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How Do I AI?

The CXO Masterclass to Close the AI Confidence Gap

If you're a CXO, the pressure is real. You're busy, accountable, and tired of experimenting.

4+ hours. 12 senior peers. Walk out with at least one clear, deployable AI opportunity and the next-steps you'll actually use.

Reserve Short Pump — Super Early Bird $555 Reserve Midlothian — Super Early Bird $555

September 23 or 24, 2025 • Richmond, VA • Two locations • Maximum 12 Participants Per Session

Seats strictly limited to 12 executives per session • Super Early Bird ends Sept 15 • Corporate invoice available • 30-day satisfaction guarantee

Super Early Bird: $555 (55.5% off) — ends Sept 15 • Early Bird: $898 (Sept 16–19) • Full Price: $1,247 starting Sept 20

Why this matters

Executives tell me the same thing: they feel behind on AI, swamped with vendor noise, and anxious about making the wrong investment. They don't need another vendor demo — they need clarity, a practical next play, and a peer-soundboard to stop guessing.

This masterclass is designed for senior leaders who want to lead, not chase. We cut through the noise, translate AI capabilities into business actions, and create a clear path you can test within 30 days — no pilot theater, no vague "we'll get back to you."

If you want tactical, executive-grade guidance (not a marketing pitch), this is how you get it.

The Executive AI Gap is Real

Your Marketing Manager...

Creates compelling presentations in 15 minutes that used to take 3 hours.

Generates market research reports in 30 minutes instead of 2 days.

Spots patterns commonly missed in spreadsheets using AI-powered analysis.

Automates routine tasks that consume hours of your week.

Your Sales Manager...

Uses AI to analyze customer conversations and identify buying signals you're missing.

Generates personalized proposals in minutes using AI-powered templates.

Predicts which leads will close using AI scoring models.

Automates follow-up sequences that increase conversion rates by 40%.

Your HR Director...

Screens resumes in seconds using AI to identify top candidates instantly.

Creates job descriptions that attract better applicants using AI optimization.

Analyzes employee sentiment from surveys using AI-powered insights.

Automates onboarding workflows that reduce time-to-productivity by weeks.

Your Customer Satisfaction Supervisor...

Analyzes customer feedback patterns using AI to predict churn before it happens.

Generates response templates that resolve issues 60% faster.

Identifies upsell opportunities from support conversations automatically.

Creates satisfaction surveys that get 3x higher response rates.

Meanwhile, Are You Still...

Spending entire weekends preparing board presentations?

Manually researching competitors and market trends?

Struggling with email overload and calendar chaos?

Feeling behind on AI while your team gets smarter?

The uncomfortable truth: Your team is becoming more AI-literate than you are.

And that gap widens every day you wait.

The Hidden Costs of AI Illiteracy

Strategic Blindness

You're making million-dollar decisions without understanding how AI impacts your industry, competitors, and customers.

Productivity Plateau

While AI-savvy executives save 5+ hours weekly, you're stuck in manual processes that drain your strategic thinking time.

Competitive Disadvantage

Your competitors are using AI for market intelligence, customer insights, and operational efficiency. You're not.

Team Credibility Gap

How can you lead AI initiatives when you lack hands-on experience with AI tools or stumble through it trying to figure AI tools out on your own?

The AI Revolution Isn't Coming. It's Here.

Every day you delay AI mastery is a day your competitive position weakens.

What you'll walk away with

AI Training Designed Specifically for Mid-Market CXOs

Deployable AI Opportunity

A prioritized, deployable AI opportunity you can pilot within 30 days (you'll identify and map this during the session).

30-60-90 Adoption Canvas

A completed adoption canvas created in-session with my guidance and the group's feedback.

Clear Success Metrics

A clear set of success metrics, owners, and what must be true for the pilot to succeed.

Executive Confidence

Confidence and language to brief your board, stakeholders, or budget owner the next business day.

These are outcomes we'll build during the masterclass — you leave with clarity, not vague next-steps.

Session Flow (4+ hours)

Each session is structured to maximize executive time and group learning. Demos are presenter-led; the workshop work is done in peer cohorts with your direct input.

Doors / Networking

30 minutes

Arrival, coffee, peer introductions

The State of AI & Executive Framing

45 minutes

What leaders must know now; core mistakes to avoid

CXO AI Confidence Clinic

40 minutes

Rapid diagnostics to map your top 1–2 opportunities

Present & Align

30 minutes

Group feedback and prioritization of topical demos

Demonstration

25 minutes

Presenter-led, deep demo of a CXO-grade AI workflow (how it runs, KPIs, failure modes)

Roadmap Workshop

45 minutes

Build your 30-60-90 adoption canvas with guided templates (you'll leave with an executable plan)

Commit & CTA

15 minutes

Fast-win checklist, next steps, optional VIP follow-up signup ($200)

Networking + Q&A

30 minutes

Follow-up conversations, invites to cohort community

How this session runs — clear expectations

Presenter-Led Demos

The demos are presenter-led, deeply technical, and designed to show exactly how an executive-grade AI workflow behaves in production.

Your Data Stays Private

You won't be asked to hand over proprietary data during demos — we use anonymized/representative examples.

Live Coaching

You will be working on your own 30-60-90 canvas during the session with my direct coaching and peer feedback.

Post-Event Support

60-day post-workshop cohort support to help you implement what you learn. Private event follow-up is available as paid advisory.

Your Investment in AI Mastery

Register Early to Save

Super Early Bird: $555 (55.5% off) thru Sept 15
Early Bird: $898 (28% off) Sept 16–19
Full Price: $1,247 starting Sept 20

What's Included:

  • 4+ hour intensive AI mastery workshop
  • Comprehensive AI tools resource guide
  • Strategic Planning: 30, 90, and 180-day implementation roadmap
  • Access to cohort community for peer follow-up
  • Exclusive alumni network access
  • Premium refreshments and networking
Register Now

30-day money-back guarantee.

Choose Your Session

Short Pump Session

Monday, September 23, 2025
1:00 PM - 5:30 PM
Short Pump Location
Richmond, VA
Attend Short Pump Masterclass

Midlothian Session

Tuesday, September 24, 2025
8:00 AM - 12:30 PM
Midlothian Location
Richmond, VA
Attend Midlothian Masterclass

Risk-Reversal

30-Day Satisfaction Guarantee

If you don't leave the workshop with at least one clear, deployable AI opportunity and the next steps to run it within 30 days, you may attend the next cohort free or request a full refund.

An Illustrative Outcome

A mid-market services company identified a single quoting workflow as their top opportunity. After the masterclass they piloted an automated draft proposal workflow in 21 days, reducing proposal assembly time by ~70% and improving win-rate clarity.

This is an illustrative scenario to show the type of outcome this workshop is designed to produce.

Why Jim Washok is Your Guide

AI Implementation Expert

Creator of the "How Do I AI?" methodology specifically designed for mid-market executives.

Real-World Experience

Founder of Aigentiv™ AI automation consulting and author of the "How Do I AI?" book series.

Executive Network

Active in Richmond's business community for 30 years with deep understanding of mid-market company challenges and constraints.

Proven Track Record

Successfully guided dozens of executives and teams through technological transformations with measurable productivity improvements and strategic advantages.

"I've tested 100+ AI tools so you don't have to."

This masterclass represents 2+ years of systematic testing focused on tools that provide immediate ROI for busy executives.

Frequently Asked Questions

Is this event right for me?

This masterclass is designed for C-level executives and direct reports responsible for AI decisions and budgets. If you sit at the strategy table and must answer "what do we do about AI," this session is for you.

What will I leave with?

You'll leave with at least one prioritized, deployable AI opportunity and a completed 30-60-90 adoption canvas created during the masterclass with my guidance.

Will we work on our company's confidential data in the session?

No. Live demos use anonymized or representative data. You may bring descriptors of your opportunity for group coaching, but no one is asked to expose proprietary data.

Are demos hands-on? Will I need to install tools?

Demos are presenter-led and detailed; you will not need to install software during the session.

What support is included post-session?

The session includes access to the cohort community for peer follow-up. Deeper advisory or implementation support is available as a paid service.

What is the VIP add-on?

The VIP add-on is a $200 option that reserves a 60-minute private strategy follow-up call to be scheduled after the event.

How many seats are available?

We cap each session at 12 seats to preserve a high-quality, peer-driven conversation.

Do you provide an invoice for company reimbursement?

Yes. Use the Square "Request Invoice / PO" option or contact us and we'll issue a corporate invoice.

Ready to Close the AI Confidence Gap?

Limited seats remain. Choose your session and secure your spot.

Reserve Short Pump Session Reserve Midlothian Session
Super Early Bird: $555 (55.5% off) — ends Sept 15 • Early Bird: $898 (28% off) Sept 16–19 • Full Price: $1,247 starting Sept 20