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.

Mike Groeneveld

GTM Advisor | Extreme Ownership | Servant Leader | Angel Investor | VP of Global Sales at Everstage

Vice President of Global Sales

Everstage can help you unlock the power of incentives and turn your sales teams into a revenue-generating weapon. Sales commissions automation saves time, motivates your payees, achieves high-accuracy commissions and wins more deals. Hyper-growth companies like Chargebee, Postman, Nitro, Thought Machine and Sosafe trust Everstage to automate their commissions process.

Learn more about Everstage here - www.everstage.com

A prospect asked for a proposal. The rep sent it same day. The $60k deal disappeared overnight.

I still remember the rep’s face the next morning. Pure human emotions: not angry or dramatic. Just that quiet drop, like, “I really thought we had it.”

And honestly, I get why they rushed.

The demo went well. The prospect was engaged. Asked smart questions. Nodded at the right moments. Said the magic line: “Send me a proposal.”

That line hits a rep’s brain like dopamine. You feel the deal tightening up. You feel the quarter getting easier. You want to be fast, helpful, on it.

But in B2B, “send the proposal” often doesn’t mean “we’re close.” It often means, “I need something to forward.”

And when you send it too early, three things happen.

First, the proposal gets judged by people you’ve never met. Finance, procurement, IT, a VP. They see a number and a scope with zero context. That’s not evaluation. That’s a drive-by.

Second, price lands before alignment does. If you haven’t sanity-checked budget range and what they’re actually buying, the proposal creates sticker shock. Sticker shock creates ghosting.

Third, you confuse interest with authority. The person who loved the demo might not be the person who can defend the spend internally. The proposal becomes their way to work without committing to a decision.

This is the part reps don’t get taught early enough: Your job isn’t to be the most available vendor. Your job is to be a premium partner.

And premium partners don’t rush documents. They slow the moment down and clarify reality.

So now, when someone asks for a proposal, don’t say “sure” and sprint.

Ask one calm question first: "Happy to send it. Do you have a few minutes to review it together?"

That one question changes many things.

Because the space in B2B SaaS is tight. Competition is everywhere. You need to understand their feedback on your pricing. Explain how it's unique vs. your competitors. Get mutual alignment on how it will provide ROI for your customer. 

The reps who win long-term are the ones who can feel that trigger and still choose patience.

Not because they’re slow. Because they’re serious.

SVP of Global Sales @ Everstage | Scaling B2B SaaS from 0-$100M | Extreme Ownership | Angel Investor

Your forecast accuracy tells me more about your culture than your pipeline.

When a rep gives you a number, they aren't just looking at a CRM. They're making a choice: Do I tell the truth, or do I tell the manager what they want to hear so I can get off the call?

The Three Forecast Lies:

1. The Safe Number:

The team always beats their number, but only at the last second. They aren't being disciplined, they're sandbagging. They've learned that being wrong hurts more than being honest helps. They're protecting themselves, not the business.

2. The Comfort Story:

Every deal is "in a good place." No concrete facts, just vague stories. This happens when the culture treats bad news like a personal failure. If honesty creates tension, people will start bringing you comfort instead of reality.

3. The Punished Risk:

You ask why you didn't hear about a slip sooner. The answer is simple: Early risk gets punished. If you give a rep "heat" for a deal slipping in week three, they will wait until week twelve to tell you next time.

How to Get the Truth?

Forecasting doesn't get better with a new template. It gets better when you change the environment:

- Reward early truth:

If someone flags a deal slipping in week two and they get heat for it, next time they'll wait until week eight. That's human nature. People avoid pain.

- Stop tying the number to the person:

Reps lie when they feel like a miss makes them look incompetent. When the number becomes identity, reality disappears.

- Ask questions that pull out the real risk:

What has to happen next for this to close on time? What are we waiting on that we can't control? If this slips, what will the reason be?

Accuracy is a result of trust. 

When your team feels safe enough to be honest, your forecast becomes boring. And in sales leadership, boring is a compliment.

The Sales quarters I feel happy about have no noise, shouting, or fireworks.

I learned that over the years.

Early on, when you’re leading a team, you chase the dopamine. The late-night war room. The last-week scramble. The comeback story. The moment you hit the number and everyone feels like a genius.

It feels like leadership.

But after you’ve done this long enough, you realize something uncomfortable: If your quarter needs drama to win, you’re borrowing from the next one.

The quiet quarters are harder. Because when things look “fine,” that’s when teams get lazy.

- You skip the prospecting block because you’re technically covered.
- You push the deal review because the notes look clean.
- You respond a day late because it doesn’t feel urgent.
- You stop staying close to customers because renewal is months away.

So the discipline became the whole game for us.

Forecast hygiene. Fast responses. No fantasy commits. Coaching when it’s calm, not when it’s on fire.

And then you hit a quarter where nothing heroic happens.

No miracle deal. No last-minute save. No fireworks.

You still close the quarter well.

And you feel happy for a different reason: Because you didn’t need adrenaline to be good.

How many follow-ups in sales is a good amount of follow-ups?

This is the most debatable question in B2B. Everyone wants a clean rule. Two follow-ups. Three follow-ups. Five touches. Ten days.

I don’t think the answer lives in a number. I think you as a rep already know the answer, because you were in the conversation.

After a demo, when you’re waiting on a buyer to respond, your job is not to “follow up the right number of times.”

Your job is to adapt to what you already saw.

There are buyers who are genuinely serious, but their company is a mess. They are in back-to-back internal meetings. They are dealing with security, finance, politics, or a fire drill.

With those buyers, even one follow-up works, because they will answer like an adult.

They will say something specific.

"Give me five days" or "I’m traveling until Thursday" or "We need security sign-off, I’ll come back after that" or "I need to align with my VP, can we reconnect next week?”

Serious buyers give timelines. Even when they are delayed.

Then there is the other kind.

The buyer who is “interested” but vague. The buyer who replies with soft words and zero commitments.

"Let’s circle back", or "Send me the deck", or "We’re evaluating".

You can feel it when it happens. The energy is different. The conversation is slippery. No one is owning the next step. Sometimes they’re shopping. Sometimes they’re using you to benchmark competitors. Sometimes they’re convincing themselves they are doing diligence.

And the more you chase that buyer, the worse your posture gets.

So if you want a practical way to think about follow-ups, use this instead of a number:

Ask yourself one question after the demo: Did this buyer behave like someone who can give a real yes or a real no?

If the answer is yes, one or two follow-ups are enough. They’ll tell you what’s going on and they’ll give you a timeline.

If the answer is no, do not turn yourself into a reminder system. Close the loop fast.

A rep who was in the room is the best person to decide what to do next.

Because follow-ups are not a math problem. They’re a read of the buyer in front of you.

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