Ryan Staley

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 2,500 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

Podcast Host

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.

I've spent 3 years helping executives navigate the fastest transformation in human history.

Here's what I've learned:


The ones who perform under pressure all have something in common.


A center. An anchor. 
Something they control when everything else is chaos.


For me? It's this. 5am. 
Weights. 
Silence before the storm.


This isn't a "wake up at 4am and crush it" motivational post.

It's reality:
→ My energy stays higher throughout the day
→ My decision-making stays sharper under pressure
→ I'm building health proactively instead of reacting to burnout


I've watched too many CROs and CMOs grind themselves into the ground chasing numbers.


Hit the target. Miss their health. Miss their families. Miss themselves.

The irony? When you lose your center, you lose your edge.


NOTE: This doesn't have to be the gym. 
It could be running. Meditation. 
Playing guitar. 
Coaching your kid's team.


The point is having SOMETHING that's yours. 


That doesn't depend on board approval, pipeline coverage, or the next AI announcement.


What's your anchor?

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 did something from Thanksgiving to New Year I haven't done in 5.5 years.
I stopped.

No podcasting. No YouTube. No content treadmill.
Instead:
→ Closed out the year strong
→ Set up massive foundational moves for 2026
→ Actually recharged with family in Napa-Russian River Valley
→ Did deep work when things got quiet

Here's what happened when I created space:

I spent serious time with Claude Code and orchestration workflows.

What I discovered completely rewired what I think is possible.

The jump I'm seeing in AI orchestration isn't incremental.
It's exponential intelligence at the speed of thought.

2026 is going to be different. Not because of hype.

Because of what I've built in the silence.

Sometimes the best move is to step back so you can leap forward.

What's one thing you stepped away from that gave you unexpected clarity?

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I just finished another AI Transformation Sprint with a SAAS leader-QT9 Software  software

The results blew me away.

Here's what 45 days of focused AI implementation produced:

→ 18 AI use cases deployed across Sales, Marketing, and Leadership
→ 139 hours saved WEEKLY across the team
→ Equivalent of 3.5 Headcount gain to drive greater efficiency and output
→ 12.4x return on program investment

But here's the metric that matters most:

Workflow confidence jumped 103%.

Before: 1.94/5
After: 3.94/5

This is the real unlock.

Most AI training programs teach tools. We transformed how the team THINKS about AI.

The 3 biggest wins:

🔹 Demo Prep: 2+ hours → 10 minutes (92% reduction)
🔹 Account Research:** 4 hours → 30 minutes (87.5% reduction)
🔹 Business Case Creation:** 4 hours → 15 minutes (94% reduction)

Here's what most companies get wrong:

They measure AI adoption by "ROI on Day 1 like a slot machine"
That's like measuring fitness by gym membership.

Leadership doesn’t set the non-negotiables

The real ROI comes from:

1. leading indicators=time
2. lagging indicators=increase in tasks, activity, pipeline , etc
3. Results= Increases in revenue and profit 

When confidence doubles, adoption becomes automatic.

NOTE: 

74% of the ROI came from SALES use cases. 

The Executive leadership was committed

-leading by example, setting expectations and driving adoption

The team was amazing

-hungry, curious and grew exponential by doing

What's blocking your team from this kind of transformation?

Feel stuck or don’t know where to start, DM me and I’ll give you a few ideas of what has been working over the last 3 years.

Amazing work Jim Ellward Jared Brady Brian Kulaga Cole Gardner, MBA Jake Ninowski Kertrina Justice Blake Carlson Christian Reyes 

And the rest of the QT9 team (who are not showing up in LI for me.)

15 hours in, three operating systems later, and I'm officially hijacked by Claude Code.

Not in the way you think.

Let's skip the AI hype and get real.

I stopped reading about "AI use cases" and got my hands dirty.

Fifteen solid hours, two weeks, zero fluffy prompts.

Just building actual operating systems.

Not content.

Not lists.

Real, working systems that actually run my business better.

Here's what happened:

1. The CEO Operating System (Annual Planning)

Forget hope and guesswork. This system turns chaos into a clear plan.
- Pick the few things that matter (not 27 "priorities")
- List what we're not doing
- Map risks and constraints
- Build a real 90-day action plan
- Log decisions, assumptions, and learnings as we go
- Use 10 battle-tested frameworks for tough calls

The result? Not a plan that "looks good" in a slide deck, but one that actually runs when the rubber meets the road.

2. The Sales Intelligence Operating System (Client Interaction Analysis at scale)

My new force multiplier.
It chews through a mountain of sales calls, client emails, and feedback in seconds, not weeks.
- Finds trends, patterns, and recurring objections
- Spots churn risk and expansion signals
- Surfaces the REAL words buyers are using, not what we wish they'd say
- Highlights opportunities we're missing

This thing can scrape thousands of data points and hand me something actionable before the coffee gets cold.

3. The Product Intelligence Operating System (Continuous Improvement)

Where delivery drifts, this system pulls it right back.
Because my edge is delivering actual AI transformation training, not just talking about it.
This OS hunts for patterns in:
- What features clients love (and which get ignored)
- What gets real results vs. wasted effort
- Where new modules, examples, or sequences are needed

It's the antidote to vibes-only product improvement. Decisions made on facts, not feelings.

Let's get honest about what made this work.

It wasn't "AI did it for me."

It was orchestration.

I skipped the mega-prompt lottery and ran swarms of specialized agents, each with a clear job.

Every OS had something even more important: memory. They don't just spit out answers and forget. They get smarter. They remember what works, what doesn't, why we made certain calls, and how we define "good."

Every week, outputs compound instead of vanish.

Here's your anti-hype PSA: it's not magic. If you feed it garbage, you get garbage,just a lot faster, and prettier.

The unlock isn't the tech.

It's having:

- Real-world skills 
- Guardrails
- Repeatable workflows
- And, most important, systems that learn instead of reset every time you open a new chat window

Thinking about breaking this down in detail on LinkedIn, YouTube, maybe even my podcast.

Would you want to see how each OS works under the hood, or should I just go back to writing about "top 5 AI tools for 2026" instead?

Drop a comment, tag someone who needs to see this, or just tell me if you want more.

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whale-boss

We’ve trained 1,850+ sales and marketing professionals on AI in 2025.
Here are the 10 most jaw-dropping ROI outcomes they achieved:

(With real quotes from real people. No theory. Just results.)

#10: Personalized Demo Configuration
"Prospects are more engaged because demos are tailored to their exact industry and use case." — Account Executive, B2B SaaS
Result: 10%+ conversion lift → 500 more closes/year potential

#9: Executive Alignment Strategy
"We're getting meetings at higher levels than ever before. The AI research helps us speak their language." — Enterprise Account Manager, $4B BPO Company
Result: 20%+ larger deal sizes → $2M incremental revenue

#8: Shark Tank Hackathon Model
"Teams built actual tools they're still using. It wasn't just training—it was delivery." — Leadership Teams, Multiple Companies
Result: 100 tools built → 200 hrs/week saved → $520K/year

#7: ROI Builder for Champions
"Building a business case for my champion used to take half a day. Now I can generate one in 15 minutes." — Account Executive, B2B SaaS
Result: 94% time reduction → $225K/year saved

#6: Competitive Intelligence GEM
"Instead of spending hours every week tracking competitors, the GEM does it automatically and alerts me." — Sales Rep, Life Sciences Company
Result: 4+ hrs/week → Fully automated → $1.04M/year

#5: Prospect List Generation
"It took us days to build a prospect list. Now we generate 300+ qualified companies in minutes." — Sales Team, Life Sciences Company
Result: 95%+ time reduction → $480K/year saved

#4: Crawl-Walk-Run Framework
"Every department now has a structured AI project in flight. We went from pockets of use to organization-wide." — COO, Industrial Software Company
Result: Org-wide adoption → 500+ hrs/week saved → $1.3M/year

#3: Call Transcript Analysis
"I don't spend 30 minutes after each call reviewing notes. The AI extracts everything instantly." — Multiple Participants
Result: 30 min → Instant (100% automated) → $2.6M/year for a 100-person team

#2: Account Research Workflow
"I was spending 4 hours researching each strategic account. Now I get better insights in 30 minutes." — Marketing Specialist, B2B SaaS
Result: 87.5% time reduction → $1.75M/year saved

#1: Demo Prep Automation
"What used to take me 2+ hours now takes 10 minutes. I can prep 5 demos in the time it used to take for 1." — AE, B2B SaaS
Result: 92% time reduction → $1.37M/year saved

The math doesn't lie:
📊 Total Annual Impact: $14.21M (for a 100-person team) 
⏱️ Hours Recaptured: 5,935 hrs/week 
🎯 Sales drove 79% of total ROI

The bottom line:

AI transformation isn't about technology. It's about closing the deal with your own organization. 

The companies seeing these results treated internal AI adoption like an enterprise sale: → Identify the pain → Find champions → Build the business case → Close the deal

Your team already knows this framework. Now apply it internally.

Which of these outcomes would move the needle most for your team?
Drop a comment 👇

I've presented growth strategies to C-Suites for the past 15 years.

Here's the brutal truth:

Most strategies die in the boardroom because they're built on gut feel and outdated playbooks.

The C-suite doesn't want more slides. They want conviction backed by data they can actually verify.

That's why I've spent the last 3 years building AI workflows that pressure-test strategy BEFORE it hits the executive table.

What used to take my team 3 weeks of analyst work now happens in 2 hours.

On January 28, I'm teaching this exact approach in Pavilion's AI in GTM School:

**Growth Strategy Design for an Enterprise (with AI Workflows)**

What you'll walk away with:
→ How to stress-test positioning against real market data using AI
→ Frameworks for validating competitive threats before they become surprises
→ The exact process I use to build strategies the C-suite actually trusts

This isn't theory. It's the same workflow I've used with 2,400+ executives over the past 3 years.

If you're a CRO or CMO tired of defending strategies built on hope, this session is for you.

Link in comments to register.

What's the last AI growth strategy you presented that got challenged in the boardroom?

This is taken from an AI Agent social network - Moltbook

It is the third most upvoted post and the first 2 aren’t any better.

Things are going to go off the rails really fast if someone doesn’t have some standards or safety measures to this site. 


Although this is an amazing concept and idea we need to make sure bad actors that have social burner accounts don’t poison the well.

Please comment for reach and let’s make sure we act smart when working with this insanely powerful technology.

WHAT keeps me up at night about AI in GTM:

The window is closing.

Right now, companies who implement AI systematically have a MASSIVE competitive advantage.

By 2027? AI capabilities will be table stakes.

Everyone will have access to the same tools.

The differentiator will be:
→ How fast you implemented
→ How deeply it's embedded in your operations
→ How skilled your team became during the transition

I've watched this pattern before.

Companies that moved early on CRM, marketing automation, sales engagement—they dominated for years.

The laggards spent the next decade catching up.

AI is that same moment. Compressed into 24 months.

This is why I partnered with Pavilion to teach a session for the **AI in GTM School**.

It's designed for GTM leaders who:
🔹 Know AI matters but don't have a systematic approach
🔹 Want alignment across teams, not scattered experiments
🔹 Need a 90-day plan they can actually execute

The next cohort starts next week.

If you're a CRO or CMO who's ready to move from AI experimentation to AI transformation—this is your moment.

Here is the link to sign up: 
https://lnkd.in/gekG_R6t

McKinsey just announced they have 25,000 AI agents.

My reaction? That's not a flex. That's a warning sign.

Here's what I've learned from 3 years of AI itransformation implementations across startups and fortune 500s:

MORE IS NOT ALWAYS BETTER.

In fact, more is usually worse.
I've watched companies rush to build dozens of agents, custom GPTs, and AI workflows—only to end up with a graveyard of tools nobody uses.

The problem isn't building agents.

The problem is building agents without asking:
→ Who owns this?
→ Who maintains this?
→ Who actually uses this daily?

NOTE: Managing 25,000 agents currently is just as hard as managing 25,000 people.
Maybe harder.

Because agents don't tell you when they're broken.
They don't raise their hand when they're producing garbage.
They just keep running.

The companies winning with AI right now aren't the ones with the most agents.

They're the ones with the RIGHT agents.

Fewer. More precise. Actually used.

What's your take—is agent quantity becoming the new vanity metric?

I spent 4 hours watching a single Anthropic video over break.

Rewound it. Took notes. Implemented immediately.

Here's the insight that's changing how I build AI systems:

STOP building agents. START building skills.

Here's what most people get wrong:

They think an "AI agent" is some magical autonomous entity that figures everything out.

Wrong.

Agents without skills are just expensive guessing machines with massive drift.

🔹 They go off path
🔹 They hallucinate next steps
🔹 They deliver inconsistent outputs

The Anthropic team broke it down into 3 layers that change everything:

**Layer 1: Foundational Skills**
The basics. File creation. Web search. Code execution.
Every agent needs these—but they're just the table stakes.

**Layer 2: General-Purpose Skills**
Document creation. Data analysis. Spreadsheet generation.
These are the workflows that apply across industries.

**Layer 3: Custom Enterprise Skills**
YOUR specific processes. YOUR playbooks. YOUR workflows.
This is where the magic happens.

The shift?

Instead of asking an agent to "figure it out," you're giving it a SKILL.md file that says: "Here's exactly how we do this."

No guessing. No drift. No inconsistent outputs.

NOTE: I've been implementing this for 2 weeks and the quality of outcomes is dramatically better across everything from content to research to data analysis.

The companies that master skills will have AI that actually performs.

The companies that keep building generic agents will keep wondering why their AI is inconsistent.

Which approach is your team using right now?

I just burned through 115 million tokens on Claude Code in 30 days.

That's not a typo.

I kept hitting usage limits and upgrading—which tells you something about how deep I went.

Here's the thing nobody talks about:

Building agents is EASY.

Building GOOD agents is hard.


You can spin up a swarm of AI agents in minutes. I've done it. Command it, and it creates.


But here's what happens next:


The output is a fraction of what you actually need.
It's the exact same pattern as Custom GPTs.
Anyone can build one in 60 seconds.
Almost no one builds one worth using.


The difference between "agent that exists" and "agent that performs"?
🔹 Rigor in testing
🔹 Quality examples baked in
🔹 Clear success criteria
🔹 Iteration cycles (lots of them)

After 30 days of intensive building, here's my take:


The barrier to entry has collapsed.
The barrier to excellence hasn't moved.


That gap is where the real opportunity lives for revenue leaders willing to put in the work.


What's been your experience building agents—easy to start, hard to finish?

I've been wrong about where the next AI breakthrough is coming from.
Prompting. Workflows. Automation.

But here's what I'm realizing now:

The real unlock isn't better prompts.

It's agentic tools like Claude Code.

I've been fine-tuning how I use it across everything I do—content, research, client work, operations.

And it's not incremental improvement.


It's a different category entirely.

So I'm going to start sharing what I learn with you in real-time.

Frameworks.
Cheat sheets.
What works. What doesn't.


No polish. No waiting until it's "perfect."

Because this is the bridge to the next exponential value creation with AI.

And I'd rather you learn from my mistakes now than figure it out alone 6 months from now.

Here is quick cheat sheet that will get you started on how to use it the right way!

What AI tools are you experimenting with right now that feel like a step-change, not just an improvement?

I've spent the last 3 weeks building what I call an "Agentic Operating System" for my company.

Here's the breakthrough:

What if your AI didn't just answer questions...

But held the ENTIRE CONTEXT of how your company operates—and helped you see what you're missing?

This is orchestration engineering.

And it's the skill that will separate 10x knowledge workers from everyone else.

Here's how I'm building it:

**5 interconnected "Operating Systems" that form a company brain:**

1️⃣ **CEO/Executive OS**

- Annual goals
- Quarterly priorities
- Weekly operating rhythm
- Action plans with tracking

2️⃣ **Sales Intelligence OS**

- Pipeline analysis
- Call transcriptions → next best actions
- Executive overviews
- Hidden opportunities across deals

3️⃣ **Product Intelligence OS**

- Training transcripts
- Customer feedback loops
- Win/loss analysis
- Engagement and expansion signals

4️⃣ **Marketing OS**

- Campaign performance
- Content byproducts
- Dream 100 prospecting
- Competitive intelligence

5️⃣ **Internal Operations OS**

- Slack messages
- Email threads
- Meeting transcriptions
- All aligned to strategic goals

**The magic happens when they INTERCONNECT.**

🔹 Your sales calls inform product improvements
🔹 Your product intelligence informs marketing messaging
🔹 Your internal operations stay aligned to executive priorities
🔹 Every signal gets processed against your strategic goals

This creates what I'm calling the "company brain."

It helps you see:

- If you're on track
- What you're doing right
- How to optimize
- 10x opportunities hiding in plain sight
- 100x possibilities you never considered

NOTE: I used to think the future was individual AI agents doing tasks.

Now I realize it's ORCHESTRATED SYSTEMS where agents work together with shared context.

That's the 10x multiplier.

The Leaders who build this capability in 2025?

They won't just outperform their peers.

They'll operate in a different dimension entirely.

Which of these 5 operating systems would unlock the most value for your team?

I spent 25 years learning how to build pipeline, increase close rates, and shorten sales cycles.

Then I asked an AI agent: "How would YOU solve these problems?"

The answer exposed a blind spot I didn't know I had.

Here's what I learned: We've been giving agents human playbooks and asking them to execute faster.

That's backwards.

Here are the 4 questions that changed how I work with agents in 2026:

1. "How would you approach this AS an agent—not as a faster human?"

Stop giving agents your methodology. Ask them what methodology makes sense given THEIR capabilities.

An agent doesn't need to "qualify" leads the way a human does. It can score 1,000 signals simultaneously. Let it design the process.

2. "Given these raw materials, what would you build?"

Feed it the data: transcripts, CRM records, emails, call recordings, Google Drive docs.

Then ask: "What system would you create to solve [goal]?"

You'll get architectures you never would have imagined.

3. "What patterns do you see that I can't?"

This is the unlock.

Humans are pattern-matching machines—but we max out at ~7 variables.

Agents can correlate hundreds. Ask them what YOU'RE missing.

4. "Using first principles, how would you solve this if you had no constraints?"

Agents don't carry your limiting beliefs, your "that's how it's always been done," your organizational politics.

Let them design from scratch. Then adapt to reality.

NOTE: These questions assume you've given the agent CONTEXT—not just instructions. Context is the fuel. Instructions are just steering.

The skill of 2026 isn't prompting.

It's knowing what to ask.

What question would you add to this list?

WHEN I started using AI 3 years ago, I focused on prompts.

HOW to write better questions.
HOW to get better outputs.
HOW to save time on individual tasks.

That approach 10x'd my productivity.

But what I discovered this week will 100x it.

**The shift: Prompt engineering → Orchestration engineering**

Here's the difference:

Prompt engineering is asking AI a great question.

Orchestration engineering is building SYSTEMS where AI holds your entire business context and synthesizes insights you'd never see on your own.

It's the difference between:

- Using GPS for one trip
- And having a co-pilot who knows every route you've ever taken, every destination you're considering, and every traffic pattern across all your priorities

I've been building what I call "operating systems" inside Claude Code:

A CEO OS that synthesizes my annual goals, quarterly priorities, and weekly rhythms.

The AI doesn't just answer questions.

It eliminates disparate information across areas.

It turns goals into action plans and tracking sheets.

It shows me where I'm off track before I even ask.

**Here's why this matters for YOUR career:**

The executives who master orchestration engineering won't just be more productive.

They'll have a STRATEGIC ADVANTAGE that compounds every single day.

While others are still asking ChatGPT individual questions...

You'll have an intelligent layer synthesizing every:

- Sales call
- Customer interaction
- Internal communication
- Market signal
- Team execution detail

Against your strategic priorities.

In real time.

NOTE: I predict "Orchestration Engineer" will be one of the most valuable skill sets in business by 2027.

It won't require you to be technical.

It will require you to think in SYSTEMS, not prompts.

The 10x knowledge workers of the next decade won't be the best prompt writers.

They'll be the best orchestration architects.

This is the fastest transformation mankind has ever had.

And the window to get ahead?

It's closing faster than most people realize.

What's the first "operating system" you'd build for your role if you could connect all your disparate information in one intelligent layer?

I'm in this photo with the cast of Severance.

Except I've never met them.

I strung together a couple commands in ChatGPT's new image generator and this was the result.

2026 is going to be WEIRD.

Here's what I'm seeing after 3 years of AI implementation work:

The line between real and synthetic is disappearing faster than anyone predicted.

🔹 Veo 3.1 just dropped
🔹 Image generation hit a new threshold
🔹 Video is about to follow

And we're only in January.

NOTE: This isn't fear-mongering. This is pattern recognition.

When you can't trust what you see online, something else becomes infinitely more valuable:

Human-to-human connection.

Not text. Not email. Not async.

→ Live conversations
→ Phone calls
→ In-person presence

These will be at a PREMIUM in 2026.

The irony? The more powerful AI becomes at mimicking reality, the more we'll crave what's actually real.

What's your prediction for how this plays out?

I just looked at my ChatGPT annual summary.
I don't know if I'm excited or disturbed.

The data showed me exactly how much of my thinking, creating, and problem-solving now runs through AI. Every day. 

Multiple times per day.


Three years ago, I had my "ChatGPT moment" that changed everything.

What I'm seeing now makes that look like a warmup.

The agents. The systems. The orchestration capabilities.


My mind is genuinely blown.


Here's what I've accepted: This is short-term sacrifice for long-term gain.

The hours I'm investing now in understanding these systems? 
They're not optional anymore.
They're the price of admission for what's coming.


I've worked with 2,600+ executives over the past three years. 

The ones who leaned in early are operating at a completely different level than those who waited.

That gap is about to become a canyon.


What did your AI usage summary reveal about how you're working now vs. a year ago?

HOW would an AI agent approach pipeline differently than your sales team?

I ran the experiment.

I asked an agent to solve evergreen pipeline problems that every sales org faces. But I didn't just give it the task—I asked it to map out:

→ Its approach
→ The steps it would take
→ How it would "attack" the problem

Here's what I learned:

**What impressed me:**

🔹 The level of detail was exceptional
🔹 It viewed pipeline stages through a different lens than most humans
🔹 It identified optimization points I hadn't considered

**What missed the mark:**

🔹 Its assessment of how humans handle pipeline undersold us
🔹 It didn't account for relationship nuance that top GTM pros leverage
🔹 It assumed more process consistency than exists in real orgs

NOTE: This isn't about agents being better or worse than humans.

It's about understanding WHERE each excels.

The takeaway for revenue leaders:

Before you deploy an agent on any workflow, ask it to explain its approach first. Compare it to your team's approach. The gaps tell you exactly where human oversight matters most.

This is how you build agent + human workflows that actually work.

What's the first sales problem you'd ask an agent to map out? Drop it below—I'll share what I've seen work.

I've never written a line of code in my life. 

30 days ago, I went all-in on Claude Code—a coding platform.

Here's what I learned as a complete non-coder doing extensive coding for the first time:

Orchestration platforms like Claude Code require you to master 4 things in a specific sequence:

1. Foundational Concepts First

There's a language barrier that has nothing to do with code.

It's like learning to ice skate. You need to understand the lingo, the logic, how things connect.

Skip this step? You'll be frustrated within 48 hours.



2. Learn By Doing (After Foundations)

Once you understand the vocabulary, execution becomes your teacher.

I built. I broke things. I rebuilt.

No course can replace actually shipping something—even if it's messy.



3. Return to Foundations

This is the step 95% of people skip.

After building, go BACK to foundational concepts.

You'll discover entire categories you missed:
→ Continuous automation
→ Skills architecture
→ Edge cases you never considered



4. Context Engineering

This might sound like a buzzword.

It's not.

If you align context properly, prompting becomes almost effortless.

It unlocks capabilities you didn't think were possible.

NOTE: Context engineering isn't prompt engineering. It's the architecture that makes prompts work.

The sequence matters: Foundations → Doing → Foundations Again → Context Architecture.

Miss any step and you'll plateau fast.


What step are you currently stuck on?

What if cheat sheets/frameworks are actually holding you back?

I've taught thousands of executives about AI.

Frameworks everywhere.

Slides. Decks. Cheat sheets.


And here's what I've realized after 3 years of implementation work:

Frameworks are the START.
Systems are the SCALE.


Last week I built something I'm calling Atomic Claude Code.


It takes James Clear's Atomic Habits—one of the best frameworks ever created—and turns it into a living, breathing agentic system inside Claude Code.


Not a document I reference.
Not a poster on my wall.
Not a "note to self."


An actual system that:
→ Tracks my 1% daily improvements
→ Compounds learning over time
→ Holds me accountable without willpower


Here's the honest truth:
I've been teaching AI transformation for 3 years.
But the biggest unlock in the last 90 days?
Realizing I can BUILD the frameworks I teach INTO the AI systems I use.


The framework becomes the infrastructure.
The concept becomes the code.
The theory becomes the transformation.


NOTE: We're at an inflection point where the gap between "people who know frameworks" and "people who implement frameworks as systems" will determine who wins the next 12 months.


So here's my question:

Is this crossover from frameworks to agentic implementations something you're interested in?


Something you've already done?


Or something you're waiting to explore?


Drop your answer below—I'm genuinely curious where you are in this journey.

Warren Zenna

Founder of The CRO Collective—the first company built exclusively around the Chief Revenue Officer role. As a former CRO myself, I bring real-world experience to the work I do with revenue leaders and growth-stage companies. I created the concept of CRO Readiness—a framework that separates individual CRO competency from an organization’s ability to support and enable the role effectively. I also built the first executive development program designed to create successful CROs from the ground up.

I’m known for a no-BS approach to revenue strategy. I challenge outdated thinking, ask hard questions, and help companies stop guessing and start aligning—across people, process, and go-to-market execution.

I advise Founders, CEOs, Chief Revenue Officers and Aspiring CROs on CRO readiness, career decisions, and high-stakes leadership challenges.

Over the past three decades, I’ve worked closely with CROs, founders, boards, and investors—seeing firsthand why some CRO roles succeed and many fail.

Because of inbound volume, advisory conversations are conducted through structured, paid sessions. This allows me to go deep, be direct, and deliver real value rather than surface-level advice.

If you’re navigating a CRO role, evaluating an opportunity, or pressure-testing a decision, you can book time directly via my website.

Founder 

The CRO Collective helps B2B companies succeed by Ensuring the Success of Chief Revenue Officers.

We help CROs win and help CEOs mitigate the risks that come with hiring one.

CEOs must first understand why they really need a CRO, and how to structure their company properly to ensure the CRO succeeds. 

CROs cannot afford to walk in without a clear understanding of the role and a defined roadmap for success.

I've been fired 5 times.

Yup. 5. 

Two of them I was the CRO. 

Both times, I owned "revenue." Both times, I didn't control marketing, product roadmap, or pricing.

The first time, I thought it was my fault. I replayed every decision. What could I have done differently?

The second time, I realized something: The role itself is structurally broken.

You're accountable for everything. You control almost nothing.

That's not a talent problem. It's an architecture problem.

It's why average CRO tenure is 17 months. It's why we built The CRO Collective.

Not to blame the system. But to fix it.

Founder, The CRO Collective—the only GTM consultancy exclusively built for Chief Revenue Officers. We help growth-stage companies become ‘CRO-Ready’—and turn high-potential revenue leaders into high-performing CROs.

25 CROs in San Francisco. 

January 21st. 

No pitches, no panels—just honest conversation about what's actually broken in our role -

and what to do about it.  

We're discussing:

- Why CROs get fired faster than any other C-suite role
- The revenue responsibility/authority mismatch nobody talks about
- How to stop being the scapegoat when the product isn't ready

The CRO Roundtables aren't just networking events. 

We curate a room full of peers who understand why this role is so damn hard.

and have constructed a dialogue framework that goes deep and delivers actionable value. 

Limited to 25 people. Invite-only. 

For currently appointed GTM Operator/Leaders at companies above $25m in ARR. 

Comment or DM if you want in.

CROs: 

Remember - 

Revenue is a system.

Not a department. Not a slide. Not a single leader’s force of will.

Revenue is the output of:

- customer selection and positioning
- pipeline creation and conversion
- pricing and value articulation
- onboarding and time-to-value
- expansion and retention mechanics
- talent density and management standards
- decision rights, incentives, and operational cadence

You are a builder - an architect - of a machine. 

Not the fixer of the transmission. 

Your Leadership will ask you to lead a vision - and close a deal. 

You will be torn between the pull of quarterly revenue targets and vital long term foundation building. 

And you will fall back on your comfort zone when things get ugly.

Don't. 

Build. Build trust to gain the Authority, Autonomy, Resources and Runway you need to serve your customers the value that they have entrusted you to deliver. 

We are building the single best organization in the world for CROs. 

Partake in our offerings. 

And win.

CROs want to meet live.

This is the #1 thing they ask of me. 

"I really want to develop a network of other CROs". 

Thats why we built the CRO Roundtable Series.

Our San Francisco event on January 21st still has a few remaining open seats.

These events are unique deep discussions and investigations into the role, what makes it so complex, how it's evolving and whats needed to keep pace with its trajectory. 

If you are a currently operator at a growth stage company with a CRO or Revenue Leadership role - this is the place for you. 

Fullcast GTM Leader Society

The Revenue Disease.   

Marketing blames sales for not closing leads.

Sales blames marketing for garbage pipeline.

Customer success blames both for overpromising.

Sound familiar?

Congrats. You’ve got the Three-Org Disease.

It’s not a people problem. It’s an architecture problem.

Each team runs on its own logic. Uses its own definitions. Optimizes for its own metrics.  Even though they’re supposedly working toward the same goal.

Marketing celebrates MQL volume while sales struggles with quality.

Sales hits quotas but churn spikes three months later.

Success metrics don’t connect to revenue outcomes.

The cure isn’t another “alignment workshop.”

It’s appointing one leader who builds and owns the entire revenue system. 

Creating one playbook with shared definitions. 

Installing operating rhythms that make coordination automatic.

Developing automation agents to run key operations. 

Your revenue teams want to work together. 

They just need a system that makes coordination possible instead of optional.

If you want to participate in the single greatest CRO architecture discussion available right now - join us at the next CRO Roundtable. 

It’s in San Francisco on Jan 21.

I get about 5 inbound emails a day from PR People people asking to have their clients be guests on my podcast. 

I got 6 today alone. 

I say no to 99% of them.  

Not necessarily because the people that they propose are bad people. Or necessarily undesirable.  

It’s because these PR firms are completely clueless how to make this request in a persuasive way. 

PR people: Here are a few tips for how to effectively recommend someone to be on my podcast: 

1) Actually listen to my podcast. 
It’s insane.  Most of these people clearly never even listened to the damn thing.  I get requests to interview (which by the way will be discussed in #2) who have absolutely nothing to do with revenue or cros. Like I get requests from people who offer franchise deals or help people manage stock picks. I interview CROs, Founders, business builders, makers, creators, leaders - about business. And leading and managing people. And how they handle change and challenges. 

2) I don’t do “interviews”.  I have conversations.  Those are a lot different.  It’s not an interview show.  Send them to Larry King. 

3) when you tout your clients,  do not mention their product or service. If you do, it’s explicitly clear that you want me to talk about a product or service. I only do this under 2 conditions: 1) I use the product or service and really love it and think people should know about it.   2) I was paid by someone who’s product I use and love and want people to know about it.  Other than that I won’t talk about a product or service.  

4) when you suggest your guest, I want to know about their ideas.  I want to learn how and what they think about business and people and leadership and building things. I like really interesting people who are smarter than me (a low bar anyone can hit) who will intrigue and educate my audience.  I don’t care about the fact that they had 5 exits and grew acme toilet consulting from $100 to $50m in two trips to the loo. I am far more interested in how and what they learned along the way. And how they have developed their skills and themselves.  

5) if I do accept a request, don’t offer to “join the prep call and sit in on the video to observe”.  I don’t want a lurker in the room when I’m talking to your client and I am quite sure your client does not need a babysitter holding his or her hand while we converse.  It’s really annoying- and it’s really weird. Stop this. Please.  

Remember that the most important thing to me is my listening audience.  That’s all that matters.  So think about them and not your clients product or service.  Ask yourself how your client would best be presented in a manner that would make them irresistible to my audience.  

And listen to my podcast. Like at least 20 episodes.

Revenue is not a department. It's a system.

And like any system, it has constraints, feedback loops, and failure points that most revenue leaders never see

because they're too busy playing hero.

The old model was simple: hire a VP of Sales, give them a quota, and hope they figure it out. 

And when they miss?  Just fire and repeat.

We reject this.

Revenue is an interconnected system where sales, marketing, and customer success are one engine.

Not three competing departments. 

Your missed number isn't because your team didn't want it enough. It's because your architecture is producing exactly what it was designed to produce.

The unit of progress isn't heroics. It's automated variable reduction.

When 80% of your team can hit 90% of quota, you have a system.
When 20% of your team delivers 80% of revenue, you have a prayer.

What percentage of your revenue comes from your top 3 reps?

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The Battle

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Warren Zenna

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