” models.
  • The pandemic accelerated the digitization of business-to-business (B2B) buying and selling.
  • Legacy sales technologies, namely CRM systems, must now share the stage with other more seller-friendly platforms.
  • Millennials are taking their places in the C-Suite.
  • Political and cultural divides are widening.
  • A war is raging in Eastern Europe.
  • Inflation is changing consumer purchasing habits.
  • Shifting demographics, evolving buyer preferences, and the rapid maturation of automation and artificial intelligence (AI) mandate that all sales organizations transform.

This dynamic environment has created new challenges. In our recent Forrester study, sales leaders identified their top three as:

1. Leading a multi-generational, sales force;
2. The pace at which buyer preferences are evolving; and
3. An uncertain economic environment

Addressing these means embracing new methods and expanding core skills. Modern sales leaders must be empathetic while creating a culture of accountability; they must design growth strategies with buyer preferences in mind; and they must recruit and retain a sales force that reflects the world around them. Here are six attributes required to enable them, their organizations, and their companies to succeed:

1. Empathy and Accountability

While holding teams accountable has always been a key tenet for sales leaders, leading today requires more sophistication and nuance than simply leveraging the two-dimensional carrot and stick. As work becomes more distributed and external global complexities increase, human connections, and empathetic leadership matter even more. Top sales leaders pay close attention to the details of what customers and staff are facing and meet both where they are. These leaders empathetically support their customers and teams — even when it takes them outside of their traditional comfort zones.

Empathetic leaders understand that buyers are people first. During the worst days of the pandemic, Anna Baird, CRO at Outreach, had her team create a digital bereavement card that could be emailed to customers who had lost loved ones. Today’s sales leaders must also be keenly attuned to the mental health and wellbeing of their sellers. According to Baird, “A new era of providing mental wellness services for sales teams has risen out of these challenging times.” Baird has instituted a series of self-care tips and training to go along with go-to-market refresh days that provide her team with the ability to plan ahead for scheduled breaks with family and friends and to pursue their non-work passions.

2. Commitment to Diversity, Equity, and Inclusion

Modern sales leaders understand that employees and buyers expect to work for and purchase from companies that value diversity. According to the Forrester sales leader study, 67% of respondents said that it’s important for their sales teams to reflect the world around them.[1] And in a recent Forrester study commissioned by LinkedIn, 82% of respondents predicted that the racial or ethnic diversity of their sales teams will be equally or more important in the next two years.[2] There is plenty of work to be done here, as data from the U.S. Bureau of Labor Statistics shows that 80% of Americans in “sales and related occupations” are white.
The Forrester/LinkedIn study2 revealed that sales organizations with leading DEI practices have higher conversion rates, higher sales attainment, and higher customer satisfaction. In a scorching hot labor market where choices abound for top-tier sales talent, organizations that treat DEI as a business priority will be able to recruit and retain the best talent and deliver superior business results.

Top sales leaders are intentional about their talent strategies as they pursue new channels to source diverse talent and create internal programs to nurture existing diverse talent. According to Hang Black, vice president of revenue enablement at Juniper Networks, “It’s time to re-imagine how we recruit, retain, and nurture sales talent. We must challenge the notion of ‘best caliber’ as defined by direct experience or by being part of prestigious networks.” Juniper partners with sales programs at universities that have multicultural student populations, and the company strives for 20% of their sales interviewees and interviewers to be diverse. Once talent is in the door, Juniper focuses on retention by providing clear career benchmarks over the course of two years with career lattices that address different intergenerational needs for achievement and impact. In 2021, 46% of Juniper’s global virtual sales organization’s managers were women and 26% were ethnic minorities.

3. Expertise in Delivering Predictable, Agile Growth

Every sales leader wants to deliver predictable, efficient growth. In today’s unpredictable business climate, having real-time, data-driven visibility into the health of deals, pipelines, and forecasts is more crucial than ever. Unfortunately, forecasting at many companies is inefficient and ineffective. In the Forrester study, 60% of sales leaders said they don’t have a well-defined or scientific approach to forecasting, and only 38% said they forecast within 10% accuracy.[1]

Timothy Hudson, Honeywell’s global vice president of sales excellence, believes the current economic uncertainty dictates that leaders must be creative, flexible and agile. According to Hudson, “Things in the past that would take a couple of weeks to complete now must be executed in 24 hours or less.” Agile and effective sales leaders need the tools and skills to course-correct at a moment’s notice and to forecast with great accuracy.

To reset on what’s currently happening versus what happened last quarter or last year, leaders are adopting solutions that use automation to capture buyer behavioral and sentiment data. With accurate and complete data sets they can minimize reliance on historical trending and gain insights derived from buyer actions leading to more accurate forecasts and predictable growth.

4. Sales Technology Proficiency

“Smart tooling,” — having the right collection of technologies for revenue team members to excel — is playing an increasingly important role in the successful execution of sales strategies. Today’s sales leaders must have an effective working knowledge of new sales technologies and an awareness of the most innovative providers. According to Honeywell’s Hudson, the company uses the “latest and greatest sales technologies to drive efficiencies and gain competitive advantage for the sales force.”

Thankfully, sales leaders are seeing their budgets increase. In Gartner’s “The Chief Sales Officer Study 4Q 2021,” 70% of CSOs said they expect to receive a budget increase for technology. Currently, only 2% of those CSOs report they are very satisfied with their current sales technology stack.[3]

Sales leaders are conducting inventories of their “tech stacks,” the set of sales technologies their teams use to do their work and are consciously moving away from unique point solutions toward unified platforms that serve every member of the revenue team and leverage automation to capture buyer behavioral and sentiment data. These platforms additionally provide a singular data repository from which insights can be gleaned and a more streamlined and cost-effective approach to managing vendors.

5. Financial Acumen and Data Literacy

Modern sales leaders must have strong financial acumen and operational management skills. Sales leaders told Forrester that they believe the most valuable competencies for a CRO are strong financial skills, strong forecasting skills, and the ability to deliver predictable growth.[1] In an increasingly digital environment, the ability to consume data and turn it into insights that drive meaningful business outcomes, is a significant competitive differentiator. According to Mark Bedard, global vice president of sales for Cognism, “The modern CRO is becoming more of a finance and ops professional. They are becoming less of the old-school salesperson with soft skills to someone who is data-driven and data literate.”

Sales leaders are focused not only on data competencies for themselves but also for their managers, as 58% said the ability to consume, analyze and act on data and analytics was the top attribute in a sales manager. Unfortunately, those same respondents said only 30% of their managers had mastered that skill. Bedard directs his managers to the “data points that actually matter” to ensure they are focused on the right metrics.

6. Buyer-First Mentality

While creating buyer-centric strategies sounds simple enough, many sales organizations still miss the mark. In LinkedIn’s “State of Sales 2021” study, only 23% of respondents agreed that sellers “always” put the buyer first. Whether it’s having buyer-centric sales stage milestones or increasing collaboration and coordination between buying and selling groups, the best sales leaders devise strategies and acquire technologies that enable their organizations to engage with customer-centricity.

Outreach’s Baird believes, “Buyers want a partner to guide them through key milestones that occur in purchases and to help them and other stakeholders understand the business value their product or solution provides.” Cognism’s Bedard is intentionally building a sales culture with a buyer-first mentality. “If we feel there is a better solution or better alternative for a customer, we’re going to recommend that. We always put the customer first, even if that doesn’t mean our solution.”

Step Up To Lead an Evolved Sales Force In a Disrupted World

For more than two-and-a-half years, sales leaders have been unwitting participants in a master class on how to be adaptable, resilient, and empathetic.

For more than two-and-a-half years, sales leaders have been unwitting participants in a master class on how to be adaptable, resilient, and empathetic. The barrage of uncontrollable external events mandates that these leaders reimagine their talent, technology, and go-to-market strategies. In the face of these realities, sales leaders must adapt and evolve their skills.

While this research focused specifically on sales leaders, the same set of challenges and opportunities face all leaders from entrepreneurs to CEOs to politicians. Many of the attributes discussed here including empathy and accountability, commitment to diversity, equity and inclusion, and a greater need for financial and technical literacy across the board will no doubt be needed by leaders of all kinds. Staying on top of rapidly changing external and industry trends is not easy, but leaders who expect to thrive must evolve their skills. For many — especially those who come from more traditional backgrounds — these are new muscles to flex. But when learned and applied, they will set leaders and their organizations up for success. Mary Shea, PhD, is Outreach’s Global Innovation Evangelist. In this role, Mary conducts research on the future of buying and selling, the sales technology landscape, and diversity, equity, and inclusion in B2B sales. In her 20-plus year sales career, Mary has been a sales leader, an academic, and an analyst.

1Source: “B2B Leaders Usher in a New Era of Sales,” Forrester Research, Inc. on behalf of Outreach, December 2021.

2Source: “Diversity Drives Sales Success,” Forrester Research, Inc. on behalf of LinkedIn, November 2021. Base: 500 managers and above responsible for a sales team in the United States.

3Source: “The Chief Sales Officer Study 4Q 2021.” Gartner, November 23, 2021.

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