Uploaded August 2026 | Updated September 2026, 2 weeks ago
*Build your AI Knowledge base (free template + starter kit):* clickhubspot.com/78j2
Everyone online is telling marketers the same thing: if you can't build AI systems, you won't survive. Nobody tells you where to start. Kieran does, and then he hands you the whole thing in a single prompt.
In this episode, Kieran walks through his V1 marketer's AI stack, layer by layer. It starts with an intelligence layer (goals, ICP, competitors, positioning, team, execs) that everything else reads from, then builds up through skills that scale you across your team, sharpen your thinking, pressure-test your product story, and run your day. He shows the AI coach that grades your own AI usage, the exec panel that pokes holes in your pitch before your execs do, the voice-of-the-customer and voice-of-the-competitor skills, and the blocker watcher he uses to unblock his team. At the end, one prompt builds the entire stack for you, then interviews you to tailor it to your role.
EP 445 Mentions
Loop: Outlearn. Outmarket. Outgrow hubspot.com/loop-marketing-book
Claude claude.ai/
ChatGPT chatgpt.com
📌 WHAT WE COVER:
→ Why "only systems builders will survive" is half right and half nonsense
→ Which marketing roles actually need to build systems (and which don't)
→ Why every AI system starts with an intelligence layer, not a prompt
→ The six context files that anchor the whole stack
→ Why skills should only read the context they need, not everything
→ Building an AI coach that grades your three weakest prompts and habits
→ Using Claude's Record Skill to turn how you work into a reusable skill
→ The People Brief: one-on-ones with follow-ups, KPIs, blockers and wins built in
→ Voice of You: let your team get your answer before they interrupt you
→ The Storyteller skill for telling marketing's story to execs
→ Building an exec panel that critiques your pitch before you deliver it
→ Inversion and pre-mortem prompts that challenge how you think
→ Voice of the Customer and Voice of the Competitor, built from your own files
→ "Are we really different?" Grading your positioning against the competition
→ Daily priority lists, what-did-I-miss sweeps, and blocker watching
→ Building custom dashboards with Claude's Live Artifacts
→ How to copy the whole stack and tailor it in one conversation
🎙️ Host: Kieran Flanagan
⏱️ CHAPTERS:
00:00 - "You won't survive AI unless you're a systems builder"
00:40 - Where that narrative is right and where it's wrong
01:20 - Why systems are hard to start if you're not an engineer
01:50 - The marketer's AI stack, layer by layer
02:20 - Layer 1: the intelligence layer everything reads from
02:50 - The six context files: goals, ICP, competitors, positioning, team, execs
04:20 - The prompt that builds your intelligence layer
04:50 - Your AI coach: let AI grade your AI usage
05:30 - Your 3 weakest prompts and the 3 skills you should build next
06:10 - Record Skill: screen record how you work, get a skill back
07:20 - Layer 2: scaling more of you across the team
07:40 - The People Brief: one-on-ones that actually go somewhere
08:30 - Voice of You: answering your team before they reach out
09:25 - The Storyteller: showing execs what marketing is doing
09:55 - Layer 3: better thinking
10:00 - The exec panel that critiques your pitch first
10:35 - Challenge Me: inversion, pre-mortems, and thinking models
11:25 - Layer 4: product story, the most important job in marketing right now
11:45 - Voice of the Customer, built from your ICP file
12:15 - Voice of the Competitor, and keeping that file current
13:10 - "Are we really different?" Scoring your positioning 1-10
14:45 - Layer 5: how I run my day
14:50 - The daily priority list from goals, team, execs, email and Slack
15:30 - "What did I miss?" Everything you owe someone, oldest first
16:15 - Blocker Watcher: find who's stuck and why
16:55 - Custom dashboards with Claude Live Artifacts
17:40 - The full recap: your V1 marketing AI stack
19:10 - Copy the whole stack and tailor it to you
📺 Subscribe to Marketing Against the Grain for weekly episodes on AI, marketing, and growth.
#AI #Claude #ChatGPT #AIforMarketers #AITools #MarketingAI #AIAgents #AIWorkflow #MarketingStrategy #AIProductivity #AITutorial #PromptEngineering #B2BMarketing #AISkills #HubSpot
Host Links:
📲Kipp Bodnar, twitter.com/kippbodnar
📲Kieran Flanagan, twitter.com/searchbrat
‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Produced by Darren Clarke.
About the Show
Kipp Bodnar, HubSpot’s CMO and Kieran Flanagan Hubspot's SVP of Marketing, lead you down the rabbit hole of marketing trends, growth tactics and innovation.
*Build your AI Knowledge base (free template + starter kit):* clickhubspot.com/78j2
Everyone online is telling marketers the same thing: if you can't build AI systems, you won't survive. Nobody tells you where to start. Kieran does, and then he hands you the whole thing in a single prompt.
In this episode, Kieran walks through his V1 marketer's AI stack, layer by layer. It starts with an intelligence layer (goals, ICP, competitors, positioning, team, execs) that everything else reads from, then builds up through skills that scale you across your team, sharpen your thinking, pressure-test your product story, and run your day. He shows the AI coach that grades your own AI usage, the exec panel that pokes holes in your pitch before your execs do, the voice-of-the-customer and voice-of-the-competitor skills, and the blocker watcher he uses to unblock his team. At the end, one prompt builds the entire stack for you, then interviews you to tailor it to your role.
EP 445 Mentions
Loop: Outlearn. Outmarket. Outgrow hubspot.com/loop-marketing-book
Claude claude.ai/
ChatGPT chatgpt.com
📌 WHAT WE COVER:
→ Why "only systems builders will survive" is half right and half nonsense
→ Which marketing roles actually need to build systems (and which don't)
→ Why every AI system starts with an intelligence layer, not a prompt
→ The six context files that anchor the whole stack
→ Why skills should only read the context they need, not everything
→ Building an AI coach that grades your three weakest prompts and habits
→ Using Claude's Record Skill to turn how you work into a reusable skill
→ The People Brief: one-on-ones with follow-ups, KPIs, blockers and wins built in
→ Voice of You: let your team get your answer before they interrupt you
→ The Storyteller skill for telling marketing's story to execs
→ Building an exec panel that critiques your pitch before you deliver it
→ Inversion and pre-mortem prompts that challenge how you think
→ Voice of the Customer and Voice of the Competitor, built from your own files
→ "Are we really different?" Grading your positioning against the competition
→ Daily priority lists, what-did-I-miss sweeps, and blocker watching
→ Building custom dashboards with Claude's Live Artifacts
→ How to copy the whole stack and tailor it in one conversation
🎙️ Host: Kieran Flanagan
⏱️ CHAPTERS:
00:00 - "You won't survive AI unless you're a systems builder"
00:40 - Where that narrative is right and where it's wrong
01:20 - Why systems are hard to start if you're not an engineer
01:50 - The marketer's AI stack, layer by layer
02:20 - Layer 1: the intelligence layer everything reads from
02:50 - The six context files: goals, ICP, competitors, positioning, team, execs
04:20 - The prompt that builds your intelligence layer
04:50 - Your AI coach: let AI grade your AI usage
05:30 - Your 3 weakest prompts and the 3 skills you should build next
06:10 - Record Skill: screen record how you work, get a skill back
07:20 - Layer 2: scaling more of you across the team
07:40 - The People Brief: one-on-ones that actually go somewhere
08:30 - Voice of You: answering your team before they reach out
09:25 - The Storyteller: showing execs what marketing is doing
09:55 - Layer 3: better thinking
10:00 - The exec panel that critiques your pitch first
10:35 - Challenge Me: inversion, pre-mortems, and thinking models
11:25 - Layer 4: product story, the most important job in marketing right now
11:45 - Voice of the Customer, built from your ICP file
12:15 - Voice of the Competitor, and keeping that file current
13:10 - "Are we really different?" Scoring your positioning 1-10
14:45 - Layer 5: how I run my day
14:50 - The daily priority list from goals, team, execs, email and Slack
15:30 - "What did I miss?" Everything you owe someone, oldest first
16:15 - Blocker Watcher: find who's stuck and why
16:55 - Custom dashboards with Claude Live Artifacts
17:40 - The full recap: your V1 marketing AI stack
19:10 - Copy the whole stack and tailor it to you
📺 Subscribe to Marketing Against the Grain for weekly episodes on AI, marketing, and growth.
#AI #Claude #ChatGPT #AIforMarketers #AITools #MarketingAI #AIAgents #AIWorkflow #MarketingStrategy #AIProductivity #AITutorial #PromptEngineering #B2BMarketing #AISkills #HubSpot
Host Links:
📲Kipp Bodnar, twitter.com/kippbodnar
📲Kieran Flanagan, twitter.com/searchbrat
‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Produced by Darren Clarke.
About the Show
Kipp Bodnar, HubSpot’s CMO and Kieran Flanagan Hubspot's SVP of Marketing, lead you down the rabbit hole of marketing trends, growth tactics and innovation.
