A tailored course, built for your situation
Mastering AI-Driven Sales Execution for Enterprise Account Executives
Build repeatable, insight-led deal momentum that positions you as the trusted advisor in complex sales cycles
$199 one-time
30-day money-back guarantee
Verified against latest insights, updated access provided within 24h
Each order is checked and updated against the latest insights before delivery. That is why access takes up to 24 hours rather than being instant.
12 modules. 12 chapters per module. 144 chapters total.
12 modules, each with 12 chapters (144 chapters total), text-based, plus downloadable templates and a hand-built implementation playbook delivered alongside course access.
Discovery calls that don’t translate into clear next-step momentum
The situation this course is for
In complex enterprise sales, reps often invest hours in discovery only to find the conversation doesn’t create urgency or unlock new stakeholder engagement. Without a structured way to generate and validate strategic insights during customer calls, even strong relationships stall before deal progression.
Who this is for
Enterprise Account Executive selling enterprise software into large, multi-department organizations with long sales cycles and multiple stakeholders
Who this is not for
This course is not for SDRs, inside sales reps, or those selling transactional products with sub-30-day cycles. It’s designed for strategic hunters in complex B2B environments.
What you walk away with
- Generate strategic insights during customer conversations that position you as the advisor, not just the vendor
- Convert discovery calls into documented next-step momentum with executive stakeholders
- Build a personal framework for identifying unspoken business priorities in enterprise accounts
- Accelerate consensus-building across buying committees by surfacing shared pain points
- Create a track record of delivering value in every customer interaction, making renewal and expansion conversations effortless
The 12 modules (with all 144 chapters)
Module 1. The Insight-First Mindset for Enterprise Selling
Shift from feature-led to insight-led selling by mastering the mental model of high-impact account executives who drive strategic conversations.
12 chapters in this module
- Why insight creation beats relationship management in modern enterprise sales
- The psychology of buyer receptivity to unsolicited insights
- How top reps reframe customer challenges before the first call
- Building confidence to lead with insight, not questions
- Mapping your existing strengths to insight generation opportunities
- Identifying the gap between product knowledge and strategic relevance
- Recognizing early signals of insight-ready conversations
- Avoiding the 'expert trap' while positioning as an advisor
- The role of curiosity in structured insight development
- Balancing preparation with adaptability in live calls
- Creating personal insight triggers for common enterprise pain points
- Tracking and refining your insight effectiveness over time
Module 2. Pre-Call Intelligence Gathering
Leverage public and internal signals to enter every customer conversation with a validated hypothesis.
12 chapters in this module
- Extracting strategic insights from earnings call transcripts
- Using job postings to identify upcoming transformation initiatives
- Analyzing leadership changes for shifting priorities
- Mapping technology stack changes through public repositories
- Interpreting recent M&A activity for integration pain points
- Leveraging analyst reports without regurgitating them
- Structuring internal stakeholder insights from past interactions
- Validating hypotheses with cross-functional teams pre-call
- Prioritizing intelligence based on deal stage and risk
- Documenting pre-call insights in a reusable format
- Avoiding over-preparation that kills conversational flow
- Updating intelligence between follow-up meetings
Module 3. Designing Insight-Generating Questions
Craft questions that surface unstated business challenges and create opportunities for strategic positioning.
12 chapters in this module
- Moving beyond 'What keeps you up at night?' to targeted discovery
- The three types of insight-generating questions and when to use them
- Using contrast framing to reveal hidden priorities
- Embedding data points to elevate question credibility
- Sequencing questions for cumulative insight development
- Adapting question style for technical vs executive stakeholders
- Handling defensive responses while maintaining insight flow
- Using silence strategically after high-impact questions
- Transitioning from insight discovery to solution exploration
- Avoiding leading questions that undermine credibility
- Testing question effectiveness across different industries
- Building a personal question bank by deal type
Module 4. Real-Time Insight Validation
Confirm the relevance and accuracy of insights during live customer interactions.
12 chapters in this module
- Using verbal cues to test insight resonance in real time
- Reframing customer responses as validation signals
- The 'mirror and extend' technique for insight confirmation
- Handling disagreement as a path to deeper understanding
- Documenting validation moments during the call
- Adjusting insight depth based on stakeholder seniority
- Using silence to invite expansion on high-value insights
- Balancing validation with forward momentum
- Recognizing when to abandon an insight path
- Linking validated insights to documented business outcomes
- Transitioning from validation to next-step negotiation
- Creating a post-call validation scorecard
Module 5. Post-Call Insight Packaging
Transform raw conversation insights into structured, shareable value for stakeholders.
12 chapters in this module
- The 30-minute post-call insight packaging routine
- Summarizing insights using the 'Challenge-Context-Impact' framework
- Creating stakeholder-specific insight summaries
- Linking insights to measurable business outcomes
- Using visuals to enhance insight clarity without overdesign
- Sharing insights with internal teams to align support
- Archiving insights for long-term account knowledge
- Avoiding information overload in insight delivery
- Timing insight delivery for maximum impact
- Requesting feedback to refine future insight quality
- Measuring stakeholder engagement with your insights
- Building a reputation as the insight source across accounts
Module 6. Insight-Led Follow-Up Sequences
Design outreach that continues the insight conversation between meetings.
12 chapters in this module
- Crafting follow-up emails that extend the insight thread
- Using data snippets to reignite stalled conversations
- Sharing third-party content with personalized insight layers
- Scheduling insight-focused check-ins between formal meetings
- Creating micro-insights for time-crunched stakeholders
- Using LinkedIn engagement to reinforce insight positioning
- Tracking follow-up effectiveness by insight type
- Avoiding over-communication while staying top of mind
- Seeding future insights in current follow-ups
- Adapting tone for executive vs technical audiences
- Building a library of reusable insight templates
- Automating insight reminders without losing personalization
Module 7. Multi-Stakeholder Insight Alignment
Use insights to create alignment across buying committees and accelerate consensus.
12 chapters in this module
- Mapping stakeholder perspectives on a single business challenge
- Creating cross-functional insight summaries
- Positioning insights as shared solutions, not departmental fixes
- Using insights to identify hidden allies in the buying group
- Facilitating insight-driven conversations between stakeholders
- Avoiding insight overload in group settings
- Tailoring insight delivery by stakeholder influence level
- Documenting consensus points from insight discussions
- Using insights to depersonalize decision criteria
- Handling conflicting interpretations of the same insight
- Building coalition support before formal decision meetings
- Measuring stakeholder alignment progress through insight adoption
Module 8. Insight-Driven Negotiation
Leverage validated insights to shape deal terms and create mutual value in negotiations.
12 chapters in this module
- Using insights to reframe pricing discussions
- Linking commercial terms to documented business impact
- Anticipating negotiation pushback with insight preparation
- Creating trade-off scenarios based on stakeholder priorities
- Using third-party benchmarks to support insight-based positions
- Avoiding concession traps while maintaining goodwill
- Documenting negotiation insights for future deals
- Sharing negotiation insights with internal stakeholders
- Timing insight reveals for maximum negotiation impact
- Handling 'we’ve done this before' objections with fresh data
- Building a negotiation playbook from past insight outcomes
- Measuring negotiation success beyond win rate
Module 9. Expanding Within Existing Accounts
Use accumulated insights to identify and unlock expansion opportunities.
12 chapters in this module
- Auditing existing insights for expansion triggers
- Identifying adjacent pain points from current implementations
- Using operational feedback as expansion insight fuel
- Positioning expansions as continuity, not new projects
- Creating cross-departmental expansion narratives
- Leveraging leadership changes for new initiative launches
- Packaging expansion insights for executive audiences
- Timing expansion conversations with budget cycles
- Avoiding expansion fatigue in long-term accounts
- Documenting expansion insight patterns by industry
- Measuring expansion success through insight density
- Building a reputation as the growth partner, not just a vendor
Module 10. Building a Personal Insight Brand
Establish yourself as the go-to advisor through consistent insight delivery.
12 chapters in this module
- Defining your unique insight niche within enterprise sales
- Creating a signature insight framework or model
- Sharing insights internally to build cross-functional credibility
- Presenting insights at internal sales forums
- Documenting insight success stories for performance reviews
- Using insight metrics in career development conversations
- Balancing humility with visibility in insight sharing
- Handling requests for your insights from peers
- Protecting your insight IP while fostering collaboration
- Measuring your growing influence through stakeholder feedback
- Avoiding burnout in continuous insight generation
- Planning long-term insight brand evolution
Module 11. Insight Automation and Scaling
Use templates, tools, and team practices to scale insight quality without sacrificing personalization.
12 chapters in this module
- Creating reusable insight templates by use case
- Using CRM fields to track insight progress
- Building team insight libraries without losing individual voice
- Training SDRs to surface insight opportunities
- Using AI tools to enhance, not replace, insight creation
- Setting insight quality standards for team adoption
- Reviewing insights in team meetings for collective learning
- Onboarding new reps with your insight methodology
- Balancing efficiency with authenticity in scaled insights
- Measuring team insight effectiveness over time
- Adapting frameworks for different product lines
- Creating a feedback loop from customers to insight refinement
Module 12. Sustaining Insight Leadership
Maintain your position as the trusted advisor through continuous learning and adaptation.
12 chapters in this module
- Creating a personal insight refresh routine
- Identifying emerging industry trends for early insight positioning
- Using customer feedback to refine your insight approach
- Balancing new insight development with proven frameworks
- Teaching insight skills without diminishing your value
- Handling increased expectations from being the 'go-to' advisor
- Avoiding insight stagnation in long-tenured accounts
- Measuring long-term impact of your insight leadership
- Planning succession while maintaining influence
- Adapting to organizational changes in your customer base
- Maintaining energy and curiosity over time
- Defining your next-level insight evolution
How this maps to your situation
- Pre-call preparation
- Live customer engagement
- Post-call follow-up
- Long-term account growth
Before vs. after
Before
Spending hours in discovery without creating clear momentum, relying on relationship capital rather than strategic insight to move deals forward.
After
Consistently being the first to surface valuable insights that reframe buyer priorities and accelerate consensus across stakeholder groups.
What's included with your purchase
- 12 modules with 12 chapters each (144 chapters)
- Downloadable templates and worked examples for every module
- Hand-built implementation playbook delivered alongside course access
- 30-day money-back guarantee
Delivery and format
- Course and learning environment access provisioned within 24 hours of purchase
- Hand-built implementation playbook delivered alongside course access
Format: Text-based modules and chapters in the Art of Service learning environment, plus downloadable templates and worked examples for every chapter, plus the hand-built implementation playbook delivered alongside course access.
Time investment: 90 minutes per week for five weeks, with self-paced access to all materials.
If nothing changes
Continuing with traditional discovery approaches risks being seen as a vendor who responds to needs, not one who anticipates them, reducing influence in complex deals and limiting expansion potential.
How this compares to the alternatives
Unlike generic sales training, this course focuses on the specific skill of insight generation in enterprise software selling, with concrete frameworks used by top performers in complex, multi-stakeholder environments.
Frequently asked
Is this course about using AI tools in sales?
No. 'AI-Driven' refers to insight-driven execution. The course focuses on human-generated insights using structured thinking, not artificial intelligence tools.
How is the course structured?
12 modules, each containing 12 chapters (144 chapters total).
Can I apply this to my current deals?
Yes. Each module includes templates and examples designed for immediate application to active accounts.
$199 one-time. 90 minutes per week for five weeks, with self-paced access to all materials..
Within 24 hours your account in the learning environment is provisioned and the tailored implementation playbook is delivered alongside it.
30-day money-back guarantee·
144 chapters·
Hand-built playbook included·
Account access within 24 hours