Future-Proof Your Sales Strategy: The Senior Sales Leader Playbook for Adopting AI and Automation

Table of Contents

As a senior sales leader, you must scale your approach to succeed. And AI can enable you to do just that, according to Harvard Business Review, “With generative AI…sales planning tasks that took weeks can be performed in an hour, as managers dialog with the system to discover opportunities, formulate key account strategies, and determine how to allocate effort to geographies, customers, products, and activities.” Here are proven ways to use AI to achieve repeatable success and consistently exceed your goals.

Part 1. Pave the Path to Repeatable Success with AI and Automation

Step 1. Identify the areas of your sales organization that need to change. Start by identifying inefficiencies and the roadblocks standing in the way of your desired state. Then, start to think through solutions that will help get you there. Here are some challenges you may be experiencing.

Functional Area
Desired State
Roadblocks
Solution
Deal execution
Ability to recognize patterns, optimize processes, and shorten sales cycles
  • Inaccurate CRM and sales data makes it hard to understand the reasons for deal success or failures. 
  • Managing larger teams with fewer resources.
360-degree inspection of every account and opportunity
Pipeline risk management
Proactively identify and manage risk 
  • Organizational blind spots due to missing and inaccurate data
  • Actions based off of feelings instead of facts
Automatically generated insights provide clarity into current deal health and engagement levels of contacts, accounts, and opportunities
Sales velocity
Give reps more time in the field, shorten sales cycles, and improve sales velocity
Day-to-day tasks are manual, time-consuming, and keep reps from spending time with accounts
Automated and data-driven forecasts, QBRs, account planning, meeting preparation, and buyer benchmarks

Step 2. Align expectations with stakeholders.

Once you’ve identified the areas of your sales organization that need to change and how you propose to address those challenges, it’s time to gain support from senior leadership and align with your frontline sales managers. By aligning expectations with leaders, you’re making sure they understand the impact for themselves and the organization and gaining champions for your programs. And gaining the support of your frontline leaders is critical since they will be the one implementing any new programs. 

Step 3. Define success metrics.

Determine appropriate program KPIs and reporting cadences for your programs and communicate those with leadership and direct reports. What does success look like for you and your team? For example, is it a matter of how accurate your forecasting should be? What behavior are you looking to change, and how are you going to measure success?

Step 4. Develop your AI roadmap.

Your new program should have a complete set of activities, assets, tools, and technologies — all clearly aligned to measurable and observable outcomes that can be assessed by you and your team of managers and reported to senior leadership. Here is a detailed explanation on how to develop an AI roadmap your organization can trust

Step 5. Implement and iterate using the right tools.

It isn’t impossible to build AI sales tools in-house but it can be a months-to-years long process. There are many out of the box sales AI tools that can help make an impact right away. It’s important to select sales technology that offers A. the capabilities you need to help solve your challenges, B. the insights and reporting capabilities you need to measure success, and C. robust and up to date security and data privacy protections. 

Functional Area
Desired State
Roadblocks
Solution
Deal execution
Ability to recognize patterns, optimize processes, and shorten sales cycles
  • Inaccurate CRM and sales data makes it hard to understand the reasons for deal success or failures.
  • Managing larger teams with fewer resources.
360-degree inspection of every account and opportunity
Pipeline risk management
Proactively identify and manage risk 
  • Organizational blind spots due to missing and inaccurate data
  • Actions based off of feelings instead of facts
Automatically generated insights into deal health and engagement levels of contacts, accounts, and opportunities
Sales velocity
Give reps more time in the field, shorten sales cycles, and improve sales velocity
Day-to-day tasks are manual, time-consuming, and keep reps from spending time with accounts
Automated and data-driven forecasts, QBRs, account planning, meeting preparation, and buyer benchmarks
Relevant AI
Sales Technologies
  • Sales AI + Generative AI for sales
  • Automated activity capture
  • Engagement measurement and visualization dashboards
  • Activity-based forecasting
  • Opportunity management
  • Conversational intelligence
  • Sales AI + Generative AI for Sales
  • Buyer benchmarks (a tool that provides the ability to infer win rates and predict buying power)
  • Activity-based forecasting software
  • Generative AI for sales
  • Automated account research and planning
  • Historical analysis for identifying patterns of success

Part 2. Measure Success

Once you have the organizational alignment in place and the technology you need to implement changes, you can kick off your new AI-driven sales programs. Here is a table to measure if your new programs are working:

Functional Area
Desired State
Deal execution
Ability to recognize patterns and optimize processes
Pipeline risk management
Proactively identify and manage risk 
Sales velocity
Give reps more time in the field and shorten sales cycles
Sales Leader Evidence
  • Leverages unified dashboard view to ensure reps are updating and following account plans
  • Leverages accounts engaged to ensure adequate territory and account coverage
  • Coaches reps to capture Total Addressable Market (TAM)
  • Team hits quarterly and annual goals
  • Leads team to shorten sales cycles, improve customer experiences, improve onboarding, and execute quicker upsell/cross-sell opportunities
  • Uses AI and revenue software to easily inspect all accounts and opportunities at scale
  • Ensures all deals are in the correct sales stage and the correct people are engaged
  • Uses AI sales tool to uncover blind spots in pipeline and offer actionable solutions for problems
  • Percentage of closed-won deals increases YoY
  • Shorter sales cycles
  • Reduced customer churn
  • Able to effectively manage a larger sales organization
  • Able to identify deals with most revenue potential and quickly allocate resources to those opportunities 
  • Deals are closing faster YoY (shorter sales cycles)
  • Average deal size increases YoY
  • Customer lifetime value increases YoY
Sales Team Evidence
  • Reps and frontline leaders use the prescribed AI sales tools
  • Team follows a consistent sales process
  • Opportunity scorecards are created and updated for every account
  • Team maintains a healthy pipeline
  • Team improves forecast accuracy
  • Frontline leaders are using data to coach effectively and consistently
  • Frontline leaders are using new processes to help reps ramp much faster 
  • Frontline leaders are using unified dashboard view to ensure reps are updating and following account plans
  • Qualifies deals in or out early in the process
  • Uses AI-generated relationship maps to navigate complex buyer groups 
  • Proactively identifies which accounts are at risk using AI
  • Frontline leaders using AI sales tools to identify next best steps on opportunities at risk 
  • All sales activity is being automatically captured and assigned to the right accounts, opportunities, contacts, and leads in CRM
  • New contacts are being automatically created and enriched with persona, title, seniority in company, etc in CRM
  • Reps use AI to help write customer emails, understand accounts, and prepare for customer meetings and presentations
  • Frontline leaders using AI to help automate QBRs, forecasting, deal reviews, and coaching
  • Reps spending more time interacting with customers than on administrative tasks (ratio should be flipped from what it was before AI was introduced)
  • Team proactively identifying upsell/cross sell whitespace in accounts 
  • Reps first contribution happens faster

Learn more about how you can leverage AI and better data to identify and understand patterns in order to scale your sales strategy.

As a senior sales leader, you must scale your approach to succeed. And AI can enable you to do just that, according to Harvard Business Review, “With generative AI…sales planning tasks that took weeks can be performed in an hour, as managers dialog with the system to discover opportunities, formulate key account strategies, and determine how to allocate effort to geographies, customers, products, and activities.” Here are proven ways to use AI to achieve repeatable success and consistently exceed your goals.

Part 1. Pave the Path to Repeatable Success with AI and Automation

Step 1. Identify the areas of your sales organization that need to change. Start by identifying inefficiencies and the roadblocks standing in the way of your desired state. Then, start to think through solutions that will help get you there. Here are some challenges you may be experiencing.

Functional Area
Desired State
Roadblocks
Solution
Deal execution
Ability to recognize patterns, optimize processes, and shorten sales cycles
  • Inaccurate CRM and sales data makes it hard to understand the reasons for deal success or failures. 
  • Managing larger teams with fewer resources.
360-degree inspection of every account and opportunity
Pipeline risk management
Proactively identify and manage risk 
  • Organizational blind spots due to missing and inaccurate data
  • Actions based off of feelings instead of facts
Automatically generated insights provide clarity into current deal health and engagement levels of contacts, accounts, and opportunities
Sales velocity
Give reps more time in the field, shorten sales cycles, and improve sales velocity
Day-to-day tasks are manual, time-consuming, and keep reps from spending time with accounts
Automated and data-driven forecasts, QBRs, account planning, meeting preparation, and buyer benchmarks

Step 2. Align expectations with stakeholders.

Once you’ve identified the areas of your sales organization that need to change and how you propose to address those challenges, it’s time to gain support from senior leadership and align with your frontline sales managers. By aligning expectations with leaders, you’re making sure they understand the impact for themselves and the organization and gaining champions for your programs. And gaining the support of your frontline leaders is critical since they will be the one implementing any new programs. 

Step 3. Define success metrics.

Determine appropriate program KPIs and reporting cadences for your programs and communicate those with leadership and direct reports. What does success look like for you and your team? For example, is it a matter of how accurate your forecasting should be? What behavior are you looking to change, and how are you going to measure success?

Step 4. Develop your AI roadmap.

Your new program should have a complete set of activities, assets, tools, and technologies — all clearly aligned to measurable and observable outcomes that can be assessed by you and your team of managers and reported to senior leadership. Here is a detailed explanation on how to develop an AI roadmap your organization can trust

Step 5. Implement and iterate using the right tools.

It isn’t impossible to build AI sales tools in-house but it can be a months-to-years long process. There are many out of the box sales AI tools that can help make an impact right away. It’s important to select sales technology that offers A. the capabilities you need to help solve your challenges, B. the insights and reporting capabilities you need to measure success, and C. robust and up to date security and data privacy protections. 

Functional Area
Desired State
Roadblocks
Solution
Deal execution
Ability to recognize patterns, optimize processes, and shorten sales cycles
  • Inaccurate CRM and sales data makes it hard to understand the reasons for deal success or failures.
  • Managing larger teams with fewer resources.
360-degree inspection of every account and opportunity
Pipeline risk management
Proactively identify and manage risk 
  • Organizational blind spots due to missing and inaccurate data
  • Actions based off of feelings instead of facts
Automatically generated insights into deal health and engagement levels of contacts, accounts, and opportunities
Sales velocity
Give reps more time in the field, shorten sales cycles, and improve sales velocity
Day-to-day tasks are manual, time-consuming, and keep reps from spending time with accounts
Automated and data-driven forecasts, QBRs, account planning, meeting preparation, and buyer benchmarks
Relevant AI
Sales Technologies
  • Sales AI + Generative AI for sales
  • Automated activity capture
  • Engagement measurement and visualization dashboards
  • Activity-based forecasting
  • Opportunity management
  • Conversational intelligence
  • Sales AI + Generative AI for Sales
  • Buyer benchmarks (a tool that provides the ability to infer win rates and predict buying power)
  • Activity-based forecasting software
  • Generative AI for sales
  • Automated account research and planning
  • Historical analysis for identifying patterns of success

Part 2. Measure Success

Once you have the organizational alignment in place and the technology you need to implement changes, you can kick off your new AI-driven sales programs. Here is a table to measure if your new programs are working:

Functional Area
Desired State
Deal execution
Ability to recognize patterns and optimize processes
Pipeline risk management
Proactively identify and manage risk 
Sales velocity
Give reps more time in the field and shorten sales cycles
Sales Leader Evidence
  • Leverages unified dashboard view to ensure reps are updating and following account plans
  • Leverages accounts engaged to ensure adequate territory and account coverage
  • Coaches reps to capture Total Addressable Market (TAM)
  • Team hits quarterly and annual goals
  • Leads team to shorten sales cycles, improve customer experiences, improve onboarding, and execute quicker upsell/cross-sell opportunities
  • Uses AI and revenue software to easily inspect all accounts and opportunities at scale
  • Ensures all deals are in the correct sales stage and the correct people are engaged
  • Uses AI sales tool to uncover blind spots in pipeline and offer actionable solutions for problems
  • Percentage of closed-won deals increases YoY
  • Shorter sales cycles
  • Reduced customer churn
  • Able to effectively manage a larger sales organization
  • Able to identify deals with most revenue potential and quickly allocate resources to those opportunities 
  • Deals are closing faster YoY (shorter sales cycles)
  • Average deal size increases YoY
  • Customer lifetime value increases YoY
Sales Team Evidence
  • Reps and frontline leaders use the prescribed AI sales tools
  • Team follows a consistent sales process
  • Opportunity scorecards are created and updated for every account
  • Team maintains a healthy pipeline
  • Team improves forecast accuracy
  • Frontline leaders are using data to coach effectively and consistently
  • Frontline leaders are using new processes to help reps ramp much faster 
  • Frontline leaders are using unified dashboard view to ensure reps are updating and following account plans
  • Qualifies deals in or out early in the process
  • Uses AI-generated relationship maps to navigate complex buyer groups 
  • Proactively identifies which accounts are at risk using AI
  • Frontline leaders using AI sales tools to identify next best steps on opportunities at risk 
  • All sales activity is being automatically captured and assigned to the right accounts, opportunities, contacts, and leads in CRM
  • New contacts are being automatically created and enriched with persona, title, seniority in company, etc in CRM
  • Reps use AI to help write customer emails, understand accounts, and prepare for customer meetings and presentations
  • Frontline leaders using AI to help automate QBRs, forecasting, deal reviews, and coaching
  • Reps spending more time interacting with customers than on administrative tasks (ratio should be flipped from what it was before AI was introduced)
  • Team proactively identifying upsell/cross sell whitespace in accounts 
  • Reps first contribution happens faster

Learn more about how you can leverage AI and better data to identify and understand patterns in order to scale your sales strategy.

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