Welcome to Cannonball GTM!
Marketing at Max
Learn the System
From AI confusion to marketing precision in four simple steps
Ever wonder how top growth hackers build campaigns so quickly? Our Substack teaches you the exact four-step method that we developed and refined through years of GTM engineering. While others struggle with each AI update, we keep improving these techniques and share them in a clear system that anyone can use.
What You'll Get
- Weekly live videos showing how to build real campaigns from scratch
- Clear lessons on using AI for better marketing
- Access to our collection of tested AI prompts
Community Benefits
- Weekly Q&A time with marketing experts
- Useful data about what works in different markets
- Join forward-thinking marketers who use AI to enhance ideas, not replace them
Whether you're a tech expert or marketing leader, our GTM engineer and growth hacker disciples use these strategies right away and see better campaign results. Join the group that's changing what's possible with AI-powered marketing.
Stuff From our Substack
This Is The Way: The SDR Manager's Guide to Cannonball GTM
June 26th, 2025
TL;DR: Your SDR just came to you asking to try "this Cannonball thing" instead of following the playbook. Before you say no, consider this: the number of quality conversations per SDR has plummeted 55% since 2014, 36% of companies downsized their SDR teams in 2025, and cold email response rates have dropped 27% in just the last year. The traditional model isn't just broken, it's mathematically unsustainable. Here's why letting your SDR innovators try Cannonball GTM might be the smartest risk you take this quarter.
June 11th, 2025
Jon Miller, co-founder of Marketo, one of the most respected voices in B2B marketing, dropped what we're calling the "attribution extinction event." In a single LinkedIn post, he declared attribution "BS" and dismantled the fundamental assumptions that an entire industry built its promises on.
This wasn't just another hot take. This was a category killer.
When someone with Miller's credibility (29,000+ LinkedIn followers, three successful exits, board positions) publishes a detailed takedown of attribution, every CEO who read it immediately started questioning their marketing tech spend. We predict that within six months, any CMO currently evaluating attribution platforms will face serious scrutiny from leadership who saw Miller's post.
The dinosaurs just got their meteor.
June 2nd, 2025
This June 2025 edition introduces a shift from demographic theater to existential reality. We're retiring the traditional ICP approach (don't worry, it's living happily on a farm upstate with all those childhood pets) and replacing it with a methodology that identifies and targets genuine customer pain through Existential Data Points.
What's New in This Edition
Three Game-Changing Prompts:
- SaaS Category Market Analysis - Deep market research for EDP discovery
- Existential Data Point Analysis Framework - Transform research into actionable pain insights
- Pain-Based Segment Evaluator - Quantify and score segment viability
Methodology Evolution:
- Complete shift from ICP demographics to pain-based segmentation
- Introduction of Existential Data Points as the core targeting mechanism
- Data-driven approach to identifying segments that convert
June 5th, 2025
The Future of Outbound Isn't Dead - It's Just Getting Smarter
Let me paint you a picture.
You're scrolling LinkedIn (because of course you are), and another growth guru with perfect teeth and a ring light is declaring the death of outbound sales. "Cold email is dead!" they proclaim. "The future is community-led growth and authentic relationships!"
Meanwhile, across town, one of Jordan’s clients just booked a meeting with their dream prospect using a cold email. Not just any meeting, a "holy shit, how did you know exactly what keeps me up at night?" kind of meeting.
Here's what the LinkedIn gurus aren't telling you: Outbound isn't dead. Shitty outbound is dead.
And thank God for that.
Cannonball GTM Livestream Season 3
See marketing mayhem every Friday at 9am PST on LinkedIn
Season Three delivers twelve weeks of pure AI-powered marketing precision: 4 OG Cannonballs where we transform WingWork, Bolo.Ai, Evvhq.com, and Rematter from zero to campaign using Cannonball GTM 3.0, plus six Agent Builds that create research and messaging automation so sophisticated they'll make your current processes look like they were designed by cavemen. Same chaotic energy, now with hyper-focused agent development that turns everyday AI into your unfair competitive advantage—because why do manual research when you can build agents to do it better?
The Season Three Lineup
No Show for September 19th!
Jordan and Doug will be taking a break to recover from AI Barfed. If you haven't signed up yet and Lu.ma is telling you the event is fully booked, ping Doug on LinkedIn…..he may have stashed a ticket or two away for our Cannonball community.
Season Three Lineup
No Show on 9/19: Check out Barfed!
September 18th | 1:00 pm PDT
Jordan and Doug will be heads down in San Francisco getting ready for AI Barfed…..yup, the name was intentional, and yes, we're bad at brand marketing.
The Territory-Campaign Bridge with Boogie Board
September 26th | 9:00 am PDT
Episode 11: Season Finale Join Doug and Boogieboard.AI CEO Kevin Davis for a live, end-to-end build of a complete market map, from segmentation to micro-sales territory.
Explore Our Livestream Archives
Two seasons of marketing chaos that left a trail of inadvertent brilliance you can binge-watch like that show you pretend not to love.
From diagnosing campaigns for Overjet.ai and developing permissionless value props for Arborgold, to Battle of the Brands showdowns (Doug totally cheated), Clay Day wizardry, and AI-powered systems discovering 1,800 personalized value props in one hour, we've proven systematic pain-based segmentation works across every industry we could cover in 24 episodes (so, you know, vertical SaaS). Consider it your master class in "what to do" and sometimes "what definitely not to do."
Season Three Archive
Cannonball GTM for (but not with) WingWork
Season 3 | Episode 1 - July 11th, 2025
We went back to our roots to kick off Season Three with an OG Cannonball, this time with a single prompt that took us from Focus to Narrate with a few clicks.
Building a Research Agent for WingWork
Season 3 | Episode 2 - July 18th, 2025
Watch the instant classic - yes, it's up there with Texada and the 'Blue Doug' episode. Watch us as we delivered an agent-ready data framework for the aircraft maintenance industry with the typical chaotic flare you know and love.
The Headless PVP: A Permissionless Value Prop In Search of a HC Brand
Season 3 | Episode 3 - July 25th, 2025
We were at our inverting best as we tackled our first Headless PVP using the Mimilabs.AI healthcare database.
Season 3 | Episode 4 - August 1st, 2025
Watch to get a masterclass in why most companies are applying the wrong go-to-market methodology to their market segment.
Cannonball GTM Data Layer Build for (but not with!) Bolo.AI
Season 3 | Episode 5 - August 8th, 2025
By the end of the livestream, Jordan had accidentally built something that looked less like traditional AI usage and more like conducting an orchestra, with Claude Code as the lead violinist, GPT agents handling percussion, and regular Claude keeping everyone in time.
The Headless PVP: A Permissionless Value Prop for Transportation and Logistics
Season 3 | Episode 6 - August 15th, 2025
We created a data architecture and pathway for a teddy bear Jordan will forever treasure for the multi-modal transportation and logistics sector (aka, we developed a headless PVP and sorta bit off more than we could chew).
The Mega Prompt Generator: How We Turned 60 Minutes of GTM Research Into a Single Automated Workflow
Season 3 | Episode 7 - August 22nd, 2025
Transform any brand website into qualified leads in 60 minutes using our systematic research-to-outreach methodology that compressed months of GTM trial-and-error into a single automated workflow.
The Free TAM Hack: How We Built RevHQ's Entire Market Analysis Using OpenStreetMap + AI
Season 3 | Episode 8 - August 29th, 2025
'It builds the AI data framework layer or it gets the hose again'….join us for more random movie quotes to see how you to can build a data layer that allows you to PVP like a master, this time for Revv.
How We Turned Lenders from Enforcers to Advisors Using Nothing But Public Data
Season 3 | Episode 9 - September 5th, 2025
We dissected Trustpoint.AI live on Friday and accidentally recreated their entire value proposition using only publicly available data. Along the way, we discovered that construction projects failing inspections twice have an 80% correlation with budget overruns appearing 45 days later.
OG Cannonball for Rematter: When AI Meets Scrap Metal
Season 3 | Episode 10 - September 12th, 2025
We went from soup to nuts with Rematter.com, a SaaS platform that helps scrap recycling operations actually run their businesses. And we did it the hard way: no pre-loaded context, no safety nets. Just pure methodology and Jordan's terrifying ability to make AI do exactly what he wants.
Season Two Archive
Brand Blitz: Finding Pain-Based Segments for 4 Vertical SaaS Brands from Legal Services
Season 2 | Episode 1 - April 4th, 2025
Watch our livestream where we battle AI to identify high-converting pain segments for legal tech companies—proving that even when tech fails (hello, StreamYard issues), the methodology prevails.
Battle of the Brands: Narrative Showdown for 2 vertical SaaS Brands from Legal Services
Season 2 | Episode 2 - April 11th, 2025
Doug and Jordan went toe-to-toe on the Battle of the Brands to see who could deliver the best PVP for DISCO and Evisort. The result? A tie (though Doug cheated, a lot).
Clay Day: Strategic Deployment
Season 2 | Episode 3 - April 18th, 2025
After summarizing the Focus, Investigate, and Narrate steps of our methodology, we dedicated an entire hour to Clay.com deployment strategies for two vertical SaaS brands. Note: paid annual subscribes only.
Vertical Voyage: SaaS Discovery Hour
Season 2 | Episode 4 - April 25th, 2025
We took viewers through the complete methodology for two vertical SaaS brands except without the FIND bit….intrigued? We're unveiled the simple, two step Cannonball 2.0, don't miss it!
Mapping a Pain-Based Category in One Hour
Season 2 | Episode 5 - May 9th, 2025
Watch as we map the EHR and Practice Management Category.
Clay Day: Strategic Deployment with Jeremy Ross
Season 2 | Episode 6 - May 16th, 2025
Watch as Jeremy and Jordan explore self-improving AI and an example of wave 1 MCP servers.
AI Agents in the Enterprise with David Boscovic
Season 2 | Episode 7 - May 23rd, 2025
Watch how Flatfile turned the Cannonball GTM methodology into a $50-per-vertical AI system that discovers existential pain points across hundreds of markets simultaneously, proving that systematic pain-based segmentation isn't just theory anymore.
OG Cannonball with Numeo.AI
Season 2 | Episode 8 - May 30th, 2025
We mapped the transportation and logistics technology sector and performed an end-to-end Cannonball for Numeo.ai, an AI-powered dispatch automation platform that handles broker calls, negotiates freight rates, and secures loads for trucking carriers and dispatchers.
The Clinical Trial Approach to Message-Market Fit with Kellen Casebeer
Season 2 | Episode 9 - June 6th, 2025
We explored Kellen's Market → Segment → Persona → Angle methodology for horizontal SaaS, proving that systematic message-to-market fit testing can create the same precision for broad markets that our pain-based approach delivers for vertical plays.
Shovels MCP Server: Programmatic Pain Point Discovery
Season 2 | Episode 10 - June 13th, 2025
Jordan deployed the Shovels database via MCP server in Clay to demonstrate programmatic PVP (pain-based value propositions) for 1,800 construction industry prospects from the International Builders Show—proving that systematic pain discovery can scale beyond manual research to deliver personalized insights for every company in your target market.
Shovels MCP Clay Campaigns with Kellen Casebeer
Season 2 | Episode 11 - June 20th, 2025
Watch as we demonstrate how to operationalize AI-generated value propositions using a complete end-to-end automated campaign for Shovels, targeting leads from the International Builders Show.
Demo and Q&A of the Latest Features from Clay.com
Season 2 | Episode 12 - June 27th, 2025
Check out the OG GTM Engineer and Head of Education @ Clay, Yash Tekriwal, demo four fresh AI features that can transform how GTM engineers build campaigns: native AI chat for troubleshooting tables, document upload for personalized outbound, Claygent Navigator for form automation, and AI image generation.
Season One Archive
Check out this masterclass in defining ICP and discovering pain-based segments.
