The Indispensable Boatswain: Guiding Sales Teams to Success

Welcome to this companion blog post to our latest podcast episode, 7. Does sales enablement excellence require process expertise or subject matter expertise? Lisa Skillern and I duke it out! In this episode, I had the pleasure of speaking with Lisa Skillern, a seasoned sales enablement leader, about the multifaceted role of sales enablement and the skills necessary for success. This post will delve deeper into the key themes we discussed, particularly the powerful metaphor of the 'boatswain' in sales enablement. We'll explore how sales enablement professionals can effectively guide their teams to achieve both group and individual objectives, manage stakeholders, and build a high-impact enablement organization.

Introduction: Setting the Stage for Sales Success

In today's dynamic business landscape, sales teams face unprecedented challenges. From navigating complex sales cycles to keeping up with rapidly evolving technologies and customer expectations, the pressure to perform is immense. Sales enablement emerges as a critical function, designed to equip sales teams with the knowledge, skills, and resources they need to succeed. However, simply providing tools and training is not enough. Effective sales enablement requires a strategic approach, a deep understanding of the sales process, and the ability to align all stakeholders towards a common goal.

This is where the concept of sales enablement as a guiding force comes into play. Just as a boatswain leads a ship's crew, sales enablement professionals must steer the sales team, ensuring everyone is working in harmony towards a shared destination. This involves more than just providing resources; it requires leadership, communication, and a keen understanding of the individual and collective needs of the sales team.

The Boatswain Metaphor: Guiding the Sales Team

The metaphor of the 'boatswain' provides a powerful framework for understanding the role of sales enablement. On a ship, the boatswain is responsible for overseeing the crew, ensuring that everyone is performing their duties effectively, and maintaining the ship's readiness. Similarly, in a sales organization, the sales enablement professional acts as the boatswain, guiding the sales team, ensuring they are equipped and prepared to execute their tasks, and maintaining the overall effectiveness of the sales function.

Here are some key parallels between the boatswain's role and that of a sales enablement professional:

• Direction and Alignment: A boatswain ensures that the crew is pulling in the same direction, literally and figuratively. In sales enablement, this means aligning the sales team with the company's overall goals and objectives, ensuring that everyone understands the strategy and their role in achieving it. This involves clear communication, setting expectations, and providing the necessary context for the sales team to make informed decisions.
• Training and Development: Boatswains are often responsible for training new crew members and providing ongoing development opportunities. Sales enablement professionals play a similar role, providing training on products, sales processes, and industry best practices. They also identify skills gaps and develop programs to address them, ensuring that the sales team is constantly improving and adapting to the changing market conditions.
• Resource Management: A boatswain manages the ship's resources, ensuring that the crew has the tools and equipment they need to perform their duties. Sales enablement professionals manage the sales team's resources, including content, technology, and tools. They ensure that these resources are easily accessible, up-to-date, and aligned with the sales team's needs.
• Problem Solving: Boatswains are skilled problem solvers, able to address any challenges that arise on the ship. Sales enablement professionals also need to be adept at problem solving, identifying and addressing any obstacles that are hindering the sales team's performance. This requires a proactive approach, anticipating potential problems and developing solutions before they impact the sales team.
• Motivation and Morale: A good boatswain inspires and motivates the crew, creating a positive and productive work environment. Sales enablement professionals play a similar role, fostering a culture of learning, collaboration, and continuous improvement. They celebrate successes, provide recognition, and create opportunities for the sales team to connect and learn from each other.

Lisa Skillern's Expertise: A Blend of Process and Domain Knowledge

Lisa Skillern's career exemplifies the ideal combination of process expertise and domain knowledge in sales enablement. Her experience spans both sales and marketing, giving her a unique perspective on the challenges and opportunities facing sales teams. She has worked in both large and small organizations, driving revenue and sales productivity in diverse industries. Her deep understanding of the sales process, coupled with her domain expertise in security, has made her a highly effective sales enablement leader.

One of the key takeaways from my conversation with Lisa was the importance of understanding the specific needs of the sales team. This requires a deep dive into their day-to-day activities, the challenges they face, and the resources they need to succeed. By understanding these needs, sales enablement professionals can develop programs and initiatives that are directly relevant and impactful.

Lisa's expertise also extends to stakeholder management, a critical skill for any sales enablement professional. She emphasizes the importance of building strong relationships with stakeholders across the organization, understanding their perspectives, and aligning their goals with the sales enablement strategy. This requires strong communication skills, the ability to influence without authority, and a willingness to collaborate and compromise.

Pragmatic Sales Enablement: Focusing on Impact

Lisa Skillern is a strong advocate for pragmatic sales enablement, focusing on initiatives that will make a tangible difference to the sales team today, this month, this quarter. This approach emphasizes the importance of prioritizing projects that will have the greatest impact and delivering results quickly. Rather than focusing on long-term, complex projects, pragmatic sales enablement focuses on addressing immediate needs and delivering quick wins.

This approach requires a deep understanding of the sales process and the challenges facing the sales team. It also requires the ability to prioritize projects based on their potential impact and feasibility. By focusing on pragmatic initiatives, sales enablement professionals can build credibility with the sales team and demonstrate the value of their work.

One of the key principles of pragmatic sales enablement is to start small and iterate. Rather than trying to implement a comprehensive sales enablement program all at once, it's often more effective to start with a small pilot project and then expand based on the results. This allows for continuous learning and improvement, ensuring that the sales enablement program is constantly evolving to meet the changing needs of the sales team.

Stakeholder Management: Building Influence Without Authority

Stakeholder management is a crucial skill for sales enablement professionals, who often need to influence decisions and drive change without having direct authority over the sales team. Building strong relationships with stakeholders across the organization is essential for gaining buy-in and ensuring that the sales enablement strategy is aligned with the company's overall goals.

Lisa Skillern emphasizes the importance of understanding the perspectives of different stakeholders and tailoring your communication accordingly. This requires active listening, empathy, and the ability to see things from their point of view. It also requires the ability to communicate the value of sales enablement in a way that resonates with each stakeholder's specific needs and priorities.

Building influence without authority also requires demonstrating expertise and credibility. Sales enablement professionals need to be seen as trusted advisors who can provide valuable insights and guidance. This can be achieved by sharing data, demonstrating results, and showcasing the impact of sales enablement initiatives.

Another key aspect of stakeholder management is collaboration. Sales enablement professionals should work closely with other departments, such as marketing, product, and customer success, to ensure that everyone is working towards a common goal. This requires strong communication skills, the ability to build consensus, and a willingness to compromise.

Evaluating a Sales Enablement Organization: Cohesion and Impact

Evaluating the effectiveness of a sales enablement organization requires looking at both its cohesion and its impact. A cohesive sales enablement team works together seamlessly, with clear roles and responsibilities, and a shared understanding of the organization's goals. A high-impact sales enablement organization delivers tangible results, improving sales productivity, increasing revenue, and driving customer satisfaction.

Lisa Skillern outlines several key factors to consider when evaluating a sales enablement organization:

• Alignment with Business Goals: Is the sales enablement strategy aligned with the company's overall business goals? Does the sales enablement team understand the company's priorities and how their work contributes to achieving them?
• Stakeholder Satisfaction: Are stakeholders satisfied with the services provided by the sales enablement team? Do they feel that their needs are being met?
• Sales Team Adoption: Are sales team members actively using the resources and tools provided by the sales enablement team? Are they finding them valuable?
• Impact on Sales Performance: Is sales performance improving as a result of the sales enablement initiatives? Are sales cycles shortening? Are win rates increasing?
• Team Cohesion: Is the sales enablement team working together effectively? Are there clear roles and responsibilities? Is there a culture of collaboration and support?

By evaluating these factors, organizations can identify areas for improvement and ensure that their sales enablement function is delivering maximum value.

Key Takeaways: Stakeholder Management and Expertise

Two key takeaways emerged from my conversation with Lisa Skillern: the importance of effective stakeholder management and the need for both domain or subject matter expertise and lots of process experience for the sales enablement professional. These two elements are critical for ensuring the success of any sales enablement initiative.

Effective stakeholder management ensures that the sales enablement strategy is aligned with the company's overall goals and that stakeholders are supportive of the initiatives. Domain expertise ensures that the sales enablement professional understands the specific needs of the sales team and can provide relevant and valuable resources. Process expertise ensures that the sales enablement initiatives are implemented effectively and efficiently.

By focusing on these two key areas, sales enablement professionals can maximize their impact and drive significant improvements in sales performance.

Connecting with Lisa Skillern

If you'd like to connect with Lisa Skillern and learn more about her approach to sales enablement, you can find her on LinkedIn. She is a valuable resource for anyone looking to improve their sales enablement skills and drive better results.

Conclusion: The Indispensable Role of the Boatswain in Sales Enablement

As we've explored in this blog post, inspired by my conversation with Lisa Skillern, the role of the sales enablement professional is akin to that of a boatswain, guiding the sales team, ensuring they are equipped and prepared to execute their tasks, and maintaining the overall effectiveness of the sales function. By understanding the needs of the sales team, building strong relationships with stakeholders, and focusing on pragmatic initiatives, sales enablement professionals can have a significant impact on sales performance.

The indispensable boatswain in sales enablement brings direction, training, resources, problem-solving skills, and motivation to the sales team. This leadership role fosters alignment and ensures every team member contributes to achieving both individual and group goals, driving the organization towards sustainable sales success.