AI-Powered Sales Leadership: Transforming the Playbook for World-Class Coaching

Jason Creane
February 23, 2024

We are in an era of change brought about by AI. There’s a lot of positivity but also uncertainty.


For sales leaders, the advent of artificial intelligence (AI) presents an opportunity to rewrite the playbook for optimising our impact across our whole team. There’s an opportunity to capitalise on the processing power of AI to amplify sales leaders’ experience and talent.

Currently, I have the privilege of running our sales leadership enablement in EMEA at Zscaler, and advising external GTM leaders. I’ve also been doing some independent research into AI. As such, I have developed a good understanding of the current challenges sales teams face and how AI could assist us in being more effective leaders in the future.

Current State: Human-Powered Sales Forecasting

In sales, managing the forecast is one of the key challenges for leaders. Managing the forecast today can mean getting intimately involved in as many deals as possible so that you can spot risk, coach the people involved, and drive the right actions and urgency directly.

This approach has, in the past, worked effectively at delivering the forecast, but with clear drawbacks: inconsistency, time drain, and inability to scale. Sometimes referred to as the “hero” approach, “saving” deals can be exhausting for leaders and can unintentionally create a micro-management style of culture that can lead to other challenges. In addition, a sales leader can only focus on a few key deals at a time, sometimes sacrificing support for the vast majority.

The Data Dilemma

Sales leaders are not data analysts. Currently, they are expected to review large amounts of performance data constructively, extract the necessary insights efficiently, and translate these insights into coaching opportunities for their salespeople.  

Traditionally, we use leading indicators to help us understand what activities will deliver success for our salespeople and sales leaders. These are powerful metrics that shape the weekly and quarterly operating cadence for our teams. These leading indicators are manual inputs. E.g.:

  • Number of new business meetings
  • Number of opportunity progression meetings
  • Proof of values
  • Pipeline coverage, etc.

Leading indicators have always been very important because we need a scalable way of measuring how to protect the business now and in the future. However, what every good sales leader knows is that for each person, business unit, region, and market, there are always discrepancies based on the skill of the individual, their tenure, the market, the culture of the region, etc. Therefore, it becomes challenging to cater for these nuances at scale and the manual inputs can feel limited. In an age when we can develop deeper insights, imagine if we could tailor make leading indicators that are fit for each individual, team, or region.

The human-powered playbook for sales leaders stops working at scale

As the needs of our employees change and the metrics for success remain constant, there is an opportunity to evolve this traditional playbook, looking toward new tools for assistance. Specifically, AI can help us to scale our ability to coach our people, understand potential business risks, and deliver for the business.

Future State: AI-Assisted Analysis & Insights to Optimise Sales Coaching

The charter for sales leadership has always been about prioritising their people – putting them before the deal and providing the right tools to be successful. Now we have an opportunity to expand our coaching at scale using data to guide us to the right areas of focus.

There is a huge opportunity for sales leaders to develop their management style and transition from being dealmakers to being transformative coaches, assisted by AI.

You may have heard of the term “Building a Second Brain,” coined by Tiago Forte:

“Building a Second Brain is a methodology for saving and systematically reminding us of the ideas, inspirations, insights, and connections we’ve gained through our experience … . A Second Brain ultimately expands our memory and our intellect using modern tools of technology.”

AI presents the potential to serve as a second brain, helping bridge the gap between a sea of data to having effective coaching conversations. Ultimately, helping leaders scale.

For instance, imagine an AI tech stack that can help us ingest the sea of data across deals, learn the patterns and trends across the entire GTM salesforce, benchmark the performance data against the norm, trend this information and tailor it at scale for specific individuals, then create intuitive, human-like written insights that are easy for sales leaders to understand in the moment so that they can coach their team effectively on where to focus their time and energy.

AI could finally be the technology that can help sales leaders develop insights from the pool of performance data in real time so that they can deliver impactful coaching for their people. I’m privileged to be a part of this game changing transformation. It’s an exciting time for all sales leaders if we adapt and evolve the way we think and behave.


This topic is top of mind for myself and the other sales leaders at Zscaler and across industries. I welcome you to join the conversation, perhaps by responding to this prompt:

How can AI help us rewrite the Sales Leader playbook, and help us become world class coaches?

If you’re interested in learning more about the advancements we’re driving and the opportunities for growth within Zscaler’s sales organisation, please DM me directly to begin the conversation.