How CSOs Can Train and Manage Sales Talent Effectively (2024)

The seller role of the future is about asking salespeople for less and getting more. Changing technologies, buyer needs and behaviors are driving the seller role to near-impossible levels of complexity — and 94% of CSOs agree that their sales organizations will have to update the talent profile of sellers to meet revenue goals.

To lessen the burden on sellers, reduce the scope of the seller role in two ways:

1. Treat technology as a full-fledged member of the sales team and allow it to independently navigate the buying environment. Rather than giving salespeople more tech, give the tech itself more responsibility.

2. Narrow the scope of the seller role to focus on the unique human behaviors that drive high-quality deals: addressing the emotional component of purchase decisions through a set of skills called mentalizing, and collaborating with AI teammates.

Advancements in AI will require a paradigm shift in how sales leaders think about tech deployment. The following four stages of RevTech maturity outline technology’s changing role in sales:

• Simple automation. Salespeople use basic automation tools and AI that assist with simple activities. Technology supports efficiency, but its benefits depend on seller adoption.

• Assisted selling. Salespeople use AI-assisted automation tools to improve productivity. Technology is integrated into the sales process to provide passive assistance around prioritization and execution.

Automated selling. Technology is a full part of the sales team and plays an active role in decision making and execution. Technology automates most sales activities and acts as a virtual assistant able to perform many tasks more efficiently and accurately than human sellers.

Autonomous selling. Technology completely automates the sales process and makes decisions on its own. Salespeople act as strategic overseers providing guidance and prioritization, but technology performs nearly all tasks, and more digital interactions are done by automated selling tech.

High-tech enablement methods, learning science, and a multichannel approach to increasing employee performance are shifting the focus of sales enablement to “learning” over “training.”

Forty-nine percent of sales training still takes place in virtual or in-person facilitated sessions. But by 2026, sellers will spend 65% fewer hours in training compared to 2022 as enablement evolves from owning training to owning learning more holistically.

People learn differently in corporate environments now, and sales talent is no different. Learning trends like microlearning, blended learning, video-powered social learning and adaptive learning are increasingly available to sales enablement organizations. To align with these trends, replace sales enablement training hours with the following:

• In-workflow programs leading to just-in-time enablement

• Buyer-centric enablement programs

• Provision of support for more customer-facing roles

• Rollout of end-to-end interconnected workflows

Currently, less than 10% of the sales enablement technology budget is used for adaptive learning, algorithmic-guided selling and conversation intelligence for sales. Yet these areas are critical to sales enablement, which will use AI to identify, infer and track sales skills, and avoid relying on competency libraries or time-consuming manual skill updates.

Technology will aid this shift and allow sellers to learn according to their own preferred times, methods and locations. Just-in-time enablement will deliver sellers information they need at the moment within their daily workflow.

The traditional sales training that remains will change in terms of format. Some elements of classroom-based sales training will still be appropriate, but enablement must recognize that training will happen in a variety of ways, including immersive sales training via virtual reality (VR).

Enablement’s scope will break out of its traditional “sales” focus and encompass roles across the broader commercial organization. Enablement will have to adapt to deliver learning for diverse roles with diverse skill sets to ensure that all customer-facing roles have the technology, content, knowledge and skills needed to maximize revenue production.

This expansion of who needs to learn will not be limited to an internal audience. Sales enablement will also be a key stakeholder in creating and distributing cross-channel support for customer learning objectives throughout the purchase journey.

To improve the effectiveness of your sales enablement function, consider the following actions:

• Figure out how much time you’re spending on sales-enablement-led sales training.

• Assemble a task force to experiment with innovative media methods for sales training activities, such as VR and microlearning.

• Create program management roles responsible for cross-functional enablement, both by geography and business unit.

Several years of disruption in the sales environment have led to an increasingly burned out workforce. Keeping sales teams motivated, engaged and productive is becoming more challenging — but building a high adversity quotient (AQ) can enable your team to thrive in future uncertainty.

To create a culture that values grit and determination in the face of adversity, align sales skills to the four core components of AQ — control, ownership, reach and endurance:

• Control is the ability to influence sales outcomes, which relies on the ability to identify the factors within seller control and take action (using “Reach” below) to improve sales performance. For example, in a nonlinear buying journey, a salesperson leverages a variety of channels to reach potential customers, such as social media, email marketing or targeted cold calling.

• Ownership is taking proactive steps to address selling and buying challenges. For instance, even in a purely digital context, a seller must own their ability to actively listen to customers, effectively handle objections, build trust and establish credibility with buyers.

• Reach is the extent to which sales reps believe they have the resources and support necessary to overcome adversity. For example, when clients prefer “rep-free” buying, reps must believe they have the infrastructure necessary to create engaging and memorable virtual sales experiences. Additionally, a supportive organization that provides guidance and coaching on physically penetrating seller-resistant accounts exemplifies reach.

• Endurance is perseverance through difficult sales situations, the ability to bounce back from lost deals, and the ability to continue to pursue opportunities. For example, teams may face multiple rejections within a complex major account because buyers can produce extensive research and information that challenges seller assertions.

Make AQ a core capability in your sales enablement programs with the following actions:

• Baseline your sales teams’ AQ using assessments.

  • Use a standardized questionnaire to analyze the team’s resilience, adaptability and problem-solving skills.

  • Conduct structured interviews related to past challenges, problem-solving approaches and ambiguity.

  • Observe the sales team in action to assess the team’s ability to handle adversity, and provide an opportunity for immediate feedback and coaching.

• Adapt sales training programs to build AQ and improve salespeople’s resilience, adaptability and problem-solving skills. The training programs can include techniques to manage stress, strategies to overcome obstacles, and approaches to managing ambiguity.
  

• Provide AQ seller coaching and ongoing support. Target sales coaching to review past experiences and identify areas for improvement. Focus on developing specific sales skills, such as emotional regulation, risk-taking and perseverance.
  

• Build AQ recruitment criteria for HR and hiring managers.

  • Source sales talent with a proven track record of overcoming challenges and setbacks indicated through past work experiences, education or personal accomplishments.

  • Incorporate AQ assessments to objectively measure a candidate’s resilience and ability to handle adversity in the sales environment.

  • Conduct behavioral interviews that focus on how candidates have handled adversity in the past and where they may need additional onboarding or training.

By 2027, statistical analysis, application development, data visualization and strategic planning will be the top skills for sales operations. Delivering these skills is key to unlocking the sales technology stack and the ability to drive actionable insights.

To build a talent cohort that will meet sales operations’ long-term needs, work with HR on a talent plan using the following four steps:

1. Identify and prioritize skills. Identify the future skills needed to advance your company’s strategy and goals by using a capabilities roadmap. Begin to prioritize by capturing a baseline of current function capabilities and their associated skill proficiency level. Next, conduct a forward-looking exercise to assess expectations of how the function will change through planned developments in areas such as automation, analytics, technology and the expansion of stakeholders needing support. This will enable you to craft a maturity path for projects on your change agenda.
   

2. Create a workforce plan. Collaborate with HR to choose the best route(s) to upskilling your team. Hiring permanent talent is typically the fastest way to deliver needed skills, but developing your existing workforce provides opportunities to create positive employee experiences through engagement in continuous learning. Once you’ve decided on your approach, set talent objectives and success metrics, confirming risks to foster urgency around your narrative for investing in talent.

3. Initiate talent activities. Promote actions that attract and retain talent to deliver against your capabilities roadmap. Co-create a human-centric employee value proposition (EVP) with HR and other functions so that it resonates with existing employees and potential new hires. Bolster the EVP with the following initiatives:

• Showcase how sales operations uses the sales tech stack to deliver insights, drive business performance and strengthen customer relationships.

• Demonstrate brand presence through customer success stories and testimonials.

• Partner with local colleges to support programs that focus on sales operations’ future talent and capabilities needs.

• Form a “sustainability champion” network to improve team engagement and drive action through pledges of activity.

• Create a continuous learning culture by committing to formal learning plans that maximize organic skill growth and attract talent.
  

4. Track results and evaluate. Assess the talent plan’s impact on business deliverables. Budget and track costs against your talent acquisition approach. For new hires, include recruitment costs and onboarding time to productivity. For workforce reskilling, include training costs and staff time to upskill.

Eighty-two percent of sales leaders believe that sales enablement content and/or delivery must significantly change to meet revenue goals in five years. When seller skills gaps or execution challenges threaten commercial results, enablement leaders often find themselves responding to leadership requests and trying to fix problems in a reactive mode.

Although many enablement leaders seek to be a true strategic partner to the CSO, three distinct gaps keep sales enablement from functioning proactively:

• Limited focus on strategic vision. Only 43% of enablement organizations have a formalized charter that outlines their purpose, scope, strategies and responsibilities. And only 37% of organizations have an annual planning process aligned with sales strategy. This essentially puts the enablement organization in a reactive position.

• Overemphasis on formal training and communication. For many sales organizations, “enablement” equates to training — e.g., live or virtual classroom sessions, e-learning and peer-to-peer learning — which can help develop seller skills and competencies, but doesn’t always support the behaviors that help achieve sales goals.

• Measurement uncertainty. The emphasis on training is also reflected in the metrics used for enablement. “Vanity metrics” such as training attendance or satisfaction are easy to capture and understand, but most organizations don’t correlate these metrics to higher-level sales KPIs.

For sales enablement to become a strategic actor in the sales organization, refocus the team on identifying behaviors that drive commercial success, scaling them across the sales force, and measuring the impact.

Two key approaches are highly effective in changing seller behavior:

• Behavioral nudges. Small noncoercive tweaks to how choices are presented to decision makers can shape their behavior by “nudging” them to a desired action. Nudges can be as simple as nutrition information about a menu item that subtly encourages us to make a healthier food choice. Organizations that used nudges in instructional design are 2x more likely to exceed new customer acquisition targets than organizations that didn’t use nudges.

• Just-in-time learning. As the name implies, just-in-time learning is about providing the exact information a seller needs exactly when they need it. For example: A seller hasn’t had time to prepare for a prospect call. But the calendar reminder for the call includes a pop-up with the top 3 discovery questions to use with a new prospect and a one-page prospect profile. Organizations that use just-in-time learning are 2.5x more likely to exceed seller revenue target, 3.5x more likely to exceed customer retention target and 2.3x more likely to exceed retention target.