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

I just built a fully functional AI agent in under 8 minutes.
No code. No API headaches. Just OpenAI's new Agent Builder.

But here's what the hype machine WON'T tell you:

The Raw Truth After Testing:
✅ Templates make it stupid-simple to start
✅ Visual drag-and-drop actually works
✅ Enterprise teams will love this for internal tools

❌ Pricing? Complete mystery still
❌ It's NOT killing Zapier (actually uses it)
❌ Still needs technical + business logic combo


The Real Play for Revenue Leaders:

This isn't about replacing your tech stack tomorrow.


It's about building internal agents that:
→ Actually understand your business logic
→ Deploy in days, not quarters
→ Scale team capacity without headcount

I've spent 3 years implementing AI for 2,400+ execs.


Agent Builder is the first time I've seen OpenAI truly simplify the "how" for non-developers.


What I built in those 8 minutes:
An AI that maps sales enablement use cases, builds implementation roadmaps, and generates prompts for each stage.


My 2026 prediction: Companies NOT building custom agents will be at a massive disadvantage.
The question isn't IF your team needs this.
It's WHO on your team learns it first.


What's the first internal agent you'd build for your team?

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

Claude just dropped a feature that will make 99% of "AI experts" irrelevant.

It's called Claude Skills.

And here's why this changes everything:

You can now customize AI for your business in under 5 minutes. 
Zero coding.
Zero technical knowledge required.
ZERO

I've been stress-testing this for the past week with my clients (companies doing $30M to $20B in revenue).

The results? Absolutely mind-blowing.


Here are the 3 reasons why Claude Skills > MCP servers:
1. Token Efficiency
🔹MCP servers are heavyweight and constantly running
🔹They suck up massive amounts of tokens
🔹Claude Skills only activate when needed—saving you serious compute costs

2. Setup Speed
🔹MCP servers require technical configuration
🔹Skills are literally drag-and-drop
🔹I built a complete enterprise sales qualification system in 12 minutes

3. Practical Business Value
🔹Skills come with built-in workflows and decision trees
🔹They auto-trigger based on your specific use cases
🔹They generate complete reports, visualizations, and action plans automatically

Here's what I created in ONE afternoon:
→ Data journalism analyzer (pulls live Census data, creates trend reports)
→ Enterprise sales qualifier using MEDDICC framework (scores deals, predicts win rates)
→ Custom AI agents for specific GTM workflows


The craziest part?
Each skill I built would have taken weeks to code manually. Now it's done in minutes.


If you're still using basic ChatGPT prompts while your competitors are deploying custom AI skills...
You're already 6 months behind.


Which business function would you build a custom AI skill for first?

Sales? Marketing? Operations? Customer Success?


Drop your answer below. The AI skills revolution just started.

"AI will replace sales reps."

I've heard this 1,000 times in the past year.

Here's what's ACTUALLY happening after $700M in AI agent funding:

The Fear:
AI agents = Sales rep replacement

The Reality:
AI agents = Sales rep multiplication

Let me break down what 2,400+ executive implementations taught me:

━━━━━━━━━━━━━━━━━

What AI Agents ARE Doing:

✅ Prospecting research (10 min vs 3 hours)
✅ Email personalization at scale
✅ Meeting prep automation
✅ CRM data entry (finally!)
✅ Follow-up sequencing

What AI Agents ARE NOT Doing:

❌ Building relationships
❌ Handling complex objections
❌ Negotiating deals
❌ Understanding nuanced buyer needs
❌ Closing six-figure contracts

━━━━━━━━━━━━━━━━━

Here's the Data:

Companies using AI agents report:

→ 60% more demos booked (by reps, not agents)
→ 90% improvement in email response rates (agents write, reps send)
→ 10 hours/week saved per rep (time redirected to selling)

Notice the pattern?

Agents don't replace reps.

Agents free up reps to do what they do best: SELL.

━━━━━━━━━━━━━━━━━

The "Virtual Coworker" Model:

Think of AI agents as:

→ A junior SDR who never sleeps
→ A research assistant with infinite memory
→ An admin who loves CRM updates

Would you fire your top rep and replace them with a junior SDR?

No.

You'd give your top rep a junior SDR to maximize their output.

That's exactly what AI agents do.

━━━━━━━━━━━━━━━━━

**Real Example:

Before AI agents:
→ Rep spends 15 hours/week on research and admin
→ 25 hours/week actually selling
→ Books 8-10 meetings/month

After AI agents:
→ Agent handles 12 hours of research and admin
→ Rep spends 37 hours/week actually selling
→ Books 18-22 meetings/month

Same rep. Better results. More time selling.

━━━━━━━━━━━━━━━━━

**The Bottom Line:**

If you're worried about AI replacing your sales team, you're asking the wrong question.

**Wrong question:**
"Will AI replace my reps?"

**Right question:**
"How do I give my reps AI superpowers?"

━━━━━━━━━━━━━━━━━

The future isn't AI OR humans.

It's AI AND humans.

The sooner you embrace that, the faster you'll 2x your team's output.

---

What's your take? Are you using AI agents yet?

"Just implement AI agents across your revenue team."

Worst advice I've heard this year.

Here's why that approach fails (and what to do instead):

The Problem with "Just Implement Agents":

You're asking your team to:
→ Learn entirely new tools
→ Trust autonomous systems
→ Change workflows overnight


Without:
→ Foundation in AI basics
→ Understanding of what's possible
→ Quick wins to build confidence


It's like asking someone who's never driven to race Formula 1.


━━━━━━━━━━━━━━━━━

What Actually Works:

Think of AI adoption like learning a language.

You don't start with Shakespeare.

You start with "Hello, how are you?"

**Level 1: AI Literacy (Augmentation)**
→ Everyone uses ChatGPT daily
→ Team learns basic prompting
→ Quick wins in email, research, prep

**Time investment:** 2-3 hours/week
**Result:** Immediate productivity gains

**Level 2: AI Fluency (Automation)**
→ Build automated workflows
→ Integrate AI into existing tools
→ Systemize repeatable processes

**Time investment:** 2-4 weeks setup
**Result:** 3-5 processes running automatically

Level 3: AI Mastery (Orchestration)
→ Deploy semi-autonomous agents
→ Multi-tool coordination
→ Complex workflow automation

**Time investment:** 8-10 weeks implementation
**Result:** True AI-first operations

━━━━━━━━━━━━━━━━━

**Here's the data from 2,400+ implementations:**

Teams that start with Level 1:
• 95% adoption rate
• Results in 1 week
• 90% stay with the program

Teams that jump to Level 3:
• 20% adoption rate
• Results in 6+ months (if ever)
• 60% abandon within 90 days

━━━━━━━━━━━━━━━━━

**The Bottom Line:**

AI agents are incredible.

But you can't skip the foundation.

Start with augmentation.

Build to automation.

Scale to orchestration.

60 days.

Not 6 months.

That's the difference between transformation and chaos.

━━━━━━━━━━━━━━━━━

What level is your team at today?

Level 1: Basic AI use
Level 2: Automated workflows
Level 3: AI agents in production

Comment your level below. 👇

No alternative text description for this image

I've been implementing AI for 3 years. Yesterday, I had my "holy shit" moment.

Not because I discovered something new.

Because I finally connected the dots on what I've been building.

24 hours. Here's what happened:
- Used AI to audit my own AI usage (meta, I know)
- Identified 6 automation opportunities I was blind to
- Generated 30 content pieces with Claude Code
- Collapsed 8 separate prompt chains into 1 autonomous system

But here's what actually stopped me in my tracks...

I dug up prompts from September 2022—when I first started this journey.

Prompts that gave me mediocre results back then.
Ran them through Google's latest model.

The output was 10X better than what I could manually create.

Same prompts. Different model. Completely different reality.
And it hit me:


We're not in an AI evolution anymore. We're in an AI revolution.

The gap between people who implement and people who wait?
It's not months anymore.


It's weeks.

After working with 2,400+ executives on AI transformation, I can tell you this:

The ones who win aren't the ones with the most tools.

They're the ones who ruthlessly automate what they've already proven works.

Then they use that freed capacity to go deeper on strategy.


Question for the practitioners in here:

What's the oldest prompt or workflow you have that might be producing different results today?

Could be worth 10 minutes to find out

🚨 Just built a fully functional AI agent in under 8 minutes — no code, no API config.

OpenAI's Agent Builder just changed the game.

After hands-on testing, I can confidently say: this might be one of the most disruptive tools for startups and enterprise AI teams in years. Why?

Because it allows non-developers to drag, drop, and deploy complex AI workflows with minimal friction — while still offering the depth needed for serious, scalable use cases.

💡 Here's what I cover in the video:
✅ What Agent Builder and AgentKit actually are
✅ Who should care (hint: AI-first startups, internal AI teams, consultants)
✅ A walkthrough of how I used a template + light prompting to build a reasoning agent for internal AI ops
✅ Real examples of how it outputs knowledge bases, sales agents, report generators, and more
✅ What ChatKit, Widget Builder, and ChatKit Studio bring to the table
✅ My honest take on how this stacks up against tools like Zapier, N8N, and custom GPTs

🔍 Key Takeaways
Agent Builder is still in beta, but it’s already showing serious potential. If you're developing AI-first products or want to automate internal workflows, this tool is worth your attention.

While it’s not fully no-code yet — especially for non-technical users — the direction is clear: building custom AI agents is about to get dramatically easier and more integrated into everyday business operations.

As business logic and technical workflows begin to merge, the real competitive advantage will go to those who understand both.

👉 Watch the full demo to see exactly how it works in under 8 minutes.

#OpenAI #AgentBuilder #AIworkflow #AgentKit #ChatKit #AIAutomation #EnterpriseAI #nocode #AITools #DevDay #AITransformation #LLMs

I still feel this way 2 years later.

However this was a lot of fun.  

Super simple to animate any picture on Grok and when scrolling through my gallery I had to see what would happen here.

Veo 3, Sora 2 and Nano Banana are wild as well.

Last Week’s conversation with a President of a company approaching $1B in revenue:

Him: "We're budgeting for 12 new hires to hit our growth targets."

Me: "Before you post those reqs, can I show you something?"

15 minutes later, he's rewriting his entire people strategy.

Here's what shifted:

WHEN I walked him through one agentic workflow, he immediately saw that his "hiring problem" was actually a "capacity awareness problem."

His current team wasn't at capacity.

They were spending 50-60% of their time on work that AI can augment right now—not someday, not when agents are perfect, but THIS WEEK.

The workflow I showed him:
- Takes 90 minutes to train
- Requires 3 days to embed into their process
- Creates 15-20 hours per week of additional capacity per person
- Keeps humans making all strategic decisions

The math that changed everything:

12 planned hires × $180K average comp = $2.16M in additional payroll

OR

40 current employees × 20% capacity gain = equivalent of 8 full-time people

Cost to implement agentic workflows: $40K

Ramp time: 3 weeks vs. 6+ months

Here's what most executives don't realize:

The biggest AI opportunity in 2025 isn't full automation.

It's capacity multiplication of your proven performers.


WHY this matters NOW:

Your competitors are having this same conversation.

The ones who act in Q1 will have a 12-18 month advantage over those who wait for "perfect" AI solutions.

By the time full automation arrives, the winners will have already captured the market share.

I'VE watched this play out across cybersecurity, SaaS, and industrial tech companies.

The pattern is identical: Early adopters of agentic workflows are growing 20-30% faster than their peers—with the same headcount.

The question that should keep revenue leaders up at night:

Are you solving for capacity with 2024 thinking (more people) or 2025 reality (amplified capability)?

Your hiring plan for the next 12 months might need a complete rewrite.


WHAT would change in your growth strategy if your current team could operate at 120-140% of current capacity?

2025 was supposed to be "The Year of the AI Agent."

It's not.

Here's what's actually happening:

The Marketing Promise:
→ Autonomous AI agents handling entire workflows
→ 25% of companies launching agent pilots
→ Revolutionary transformation of revenue teams

The Deployment Reality:
→ 60% cite integration challenges as blockers
→ Most "agents" are just fancy chatbots
→ Implementation takes 6-12 months, not weeks

I've spent 3 years implementing AI for 2,500+ executives.

Here's what I've learned about AI agents:

What Actually Works Today:
• AI augmentation (copilots, not replacements)
• Task-specific automation (not end-to-end agents)
• Human-in-the-loop workflows (not autonomous)
• Point solution agents
• General purpose agents like Deep research, Genspark and Claude code



What's 6-12 Months Away:
• General Purpose Multi-step autonomous workflows
• Cross-platform agent orchestration
• True "set it and forget it" automation

The gap between AI agent demos and production deployment is MASSIVE.

And nobody's talking about it.

3 Questions Before Adopting Any AI Agent:

1. Can it integrate with your existing systems TODAY?
2. What's the fallback when it fails? (It will fail)
3. Do you have the internal expertise to maintain it?

If you can't answer all 3, you're not ready for agents.

You're ready for copilots.

And that's okay.

Because copilots deliver 2x productivity gains without the deployment headaches.

The near future is agents.

The present is augmentation + automation (with AI).

Know the difference.

---

P.S. I help PE-backed SaaS companies and publicly traded companies implement AI without the hype. 60-day transformations, not 6-month pilots.

The biggest lie about AI productivity?

That you need to learn 47 different tools.

I just spent 24 hours proving the opposite.

Here's what I automated with AI that most "experts" say requires a tech stack:

🔹 Automated my entire ChatGPT evaluation system
- Identified which automations actually move the needle
- Mapped agentic use cases across my business
- Zero manual analysis required

🔹 Generated 30 LinkedIn posts in one session
- Claude Code researched trending topics
- Applied my exact brand voice automatically
- Followed my proven structure without thinking

🔹 Consolidated 8 prompt chains into 1 autonomous cluster
- What used to take multiple passes now happens once
- Claude Code handles the orchestration
- I just hit enter and walk away

Here's the kicker:

I found prompts I wrote 18 months ago that were "meh" with GPT-3.5.

Ran them through Google's new model yesterday.

Mind. Blown.

The world isn't just changing. It's already changed.

While everyone's waiting for the "perfect" AI setup, the window for competitive advantage is closing FAST.

You don't need more tools.

You need better implementation.

What's one AI workflow you automated in the last 30 days that saved you 5+ hours?

I've implemented AI transformations for 2,400+ executives over 3 years.
Here's the pattern I see in EVERY organization:

The 20/80 AI Adoption Split is killing your competitive advantage.

20% of your team are hand-raisers. They see ChatGPT, Claude, Zapier as career accelerators.

The other 80%? They won't touch it. The learning curve feels steeper than the payoff.


Here's what nobody's talking about:
That 20% will be doing 2-3x the work of the 80% within 6 months. Same headcount. 

Same compensation. Wildly different output.


The math is brutal: 
🔹 Your top performers multiply their capacity 
🔹 Your middle 80% stagnates 
🔹 The performance gap becomes unbridgeable 
🔹 You've accidentally created a two-tier organization


I watched this exact scenario play out at a $100m+ SaaS company.


Their AI-adopting reps were booking 2.7x more meetings with LESS effort. 

The non-adopters? Grinding harder for declining results.


Here's how forward-thinking leaders are solving this:

1. They stop treating AI adoption as optional.
2. Make it explicit. Make it mandatory. Make it measurable.


WHEN I work with CROs who successfully drive mass adoption, they do 3 things:

1. Declare AI competency a core requirement (not a "nice to have")
2. Build it into performance reviews (measure skill development quarterly)
3. Create consequence and reward systems (tie compensation to AI utilization)


The companies that figure this out in 2025 will double their team's capacity without hiring in 2026.


The ones that don't? 

They'll watch their 20% leave for competitors who value AI skills—and they'll be stuck with teams that can't compete.


WHAT'S your approach to driving AI adoption across your entire team?


Are you treating it as optional or mandatory?

whale-boss

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

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