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About our guest — Josh Whitfield
Josh Whitfield is founder of Content Marketing Media (CMM), the only agency globally certified across Clay, Instantly, HeyReach, and Octave — the four cornerstone platforms powering modern outbound strategy. He's also building Signaliz.com while sharing innovative GTM workflows and AI agents across LinkedIn and X.
Before diving into go-to-market engineering, Josh spent 15 years in insurance leading agile teams focused on intelligent automation solutions including process mining, API integrations, and robotic process automation. His technical background in AI and automation— before it was mainstream — gives him unique perspective on what truly matters as these technologies democratize.
Josh's philosophy centers on creativity over technical prowess, arguing that as AI handles the complex technical work, success comes from institutional knowledge, business understanding, and the ability to orchestrate innovative solutions that others haven't thought of.
Core takeaways
The creativity revolution — Why prompt engineering is dead and creative business thinking is the new differentiator
Institutional knowledge over coding — How understanding business fundamentals matters more than technical skills
The alpha signal methodology — Moving beyond basic demographic targeting to find unique buying indicators
AI-powered research workflows — Using Manus AI and other tools to deliver PhD-level competitive intelligence
The democratization paradox — As tools get easier, differentiation comes from creative application not technical mastery
Strategic retention model — How agencies evolve from email senders to trusted AI advisors for sustained growth
The 25% learning rule — Why dedicating a quarter of your time to exploring new tools is non-negotiable
Robotic handwritten notes case study — The wild workflow that automatically sends real handwritten notes to high-value prospects
Top quotes
New Reality of Skills: "If you'd asked me that six months ago, I'd have said prompt engineering. Today, I would tell you, I think it's creativity because you know, I don't write any of my own prompts anymore. I just ask the models to write the prompts for me."
On Institutional Knowledge: "The future true impactful GTM engineer has enough institutional knowledge of the business, knows how to go find out and fill in the gaps of what they don't know."
The Alpha Signal Philosophy: "Clay calls it the alpha signal and really find that thing that really defines, like, this person is telling me they need to get or be involved in the solution that's being offered and that they have the means or will to do so."
On Creative Differentiation: "It takes creativity to not be like everybody else and pull news and funding and job changes. It takes creativity to say, look, I'm gonna go out and I'm going to figure out every time someone inserts a geocode radius outside of a conference location in San Jose."
The Learning Imperative: "I spent 25% of my existence doing that... When you take the 10 rich companies in the world and they're all focused on the same thing, that's a clue that you probably should be paying attention to it too."
On Accessible Learning: "You could, this could be the first time you've ever heard the word GTM engineering. And if you spend enough time, even just open AI with web search, you can, it can teach you how to build clay tables."
Referenced tools and resources
Clay: The orchestration powerhouse that can make 72 API calls per row for enrichment
Octave: Most underrated GTM tool for messaging and copywriting
Claude: Superior for copywriting and email generation over other LLMs
Instantly/Maildoso: Email infrastructure and sequencing platform combination
Manus AI: Advanced research platform delivering PhD-level competitive analysis
Apify & Firecrawl: Web scraping tools for unique data acquisition
PandaMatch: Lookalike modeling for prospect identification
HubSpot/Salesforce: CRM platforms (Josh uses both depending on client needs)
Model Context Protocol (MCP): Advanced Claude integration for enhanced workflows
Cursor & Lovable: No-code development tools for rapid prototyping
Delphi: AI training platform Josh used to build his 560,000-word personal AI assistant
Want to learn GTM Engineering strategy and execution? Ticket for GTM Engineer School cohort 2 are now out (less than 45 out 75 seats available!)
Timestamps
(01:24) Josh's background: 15 years in insurance building AI before it was cool
(02:07) Definition deep dive: Why GTM engineering is broader than people think
(04:31) The evolution question: From structured enterprise AI to democratic vibe coding
(07:03) Lightning Round: CRM agnostic, Claude for copywriting, Clay for orchestration
(08:55) Most underrated tool: Octave's game-changing impact on messaging
(09:57) System design: Octave brain, Clay orchestration, Instantly distribution
(12:18) The alpha signal methodology: Finding unique intent signals
(14:07) Technology trade-offs: Managing vendor reliability and rapid AI evolution
(16:14) Client adaptation: Balancing multiple stacks and varying organizational maturity
(18:34) First play strategy: Using demo-quality builds to prove value before onboarding
(21:21) Impact metrics: Retention over conversion as agencies become advisors
(24:37) New skills: From prompt engineering to creativity and institutional knowledge
(27:15) Defining creativity: Balancing business understanding with new tool application
(29:30) The 25% rule: Why Josh dedicates 25% of his time exploring new tech
(32:38) Practical advice: Using free ChatGPT as your learning starting point
How to connect with Josh
Where to connect with Jared & Matteo
Jared Waxman, GTM Engineer School Co-founder: LinkedIn
Matteo Tittarelli, GTM Engineer School Co-founder: LinkedIn, X, Website, Newsletter
