In this episode, Ian sits down with Greer Lynch, VP of Marketing at Reprise, the AI-powered demo automation platform helping enterprise teams deliver high-stakes software demos with confidence.

Greer shares how she approaches storytelling as the foundation of effective marketing, why community-building has become a core growth lever for Reprise, and how her team balances long-term brand investments with short-term demand generation. She also breaks down how Reprise thinks about rebranding for enterprise credibility, adapting SEO strategies for an AI-first world, and using AI internally to move faster without losing authenticity.

Key Takeaways

• Storytelling is the foundation of scalable marketing. Clear positioning and narrative make every channel more effective — from demand gen to community.
• Community is a long-term growth strategy. Bringing people together authentically builds trust, insight, and future demand, even beyond your immediate ICP.
• Brand maturity matters in enterprise markets. Positioning and design must reflect who you serve today, not who you served yesterday.
• AI is changing how marketing works — not eliminating fundamentals. The best teams use AI to accelerate insight, experimentation, and execution, not replace judgment.

Episode Timestamps:

*(03:01) The Trust Tree: Focus on what you can uniquely deliver to your audience

*(07:09) The Playbook: Storytelling and understanding your audience

*(32:53) Quick Hits

Sponsor:

Pipeline Visionaries is brought to you by Qualified.com. Qualified helps you turn your website into a pipeline generation machine with PipelineAI. Engage and convert your most valuable website visitors with live chat, chatbots, meeting scheduling, intent data, and Piper, your AI SDR. Visit Qualified.com to learn more.

Links:

• Connect with Ian on LinkedIn
• Connect with Greer on LinkedIn
• Learn more about Reprise
• Learn more about Caspian Studios

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In this episode, Ian sits down with Phyllis Fang, Head of Marketing at Transcend, where she leads go-to-market strategy for a data infrastructure platform powering compliant AI-driven experiences.

Phyllis shares how she thinks about go-to-market strategy, building repeatable marketing systems, investing in thought leadership and IRL events, and creating the right culture for AI adoption inside marketing teams.

• Thought leadership compounds over time. First-party research, executive voices, and clear points of view build trust long before buyers are in-market.
  
  
• Operational rigor matters, even in startups. Repeatable playbooks and clear ownership help marketing scale without breaking.
  
  
• AI adoption is as much a cultural challenge as a tooling one. Creating space to experiment is key to long-term impact.
  
  

“Slow down to speed up. Be best friends with sales. You’re there to help the business win.”

00:27 Phyllis’s Path into Marketing
02:03 What Transcend Does and Who It Serves
03:53 Go-to-Market Strategy Overview
05:58 Marketing Team Structure
07:15 Lessons from Uber
12:26 Uncuttable Marketing Investments
14:57 Activating Executive Thought Leadership
16:22 Running Effective IRL Events
21:07 What’s Most Cuttable in the Budget
26:04 Favorite Campaigns
28:08 Building a Culture for AI Adoption
36:27 Navigating Cross-Functional Tension
41:21 Quick Hits

Pipeline Visionaries is brought to you by Qualified.com. Qualified helps you turn your website into a pipeline generation machine with PipelineAI. Engage and convert your most valuable website visitors with live chat, chatbots, meeting scheduling, intent data, and Piper, your AI SDR. Visit Qualified.com to learn more.

Connect with Ian on LinkedIn

Connect with Phyllis on LinkedIn

Learn more about Transcend

Learn more about Caspian Studios

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They explore Emily’s concept of the “gen marketer”, and why traditional silos and specialist-heavy teams struggle in today’s high-velocity environment.

• Marketing teams need more generalists who can connect strategy, creativity, and distribution.
• Speed to execution matters more than perfect alignment across functions.
• Big marketing wins come from coordinated campaigns, not isolated tactics.
• AI increases the value of orchestration and taste, not specialization alone.
• Marketing leaders should think in portfolios of bets, not incremental activities.
  

“Every big initiative needs to have a chance to really win — not just deliver incremental results.”

Episode Timestamps

(03:51) What the “Gen Marketer” role actually means

(10:04) Why speed matters more than perfect alignment

(16:42) Escaping random acts of marketing with big bets

(24:58) How CMOs should think like producers or VCs

(31:37) When founder-led marketing works (and when it doesn’t)

Sponsor

Pipeline Visionaries is brought to you by Qualified.com — the pipeline generation platform for revenue teams.
Turn your website into a pipeline machine with PipelineAI. Engage and convert your most valuable visitors with live chat, chatbots, meeting scheduling, and intent data.
Visit Qualified.com to learn more.

Connect with Ian on LinkedIn
Connect with Emily Kramer on LinkedIn

Dear Marketers Podcast

MKT1 Unboxing
Learn more about MKT1
Learn more about Caspian Studios

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Hear from Jill Wiltfong, CMO, Korn Ferry, Chris Bontempo, CMO, Johnson Controls, Shannon Sullivan Duffy, CMO, Asana, and Melton Littlepage, CMO, 1Password on their uncuttable budget items.

Timestamps:
(01:19) Jill Wiltfong, CMO, Korn Ferry,
(08:03) Chris Bontempo, CMO, Johnson Controls
(23:12) Shannon Sullivan Duffy, CMO, Asana
(28:10) Melton Littlepage, CMO, 1Password

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Ian sits down with Stacey Epstein, CEO of Magnetic, where she helps brands create clear positioning and go-to-market strategies that drive lasting demand. She talks about how to succeed in interacting with the board, outlining do’s and don’ts, and providing advice around defensiveness and preparation.

Key Takeaways:

• The board is there to help you succeed. Treat them like advisors and go to them with questions and issues that you are trying to solve. Don’t try to hide problems, do demonstrate your wins.
• There is an art to defending yourself without being defensive. Defensiveness often results in a board member feeling unheard and pushing harder. Take the note, even if you can’t take the proposed solution.
• Ditch the slide decks and excel spreadsheets, and tell the story for board members. A unified board letter from the leadership team is a great way to do this and increases alignment before a meeting.

Quote:

• “  We're all on the same team. We all wanna win. Like we're here together in this board meeting because we want the company to be successful and we want to win. And, . There should be no hiding of issues. In fact, that's what the board is there for. The board is there to help you get through the challenging times.”

Episode Timestamps:

00:53 The Role of the Board in Marketing

02:20 Navigating Board Interactions

03:06 Performance and Authenticity in Board Meetings

04:29 The Complexity of Marketing Roles

08:51 Aligning Marketing and Sales

16:56 The Importance of SDR Feedback

19:13 AI and Marketing Technology Decisions

21:44 Navigating Board Dynamics as a CMO

21:59 Building Relationships and Credibility

23:11 The Importance of Authenticity in Marketing

24:22 Handling Investor Feedback Tactfully

29:16 Defending Your Marketing Strategy

36:03 Effective Board Communication Strategies

39:10 The Value of Board Letters

Sponsor:

Pipeline Visionaries is brought to you by Qualified.com. Qualified helps you turn your website into a pipeline generation machine with PipelineAI. Engage and convert your most valuable website visitors with live chat, chatbots, meeting scheduling, intent data, and Piper, your AI SDR. Visit Qualified.com to learn more.

Links:

• Connect with Ian on LinkedIn
• Connect with Stacey on LinkedIn
• Learn more about Magnetic
• Learn more about Caspian Studios
• AI’ve Got Questions Podcast: https://www.buzzsprout.com/2497617/episodes

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Ian sits down with Shafqat Islam, President, Optimizely. They dive into AI, GEO, and the future role of websites. They also talk about how experimentation and creativity give companies the competitive edge in the current marketing landscape.

Key Takeaways:

• Your content needs to provide scarcity value to stand out. People and LLMs want original ideas.
• Most CMOs are not experimenting enough, and are not being creative enough. Experimentation is key.
• Many SEO tactics will work for GEO, and the harsh truth is that a lot of SEO content did not move the needle anyway.

Quote:

• “ Everyone should be testing. Testing allows you to be more creative.Take bigger bets, be bolder. If your bet is huge, and the return and the result is huge, it's totally disproportionate, upside uncapped. Frankly, most marketers are afraid.”

Episode Timestamps:

01:56 The Role of Product and Marketing

03:09 Origins and Evolution of Opal

10:51 Creativity in Marketing and Software

13:44 The Importance of Experimentation

19:40 Storytelling and Risk-Taking in Marketing

23:21 The Rise of AI and Podcasting

28:03 Generative Engine Optimization (GEO)

29:31 Websites' New Dual Role

32:34 The Studio Head Approach to Marketing

38:12 The Impact of AI on Creativity

40:09 The Future of Search and Marketing

Sponsor:

Pipeline Visionaries is brought to you by Qualified.com. Qualified helps you turn your website into a pipeline generation machine with PipelineAI. Engage and convert your most valuable website visitors with live chat, chatbots, meeting scheduling, intent data, and Piper, your AI SDR. Visit Qualified.com to learn more.

Links:

• Connect with Ian on LinkedIn
• Connect with Shaf on LinkedIn
• Learn more about Optimizely
• Learn more about Caspian Studios

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

This episode features an interview with Alex Halliday, the CEO at AirOps, an end-to-end content engineering platform that gives marketing teams the systems they need to win visibility across AI search and SEO with quality content. Alex gives the marketing masterclass on AI search, laying out the framework for what marketers need to be doing.

Key Takeaways:

• Understand your current State of the Union: Audit how you are currently showing up across the AI models and what is driving those results.
• Pick a strategy based on what truly matters to you as a brand and ruthlessly prioritize.
• Execute through content engineering, a combination of brand taste, technical skills and strategy.

Quote:

•   The future of, we think, content and AI search is this new role that we're pushing and championing. It's called content engineering. And content engineering is a blend of three things. It's brand taste, which you absolutely need. It's enough technical skills to use this technology well. It's strategy. It's like really a really good strategic mind of the kinds of plays that you want to put out into the world.”

Episode Timestamps:

*(04:26) The Trust Tree: Education- and Evidence-led go-to-market

*(10:19) The Influence of YouTube on AI Search Results

*(18:10) The Masterclass on AI Search: Step-by-step

*(25:35) What do LLMs actually like?

*(40:04) How should marketers be investing in content?

Sponsor:

Pipeline Visionaries is brought to you by Qualified.com. Qualified helps you turn your website into a pipeline generation machine with PipelineAI. Engage and convert your most valuable website visitors with live chat, chatbots, meeting scheduling, intent data, and Piper, your AI SDR. Visit Qualified.com to learn more.

Links:

• Connect with Ian on LinkedIn
• Connect with Alex on LinkedIn
• Learn more about AirOps
• Learn more about Caspian Studios

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

This episode features an interview with Kady Srinivasan, Chief Marketing Officer at You.com, the enterprise AI productivity platform redefining knowledge work with trusted, customizable AI agents. She breaks down GEO, storytelling in an infinite-content world, and why content now must serve both humans and LLMs.

Key Takeaways

• Demand generation has changed: Google Ads don’t work, while newsletters, advertorials, and events perform better.
• Marketing teams must operate as multithreaded groups built around outcomes rather than traditional functional silos.
• Imperfection and speed are essential to stay competitive in fast-moving AI markets.
  
  

Quote

“I just want everything to be on time and running properly… And so, particularly in AI and to your point in 2025, that is, you could just get killed if you're like that. So you need to know when to be fine with imperfection and when to, and in some cases you have to double down and really take your time.”

Episode Timestamps

03:23 Demand Generation Changes

04:56 Google Ads and New Marketing Channels

05:51 Generative Engine Optimization (GEO)

07:44 Importance of Original Content

25:12 Exploring the Future of Marketing Roles

28:10 Balancing Speed and Perfection in Marketing

Sponsor

Pipeline Visionaries is brought to you by Qualified.com — the pipeline generation platform for revenue teams.
Turn your website into a pipeline machine with PipelineAI. Engage and convert your most valuable visitors with live chat, chatbots, meeting scheduling, and intent data.
Visit Qualified.com to learn more.

Links

Connect with Ian on LinkedIn: https://www.linkedin.com/in/ianfaison/
Connect with Kady on LinkedIn: https://www.linkedin.com/in/kadysrinivasan/
Learn more about You.com
Learn more about Caspian Studios: https://caspianstudios.com

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