Uploaded July 2026 | Updated September 2026, 2 weeks ago
*Free guide + skill: build social carousels in claude cowork* clickhubspot.com/fvzf
Most marketers are still typing one-off prompts and getting generic, off-brand AI output. Grace Leung built a different way to work: a repeatable Claude system where context files, a Claude.md router, and reusable skills do the heavy lifting, so one prompt produces finished, on-brand marketing assets.
In this episode, Grace walks Kipp and Kieran through her entire setup live: the folder structure, the context layer, building a brand design system in Claude Design, turning templates into reusable skills, and running the whole workflow end to end from topic idea to ready-to-post LinkedIn carousel. Then Kieran explains why your context layer is the only thing standing between your marketing and everyone else's.
Ep 438 Mentions
Youtube: youtube.com/@graceleungyl
LinkedIn: linkedin.com/in/grace-leung-yl
Loop: Outlearn. hubspot.com/loop-marketing-book
Groove Anchor, grooveanchor.com
Claude Cowork support.claude.com/en/articles/13345190-get-started-with-claude-cowork
ChatGPT chatgpt.com
Codex openai.com/codex
📌 WHAT WE COVER:
→ The folder structure that powers every marketing discipline
→ Why setup beats prompting (work slow to work fast)
→ What claude.md actually does: file routing and tool routing
→ How skills inherit your context automatically
→ Building a reusable brand design system in Claude Design
→ Creating an on-brand carousel template once, using it forever
→ Export skills: carousel to LinkedIn PDF and Instagram images
→ Live demo: one prompt to a finished, on-brand carousel
→ Making your AI second brain portable with GitHub sync
→ Sonnet vs. Opus: the hosts' honest model hot takes
→ Context intelligence: why generic AI output kills marketing
→ Taste as the durable differentiator in the AI era
🎙️ Hosts: Kipp Bodnar & Kieran Flanagan
Guest: Grace Leung, AI Educator & Digital Growth Strategist
⏱️ CHAPTERS:
00:00 — Intro: Grace's repeatable AI marketing system
01:10 — Step 1: The folder structure and context folder
01:50 — Why setup beats prompting (work slow to work fast)
04:40 — Setting up the project in Claude Cowork
05:00 — What claude.md does: file and tool routing
05:50 — How skills inherit your context
06:50 — Building a brand design system in Claude Design
09:00 — Creating a reusable carousel template
11:50 — Export skills: from template to ready-to-post
13:30 — Converting carousels into Instagram images
14:30 — Breaking marketing tasks into reusable skills
14:50 — Live demo: one prompt, five on-brand topic ideas
15:10 — Hot take: Sonnet over Opus (and a Codex confession)
16:00 — Watching the skills fire: brand voice to finished carousel
17:20 — Making your AI second brain portable (GitHub sync)
20:00 — Kieran vs. the token-burning Claude session
20:40 — Context intelligence: why generic AI kills your marketing
23:00 — Taste is the differentiator (Loop preview)
24:30 — Wrap-up
📺 Subscribe to Marketing Against the Grain for weekly episodes on AI, marketing strategy, and growth.
#ClaudeAI #AIMarketing #MarketingSystem #ClaudeSkills #ContextEngineering #AIForMarketers #MarketingAgainstTheGrain #ClaudeCowork #AIWorkflow #MarketingStrategy
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. On the way you’ll pick up undiscovered strategies to give you that slight edge for success. These are not your typical twitter thread regurgitated marketing tactics that everyone is doing. These are new methods, with unfiltered examination of successful fresh ideas.
*Free guide + skill: build social carousels in claude cowork* clickhubspot.com/fvzf
Most marketers are still typing one-off prompts and getting generic, off-brand AI output. Grace Leung built a different way to work: a repeatable Claude system where context files, a Claude.md router, and reusable skills do the heavy lifting, so one prompt produces finished, on-brand marketing assets.
In this episode, Grace walks Kipp and Kieran through her entire setup live: the folder structure, the context layer, building a brand design system in Claude Design, turning templates into reusable skills, and running the whole workflow end to end from topic idea to ready-to-post LinkedIn carousel. Then Kieran explains why your context layer is the only thing standing between your marketing and everyone else's.
Ep 438 Mentions
Youtube: youtube.com/@graceleungyl
LinkedIn: linkedin.com/in/grace-leung-yl
Loop: Outlearn. hubspot.com/loop-marketing-book
Groove Anchor, grooveanchor.com
Claude Cowork support.claude.com/en/articles/13345190-get-started-with-claude-cowork
ChatGPT chatgpt.com
Codex openai.com/codex
📌 WHAT WE COVER:
→ The folder structure that powers every marketing discipline
→ Why setup beats prompting (work slow to work fast)
→ What claude.md actually does: file routing and tool routing
→ How skills inherit your context automatically
→ Building a reusable brand design system in Claude Design
→ Creating an on-brand carousel template once, using it forever
→ Export skills: carousel to LinkedIn PDF and Instagram images
→ Live demo: one prompt to a finished, on-brand carousel
→ Making your AI second brain portable with GitHub sync
→ Sonnet vs. Opus: the hosts' honest model hot takes
→ Context intelligence: why generic AI output kills marketing
→ Taste as the durable differentiator in the AI era
🎙️ Hosts: Kipp Bodnar & Kieran Flanagan
Guest: Grace Leung, AI Educator & Digital Growth Strategist
⏱️ CHAPTERS:
00:00 — Intro: Grace's repeatable AI marketing system
01:10 — Step 1: The folder structure and context folder
01:50 — Why setup beats prompting (work slow to work fast)
04:40 — Setting up the project in Claude Cowork
05:00 — What claude.md does: file and tool routing
05:50 — How skills inherit your context
06:50 — Building a brand design system in Claude Design
09:00 — Creating a reusable carousel template
11:50 — Export skills: from template to ready-to-post
13:30 — Converting carousels into Instagram images
14:30 — Breaking marketing tasks into reusable skills
14:50 — Live demo: one prompt, five on-brand topic ideas
15:10 — Hot take: Sonnet over Opus (and a Codex confession)
16:00 — Watching the skills fire: brand voice to finished carousel
17:20 — Making your AI second brain portable (GitHub sync)
20:00 — Kieran vs. the token-burning Claude session
20:40 — Context intelligence: why generic AI kills your marketing
23:00 — Taste is the differentiator (Loop preview)
24:30 — Wrap-up
📺 Subscribe to Marketing Against the Grain for weekly episodes on AI, marketing strategy, and growth.
#ClaudeAI #AIMarketing #MarketingSystem #ClaudeSkills #ContextEngineering #AIForMarketers #MarketingAgainstTheGrain #ClaudeCowork #AIWorkflow #MarketingStrategy
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. On the way you’ll pick up undiscovered strategies to give you that slight edge for success. These are not your typical twitter thread regurgitated marketing tactics that everyone is doing. These are new methods, with unfiltered examination of successful fresh ideas.
