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.

Hot take: The most underrated AI tool right now isn't a model.

It's a browser extension.

Claude Chrome extension works really well and I expect this to continue to increase in value.

I know that sounds ridiculous.
Browser extensions have been slow, buggy, and frustrating. Most people have written them off.


But here's what happened when I stopped ignoring Claude's Chrome extension:


I built a complete inventory of every AI assistant and agent I've created across ALL platforms in 15 minutes.


This would have taken me 2 hours of manual copying, pasting, and formatting.


And here's why this matters more than you think:


If you've been building AI systems for the past year, you probably have agents scattered across 3 to 5 platforms with no central view of what exists.


That's not an AI strategy. That's digital hoarding.

The extension handled the tedious part. Pulled the data, organized it, formatted it cleanly.


Will these tools get better? Absolutely.


But RIGHT NOW, they already work for the unglamorous work that actually matters. Data transfer. Organization. Structuring information across platforms.


The flashy stuff gets the attention.
The operational stuff gets the results.


What hidden tool has surprised you lately?

Founder & CEO, Whale Boss | Demystifying AI Agents | Helping revenue leaders 2x team results through AI Led GTM | Trusted by $50M-$20B PE-backed and Publicly Traded Companies | AI ROI for your team in 60 days

I just watched a 2.5 hour interview that changed how I see the next 3 years. And what he said should make every business leader stop and pay attention.

Dario Amodei, CEO of Anthropic, on the Dwarkesh Podcast. 

Here's the part that hit me hardest:

There are TWO exponentials happening right now. Not one. 

The first is the capability curve. Models getting smarter at research speed. 

The second is economic diffusion. How fast businesses actually ADOPT and deploy AI. Both are fast. Neither is instant. And there's a GAP between them. 

That gap is where careers are being made or destroyed RIGHT NOW. Dario put a number on AGI. 1-3 years for most knowledge work. 90% confidence within a decade. 


He said software engineering gets fully automated FIRST because code is verifiable. It works or it doesn't. But every function is next. Sales. Marketing. Operations. Finance. Strategy. 

The question isn't whether AI will transform your organization. That's settled. 

The question is whether YOU close the gap between what's possible and what your teams are actually doing. 

Anthropic went from $0 to $9-10 BILLION in revenue in 3 years. 

10x growth per year. 
That's not hype. 
That's the market screaming that AI delivers real value. 

I've been implementing AI across leadership teams for 3 years now with 3,100+ executives. 

The pattern is clear. 

The leaders who move during the gap between capability and adoption don't just win. 

They make it nearly impossible for competitors to catch up. 

Whether you're a CEO setting direction, a VP running a division, or a Director leading a team of 15, the window is the same. 


NOTE: I pulled the key visuals and takeaways from the full 2.5 hours so you don't have to watch it all. Link in comments. Where do you think your organization sits on the adoption curve right now?

AGI Transition Strategy

What if the "ruthless" ElevenLabs quota model is actually the most HUMANE way to run a sales team?


Hear me out.


Right now, most sales orgs carry 50+ reps. Half of them miss quota. 

They grind through manual research, data entry, and admin work that has nothing to do with selling.


They burn out. They churn. They blame enablement. Leadership blames them.


Everyone loses.


ElevenLabs flipped the script. 

Micro-teams of 5-10. AI handles the grunt work. 
Reps focus on what they were actually hired to do.

The result? 80% quota attainment.


And if you hit your number? 
You get paid MORE because there are fewer people splitting the pie.


This is the part nobody talks about with AI transformation.


It's not about replacing people.
It's about FREEING the right people to do their best work and paying them what they're actually worth.


The old model punishes A-players by surrounding them with B and C-players who drag down performance, culture, and comp pools.


The new model? Only A-players. Only selling. Only winning.


NOTE: After working with 3,100+ executives on AI transformation, the biggest resistance isn't from reps. It's from leaders who built their identity around managing large teams.


Smaller team = less perceived power.


But the CROs who get over that ego hurdle?


They're the ones building the future.


Would you rather manage 50 reps at 40% attainment or 10 reps at 80%?

Controversial take: The CROs and CMOs who work the MOST hours are often the worst performers.

I know. That's uncomfortable.

But after 23 years in GTM and 3 years of working with 3000+ revenue leaders across Public Traded and PE-backed SaaS, I can't unsee the pattern.

The leaders grinding 80-hour weeks aren't outperforming anyone. They're too exhausted to realize their strategy stopped working 6 weeks ago.
I've been there myself.

I used to wear exhaustion like proof I was committed. 70-hour weeks. Always on. Always grinding. I thought that's what it took to build Whale Boss while delivering for clients.

Then I hit a wall where I couldn't see what was obvious. I was making slower decisions. Recycling old ideas. Running on fumes and calling it discipline.

The moment I started treating rest as a STRATEGIC INPUT instead of a reward, everything changed.

My content got sharper. My client sessions got better. I started seeing patterns in AI implementation I'd been too fried to notice.

Think about Tom Brady.

He didn't become the GOAT by outworking everyone in the weight room. He became the GOAT by obsessing over recovery, nutrition, rest, and how he treated his body. While other quarterbacks were breaking down at 35, Brady played 4-5 years LONGER and at a HIGHER level than his peers.

That wasn't luck. That was a strategic decision to optimize for longevity and peak performance instead of brute force.

Revenue leadership is the same game.

The executives I train who ruthlessly protect recovery time?


They see market shifts faster.
They make pricing decisions with conviction instead of desperation.
They retain their best people because burned-out leaders create burned-out teams.


One CRO told me something I'll never forget:
"I made more strategic progress in 10 days off than I did in the 6 months before. Because I finally had the space to THINK instead of just REACT."

Your brain isn't a machine that performs better with more runtime.
It's a system that performs better with RECOVERY CYCLES.

The same way PE firms don't expect compound returns without reinvestment, you can't expect compound performance without rest.

NOTE: The executives who survive and thrive across multiple PE cycles aren't superhuman. They're the Tom Brady's of leadership. They figured out that strategic rest isn't soft. It's the hardest competitive edge to copy.

What's your actual recovery strategy right now? Or are you still telling yourself you'll rest after this quarter?

Canary in the coal mine, here’s why this happened…


This is going to be common moving forward if you don’t take this seriously.

I repeat, if you don’t adapt and AI upskill, companies you work for will adapt for you.

If you don’t adapt your workforce to be AI unskilled you will be disrupted by companies like this that will put you out of business.



This is an exact quote from the CEO.

“we're not making this decision because we're in trouble. our business is strong. gross profit continues to grow, we continue to serve more and more customers, and profitability is improving. but something has changed. we're already seeing that the intelligence tools we’re creating and using, paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company. and that's accelerating rapidly.”

I took inventory of every AI agent and assistant I've built for my business.

Here's a some of what my "Agent/Assistant org chart" looks like:

Operating Systems:
• CEO OS (strategy, planning, reviews)
• Sales OS (pipeline, deal coaching, forecasting)
• Product OS (curriculum, delivery, design)

C-Suite Agents:
• Chief Counsel (legal review, contracts)
• CHRO (hiring, candidate scoring, team design)
• CMO (Content, Creative, Strategy, team design)

Sales:
• Deal Coach with Next Best Action
• Research assistant

Productivity:
• Email management
• Proposal design

Marketing:
• LinkedIn content teammate

Product:
• Program design
• Agent designer
• Customer artifact designer

That's 15 agents across 6 functions. Built in 3 months. No engineering team. No dev budget.

Here's what I've learned:

The mistake most people make with AI agents is building them one at a time, like isolated tools.

The unlock is designing them like an organization.

Just like a company has:
→ Leadership (Operating Systems)
→ Departments (Sales, Marketing, Product)
→ Communication layers (how agents share context)
→ Reporting structure (which agent leads which workflow)

When you architect assistants or agents as a system instead of individual tools, every new agent you add makes the whole thing more powerful.

Not additive. Multiplicative.

The question for every leader right now:

What does YOUR agent org chart look like?

If the answer is "we don't have one" — that's your biggest AI blind spot.

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.

The CRO Collective went across the pond this week.

Our CRO Roundtable London was another epic example of what happens when operating GTM leaders gather to solve real-world problems. 

Whats clear is that CROs are oftentimes under a no-win situation. 

They inherit a system that they had no hand in creating - 

- and then are mandated to accomplish unrealistic (and unsubstantiated) revenue goals. 

The gun goes off and the playbook is always the same. 

We discussed provocative questions:

What influence can the CRO exert over a system of someone else's creation? 

What are the key levers that incoming CROs can pull to have influence over that systems redesign?

What powers does the Board and CEO need to grant the CRO in order to win? 

Huge thanks to the great people at Scalestack Elio Narciso Thomas Hughes Ellis Clearitty Gil Harel Robb Miller Peter Gillingwater and Perkins Coie. 

We are going to convene 12 more CRO Roundtables in 2026 - 

March 12: New York City
April 16: Silicon Valley
May 20th: New York City
June 24: Washington, DC
July 9th: Chicago
September 8th: Boston
September 10th: Atlanta
October 6th: Los Angeles
October 7th: Silicon Valley
October 8th: Seattle
November 10th: Dallas
November 12th: Austin

DM me if you want to get on the waitlist.

The CRO Architect | Author of “What Chief Revenue Officers Actually Do” | Founder, The CRO Collective.

We only work with a small handful of rev tech platforms.  

We have a unique perspective on this sector for a number of reasons: 

1. I come from the adtech and rev tech sector.  I spent 2014-2019 ( the “meat” of the adtech and rev tech sector heyday) cutting my teeth building and selling and marketing services revtech products. I know this shit backwards and forwards.  

2. The CRO Collective focuses exclusively on helping and developing the Chief Revenue Officer role - the core ICP for all revtech products. We understand what CROs want, what they struggle with, why they want it and what works more than any other consultancy. It’s all we do. 

So we scrutinize revtech solutions diligently. Most fall short in some way or another. 

So when we come across tools that actually work and deliver on what CROs actually need we endorse and work with them.  

The Fullcast Revenue Insights platform - formerly Ebsta (now part of Fullcast) created by Guy Rubin is one of our recommended platforms.  

Any CRO should be using this platform to ascertain what’s really happening with their GTM function. 

Without that (accurate) knowledge, all systems, processes, motions, functions and strategies will be sitting on top of unreliable and inaccurate information.  

System design requires foundational data integrity.  

We bake the Fullcast Revenue Insights platform into our CRO Readiness process because it solves this base line issue for CROs. Full stop. 

I was pleased to participate in the Revenue Insights report. 

There are gems of information in this research.  

If you want to talk to me or my colleagues about how you can build a CRO Ready system, DM me.

Founder at Ebsta and MD Revenue Intelligence at Fullcast | Revenue Intelligence & RevOps Leader | Go-to-Market Strategy | Keynote Speaker on Sales, Forecasting & Growth

Today is the day! After months of analysis, conversations, and collaboration, we’re releasing early access to the 2026 GTM Benchmark Report with Fullcast and Pavilion.

This year’s report is built from $78B in pipeline, 361,000 opportunities, and 2,500 sellers. The result is a view of how revenue engines are actually performing right now. 

There’s a lot in the data, and I’ll be sharing more about it in the coming weeks.

For now, I just want to say thank you to the incredible leaders who contributed their perspective and insight to this year’s report. I’m grateful for the time, thinking, and candor you brought to it. Sam Jacobs, Jacco van der Kooij, ☁️ Cliff Simon, Mike Slater, Matt Gallagher, Kfir Pravda, Alan Morton, Tanja Mitchell, Sandy Robinson, M.Ed., Anthony Enrico, Warren Zenna, Pete Shelton, and (last but certainly not least) Ryan Westwood. 

If you’d like early access to the full report, you can sign up here: https://lnkd.in/exbMNKbh

#GTM #RevenueOperations #SalesLeadership #RevenueGrowth #GoToMarket

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