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

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.

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

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.

‍Step 3. Define success metrics.

‍Step 4. Develop your AI roadmap.

‍Step 5. Implement and iterate using the right tools.

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

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.

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

Mariah Petrovic

Table of Contents

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

Part 2. Measure Success

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

Part 2. Measure Success

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