Ryan Staley

Whale Boss

A New Era of Revenue Leadership with AI 

Our mission is to empower 1 million Go-To-Market Executives to achieve superhuman potential through AI transformation. We help revenue leaders escape the operational grind, multiply team capacity, and accelerate revenue—all while working less and achieving more.  This can be done in less than 2 months with AI education activation, innovation and automation. 

🚀 AI as “Liberating Intelligence”
AI isn’t just a tool; it’s “liberating intelligence.” This shift redefines productivity, ambition, and control, enabling leaders and teams to reach impact levels once unimaginable—all without expanding headcount. This approach resonates with executives who seek freedom in both business and life, making AI a true transformational ally.

🔹 From Productivity to “Capacity Multiplication”
Today’s leaders don’t need mere productivity boosts; they need to multiply team capacity. AI agents, workflows, and assistants go beyond task completion, amplifying output so teams perform at peak levels without constant oversight—giving leaders time for moves that truly matter.

🌄 Liberating Leaders to Live the Dream, Not Chase It
With AI, revenue leaders can grow without the endless grind. Freed from perpetual hiring and micromanagement, you gain the power to step back, letting a self-sustaining revenue engine deliver results while you live the life you envision.

💡 AI for “Decision Density”: Minimize Decisions, Maximize Impact
AI reduces the mental load by taking on real-time tactical choices, freeing leaders to focus on fewer, high-impact decisions. It turns decision-making from a draining process into strategic momentum.

I’m passionate about helping revenue leaders not just transform their teams but redefine growth itself. 

Together, we’re building a future where AI isn’t just helpful—it’s liberating.

Founder and CEO

The Scale Up Show

I deconstruct how the top SAAS CEOs in the world grow their companies repeatedly and predictably.  

This show has featured Startup and Billion Dollar Founders, Best Selling Authors, and the World’s Top Sales and Marketing Experts like Terry Jones (Founder of Travelocity and Chairman of Kayak),  Andrew Gazdecki (Founder of Microacquire), Harpaul Sambhi (Founder of Magical with a previous exit to Linkedin) and many more.

Podcast Host

Gartner

Gartner Peer Community is Gartner's new, next-generation online destination designed to increase value through timely answers and meaningful peer connections.

Ryan Staley has been invited as a Founding Peer Community Ambassador to contribute insights on B2B sales, sales leadership, and enterprise go-to-market among other topics. Gartner Peer Community is Gartner's new, next-generation online destination designed to increase value through timely answers and meaningful peer connections. 

Ryan Staley has been invited as a Founding Peer Community Ambassador to contribute insights on B2B sales, AI for Sales, sales leadership, and enterprise go-to-market among other topics.

Peer Ambassador: B2B Sales, Sales Leadership & Enterprise GTM

Pavilion

As an instructor, I have taught over 800 VPs of Sales and CROs my proprietary methods for Enterprise Sales and Enterprise GTM.  

Pavilion is a private, invitation-only community of sales and marketing executives at growth-focused companies.

Executive Member,  Former CRO & Enterprise Sales GTM School Lecturer

RevGenius

RevGenius is a think tank networking group of revenue-generating sales and marketing professionals brought together to learn, share, support, and grow with each other. You can consider us your alt work family!

Founding Member

Sales Hacker, Inc.

Flex Technology Group

Specific examples of value delivered for net new customers listed below;

-Leading Retail Company ($15 billion in annual revenue)-$3.6 Million in expense reduction over the life of contract, 15 FTE's freed up for core IT initiatives and 300% improvement in SLA's

-High Growth Manufacturer ($9 Billion in annual revenue)-$1.8 Million in expense reduction over the life of contract, 300% improvement in SLA's and 15 vendors consolidated into 1.

-Leading National Healthcare Provider ($2.5 Billion in annual revenue)- $3.6 Million in expense reduction over the life of contract, SLA improvement of 400% and  Co-authored enhanced asset management strategy

-Top Professional Services Organization ($3 Billion in annual revenue)- 60% expense reduction, SLA improvement of 300% and asset management visibility provided across 900 locations

Vice President of Strategic Accounts

Director of Strategic Accounts

Director of Sales, Midwest Region

Regional Sales Manager

Pitney Bowes (Managed Services)

Managed Print Services Enterprise Sales (Midwest Region) for Fortune 500 and Fortune 1000 organizations.

Senior Sales Consultant

Antenna Software

Antenna is a high growth early stage Software company that provides a SaaS based applications and mobility platforms that allow Fortune 500 companies to mobilize their enterprise applications.

• Responsible for Direct and Channel Sales for the Region
• Developed new Partner/Customer relationships for an
   undeveloped territory

Director of Sales Midwest Region

Sold customized Managed Print Services and software solutions to Fortune 500 and Fortune 1000 C-level executives. 

• President's Club Winner 2004, 2005, 2006, and 2007
• Grew a new market that had no customers into the one of
   the most profitable sales markets.

I help Chief Revenue Officers & Sales Professionals Leverage AI to work 10 hours less weekly and 2x performance. Follow for cutting-edge cheat codes, prompts, and workflows🎙Scale Up Show Host🔥$0→$30M ARR in 5.5 yrs

Over the last decade, I’ve grown a division from 0-$30M ARR with 4 Sales People and have upskilled over 1,600 GTM executives on AI, Enterprise Sales and GTM Strategy  .

My mission is to inspire 1 million Go To Market Executives to work less and sell more through becoming Superhuman with Artificial Intelligence.

I help revenue leaders transform their teams by acquiring AI skills to escape the operational grind, and accelerate topline revenue.

I’m the founder of Whale Boss and The Scale Up Show.

My portfolio:

→ I’m the Founder of Whale Boss, an AI Sales & Marketing consulting and skill transformation company
→ I’m the Founder of the Scale Up Show, Top 1% Global Podcast
→ I teach Executives, Sales & Marketing teams to implement tools like ChatGPT, Copilot, Claude, etc.   
→ I provide Chief AI Officer Advisory services for human capital.  


My results:

→0-$30M without funding, marketing or SDRs with only 4 Sales people
→Identified and implemented over 500 AI use cases (internally and externally)
→Taught over 800 CROs proprietary selling strategy and tactical execution
→Consulted over 40 Technology companies on custom revenue growth strategies.  
→Voted as a TOP global AI thought leader, Gartner Ambassador & Sales Assembly thought leader. 


If you want to learn more on how to become Superhuman, you can join my newsletter.
⇒ https://superhumanrevenue.beehiiv.com/


If you want to explore AI skill transformation for your organization or Team, apply for an AI Consult.  
=> https://calendly.com/ryanstaleywss/introductory-call-with-ryan-staley-from-whale-boss


Youtube- https://www.youtube.com/channel/UCFGndSHN4KkE89kUP74U7Qg

Podcast-https://ryanstaley.io/podcast/

X-https://x.com/Ryan_Staley1

Just wrapped another CRO roundtable last week in Chicago.
Stellar group. 

The conversation was unfiltered, insightful, and honestly pretty intense.


Here's what's actually keeping revenue leaders up at night:
1. Misaligned Expectations with the Board

Targets keep rising while market conditions keep deteriorating.
The fear isn't about working harder—it's about being held to numbers that completely ignore reality. How do you prove success when the metrics everyone's watching don't actually reflect what's happening in the business?




2. The AI Shock + Everything Changing at Once

Technology, GTM motions, buyer behavior, AI capabilities, org structure—all shifting simultaneously.

Without a clear framework, every change feels like risk instead of opportunity.

The real issue? Separating AI hype from actual impact before you waste time and credibility chasing vaporware.



3. Tech Stack Evolution vs. Human Adoption

The stack evolves faster than behavior, process, and culture ever will.
You've got increasingly sophisticated tools and data while revenue outcomes lag miles behind. The gap isn't closing—it's widening.



4. Margin and Pricing Pressure
Competitors are cutting price aggressively, creating massive pressure to follow.

Leaders are stuck protecting brand value and economics while discount pressure builds every single quarter. Race to the bottom or hold the line?



5. Comp Plans, Metrics, and Governance

Designing effective comp plans is brutal when GTM motions shift and turnover stays high.

Which metrics actually matter versus which ones just look good in board decks? How do you create incentive alignment when ownership across GTM is still fuzzy?


6. Cross-Functional GTM at Scale

Scaling Sales, CS, Product, and Marketing requires a unified operating model.

At hyper-scale, collaboration collapses into silos. Everyone wants a single customer journey—until it requires giving up their kingdom.



7. Talent and Ramp Reality
Ramping and retaining top reps in this environment is harder than ever.
The challenge? Distinguishing true high performers from strong interviewers. And balancing L&D investment against the reality of high turnover.



8. CRO Role Clarity and Org Design

When do you actually need a CRO versus a Head of Sales?

The difference is structural and political, not just a title change. Position the role wrong in the leadership architecture and it becomes friction instead of leverage.

Which of these 8 is hitting hardest for you right now?

Huge thank you to Warren Zenna to hosting

Also it was an amazing group and great to see Daniel Frailey Guy Rubin Greg Leos Howard Diamond Elio Narciso Marc Sabatini Jason A Wankovsky  James Kaikis

Founder & CEO, Whale Boss | Demystifying AI Agents | Helping revenue leaders 2x team results through AI Led GTM | Trusted by PE-backed SaaS | Transform your team in 60 days

I've learned more about life than I ever had this year, so I wrote down 20 things I know at 48 that I wish I knew at 28.

This is straight from the heart.



1. Working as an employee trains you to ask for permission. Working as a founder trains you to take action because your life depends on it.

2. Every 10 years, there was a technology evolution that I ignored because I was too busy. I missed the internet explosion (in early 2000), Mobile and Social (2008-2011), and Bitcoin (2015 at $230 vs. $100K+ now). I am not doing the same with AI.

3. I used to be massively afraid of failing; things had to be perfect. However, my most painful failures pushed me to do things that I never would have dreamed of.

4. Without some separation of work from relationships, health, and fun, life can seem empty when work doesn’t meet your expectations.

5. The biggest risk to an achiever with a hard work ethic is burnout. Recovery (in whatever form you need) is sometimes better than working an extra 5-10 hours weekly.

6. It’s better to have 2-3 amazingly loyal friends you can count on rather than 15 that are mediocre.

7. Lack of focus on your own can be just as paralyzing as a job you hate.

8. You can learn anything, but you don’t have time to learn everything.

9. Nobody has all the answers, and the fastest way to evolve is to do rather than passively watching LinkedIn, YouTube, taking courses, reading books, etc.

10. If you don’t make a plan for your life, you will live within the confines of someone else’s plan.

11. I appreciate my parents way more now because I have to parent and realize how hard they worked to give me an amazing life.

12. If you help others unselfishly, it always comes back to you, whether it be a day, a month, or years later.

13. God, the universe, or whatever you believe in will often guide you in simple ways if you just ask for it and allow for grace.

14. Daily focus on gratitude will transform who you are and your view of the world if you make space for it.

15. Alcohol doesn’t need to be a big part of your life to fit into social situations.

16. Your biggest breakthroughs will happen unexpectedly after you relentlessly work to improve through massive action.

17. Every person on this earth has a unique path that no one else has ever had. Take that experience and do the best you can with your unique gifts.

18. Focus is the biggest barrier you will face when AI makes custom knowledge free.

19. Your children will bring you joy that you can’t comprehend at 28.

20. If you take care of yourself physically, mentally and psychologically you won’t feel old.

That's all for now! I am sure more will come to me for a post 2 on this:)

Every company says they're "doing AI." Few are actually seeing results.

Why? They're treating AI like a 2-year R&D project when it should be a 60-day transformation.

━━━━━━━━━━━━━━━━━

THE TYPICAL APPROACH (That Fails):

Months 1-6: Form committees, evaluate vendors
Months 7-12: Run pilots, "gather learnings"
Months 13-24: More pilots, maybe deploy something

Result: $500K spent, 2 years wasted, no impact

━━━━━━━━━━━━━━━━━

THE 60-DAY APPROACH (That Works):

Weeks 1-2: Pick ONE process, automate it, show immediate results
Weeks 3-4: Expand to 3 more processes, train team
Weeks 5-6: Connect to existing systems, measure everything
Weeks 7-8: Deploy revenue-generating applications

Result: $35K investment, 60 days, measurable ROI

━━━━━━━━━━━━━━━━━

WHY MOST FAIL:

- Analysis paralysis: Studying instead of using
 Boiling the ocean: Too many initiatives at once
 No quick wins: Team loses interest

━━━━━━━━━━━━━━━━━

THE ANTI-HYPE RULES:

1. Ship to production in Week 1 (not pilots)
2. One process at a time
3. Measure hours saved, not AI maturity
4. If it takes >60 days, you're doing it wrong

━━━━━━━━━━━━━━━━━

REAL EXAMPLE: $300M ARR Company

Day 1: Identified pain point (meeting prep), trained 30 reps
Day 14: 4.5 hrs/rep/week saved
Day 30: Expanded to email, research, CRM
Day 60: 300 hrs/week saved, pipeline up 20%, win rate up 6%

Investment: $35K | ROI: 400%+ in 90 days

━━━━━━━━━━━━━━━━━

THE BOTTOM LINE:

Stop planning AI. Start shipping AI.

60 days. Not 2 years.

━━━━━━━━━━━━━━━━━

Is your AI transformation taking too long?

whale-boss

li_at

JSESSIONID

Talks about #gtm, #sales, #chatgpt, #entrepreneurship, and #artificialintelligence

95% of executives are missing GPT-5's true potential.


WHEN I see people using GPT-5 like ChatGPT 4o...

WHAT I really see is millions in missed opportunities.

I just cracked GPT-5's three game-changing features that separate winners from wannabes:

Feature #1: 

The "Rival Intelligence" Framework ⚡ → Single prompt = 5 expert perspectives instantly → Customer + Shareholder + Employee + Competitor + Regulator analysis → I fed it Shopify's leaked AI memo - got strategic recommendations in 30 seconds


Feature #2: 

Your Data = Your Competitive Moat 🎯 → Connect HubSpot, Google Drive, Box directly to GPT-5 → Extract client dreams, fears, frustrations from 90 days of data → Generate personalized scripts + strategies from YOUR actual conversations


Feature #3: 

Agentic Workflow Mastery 🚀 → "Single-pass" prompting = no more back-and-forth → Deep market recon + strategy + execution in ONE prompt → Think strategic consulting team, not search engine


HOW to implement today:

Challenge Current Thinking: Use rival perspectives on your biggest decision

Mine Your Gold: Connect your CRM and ask for pattern analysis

Go Agentic: Create workflows that think 5 steps ahead

I'VE tested this with 2,500+ executives.

The results? Superhuman decision-making in seconds.

Most leaders are playing checkers with AI.

Smart ones are playing 4D chess.

Which game are you playing? 👇

Download The Ultimate GPT-5 Go-To-Market Prompting Toolkit: 
Profile link

Gpt 5 not Gpt 4

4 hours of GTM work → 15 minutes. Same outcome. ~2x quality.
Here’s what one AI workflow did for me last week:


The workflow (all in a single thread):

-Follow-up email with clear actions for the prospect.
-Deal coaching on how qualified it was through MEDDICC-style criteria.
-Next best actions based on my notes and pipeline context.
-Full proposal in my branding, with all the details tightened up.


🔥 Total time: ~15 minutes.

Old way: 3–4 hours of deep work.

Quality: better structure, cleaner narrative, stronger visuals than if I white-knuckled it myself.


This is why I think we need a new standard for AI ROI.

Not “I paid $100 for licenses, where’s my $40K?”


But:
Hours collapsed per workflow
Quality lift vs manual
Capacity unlocked per rep per week


The beautiful thing about it was that it wasn’t a complex Agent build.

It was a stacked workflow of 2 tools.


Those are the leading indicators that create the compounding ROI later.


Question for you: Where in your GTM motion would a “4 hours → 15 minutes” shift change the quarter?

$1.5 Trillion invested in AI in 2025.

90% of enterprises see ZERO impact on EBIT.

Let me say that again:

90% see no bottom-line impact.

Despite trillions invested.

Here's why (and what to do differently):

━━━━━━━━━━━━━━━━━

**THE PARADOX:**

What's happening:
→ 92% plan to increase AI investment
→ 70%+ have integrated AI into at least one function
→ AI is everywhere in the enterprise

What's NOT happening:
→ Revenue growth from AI
→ Profit margin improvement
→ Bottom-line impact

The question everyone's avoiding:

Where's the ROI?

━━━━━━━━━━━━━━━━━

THE 3 FAILURE MODES:

1. Pilot Purgatory

Companies run 47 AI pilots.

None reach production.

Why? They're always "testing."

2. The Integration Gap

AI tools purchased.

Can't access company data.

Sit unused. Money wasted.

3. Time to Value Problem

Implementation takes 6+ months.

People lose interest.

Tools abandoned before impact.

━━━━━━━━━━━━━━━━━

REAL DATA FROM MY CLIENTS:

Companies that SEE ROI:
→ Implementation in <60 days
→ Focus on 2-3 use cases max
→ Measure impact weekly
→ Result: 2x productivity, 10-20% revenue lift

Companies that DON'T see ROI:
→ Implementation in 6+ months
→ Try to boil the ocean (10+ use cases)
→ Measure impact quarterly (or never)
→ Result: Wasted investment, team burnout

━━━━━━━━━━━━━━━━━

THE "TIME TO VALUE" FRAMEWORK:

If people don't see results in 2 weeks, they quit.

Here's how to beat that:

Week 1:
→ Pick ONE painful process
→ Implement ONE AI solution
→ Show immediate time savings

**Week 2:**
→ Quantify the impact
→ Share wins widely
→ Build momentum

**Week 3-4:**
→ Scale what worked
→ Add ONE more use case
→ Repeat

**Result:**
→ Fast wins compound
→ Adoption spreads organically
→ Bottom-line impact in 90 days (not never)

━━━━━━━━━━━━━━━━━

**THE BOTTOM LINE:**

The $1.5 Trillion AI investment paradox isn't about bad technology.

It's about bad implementation.

**Fix these 3 things:**

1. Get out of pilot purgatory (ship to production)
2. Solve integration FIRST (data access is everything)
3. Deliver value in weeks, not quarters

Do that?

You'll be in the 10% that actually sees ROI.

━━━━━━━━━━━━━━━━━

Are you seeing AI ROI at your company?

Or are you stuck in pilot purgatory?

Comment below. 👇

It took me 10 years to learn how to qualify deals effectively.

AI can do it in 3 questions.

With 95% accuracy.

Here's how:

━━━━━━━━━━━━━━━━━

THE OLD WAY:

Years 1-3: Learn your product inside out
Years 4-6: Understand your market deeply
Years 7-10: Master pattern recognition

Result: Expert intuition about which deals will close

Time investment: 10 years

━━━━━━━━━━━━━━━━━

THE NEW WAY:

3 Questions to AI:

Question 1:
"Based on our last 100 won deals, what are the top 5 characteristics that predict a win?"

Question 2:
"Analyze this new opportunity: [paste deal details]. How does it compare to our ideal customer profile based on actual wins?"

Question 3:
"What are the 3 biggest red flags from our lost deals that appear in this opportunity?"

Result: Data-driven qualification in 5 minutes

Accuracy: 95%+ (tested against actual outcomes)

━━━━━━━━━━━━━━━━━

WHY THIS WORKS:

Human intuition:
→ Based on maybe 50-100 deals you remember
→ Influenced by recency bias
→ Misses subtle patterns

AI analysis:
→ Based on ALL your historical deals
→ No bias, just patterns
→ Sees correlations humans miss

━━━━━━━━━━━━━━━━━

REAL EXAMPLE:

Sales rep brought me a "perfect" opportunity:

Human intuition said:
→ Great fit company
→ Budget approved
→ Timeline makes sense
→ "This is closing for sure"

AI analysis revealed:
→ Company size matches lost deals (not won deals)
→ Title of decision maker is different than usual champions
→ Deal velocity is 2x slower than typical wins
→ Missing 3 key buying triggers from successful deals

Recommendation: Deprioritize

Outcome: Deal stalled at 120 days, never closed

AI was right. Human intuition was wrong.

Every company says they're "doing AI." Few are actually seeing results.

Why? They're treating AI like a 2-year R&D project when it should be a 60-day transformation.

━━━━━━━━━━━━━━━━━

THE TYPICAL APPROACH (That Fails):

Months 1-6: Form committees, evaluate vendors
Months 7-12: Run pilots, "gather learnings"
Months 13-24: More pilots, maybe deploy something

Result: $500K spent, 2 years wasted, no impact

━━━━━━━━━━━━━━━━━

THE 60-DAY APPROACH (That Works):

Weeks 1-2: Pick ONE process, automate it, show immediate results
Weeks 3-4: Expand to 3 more processes, train team
Weeks 5-6: Connect to existing systems, measure everything
Weeks 7-8: Deploy revenue-generating applications

Result: $35K investment, 60 days, measurable ROI
━━━━━━━━━━━━━━━━━

WHY MOST FAIL:

- Analysis paralysis: Studying instead of using
 Boiling the ocean: Too many initiatives at once
 No quick wins: Team loses interest
━━━━━━━━━━━━━━━━━

THE ANTI-HYPE RULES:
1. Ship to production in Week 1 (not pilots)
2. One process at a time
3. Measure hours saved, not AI maturity
4. If it takes >60 days, you're doing it wrong
━━━━━━━━━━━━━━━━━

It-took-me-10-years-to-learn-how-to-qualify-deals-effectively.pdf

Google Just Opened a 90-Day Competitive Window
Most businesses will miss it entirely.


I've watched this pattern for 3 years across 2,500+ executives:


Early movers capture 12-18 months of market advantage. Hesitators spend years catching up.


It's happening again. Right now.


The Tests That Matter
I spent 48 hours stress-testing Gemini 3 on real business scenarios:
Sales Prep: 

3 hours → 10 minutes (same quality, better output) 

Website Build: 3 weeks → 63 seconds (921 lines of functional code) 
Analytics Dashboard: 2 weeks → minutes (production-ready)

Zero exaggeration. I recorded everything.


The Business Math

Your team of 50 can now perform like 60-75. 
Your content velocity increases 5-10×. 
Your decision speed accelerates 10-20×.


Same headcount. Same budget. Different results.


Your 3-Stage Play
Days 1-30: Individual team members test on daily tasks (10-20% time savings) 
Days 31-60: Scale across departments (30-40% capacity increase) 
Days 61-90: AI-first workflows deployed (50%+ multiplication)

NOTE: After 90 days, this becomes table stakes. The advantage window closes.

The Split Happening Now
Group A: Testing this week, implementing next week, scaling by month-end Group B: "Monitoring the situation"
Group A dominates their markets by Q2 2025. Group B explains market share losses to their boards.


Your 7-Day Action Plan


Day 1-2: Identify your highest-value, most time-intensive process 
Day 3-4: Assign your best operator to test Gemini 3 
Day 5: Document time/capacity savings Day 6-7: Scale or course-correct

The Question


You won't get disrupted by AI.

You'll get disrupted by competitors using AI better than you.

Are you testing this week, or "waiting for more information"?

The 90-day clock is ticking ⏰

The GPT-5.1 rumors have my full attention.

What I’m hearing from people who actually know:

→ Not an update. A transformation.
→ Reasoning that makes current models look broken.
→ Speed + pricing that changes everything.


Here’s what happens if this is real:
The gap between AI-first and AI-last companies becomes uncrossable.
Workflows we teach today become obsolete next week.


6-month “AI strategies” get rewritten in 48 hours.


What I’m telling clients:

Don’t wait to “see what happens.”
Build the muscle of rapid AI adoption NOW.


Because if these rumors are accurate, you’ll need it in 3 weeks.


Bottom line:
The curve is about to bend.
Teams ready to move fast will capture 18 months of advantage in 60 days.


Teams still “evaluating” will be explaining to their board why they’re behind.



Which side will you be on?

BREAKING-CLAUDE 4.5 OPUS RELEASE (here's what it actually means)
I've spent 3 years implementing AI for go-to-market teams.   
Here's what I've learned about benchmarks:


Nobody cares about the scores.
They care about what the scores MEAN for their Monday morning.


So let me translate the latest Claude Opus 4.5 results into plain English:


WHAT THE NUMBERS SAY:

Agentic Coding: 80.9% (fixes 4 out of 5 real software bugs)
Tool Use: 98.1% (completes multi-tool tasks reliably)
Scaled Tool Use: 62.3% (orchestrates many tools simultaneously)
Novel Problem Solving: 37.6% (still struggles with truly creative thinking)


WHAT THIS MEANS FOR YOUR TEAM:

🔹 For CROs: Your SDRs spend hours on research before every call. AI can now do that research in 10 minutes with 80%+ accuracy. That's 2-3 extra meetings per AE per week.
🔹 For CMOs: Campaign execution bottlenecks disappear when AI handles reporting, repurposing, and distribution simultaneously. 2X output. Same team.
🔹 For RevOps: Manual CRM updates, forecast modeling, pipeline analysis—AI handles 50%+ of this autonomously now. Your analysts focus on insights, not data entry.


WHAT THIS DOESN'T MEAN:

AI isn't replacing your closers.

The novel problem solving score (37.6%) tells you where humans win: complex negotiations, relationship building, creative strategy.

That number was near 0% two years ago—so the frontier is moving.
But TODAY, the play is clear:


AI handles the mechanics. Humans handle the moments.

The companies I work with aren't debating this anymore.
They're racing to reorganize around it.


How are you thinking about deploying agentic AI this quarter? Drop your use case below—I'll share what's working.

The "Pilot Purgatory" Problem
The traditional software playbook is KILLING your AI ROI.

Here's what I mean:
I've seen dozens of Public, VC, PE-backed companies spend 6-9 months "validating" AI pilots.

By the time they're ready to scale? The technology has already evolved 3 generations.

OpenAI just released data showing they've shipped a new feature every ~3 days this year.


Your quarterly validation cycle can't keep pace with weekly capability improvements.


Here's the uncomfortable truth most consultants won't tell you:
The companies stuck in pilots aren't failing because of technology.


They're failing because they're applying OLD playbooks to NEW capabilities.
🔹 Traditional software: Start small → Test a specific use case → Scale once proven 

🔹 AI implementation: Build learning systems → Iterate in weeks → Scale while improving


The difference?
AI systems don't follow fixed rules. 
They generate outputs based on patterns, data, and context.


Success changes with new inputs.

That means quality and reliability require CONTINUOUS evaluation, feedback, and iteration.


NOT a 6-month pilot program that measures last quarter's metrics.


Here's what I've seen work in 60-day transformations:

Shorter loops (weekly, not quarterly reviews)

Decentralized learning (champions across every team)

Immediate measurement against business outcomes


NOTE: The companies reaching production consistently share one trait—they balance speed with structure and evolve as fast as the technology.



Is your AI strategy moving at the speed of ChatGPT's feature releases, or the speed of your annual planning cycle?

Gemini 3.0 in 3 Minutes: Live website & Dashboard build (INSANE RESULTS)

This one blew me away.  

After playing with this all weekend Google really knocked the cover off the ball.

Turning cold leads into warm leads.

This was a combo of Gemini 🍌and @grok 

The ability to generate an insane scene and then animate it can be done for $60 per month of what would have taken $10,000 in the past in addition.



It can be done from your phone in literally 5 minutes vs a multi-week process.



Insane that this is possible.  And opens up creativity to so many people.

40% of enterprises say they lack internal AI expertise.

This number is about to get worse.

Here's why (and what to do):

━━━━━━━━━━━━━━━━━

THE SKILLS GAP DATA:

What enterprises need:
→ AI strategy development
→ Prompt engineering expertise
→ AI workflow design
→ Integration architecture
→ Change management for AI

What they have:
→ Traditional IT skills
→ Legacy system knowledge
→ Pre-AI processes
→ No AI-native talent

The gap is widening.

━━━━━━━━━━━━━━━━━

WHY THE GAP IS GROWING:

Reason 1: AI Skills Are Brand New
→ These roles didn't exist 2 years ago
→ No traditional education path
→ Learn by doing, not by degree

Reason 2: Competition for AI Talent Is Brutal
→ Startups offering $300K+ for AI roles
→ Enterprises can't compete on salary
→ Best talent going to AI-first companies

Reason 3: Skills Evolve Monthly
→ What was cutting-edge 6 months ago is basic now
→ Constant learning required
→ Traditional training programs too slow

━━━━━━━━━━━━━━━━━

THE 3 TYPES OF AI SKILLS NEEDED:

Type 1: Foundational (Everyone needs)
→ AI tool usage (ChatGPT, Claude, etc.)
→ Basic prompting
→ Understanding AI capabilities/limitations

Current gap: 60% of employees lack this

Type 2: Applied (Power users need)
→ Advanced prompting techniques
→ Custom GPT creation
→ Workflow automation
→ AI + existing tools integration

Current gap: 80% of employees lack this

Type 3: Strategic (Leadership needs)
→ AI strategy development
→ ROI calculation
→ Risk assessment
→ Change management

Current gap: 90% of leaders lack this

Does your company have the AI skills it needs?

Or are you in the 40%?

The-Skills-Crisis-A-dollar500K-Problem-With-a-dollar35K-Solution.pdf

A CRO of a Publicly Company told me he'd trade his worst performing salesperson to fund AI transformation.

Not fire a large part of his team because of AI.

Trade the lowest performing person FOR AI.

That conversation revealed something I've now confirmed across hundreds of executive conversations:

The leaders who will win in 2026 aren't thinking about AI as a technology decision.


They're thinking about it as a RESOURCE ALLOCATION decision.

After 3 years and 2,500+ executive AI implementations, here are the 7 beliefs driving their 2026 AI strategies:

1. AI is strategically non-optional—but must be grounded in execution 
🔹 Not a side experiment. Not a pilot. 
🔹 They want AI hardwired into campaigns, daily activities, and systems.


2. Willing to fund AI by reallocating headcount, not adding spend 
🔹 One mid-performing rep = one AI transformation budget. 
🔹 They're in reallocation mode, not expansion mode.


3. Training must be the most relevant enablement they've ever had 
🔹 No theory. No hype. 
🔹 People must leave sessions doing specific things differently TOMORROW.


4. Transformation must be phased and resilient to changing priorities 
🔹 They're notorious for changing direction. 
🔹 Crawl-walk-run beats big-bang every time.


5. Time and change-capacity are the scarcest resources 
🔹 AI work must be time-neutral or time-accretive. 
🔹 It can't feel like "another initiative."


6. AI must compensate for structural underinvestment 
🔹 No dedicated data analysts. Underfunded marketing. 
🔹 AI is the force multiplier that covers the gaps.


7. The AI story must be consistent across sales + marketing + leadership 
🔹 One storyline. One SOW. 
🔹 CFO and CMO must see their words in the program.


NOTE: The bar has changed. Executives will trade headcount for AI—IF it clearly drives daily behavior change and revenue outcomes.


Which of these 7 beliefs resonates most with what you're hearing from leadership?


Struggling to figure this out? 

DM me to see how your peers are tackling this for 26 and beyond.

Save Hours Every Week With This Simple Trick!

I used to spend 10+ hours every week writing marketing content. It was a time sink.


Then I leveraged AI, and my content workflow exploded:

Generated 30 LinkedIn posts in 15 minutes.

Created 12 YouTube video outlines (including SEO/AEO research, thumbnail designs, and full scripts) in the same time.


The best part? Same quality, 95% less time.


This isn't just about speed; it's about shifting your focus from creation to strategy.

The secret is knowing exactly what’s possible with Claude Code (outside of traditional coding). It’s a game-changer for Marketing, Sales, and general Go-to-Market functions.

#AI #ContentMarketing #LinkedInStrategy #Productivity #GoToMarket

Sometimes I think we overcomplicate AI in sales.

Everyone wants the perfect playbook, the secret sauce, the one tool that will magically double revenue.

But the truth is, most of the wins I’ve seen come from small, gritty experiments.

A team tries a new AI-powered lead scoring model. It flops. They tweak it, try again. Suddenly, they’re booking 30% more meetings.

Or a manager uses AI to analyze call recordings. Finds out the top reps ask twice as many questions as everyone else. Next week, the whole team is trying it. Win rates jump.

It’s not glamorous. It’s not always scalable. But it works.

AI isn’t a silver bullet. It’s a thousand little adjustments, stacked up over time.

The teams that win aren’t the ones with the biggest budgets. They’re the ones willing to get their hands dirty, fail fast, and learn faster.

So if your AI project feels messy, you’re probably on the right track.

What’s the smallest experiment that made the biggest impact for your team?

Mixing models? 

 There’s been a lot of different opinions in terms of mixing models however, I’m absolutely blown away that I could create a video like this in five minutes by using nano banana pro 🍌with Grok 4.1 imagine.

I get for standardization purposes of ONLY ONE LLM in large organizations has huge value however, a lot of the large language models are like superheroes that each have their own special superpower.

Susan Whittemore

tax.com™

Tax.com™ solutions are powered by the insights and ingenuity of some of the most renowned tax professionals at Ryan, LLC whose experience and expertise form the bedrock on which our solutions are built. The result is responsive, intelligent technology that empowers organizations to act quickly and confidently within a dynamic tax landscape. Harness the power of tax.com™ solutions and take your organization into the future.Tax.com™ solutions are powered by the insights and ingenuity of some of the most renowned tax professionals at Ryan, LLC whose experience and expertise form the bedrock on which our solutions are built. The result is responsive, intelligent technology that empowers organizations to act quickly and confidently within a dynamic tax landscape. Harness the power of tax.com™ solutions and take your organization into the future.

VP, Revenue Operations

Hunters and Unicorns

Strategic Partner

QFlow.ai

QFlow leverages AI and advanced analytics to offer ready-to-use GTM stats, performance driver analysis, and scenario planning capabilities. Our vision is to equip every B2B company with the power of a robust 10-person GTM Finance team (including BI analysts and data engineers).

GTM and Revenue Operations Executive Advisor

Teampay

➼ Led Revenue Operations, optimizing GTM tech stack, streamlining tool integrations, and elevating cross-functional productivity.
➼ Established a comprehensive end-to-end process from Marketing to Customer Success, embedding feedback loops and key conversion and velocity metrics.
➼ Collaborated with CFO and CRO to define and harmonize crucial SaaS metrics (ARR, MRR, NRR, GRR, etc.), boosting operational efficiency and customer satisfaction.
➼ Secured advantageous vendor contracts, and managed data insights for board presentations, enhancing strategic decision-making.
➼ Implemented robust internal controls across marketing, sales, and post-sales phases ensuring data-driven transparency in GTM strategies and campaigns.

About Teampay:
Teampay is a leader in distributed spend management, providing businesses with unmatched spending oversight and empowering employees in procurement. We believe in channeling efforts towards growth over overhead.

Head of Revenue Operations

Starburst Data

➼ Revolutionized the GTM strategy and tech stack, centralizing cross-functional teams with agile methodologies to enhance both sales-marketing synergy and customer satisfaction.
➼ Leveraged PXT Select in recruitment to expedite the hiring process, ensure candidate fit, and personalize our sales coaching methods, culminating in a diverse, elite global sales team.
➼ In partnership with the VP of Sales, redefined the operating rhythm, achieving increased forecast accuracy and a cohesive, transparent forecasting process from frontline teams up to the CEO.
➼ Oversaw sales and marketing KPIs, paving the way for scalable pipelines, strategic territory planning, and propelling the company towards significant milestones like Series C Funding.

About Starburst Data:
Starburst champions the vision of unveiling the unseen for its customers. Over a decade, our founders, across three ventures, tackled data access challenges, traditionally deemed slow and inflexible. Starburst presents a solution, counteracting data silos and ensuring swift access. We amplify open source Trino's capabilities, a rapid distributed analytics engine, by integrating essential connectors, fortifying security, and ensuring 24x7 support for expansive, rapid data access.

VP, GTM and Revenue Operations

Silk

➼ Drove Silk's transition from hardware-centric to software powerhouse, overseeing comprehensive operational overhauls and reimagining the go-to-market strategy.
➼ Implemented Command of the Message and MEDDICC methodologies across all levels, resulting in a remarkable 30% sales increase.
➼ Directed a rigorous training program for sales reps, leading to improvements in pipeline velocity (25% up), sales cycle duration (20% reduction), and win rates (15% growth).
➼ Revamped the marketing funnel, achieving a 40% pipeline boost and a significant 25% revenue increase through data-driven territory planning and optimized lead strategies.
➼ Collaborated closely with top-tier leadership, including the COO, SVP of Sales, and CMO, on objectives, technological transformations, and seller adaptations, in alignment with Force Management's strategies.

About Silk:
Emerging from its earlier avatar, Kaminario, in 2020, Silk's Cloud Data Platform is the touchstone of cloud efficiency. It empowers entities to extract tenfold performance from their cloud data while incurring 30% fewer costs. Positioned between application stacks and cloud infra, it elevates the entire cloud ecosystem without modifications. With features like real-time data reduction, thin provisioning, and perpetual resource tuning, Silk tailors your cloud spending to match evolving data needs, making cloud economics more viable.

Sr. Director, Global Revenue Operations

Perfecto Mobile

➼ Drove substantial revenue growth, taking ARR from $13M to $75M.
➼ Expanded and operationalized the enterprise sales team, growing it from 4 to 60+ global sellers, focusing on enterprise value selling in tandem with the CRO.
➼ Oversaw comprehensive new hire training and enablement, ensuring consistent skill development and tool accessibility, incorporating MEDDICC & Command of the Message for optimal sales performance.
➼ Crafted an all-encompassing go-to-market strategy, utilizing both direct and indirect sales channels, in-house sales initiatives, and SDRs, while handling compensation plans for various teams.
➼ Streamlined the MEDDICC-based forecast process, providing vital sales KPI insights to the CRO and Managers for informed strategic decision-making.
➼ Directed global sales operations and development, encompassing sales forecasting, Salesforce operations, onboarding, renewals management, and business development while fostering team cohesion through events like Sales Kick Offs and Quarterly Reviews.

About Perfecto Mobile:
Perfecto Mobile offers industry-leading mobile and web automation testing solutions. We facilitate efficient testing, monitoring, and delivery of high-quality applications, supporting multiple frameworks including Selenium and Appium.

AVP, Sales Operations and Sales Development 

Rocket Software

My Role:
➼ Drove substantial growth at Rocket, increasing ARR from $200m to $500m and doubling the workforce from 600 to 1,200+.
➼ Unified 15+ distinct brands through innovative tools and systems, enhancing insight selling and fostering organizational synergy.
➼ Pioneered Rocket's first-ever sales meetings, laying the groundwork for sustained growth and cross-team collaboration.
➼ Integrated a unified sales CRM platform using Salesforce and Marketo, streamlining operations across diverse business units and refining sales processes.
➼ Designed a robust lead-to-order framework, covering lead management, CPQ, forecasting, and insight selling tools.
➼ Secured the Prosci Change Management Practitioner certification, underscoring a dedication to efficacious organizational transformation in complex growth scenarios.

About Rocket Software:
Rocket Software, a leading partner to global enterprises, addresses multifaceted IT challenges spanning infrastructure, data, and applications. Dedicated to in-place modernization through a hybrid cloud approach, Rocket assists over 10,000 customers globally. Its expansive team of 2,600 accelerates and refines modernization paths, meeting evolving market demands. Based in Boston and part of the Bain Capital Private Equity portfolio, Rocket's global centers of excellence cater to diverse clientele.

Global Sales Operations and Enablement Director

Novell

➼ Supported the VP, Americas, providing senior executive assistance as he rose through the ranks to ultimately assume the role of CEO.
➼ Expanded my Sr. Executive support to top-tier executives including the CFO, General Counsel, and SVP of HR, while also managing critical board committees.
➼ Launched the global onboarding portal on time and within budget, elevating productivity for new hires by an impressive 50% within the first quarter.
➼ Partnered closely in reshaping the Americas go-to-market strategy, leveraging transformational emotional intelligence, which led to a 13% increase in operating profit over two years and set new benchmarks in revenue growth.
➼ Jointly penned the M&A Integrations Playbook, refining Novell's approach to integrations and acquisitions.
➼ Served as a trusted internal consultant, addressing pivotal challenges like employee retention and skill development, laying the foundation for a vibrant and high-performing work environment.

About Novell:
Novell, Inc., operational between 1980 to 2014, was a renowned American software and services entity based in Provo, Utah. Its flagship product was the versatile network OS, Novell NetWare.

Sr. Executive Support & Project Management

Deloitte & Touche

➼ Started at Deloitte & Touche at 18 following the acquisition of their own start-up, Real Estate Tax Services, Inc.
➼ Partnered closely with the Boston-based leadership and the Partner-in-Charge, showing adaptability by operating out of two major locations: Boston, MA, and Manchester, NH.
➼ Successfully managed a $25M property tax liability portfolio, emphasizing compliance and financial risk mitigation.
➼ Pioneered the development of AtlasTax, a cutting-edge property tax CRM, ushering in a new era of client tax management for Deloitte & Touche.
➼ Rapidly advanced to pivotal roles such as East Region Consultant and Account Manager.
➼ Championed AtlasTax's adoption, enhancing client satisfaction and strengthening business partnerships through strategic presentations and demonstrations.

About Deloitte & Touche:
Renowned as the world's fourth-largest public accounting entity, Deloitte & Touche stands tall among the Big Six accounting magnates. Delivering a plethora of professional services, from accounting, auditing to tax and management consulting, its vast network spans 15,300 professionals across 100+ U.S. cities. As a constituent of Deloitte Touche Tohmatsu International, it amplifies its global footprint, making a mark in managerial consulting via 56,000 professionals spread over 108 countries.

Account Manager - Tax Associate

GTM Leader | Revenue Operations Executive

A transformative Revenue Operations Executive and GTM leader with over 15 years of experience. My passion lies in building elite sales teams and driving operational efficiency to scale businesses. 

Here's how I make an impact

➥Strategic Leadership: Spearheaded GTM revamps and sales optimizations in top-tier tech firms.

➥Operational Excellence: Streamlined processes from onboarding to customer journey, reducing friction and elevating performance.

➥Data-Driven Agility: Accelerated insight-driven decision making, ensuring speed, agility, and alignment across leadership teams for rapid strategic adjustments.

➥Team Building: Utilized PXT Select, DiSC, and Predictive Index for efficient hiring and tailored sales coaching, creating diverse, high-performing teams.

➥Innovative Solutions: My approach combines strategic technology application with a focus on buyer journey insights, ensuring growth and efficiency.

Revenue Operations - Consultant

Operations Consulting Services:
Onboarding, Buying-to-Customer Journey Mapping, Process Design and Workflows, LinkedIn Strategies, RevOps Strategies, Prioritization Workshops, and ICP definition / validation.

Personal Coaching Services:
Career Mapping and Pivots; Professional Branding, LinkedIn Workshops, Unstucking Yourself, Team Building, and Clarity / Prioritization Workshops.

Boston showed up. And so did the snow (at least outside the city). 



Pavilion Boston wrapped our 2025 in-person events with a full room, big energy, and conversations that reminded me why community matters.

Highlights:

 ➡️ A powerful session with Sam Jacobs on Pavilion’s origin, journey, and future
 ➡️ A holiday celebration at SPIN with 50+ members
 ➡️ Real conversations about family, career pivots, new endeavours, leadership struggles, AI in GTM, compensation, and the challenges facing the next generation

Grateful for Sam and the Pavilion team, all our Boston members, and my co-chapter head Mark, for helping build something special here in Boston.

Looking ahead to 2026:

 ⏩ More in-person local events
 ⏩ Executive compensation and negotiation content
 ⏩ P&L fluency for operators
 ⏩ The fast growing #AI in GTM program including our most active Slack channel, monthly meetups featuring real applications, and new formal content

What conversations or connections do you want more of in #2026?

#Pavilion #BostonTech #GTMLeadership #Community

#Pavilion #boston #community #leadership #GTM #Holidays #SaaS #learning 

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The Battle

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The Battle

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