The Complete 6-Month Roadmap for Sales Leaders
This comprehensive 6-month learning roadmap is designed to help sales executives confidently integrate Artificial Intelligence (AI) into their sales workflows and long-term strategies. It combines hands-on tools, essential courses, ethical insights, and Agile frameworks to transform how sales leaders think, operate, and lead.
Month 1: Try AI First
Goal: Build curiosity and confidence by experimenting with AI tools.
Why This Matters: Experiencing AI first-hand through practical tasks increases engagement and lays a motivational foundation for deeper learning.
Tools & Courses:
- ChatGPT: https://chat.openai.com/
- OpenAI Academy: https://academy.openai.com/
Key Activities:
- Generate sales emails, proposals, and replies using ChatGPT.
- Reflect on how AI might improve your day-to-day work.
Recommended Reading:
- Chapter 1: Introduction to Agile Sales and AI-Assisted Selling
https://businessagility.education/blog/agile-sales-ai-selling-chapter1/
Introduces the strategic integration of Agile and
- Chapter 2: Beyond “Always Be Closing” and “Rinse and Repeat”
https://businessagility.education/blog/agile-sales-ai-selling-chapter2/
Introduces the case for modernizing sales practices using Agile and AI. Explains why traditional sales needs an update, setting the stage for AI adoption.
Month 2: Learn AI Basics
Goal: Understand core AI concepts and terminology.
Why This Matters: Grasping fundamental AI concepts helps sales leaders make informed decisions, communicate with vendors, and guide team adoption.
Courses:
- AI for Everyone – Coursera (Andrew Ng):
https://www.coursera.org/learn/ai-for-everyone - Elements of AI – University of Helsinki & Reaktor:
https://www.elementsofai.com/ - Google AI Introduction – Grow with Google:
https://grow.google/ai/
Key Topics:
- Machine learning, deep learning, NLP, neural networks, data science.
Recommended Reading:
- Chapter 6: Merging Agile Sales with AI-Driven Enablement
https://businessagility.education/blog/agile-sales-ai-selling-chapter6/
Explains how AI can enhance sales enablement strategies, onboarding, and content workflows. Bridges the gap between AI and sales team development.
Month 3: Use AI in Sales
Goal: Apply AI tools to optimize lead generation, CRM, and outreach.
Why This Matters: Demonstrates measurable value by embedding AI into existing sales processes.
Courses & Tools:
- AI Essentials for Sales Professionals – LinkedIn Learning:
https://www.linkedin.com/learning/paths/ai-essentials-for-sales-professionals - HubSpot AI Tools for Sales:
https://www.hubspot.com/products/sales/ai - Salesforce Einstein AI:
https://www.salesforce.com/products/einstein/overview/ - Gong.io:
https://www.gong.io/
Key Activities:
- Automate lead scoring, email follow-ups, and pipeline insights.
Recommended Reading:
- Chapter 8: Spectrum of Sales Professions with Agile Sales and AI-Assisted Selling Enhancements
https://businessagility.education/blog/agile-sales-ai-selling-chapter8/
Maps how AI tools enhance specific sales roles, helping learners personalize AI implementation.
Month 4: Master Prompting
Goal: Develop skills to interact with AI more effectively using prompt engineering.
Why This Matters: Well-structured prompts produce better AI outputs, increase consistency, and reduce miscommunication.
Course:
- Prompt Engineering for ChatGPT – Coursera:
https://www.coursera.org/learn/prompt-engineering
Key Activities:
- Create a personal prompt library: objection handling, email writing, discovery questions.
Recommended Reading:
- Chapter 9: Agile Excellence in Sales: Integrating Scrum and Kanban
https://businessagility.education/blog/agile-sales-ai-selling-chapter9/
Links Agile frameworks to iterative AI interactions. Encourages structured experimentation and feedback loops.
Month 5: Learn Responsible AI
Goal: Understand how to use AI ethically and responsibly in customer interactions.
Why This Matters: Building trust through ethical AI use is essential for reputation, compliance, and long-term success.
Courses & Resources:
- Responsible AI – Google:
https://grow.google/ai/ - AI in Sales Ethics – Salesforce Guide:
https://www.salesforce.com/resources/articles/ai-in-sales/ - OECD AI Ethics Principles:
https://www.oecd.org/going-digital/ai/principles/
Key Topics:
- AI hallucinations, algorithmic bias, data privacy, customer trust.
Recommended Reading:
- Chapter 3: Customer-Centricity as a Cornerstone of Agile Sales and AI-Assisted Selling
https://businessagility.education/blog/agile-sales-ai-selling-chapter3/
Explains how customer-first thinking underpins ethical AI practices.
- Chapter 4: Human-AI Complementarity in Sales
https://businessagility.education/blog/agile-sales-ai-selling-chapter4/
Frames ethical use of AI as a collaborative force that complements, not replaces, human sales efforts.
Month 6: Build AI Sales Strategy
Goal: Design and lead your team’s long-term AI adoption plan.
Why This Matters: Strategic alignment ensures sustainable value, smoother change management, and scalable outcomes.
Course:
- AI for Business Leaders – edX:
https://www.edx.org/course/ai-for-business-leaders
Key Activities:
- Draft your team’s AI roadmap.
- Identify KPIs: lead conversion, sales cycle time, customer satisfaction.
- Plan team training and pilot phases.
Recommended Reading:
- Chapter 5: The Eight-Step Agile Sales and AI-Assisted Selling Process
https://businessagility.education/blog/agile-sales-ai-selling-chapter5/
Provides a structured sales workflow that AI tools can support and enhance.
This roadmap helps sales leaders not only adopt AI but lead it—with a strong foundation in Agile thinking, ethical responsibility, and strategic implementation. For guidance, reach out to us!