Jonathan Moss

Experity

Leading a team of senior Growth, GTM and Data leaders focused on establishing new growth vectors, building go-to-market strategies for the established and new business, and optimizing the system (data, process, and technology) that underpins the revenue machine. 

2024 results: 
↳ Grew top and bottom line by double digit % (first time in since 2021)
↳ Exceeded annual plan in revenue and EBITDA 
↳ CAC payback <12 months 
↳ LTV/CAC 5:1 
↳ Increased volume and conversion rates at every stage of the bowtie while decreasing sales cycle time across all product and service mixes 
↳ Reduced time to install by 2.5x 
↳ Reduced churn by 50%
↳ Launched 2 new revenue streams 

My teams are responsible for the following: 

Growth: establish growth vectors (e.g. adjacencies, new categories, product innovation), build out a 0 to 1 business within our incubator, and launch go-to-market 

Go-to-Market Strategy & Planning: planning and execution to accelerate durable growth across our platform of products/services 

GTM Operations: building, managing, and optimizing our GTM system that underpins our revenue factory. 

AI: building and implementing AI strategies across the GTM team, product and service lines. 

Data: structuring, aggregating, analyzing and providing insights for the GTM teams that drive our strategic decisions and operations. 

Revenue Enablement: accelerating employee productivity and knowledge across all GTM teams.

EVP - Growth, GTM Strategy and Operations

Established and lead the Executive AI committee comprising CTO, SVP of Strategic Partnerships, Chief Medical Officer and SVP of Technology. 

Implemented 5 AI initiatives 
2024/2025 roadmap for 10+ initiatives

Executive Chair - AI committee

OpenAI

Forum Member

Pavilion

Co-Chair AI in GTM

Executive Member

Winning by Design

Revenue Architect & GTM Ambassador

AI Business Network

Co-Founder

MetaVRse

✅ 140+ Metaverse / Web3 Products and Projects 

🌎 9 World-Firsts

💻 1 Award-Winning, Proprietary 3D Creation Platform (Metaverse, Web3)

👩‍💻60k+ Creators

♟️Established strategic partnership with Microsoft

Founding Team, Executive Board Member & Strategic Advisor

Led global vision, strategy, and execution for all facets of revenue generation, go-to-market, operations, customer success and product management within a high growth technology industry.

🚀Launched the Metavrse Engine from stealth April 2020 including SaaS and professional services. 

✍️Negotiated and Signed deals with Siemens Healthineers, Samsung, MasterCard, JP Morgan and other Fortune 500 companies. 

📚$2M+ booked revenue in the first 12 months. 

♟️Established strategic partnerships including NVIDIA, Qualcomm, EPIC Games, Meta (formerly Facebook), and Autodesk. 

🛣️Developed product roadmap with feature prioritization, UX/UI design, and technical integrations.

Chief Revenue Officer (CRO)

Booster

Booster is a clean technology company that provides mobile energy delivery, including renewable and sustainable fuels, through its marketplace. 

🛠️ Elevated go-to-market strategy, built the revenue engine and led sales team that secured $56M in bookings with 79% net revenue growth and 215% Enterprise segment growth

⚙️ Implemented sales motions with aligned systems across the customer journey, automated workflows and insights that led to a 60% more outbound lead volume, 2.5x meetings, and 4.6x opportunity creation, 56 day reduction in sales cycle time, 25% conversion rates and a 45% increase in deal size

✅ Transformed top of funnel strategy through diversification of marketing channels and building infrastructure which led to 10x inbound lead volume accounting for 30% of new business, up from 2%

🚀 Implemented Customer Led Growth strategy that led to a better customer experience, 2x faster growth and improved LTV/CAC

🤝 Series C ➡️ D Senior Leader

🎯 Built annual operating plan and forecasts (quarterly, monthly, weekly) with 96%+ accuracy  

🎙️Built brand and content strategies that elevated Booster to over 60%+ Share of Voice and 90%+ positive Brand Sentiment

🚀 Launched platform business (including a marketplace) with complete P&L ownership

📈Grew platform from $0 to $6M+ in ARR since launching in December 2022

🔋Built partnerships that enabled Infrastructure as a Service for EV Charging, Hydrogen, LNG, and CNG delivery 

🚚 Drove product roadmap strategy that allowed for mixed energy fleets to manage energy consumption, vehicles insights and payments for both sides of the marketplace 

📍Developed geo-spatial models and algorithms for route and location based density to enable effective dynamic pricing, sales and marketing prioritization

💰Developed pricing strategy transitioning legacy margin model to a product (SaaS) and services (Consumption) model

Vice President - Revenue & Revenue Operations

REEF

REEF is a technology company that transforms urban real estate into thriving mobility and logistical hubs via a marketplace.

🎯 Led GTM strategy and execution across sales, revenue operations, and customer success that secured $70M in new bookings and expansion that increased revenue from $30M to $100M+ throughout the United States, Canada, and Europe.

⚙️ Implemented sales process with aligned systems across the customer journey, automated workflows and insights that led to a 36 day reduction in sales cycle time, 40% increase in conversion rates and a 25% increase in deal size.

📱Developed and implemented product led growth strategies that led to a 3x revenue growth expansion from the demand side of the marketplace.

⛓️Interconnected and consolidated technology stack to increase efficiency and efficacy across marketing, sales, and customer success (Salesforce, ZoomInfo, Marketo, LinkedIn Sales Navigator).

Executive Vice President - Revenue & Global Revenue Operations

OYO USA

OYO is a global travel technology company that connects guests to owner-operators via a marketplace. It offers full-stack hospitality software and revenue management solutions to hotel owner-operators.

🎯 Led strategy and execution for go-to-market, revenue operations, and sales training that led to growth from $17M to $200M throughout the United States, Canada, and India.

📈Developed and implemented product led growth strategies that led to a 2x revenue growth and 3x margin expansion from the demand side of the marketplace.

🛣️ Create and maintain data and insights across the entire customer journey that increased direct sales close rate by 2.5x, increased deal size by 50% and decrease sales cycle by 45 days.

⛓️ Interconnected and built the sales tech stack to align with the customer journey and automated work flows to drive 2x sales efficiency and efficacy.

Vice President Revenue Operations & Enablement

T-Mobile

A demonstrated record of success and achievement, marked by a promotion to a position of increased influence, authority, and accountability. Fulfilled a critical role building and executing strategies to govern sales, communication, and training professionals in franchise stores, small business team, national retail team, and in Direct to Consumer teams encompassing over 40,000 individuals responsible for 80% of all revenue. Maintained accountability for $25M in P&L.

•Supervised a 190-person team engaged in sales enablement, learning (e.g. in-person, virtual, eLearning, and AR/VR), strategy/planning, sales tech stack, process design, LMS, other Learning technology and communication tools. 

•Recognized for Performance (Top 5%)

•Successfully accelerated the ramp-up period for new sales personnel from six months to one month, as measured by five key performance metrics - New Customer Acquistion, Renewal Rate, Average Revenue Per User, Value Added Service Attach Rate, and Emerging Product Attach Rate.  

•Positioned the company to be listed in the Great Places to Work list for 2018 to 2019.

•Sparked a 25% increase in revenue per subscriber as a result of training programs for existing sales representatives, improving their ability to promote and secure agreements for products, services, and accessories.

•Developed quantitative and qualitative analytics and dashboards to measure sales intelligence, performance, deal/funnel intelligence, and trainer performance across 40,000 employees. 

•Scope of training curricula and collateral spanned New Hire, Management Fundamentals, Advanced Leadership Programs, Behavioral Skills Workshops, Gamification, and over 250 sales and leadership videos.

•Recognized as the first training team in the world that formed a co-development partnership with the Apple Master’s Program.

Senior Director Sales Enablement | Learning

Responsible for operations encompassing 15,000 employees and 8,000 points of distribution across 22 states, representing $14B in revenue. Directed teams engaged in Go-To-Market strategy, Communications, Retail Technologies, Customer Support & Success, Performance/Competitive Analytics, Workforce Planning, Facilities and Distribution strategy.

•Developed operational and customer success strategies that led to $825MM increase in profit and 2,100 basis points in NPS.

•Executed over 20 go-to-market projects with budgets in excess of $10MM.

•Led Go-To-Market and Operational implementation of new channels including Direct to Consumer, Uber, Walgreens, and AAA. 

•Managed $1B+ budgets for labor, facilities, service and repair centers, new store builds, remodels, and equipment.

•Developed automated dashboards for 40+ operational and customer experience metrics with tangible costs and actions. 

•Implemented a variety of technology solutions to assist the sales, operations and customer support teams, including intelligent process automation, digital chatbots, Microsoft Office 365, Salesforce, and a number of SaaS tools.

Director Multi-Channel Sales Operations

Turning GTM into a revenue factory through recurring impact & helping GTM leaders do the same | GTM Executive leveraging AI ✨ | Keynote Speaker & Advisor | Podcast 🎙️ Host |

You know how companies either burn a ton of cash trying to scale or hit a growth ceiling they just can’t break through?

What I do is step in, audit their GTM strategy, financials, and operations, and then engineer a smarter, more scalable system (typically including AI). Whether that’s digitizing their physical business, refining their go-to-market motion, or unlocking new revenue streams, I build the strategies and systems that fuel sustainable, high-impact growth.

Companies I’ve worked with have seen a median growth rate of 87%

My journey has given me diverse experiences across many different industries, business models, products, and functions at different scales. 

➡️ Experience across multiple industries including Software (SaaS), Healthcare, Retail, Real Estate, Hospitality, Transportation/Logistics, Telecommunications. 

🚀 Company Stages: Venture Capital, Private Equity, and Bootstrapped at Pre-Revenue, Seed, Series A, Series C, Series D, Publicly traded 

💵 Investment Partners: Sequoia, Lightspeed, Madrona, GTCR, Warburg Pincus, Mubadala Capital, AirBnB, Microsoft, JP Morgan, UBS Asset Management, Softbank and JC2 Ventures 

💰Company Revenue: $0-$15B (87% median growth rate; over $1B of capital raised)
     👉 $0-$6M+
     👉 $0-$7M+
     👉 $17M-$200M+
     👉 $30M-$100M+
     👉 $80M-$150M+
     👉 $165M-$260M+
     👉 $190M-$2XX (Current role)
     👉 $13B-$15B+

📍Geographies: North America, LATAM, EMEA, and APAC

✅ Team Size: 1-200

🤓 Experience
👉 AI: 6+ years     
👉 GTM: 20+ years
     👉 Sales: 12 years (B2B); 10 years (B2C)
     👉 Revenue Operations: 13 years
     👉 Customer Success / AM: 9 years
     👉 Product: 9 years
     👉 Revenue / Sales Enablement: 5 years
     👉 Marketing / Demand Generation: 3 years
     👉 Business Development/Partnerships: 3 years

Healthcare should work like everything else in our lives — convenient, transparent, and built around the people it serves.

That's what we're building at Experity: a patient experience that feels less like navigating a system and more like having a concierge. 

On-demand access. 

Digital-first workflows. 

Intelligent connections between care moments. 

And critically, less administrative burden on the clinicians who make it all possible.

Our new partnership with Amazon Pharmacy is a perfect example of this vision in action. 

Patients walk out of an urgent care visit and get their prescriptions delivered fast, with full pricing transparency. 

No extra trips. 

No pharmacy lines. 

Just care that continues seamlessly after the visit ends.

This is what modern healthcare should feel like.

...and this is only one of many things we are doing to solve these problems. 

Tanvi Patel Tara DellaVecchia Kevin Clarke

Congrats to Amanda, Katie and the 1mind team for their Series A raise! 

Watching them build “always-on, infinitely knowledgeable” AI employees that anyone can access.

The implications are massive - not just for how we structure teams, but for how we think about deploying AI agents across the organization.

This is fundamentally rethinking what work gets done by humans vs. agents, and how org structures evolve when knowledge and capability can be instantly accessible to everyone.

Excited to see the evolution of 1Mind and what this team does!

A lot of people think they are behind in AI deployments based on the LinkedIn and X messages giving them FOMO. 

Let me bring some light to the situation so you don’t get a false narrative from the algorithms. 

If you aren’t experimenting daily/weekly, you are behind. 

If you haven’t deployed AI or agents at scale yet, you aren’t behind yet. 

Most deployments fail. Why? 

Data is messy. 

Most processes aren’t documented properly. 

Change management with people is hard. 

This is why you aren’t behind. 

You have do the unsexy and hard work first and then you will get success from your AI and agent deployments. 

Take your time, do it right, and you will get the outcomes you are needing. 

We see this in real life and through published research. 

Share your story of successful or unsuccessful AI deployments. Here to help and learn.

Same market. Same physics. Different systems.

Over a century ago, Amelia Earhart flew by the same laws that govern flight today... lift, drag, thrust, gravity. 

But we're flying 100x faster now. Not because the physics changed.

Because the systems evolved.

That's where GTM is right now.

You've probably seen the chart showing where we missed the pivot. 

The one that makes your stomach drop a little. 

That red zone between 2020-2023 where everyone should've been building different but kept throwing bodies at growth problems instead.

Capital was cheap. Risk-taking was even cheaper. So we hired early-career SDRs, AEs, and CSMs. 

We brute-forced our way to pipeline with headcount. 

We measured productivity per person.

And honestly? It worked. Until it didn't.

Now capital scarcity is forcing something we should've done years ago....operational efficiency. 

But here's what nobody's saying out loud: this isn't just about doing more with less.

It's about fundamentally rethinking the infrastructure.

The shift from SaaS-native to AI-native isn't a feature update. 

It's a systems overhaul.

Think about what changed from 2008 to 2023: 
→ People were the compound growth lever 
→ Hired fast, trained faster, measured activity 
→ Success = bodies in seats generating pipeline

But look at 2023 forward: 
→ Systems become the compound growth lever 
→ Low-cost intelligence via LLMs 
→ Success = growth loops built on usage data, not headcount

Here's what we're seeing:

→ Data becomes the moat, not messaging: Your CRM is full of signals about what actually works. Most companies ignore this goldmine and keep running the same plays.
→ Growth loops replace growth hacks: Product usage feeds GTM intel. GTM intel feeds product improvements. It's circular, not linear.
→ AI isn't a feature, it's the foundation: You don't bolt AI onto your existing process. 

You rebuild the process around what AI makes possible.

Look, I get it. This feels scary. Changing systems while you're flying the plane? 

That's not a metaphor—it's literally what we're all doing right now.

But the physics haven't changed. 

Customers still need solutions. 

Problems still need solving. 

Value still needs creating.

What's changing is how efficiently we can do it.

The companies that figure this out are the ones that build AI as infrastructure instead of just another tool. 

Those are the ones that'll be flying 100x faster while everyone else is still trying to hire more pilots.

Thanks Jacco for bringing forward the amazing research and POV on GTM in the AI era! 

Happy to be on the journey with you as an Ambassabor for Winning by Design and Founding Member of the Growth Institute.

Hope everyone had an amazing holiday, I took some time off and disconnected, hope you did as well. A lot happened and I am going to share thoughts on it all this week, plus some expansive thoughts on AI-native GTM. 

But first.. let's get into some of the things that happened over the last week or so. 
 
Meta just gave ChatGPT, Copilot, and Perplexity their eviction notice from WhatsApp Business API. Wonder if ChatGPT group chats accelerated this.. 
 
Official reason: "Business API is for transactional messaging, not AI assistant distribution."
 
Real reason: Meta wants Meta AI to own the playground.
 
Think about that.
 
This isn't a WhatsApp problem. It's a "building on someone else's rails" problem.
 
→ Meta wants Meta AI 
→ Google wants Gemini everywhere  
→ Microsoft wants Copilot in everything
 
That brief magical period where AI assistants could meet customers wherever they were? It's ending faster than anyone expected.
 
What does this mean for your GTM org?
 
If you're using AI chatbots on third-party platforms for customer conversations, you've got three immediate problems:
 
→ Platform risk you can't control. That Slack integration, that LinkedIn automation, that WhatsApp bot—they can all disappear with 90 days notice. Your workflows, your data, your customer relationships. Gone.

→ Data you can't move. Most of these integrations don't let you export conversation history. When the platform pulls the plug, you're starting from scratch. Every insight, every customer interaction, every qualification step—locked in someone else's system.

→ GTM strategies built on borrowed time. If your outbound motion, your customer success workflows, or your sales enablement depends on tools you don't control, you're one terms-of-service update away from scrambling.
 
The companies winning right now? They're building AI on infrastructure they own, and integrating strategically where it makes sense. But they never confuse the two.
 
The question for every GTM leader:
 
Where are you building your AI integrations?
 
Because if the answer is "on platforms we don't control," you need to answer three more questions:
 
1. What happens when they change the rules overnight?
2. Can you actually migrate your customer data if you need to?
3. Who owns the conversation history with your customers?
 
The pattern here is old. The speed is new.
 
Every platform eventually prioritizes its own ecosystem. MySpace did it. Facebook did it. Twitter did it.
 
But the AI platforms are doing it in months, not years.
 
My take:
 
Build where you own the rails. Integrate where you don't. But never confuse the two.
 
And if you're relying on third-party AI integrations for customer conversations? Audit that data portability. Today.
 
Because the walls are going up faster than anyone thought possible.

MCP has been live for a year.

Most GTM leaders still have no idea what it means for them.

That's about to change.

Anthropic just showed why Model Context Protocol with code execution is the infrastructure shift everyone's been sleeping on.

𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁'𝘀 𝗵𝗮𝗽𝗽𝗲𝗻𝗶𝗻𝗴:

Since November 2024, developers have been building on MCP. Thousands of integrations. Every major programming language. The protocol is becoming the standard for connecting AI to tools and data.

But here's the problem most companies are hitting right now.

𝗬𝗼𝘂𝗿 𝗔𝗜 𝗮𝗴𝗲𝗻𝘁𝘀 𝗮𝗿𝗲 𝗳𝘂𝗻𝗱𝗮𝗺𝗲𝗻𝘁𝗮𝗹𝗹𝘆 𝗶𝗻𝗲𝗳𝗳𝗶𝗰𝗶𝗲𝗻𝘁

Every time your AI needs to access Salesforce, check HubSpot, pull from Drive, send a Slack—it's reading every instruction manual first. Then manually copying data between systems. Word by word.

Not slow. Broken.

Most teams added MCP integrations and wondered why everything still felt sluggish.

𝗧𝗵𝗲 𝗯𝗿𝗲𝗮𝗸𝘁𝗵𝗿𝗼𝘂𝗴𝗵 𝘁𝗵𝗮𝘁 𝗷𝘂𝘀𝘁 𝗱𝗿𝗼𝗽𝗽𝗲𝗱

Code execution with MCP changes the entire game.

Instead of AI following instructions, it writes code.

The numbers are wild

Before: 150,000 tokens processed just to access your tools

After: 2,000 tokens to run the same workflow

That's 98.7% reduction in processing. 75x faster. 75x cheaper.

Same task. Different architecture.

𝗪𝗵𝘆 𝘁𝗵𝗶𝘀 𝗺𝗮𝘁𝘁𝗲𝗿𝘀 𝗳𝗼𝗿 𝗚𝗧𝗠

Remember when you tried connecting your entire tech stack... Salesforce, Gong, calendar, Drive, Slack, data warehouse... and it didn't work well?

Code execution fixes that.

You can finally run complex workflows that actually work

"Pull this week's calls from Gong → identify pricing objections → cross-reference closed-lost in Salesforce → draft personalized responses → send to reps in Slack."

Used to crash halfway through. Now runs in 2 minutes.

𝗧𝗵𝗲 𝗽𝗮𝗿𝘁 𝘁𝗵𝗮𝘁 𝗰𝗵𝗮𝗻𝗴𝗲𝘀 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴

Your AI saves its own workflows.

First time it analyzes competitor mentions, it figures it out. Every time after, it just runs the saved playbook. Your AI gets better at YOUR specific business. Not generic tasks.

𝗧𝗵𝗲 𝗮𝗱𝗼𝗽𝘁𝗶𝗼𝗻 𝗰𝘂𝗿𝘃𝗲 𝗶𝘀 𝘀𝗵𝗶𝗳𝘁𝗶𝗻𝗴

MCP launched a year ago. Code execution just showed why it matters.

Most GTM teams are still treating AI like fancy ChatGPT... one task at a time, slow, expensive, breaks on complexity.

The companies that win will be the ones whose AI actually scales across their full tech stack. 

Fast. Reliable. At cost that makes sense.

That infrastructure just became real.

𝗪𝗵𝗮𝘁 𝘄𝗼𝗿𝗸𝗳𝗹𝗼𝘄 𝗵𝗮𝘃𝗲 𝘆𝗼𝘂 𝗯𝗲𝗲𝗻 𝗮𝘃𝗼𝗶𝗱𝗶𝗻𝗴 𝗮𝘂𝘁𝗼𝗺𝗮𝘁𝗶𝗻𝗴 𝗯𝗲𝗰𝗮𝘂𝘀𝗲 𝘆𝗼𝘂𝗿 𝗔𝗜 𝗰𝗼𝘂𝗹𝗱𝗻'𝘁 𝗵𝗮𝗻𝗱𝗹𝗲 𝗶𝘁?

OpenAI is coming for where you work today, the browser. 

They bought Sky , which builds browser-based AI agents that sit 𝘪𝘯𝘴𝘪𝘥𝘦 the tools your team already uses.

And they dropped Atlas - their new "AI teammate" that can browse the web, fill forms, and execute workflows autonomously.

Connect the dots:

→ ChatGPT already has 800M+ weekly active users 
→ Sky's tech lets AI operate directly in browsers 
→ Atlas can now execute tasks across web applications 
→ Your CRM, your outreach tools, your data entry... all vulnerable

𝗧𝗵𝗲 𝗽𝗹𝗮𝘆 𝗶𝘀𝗻'𝘁 𝘀𝘂𝗯𝘁𝗹𝗲:

Phase 1: Get everyone dependent on ChatGPT for thinking 
Phase 2: Acquire the tech that lets AI act in their workspace 
Phase 3: Launch agents that can 𝘥𝘰 the work, not just suggest it 
Phase 4: Own the entire workflow from insight to execution

Your sales team uses Salesforce? Atlas can update it. 
Your SDRs use Outreach? Atlas can send sequences. 
Your ops team does data entry? Atlas can handle spreadsheets.

This isn't about making your team more efficient.

𝗜𝘁'𝘀 𝗮𝗯𝗼𝘂𝘁 𝗢𝗽𝗲𝗻𝗔𝗜 𝗯𝗲𝗰𝗼𝗺𝗶𝗻𝗴 𝘁𝗵𝗲 𝗶𝗻𝗳𝗿𝗮𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲 𝗹𝗮𝘆𝗲𝗿 𝗯𝗲𝘁𝘄𝗲𝗲𝗻 𝘆𝗼𝘂𝗿 𝘁𝗲𝗮𝗺 𝗮𝗻𝗱 𝗲𝘃𝗲𝗿𝘆 𝘁𝗼𝗼𝗹 𝘁𝗵𝗲𝘆 𝘁𝗼𝘂𝗰𝗵.

And here's the brutal truth nobody wants to say out loud:

Most AI companies spent 2024 building point solutions - better email writers, smarter dialers, faster research tools. 

OpenAI is positioning itself to make a lot of point solutions obsolete by owning the execution layer itself.

The question isn't whether your tools will integrate with OpenAI's agents.

The question is whether your tools will even matter when those agents can operate through a browser better than your team can.

We're not in the "AI features" era anymore.

𝗪𝗲'𝗿𝗲 𝗶𝗻 𝘁𝗵𝗲 "𝗔𝗜 𝗶𝗻𝗳𝗿𝗮𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲" 𝘄𝗮𝗿.

And OpenAI just fired the first real shot at the application layer where revenue teams actually live and work.

How are you rethinking your tech stack?

OpenAI is going after so many places right now to before the de facto interface for consumers…

Group chats in ChatGPT are now piloting in Japan, New Zealand, South Korea, and Taiwan.

A new way to collaborate with friends, family, or coworkers and ChatGPT in the same conversation.

WDYT?

graphical user interface, text, application, chat or text message

I used ChatGPT Voice to prep my AWS re:Invent presentation and interview.
 
Walking around my hotel. Inside. Outside. Hands-free. No typing. No switching screens.
 
I've been obsessed with conversational UX/UI since before it was cool.
 
My thesis: Voice is how humans naturally communicate. So voice will become how we interact with computers.
 
Not as a novelty. As the primary interface.
 
I now talk to my computer and phone about 80% of the time instead of typing.
 
Not because I'm trying to be futuristic. Because it's faster. More natural. Less friction between thought and action.
 
And what ChatGPT just shipped? Validation that this shift is real.
 
Voice is now just... part of the conversation. No toggle. No separate mode. You talk. Text appears. You see images, maps, code—all while speaking.
 
Mobile. Web. Everyone. Right now.
 
Here's what I actually did:
 
Presentation tomorrow. High stakes.
 
I opened ChatGPT and just... talked. While walking around the hotel. Through the lobby. Outside. Back to my room.
 
"Help me practice my presentation."
 
Then I delivered my intro. Out loud. Moving. Like I would on stage.
 
ChatGPT listened. Analyzed. Gave me specific feedback: 
→ "Your hook is strong but arrives 30 seconds late" 
→ "You used 'basically' three times in 90 seconds" 
→ "Your transition to the data point needs more punch"
 
Then we iterated. Live. Conversationally. Like having a coach beside me.
 
This isn't about voice recognition getting better.
 
It's about eliminating the cognitive load of interacting with technology.
 
What's different now:
 
Before: "Hey Siri, SET TIMER for 10 minutes" (command) 
Now: "I need to prep for a meeting in about 10 minutes" (intent)
 
The computer figures out what you need.
 
This is about eliminating context switching in the workflow that matters most.
 
Current reality:
 
A rep has a call in 12 minutes with a VP of Sales at a $50M ARR company.
 
They need to: 
→ Pull up account history
→ Review past conversations 
→ Check recent company news 
→ Find relevant case studies 
→ Draft discovery questions 
 
Five tools. Four logins. Twelve minutes.
 
That rep walks into that call underprepared. Every. Single. Time.
 
Now imagine this:
 
11 minutes before the call, they open one interface and just... talk:
 
"What do I need to know about Acme Corp before my call with their VP of Sales?"
 
And they get—while putting on their headset—account context, recent news, suggested questions, similar customer stories, and potential objections.
 
No tabs. No logins. No mode switching.
 
The best GTM tool isn't the one with the most integrations.
 
It's the one that disappears into the flow of actual selling.
 
For the last decade, we've built GTM tech like this:
 
"Here's a dashboard for analytics. Here's a portal for content. Here's a tool for sequences. Here's another tool for intelligence."
 
The future looks like this:
 
"Just talk. We'll handle the rest."

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

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

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

Executive Member,  Former CRO & Enterprise Sales GTM School Lecturer

RevGenius

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

Founding Member

Sales Hacker, Inc.

Flex Technology Group

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

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

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

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

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

Vice President of Strategic Accounts

Director of Strategic Accounts

Director of Sales, Midwest Region

Regional Sales Manager

Pitney Bowes (Managed Services)

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

Senior Sales Consultant

Antenna Software

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

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

Director of Sales Midwest Region

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

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

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

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

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

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

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

My portfolio:

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


My results:

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


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


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


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

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

X-https://x.com/Ryan_Staley1

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

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


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

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




2. The AI Shock + Everything Changing at Once

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

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

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



3. Tech Stack Evolution vs. Human Adoption

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



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

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



5. Comp Plans, Metrics, and Governance

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

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


6. Cross-Functional GTM at Scale

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

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



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



8. CRO Role Clarity and Org Design

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

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

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

Huge thank you to Warren Zenna to hosting

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

whale-boss

li_at

JSESSIONID

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

Founder, The CRO Collective—the first firm built exclusively for Chief Revenue Officers. I help companies become 'CRO-Ready'—and turn high-potential leaders into high-performing CROs.

CRO📈? Or in Subscriber Acquisition♻️💰? I’m your guy 👊 | @UChicagoBooth @JOT | xBCG xBBDO xGroupon

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

Chief Revenue Officer I General Manager I Fintech I Cybersecurity

Passionate about helping brands grow through media and technology innovation.

Co-Founder & CEO @ Scalestack | Autonomous Revenue Engine. Zero Duct Tape.

CRO / GTM Executive helping business leaders bridge the gap between vision and execution to accelerate growth. Never stop learning and improving!

Managed Services CRO | Board Member | Leader & Team Builder | Growth Focused Executive

Preparing CROs & CEOs for the future of B2B SaaS | GTMshift | CRO Functional Head @ Pavilion | Former CRO | Co-Founder @ PreSales Collective (Acquired) | Breaking The GTM Playbook |

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

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

This is straight from the heart.



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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

━━━━━━━━━━━━━━━━━

THE TYPICAL APPROACH (That Fails):

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

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

━━━━━━━━━━━━━━━━━

THE 60-DAY APPROACH (That Works):

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

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

━━━━━━━━━━━━━━━━━

WHY MOST FAIL:

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

━━━━━━━━━━━━━━━━━

THE ANTI-HYPE RULES:

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

━━━━━━━━━━━━━━━━━

REAL EXAMPLE: $300M ARR Company

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

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

━━━━━━━━━━━━━━━━━

THE BOTTOM LINE:

Stop planning AI. Start shipping AI.

60 days. Not 2 years.

━━━━━━━━━━━━━━━━━

Is your AI transformation taking too long?

$1.5 Trillion invested in AI in 2025.

90% of enterprises see ZERO impact on EBIT.

Let me say that again:

90% see no bottom-line impact.

Despite trillions invested.

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

━━━━━━━━━━━━━━━━━

**THE PARADOX:**

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

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

The question everyone's avoiding:

Where's the ROI?

━━━━━━━━━━━━━━━━━

THE 3 FAILURE MODES:

1. Pilot Purgatory

Companies run 47 AI pilots.

None reach production.

Why? They're always "testing."

2. The Integration Gap

AI tools purchased.

Can't access company data.

Sit unused. Money wasted.

3. Time to Value Problem

Implementation takes 6+ months.

People lose interest.

Tools abandoned before impact.

━━━━━━━━━━━━━━━━━

REAL DATA FROM MY CLIENTS:

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

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

━━━━━━━━━━━━━━━━━

THE "TIME TO VALUE" FRAMEWORK:

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

Here's how to beat that:

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

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

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

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

━━━━━━━━━━━━━━━━━

**THE BOTTOM LINE:**

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

It's about bad implementation.

**Fix these 3 things:**

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

Do that?

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

━━━━━━━━━━━━━━━━━

Are you seeing AI ROI at your company?

Or are you stuck in pilot purgatory?

Comment below. 👇

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

AI can do it in 3 questions.

With 95% accuracy.

Here's how:

━━━━━━━━━━━━━━━━━

THE OLD WAY:

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

Result: Expert intuition about which deals will close

Time investment: 10 years

━━━━━━━━━━━━━━━━━

THE NEW WAY:

3 Questions to AI:

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

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

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

Result: Data-driven qualification in 5 minutes

Accuracy: 95%+ (tested against actual outcomes)

━━━━━━━━━━━━━━━━━

WHY THIS WORKS:

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

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

━━━━━━━━━━━━━━━━━

REAL EXAMPLE:

Sales rep brought me a "perfect" opportunity:

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

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

Recommendation: Deprioritize

Outcome: Deal stalled at 120 days, never closed

AI was right. Human intuition was wrong.

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

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

━━━━━━━━━━━━━━━━━

THE TYPICAL APPROACH (That Fails):

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

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

━━━━━━━━━━━━━━━━━

THE 60-DAY APPROACH (That Works):

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

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

WHY MOST FAIL:

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

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

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

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


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


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


It's happening again. Right now.


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

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

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

Zero exaggeration. I recorded everything.


The Business Math

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


Same headcount. Same budget. Different results.


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

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

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


Your 7-Day Action Plan


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

The Question


You won't get disrupted by AI.

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

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

The 90-day clock is ticking ⏰

The GPT-5.1 rumors have my full attention.

What I’m hearing from people who actually know:

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


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


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


What I’m telling clients:

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


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


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


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



Which side will you be on?

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


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

WHAT I really see is millions in missed opportunities.

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

Feature #1: 

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


Feature #2: 

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


Feature #3: 

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


HOW to implement today:

Challenge Current Thinking: Use rival perspectives on your biggest decision

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

Go Agentic: Create workflows that think 5 steps ahead

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

The results? Superhuman decision-making in seconds.

Most leaders are playing checkers with AI.

Smart ones are playing 4D chess.

Which game are you playing? 👇

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

Gpt 5 not Gpt 4

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


The workflow (all in a single thread):

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


🔥 Total time: ~15 minutes.

Old way: 3–4 hours of deep work.

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


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

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


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


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

It was a stacked workflow of 2 tools.


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


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

There are two types of SaaS companies in 2025:

AI-First companies (doubling year-over-year)

AI-Last companies (struggling to hit targets)

The gap is widening fast.

Here's what separates them:

━━━━━━━━━━━━━━━━━

AI-LAST COMPANIES:

"We'll adopt AI when it's proven."

**Their mindset:**
→ Wait and see approach
→ Risk-averse pilot programs
→ 12-month evaluation cycles

Their reality:
→ Competitors moving faster
→ Best talent leaving for AI-forward companies
→ Growth slowing

━━━━━━━━━━━━━━━━━

AI-FIRST COMPANIES:

"We're implementing AI yesterday."

Their mindset:
→ Move fast, iterate faster
→ 60-day transformations
→ AI in hiring criteria

Their reality:
→ 2x productivity gains
→ Attracting top talent
→ Doubling in size annually

━━━━━━━━━━━━━━━━━

THE PE PERSPECTIVE:

I work with PE-backed SaaS companies.

Here's what boards are saying:

2024:
"AI is nice to have."

2025:
"AI is table stakes."

2026
"AI or Die"

The shift happened FAST.

━━━━━━━━━━━━━━━━━

THE COMPETITIVE MOAT:

What used to create competitive advantage:
→ Better product
→ Larger sales team
→ More marketing spend

What creates competitive advantage now:
→ AI-enhanced product velocity
→ Smaller sales team with AI superpowers
→ AI-driven marketing efficiency

The difference?

AI-First companies do MORE with LESS.

━━━━━━━━━━━━━━━━━

**REAL EXAMPLE:**

Two similar $30M ARR SaaS companies:

**Company A (AI-Last):**
→ 150 employees
→ 18-month product release cycles
→ 30% growth target (struggling)

**Company B (AI-First):**
→ 95 employees
→ 6-month product release cycles
→ 80% growth actual

Same market. Same TAM.

Different AI strategy.

Different results.

━━━━━━━━━━━━━━━━━

**THE 90-DAY PE PLAYBOOK:**

**Month 1: Assessment & Quick Wins**
→ AI audit across all functions
→ Implement AI in 2-3 key areas
→ Show immediate ROI to team

**Month 2: Scaling & Integration**
→ Expand successful pilots
→ Integrate AI into workflows
→ Train entire organization

**Month 3: Competitive Advantage**
→ AI-enhanced product development
→ AI-driven sales & marketing
→ Measure growth impact

**Result:** Competitive moat established

━━━━━━━━━━━━━━━━━

**THE BOTTOM LINE:**

You can't afford to be AI-Last in 2025.

Your competitors aren't waiting.

Your customers aren't waiting.

The market isn't waiting.

**Two choices:**

1. Transform in 60-90 days
2. Fall behind permanently

There's no middle ground anymore.

━━━━━━━━━━━━━━━━━

Is your company AI-First or AI-Last?

Be honest. 👇

40% of enterprises say they lack internal AI expertise.

This number is about to get worse.

Here's why (and what to do):

━━━━━━━━━━━━━━━━━

THE SKILLS GAP DATA:

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

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

The gap is widening.

━━━━━━━━━━━━━━━━━

WHY THE GAP IS GROWING:

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

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

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

━━━━━━━━━━━━━━━━━

THE 3 TYPES OF AI SKILLS NEEDED:

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

Current gap: 60% of employees lack this

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

Current gap: 80% of employees lack this

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

Current gap: 90% of leaders lack this

Does your company have the AI skills it needs?

Or are you in the 40%?

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

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

This one blew me away.  

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

Google

Turning cold leads into warm leads.

This was a combo of Gemini 🍌and @grok 

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



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



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

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

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

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

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


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


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


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

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


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


Success changes with new inputs.

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


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


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

Shorter loops (weekly, not quarterly reviews)

Decentralized learning (champions across every team)

Immediate measurement against business outcomes


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



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

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


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


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


WHAT THE NUMBERS SAY:

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


WHAT THIS MEANS FOR YOUR TEAM:

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


WHAT THIS DOESN'T MEAN:

AI isn't replacing your closers.

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

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


AI handles the mechanics. Humans handle the moments.

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


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

Save Hours Every Week With This Simple Trick!

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


Then I leveraged AI, and my content workflow exploded:

Generated 30 LinkedIn posts in 15 minutes.

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


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


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

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

#AI #ContentMarketing #LinkedInStrategy #Productivity #GoToMarket

Mixing models? 

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

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

taplio

The Battle

Jonathan Moss

Ryan Staley

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The Battle

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