Unlocking Success in Complex Deal Execution: The Power of AI and Guided Selling

In today's fast-paced business landscape, the art of sales has evolved significantly. Complex sales now require more than just a persuasive pitch and a charismatic salesperson. To excel in this challenging environment, organizations are turning to innovative solutions like Artificial Intelligence (AI) and guided selling to navigate the intricacies of complex deal execution.

In a recent webinar, together with Daniel Zamudio and Shaun Siler , we discussed the shifting dynamics of complex sales in 2023 and how AI-powered guided selling can become the game-changer your organization needs, illustrating this with examples stemming from the Aviso AI Platform and Playboox’s salesforce-native playbook application, Playmaker.

Let's explore the key takeaways from this discussion and understand how these technologies can be harnessed to drive sales success (enhancing the sales basics that cannot be replaced!).

Understanding the Complexity of Sales in 2023

The landscape of complex sales has transformed drastically over the years. In 2023, the characteristics of a complex sale have evolved to encompass high stakes, intricate decision-making processes, and the involvement of multiple stakeholders, all factors that can be augmented with economic headwinds.

It's no longer about selling to an individual but engaging with a committee of buyers, each with unique needs and priorities. This complexity demands a thorough understanding of the buyers' landscape, meticulous stakeholder mapping, and the ability to create internal alignment within the buying organization.

Moreover, the complexity of a sale is often influenced by various external factors such as industry verticals, market size, and specific sales motions. What works for one organization may not be effective for another. Therefore, flexibility and customization are key to addressing the diverse needs of complex sales in 2023.

Challenges in Managing Complex Sales

As the complexity of sales grows, organizations face several challenges in managing and executing complex deals effectively. These challenges are yet rooted in foundational elements and include:

1. Lack of Sales Process Maturity: Many organizations lack a mature sales process that aligns with the customer's buying journey. Often, sales methodologies focus on what the seller needs to sell rather than what the customer needs to make a buying decision.

2. Skills Gap: Successful complex deal execution requires consultative selling skills that can understand and cater to the diverse needs of stakeholders. Pitching products and features is no longer sufficient.

3. Ineffective Coaching: Sales managers play a critical role in developing and scaling the skills of their teams. However, the absence of rigor and structured coaching practices can hinder performance improvement.

The Failed Approach: Isolated Bursts of Enablement

To address these challenges, organizations often turn to traditional (and isolated) solutions such as sales process and sales methodology training or creating playbooks. While these approaches have their merits, they come with limitations.

Sales methodology training can be expensive and may not yield the desired results. Training sessions may be engaging, but the knowledge retention often dwindles within days or weeks. The forgetting curve sets in, and reps revert to old habits.

Playbooks, on the other hand, can become overly extensive and challenging to navigate. They may contain valuable insights but often end up buried in content management systems, unused and forgotten.

Even with the best of the above, organizations still fail to empower sales managers to hold their teams accountable, inspect what they are doing, and coach them to up their game.

The Recipe for Success: AI-Powered Guided Selling

To win complex deals at scale, organizations need to adopt a holistic approach that empowers sales managers and their teams. The recipe for success involves several key ingredients:

1. Sales Manager Empowerment: Equip sales managers with the tools, training, technology, and data they need to drive effectiveness within their teams. Transform your managers into expert coaches, even when they're not physically present.

2. Structured Coaching: Shift from ad-hoc, unstructured approaches to deal inspection to more structured and cadenced deal coaching. Create forums like deal win rooms and deal huddles to collaboratively strategize on moving deals forward.

3. Deal-Specific Guided Coaching: Provide sales teams with deal-specific guided coaching precisely when needed. This AI-driven approach ensures that reps receive tailored guidance throughout the deal cycle, leading to improved deal execution and higher win rates.

4. Integration of Tools: Embrace AI and technology to streamline sales processes and reduce manual work. Avoid the trap of purchasing numerous point solutions that create data silos and inefficiencies.

5. Data-Driven Insights: Leverage data to gain insights into your sales processes and performance. Identify patterns, trends, and opportunities for improvement.

Unlocking Deal Coaching Success with AI and Guided Selling

There’s a space that allows the opportunity to both inspect and coach while creating tangible immediate impact: Deal Coaching.

Follow these steps to harness the value of deal reviews and empower your teams to win:

1. Make Informed Choices to Focus on the Deals That Matter

Effective deal selection is the foundation of a successful deal review strategy. Traditionally, sales reps might prioritize deals based on their intuition or personal preferences. However, AI introduces a data-driven approach to deal selection, ensuring no potentially valuable opportunity is overlooked.

AI can analyze a wide range of data points, from customer engagement to deal progression, helping sales managers identify deals that are most likely to convert or those that may require special attention. By considering insights that humans might overlook, AI helps sales teams make informed choices about where to focus their efforts.

2. Assess Deal Health with Data-Driven Insights

The sales process is often complex, with multiple stages and various stakeholders involved. AI not only aids in deal selection but also offers data-driven insights at every stage of the sales process. It can provide real-time feedback on deal health, highlighting areas of strength and potential risks.

For instance, AI can detect changes in sentiment during customer interactions, helping sales reps understand the mood and receptiveness of their prospects. It can also analyze conversations to identify key objections or competitor mentions, enabling reps to adapt their strategies accordingly.

3. Create a Plan to Win

One of the most valuable aspects of AI and guided selling is the creation of winning playbooks. These playbooks are tailored guides that provide sales reps with the information, strategies, and best practices they need at each stage of the sales process while giving sales managers clear references to coach against.

A playbook can be used to curate and recommend plays based on specific deal attributes that can be customized for different market segments, verticals, or even specific buyer personas. This ensures that sales teams have access to the most relevant and effective strategies, when they need them, increasing their chances of success.

4. Excel in the Next Customer Interaction

The Win Plan created after the Deal Review should identify the next customer interaction to move the deal forward.

Leverage AI and applicable best practices in the playbook to plan for the coming call, defining a clear definition of success and how to achieve it. Take a step further and observe that call for coaching purposes.

AI can also be leveraged to provide in-call guidance to reps, suggesting actions or insights based on the ongoing conversation. This ensures that reps are equipped with the right information and strategies during critical interactions.

Furthermore, AI and the playbook can provide references that enable managers to observe and assess calls, offering constructive feedback and helping reps refine their skills. This coaching loop not only improves individual performance but also contributes to the overall development of the sales team.

Conclusion

Incorporating AI and guided selling into your sales strategy isn't just a trend; it's a competitive advantage. When used effectively, these technologies enhance deal selection, provide actionable insights, guide sales teams with winning playbooks, and facilitate continuous improvement through coaching and feedback.

The result? Improved win rates, larger deal sizes, shorter sales cycles, and greater accuracy in sales forecasts. In essence, it's about unlocking the full potential of your sales team and achieving consistent success quarter after quarter.

As the sales landscape continues to evolve, AI and guided selling are poised to play a pivotal role in shaping the future of sales. Embracing these technologies today could be the key to staying ahead in the fiercely competitive world of sales.