Mastering Sales: The Digital and AI Toolkit for Success

Integrate AI. Lead sales conversations. Convert opportunities at scale.

Marketing, operations and finance set the stage, but growth begins when something is sold. Organizations succeed through professionals who can sell with clarity, credibility and impact. High-performing sellers are in demand, and this program equips you to become one. Unlike many sales programs that focus narrowly on tactics or leadership models, this program integrates strategy, digital fluency, data-driven insights and the power of artificial intelligence (AI). Today’s top performers don’t just close — they lead, shape and deliver value throughout the sales cycle.

The 10-week Mastering Sales: The Digital and AI Toolkit for Success program is a structured, research-backed journey that empowers professionals with a rigorous, end-to-end approach to selling, from prospecting and client engagement to storytelling, closing and coaching. The program blends proven sales frameworks with advanced digital and AI-enabled tools, delivering world-class expertise, practical fluency and credentialed credibility to equip participants with the structure, confidence and AI-driven skills needed to accelerate performance, drive measurable outcomes and thrive in a volatile, technology-driven sales environment. Participants will gain:

  • Proven techniques and frameworks for effective selling, based on Kellogg Executive Education’s research and industry practice
  • A ready-to-use personalized sales toolkit with more than 30 tools
  • Practical strategies to build confidence, structure and discipline in every sales interaction
  • A set of tested digital and AI tools and insights to enhance sales efficiency
  • Leadership insights for coaching teams, building high-performing sales engines and driving organizational growth
  • A roadmap for developing lasting, measurable sales habits

Incentives available for groups and teams of four or more attending open enrollment programs. Learn more


Online Programs

Craig Wortmann / Academic Director

Personal Consultation

Please contact us to schedule an advising session

Who Should Attend

  • Early-career sales professionals seeking credibility and improved closing rates with a repeatable sales toolkit that turns activity into measurable conversions
  • Sales leaders and managers aiming to break performance plateaus, modernize processes, learn digital and AI-powered tools and scale results
  • Entrepreneurs and founders looking to sharpen pitches, build structured sales engines and confidently acquire and grow customers
  • Business development professionals and career shifters who need structured and proven sales techniques and engagement skills to pitch, close deals and build credibility
  • Leaders and professionals outside sales who want to sell ideas, influence stakeholders and drive impact with structured strategies

Key Benefits

By the end of this program, participants will be able to:

  • Assess their sales mindset, habits and performance using proven techniques
  • Analyze team performance using specific leadership tools and behaviors
  • Create persuasive sales stories using client context, buyer psychology and data insights
  • Apply digital tools and AI insights to improve sales preparation and engagement
  • Identify strategies to build trust and credibility in professional networking and sales
  • Build a personalized sales toolkit with tools for each step of the buyer’s journey
  • Develop a repeatable process for self-coaching and peer coaching

Program Content

Module 1: Sales Mastery Through Deliberate Practice

  • Assess how knowledge, skill and discipline work together to influence performance and mindset
  • Define personal deliberate practice techniques
  • Write a sales goal using the SMARTTSS (Specific, Measurable, Actions, Realistic, Time-Bound, Tools, Support, Stop) process
  • Plan the steps to implement and support your sales goal
  • Apply the 2X2 feedback model tool in simulated or real coaching interactions
  • Construct a personalized system for performance improvement using the five-part scaffold

Module 2: Run Fantastic Sales Meetings: Differentiate Yourself by How You Run Meetings

  • Discuss AI prompts that assist in building meeting agendas
  • Determine the difference between surface-level and connection questions
  • Execute pivots that maintain meeting momentum and reinforce meeting value
  • Discuss personalized closing strategies and post-meeting communication that reinforce your professional brand
  • Plan meeting strategy changes for virtual settings
  • Construct a complete meeting plan, from preparation through follow-up

Module 3: Practice Proactive Pursuit With Lead Generation and Cold Calling

  • Discuss proactive pursuits to define your personal pursuit checklist
  • Build a personalized preparatory plan using a tailored proactive pursuit checklist
  • Develop a prospecting script
  • Apply the four gears of a networking conversation
  • Construct a networking plan and an outreach plan for current and future networking

Module 4: Sales Qualification and Objection Handling

  • Discuss the role of connection and discovery questions in sales
  • Assess buyer readiness with qualifying questions
  • Design impact questions tailored to specific client contexts
  • Formulate layered questions that drive deeper conversations
  • Execute all five steps of objection handling
  • Integrate active listening and objection handling tools in a full client scenario

Module 5: Storytelling in Sales

  • Discuss how storytelling influences sales conversations
  • Curate stories from personal and professional experiences to fit various clients
  • Write stories that align with the four storytelling categories (success, failure, fun and legend) using the Story Canvas tool
  • Use AI to revise a constructed story to improve clarity, length and emotional impact
  • Build a story matrix template with the What’s Your Story and Story Canvas tools

Module 6: Present With Panache: Sales Presentations That Persuade

  • Design a presentation plan using the six preparation disciplines: goals, audience, structure, pro tricks, opening & closing and practice
  • Redesign an existing slide deck using the three visual impact tools: hip pocket frameworks, art and slides
  • Apply the three V’s of performance — visual, vocal and verbal — to refine presentation delivery

Module 7: Team for Impact With Elite Team Selling Strategies

  • Discuss the role of teams in meetings
  • Apply preparation strategies to team meetings
  • Apply the process leader and perspective leader roles to a team meeting
  • Apply the six rules of engagement to plan team behavior in a meeting

Module 8: Closing Sales Deals

  • Discuss strategies for getting a deal unstuck
  • Match deal-stalling factors to deal-unstalling strategies
  • Create a closing strategy
  • Create a reusable and personalized Get Deals Unstuck tool

Module 9: Bounce Back Better by Building Sales Resilience

  • Document your weekly habits in nine energy categories
  • Plan targeted actions that enhance positive energy sources and address areas of depletion
  • Apply the bounce stage to a setback
  • Create a plan with actions that provide forward motion and momentum
  • Create a personalized sales-focused resilience plan that applies the Bounce Back Better framework

Module 10: Personal Branding for Sales Professionals

  • Analyze how your personal brand affects your career
  • Define the building blocks of your personal brand
  • Create a plan to deliver and scale your personal brand online
  • Identify values within your personal brand that resonate with your clients
  • Match the sales tools to a cohesive personal brand strategy

Faculty

Craig Wortmann - Academic Director; Clinical Professor of Marketing; Executive Director, Kellogg Sales Institute

Upcoming Sessions

February 12 – April 30, 2026

Start: February 19 at 12:00 AM

End: April 30 at 12:00 AM


Accepting registrations through February 18

$2,775

April 16 – July 2, 2026

Start: April 16 at 12:00 AM

End: July 2 at 12:00 AM


Accepting registrations through April 22

$2,775

Kellogg School of Management

Kellogg Executive Education
2211 Campus Drive, Evanston, IL 60208
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847.467.6018