“Most marketers are copying what their competitors are doing without realizing they might be copying the losing version,” says Casey Hill, CMO at DoWhatWorks.



In this episode of The Content Cocktail Hour, Jonathan Gandolf welcomes back Casey Hill to explore why marketers need to question the default choices they make and how actual A/B test data is reshaping what “best practice” really means. Casey unpacks what thousands of tests reveal about things like social proof, button copy, and AI messaging, and why most marketers are accidentally copying losing strategies from their competitors. They also dig into how internal politics and funding optics can sometimes override what the data says, and how to navigate that tension without sacrificing performance.

In this episode, you’ll learn:

1. Why generic AI messaging is underperforming and what to do instead
2. How to build testable hypotheses without compromising creativity
3. How to use test data to influence stakeholders and avoid opinion-based decisions

Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Casey on LinkedIn: https://www.linkedin.com/in/caseyhill/

Explore DoWhatWorks: https://www.dowhatworks.io/

Subscribe to the DoWhatWorks Newsletter: https://www.dowhatworks.io/newsletter

Timestamps:

(00:00) Intro

(01:22) Understanding DoWhatWorks

(02:13) The importance of data in decision making

(03:00) The role of algorithms in marketing

(06:46) The power of social proof

(07:58) Effective use of customer logos

(11:34) The evolution of marketing norms

(16:54) AI messaging in marketing

(24:32) Unpopular opinions in B2B marketing

“The best thing we can do as sellers is match the urgency of the person who is reaching out to us.” says Val Riley, VP of Marketing at Unbounce, Insightly, and LeadsRX.

In this episode of The Content Cocktail Hour, host Jonathan Gandolf chats with Val about the shift from conversion to connection, both in your tech stack and your go-to-market strategy. With deep experience spanning CRM, landing pages, and attribution tools, Val shares how brands can build more meaningful customer experiences by removing friction between form fill and follow-up. She also unpacks what it looks like to move fast as a challenger brand in the AI era and how being “right-sized” in your CRM approach can actually lead to better results across your funnel.

In this episode, you’ll learn:

1. Why 25–50% of form fills are wasted and how to fix that
2. What it means to align sales and marketing around a shared funnel view
3. How mid-market CRMs can offer enterprise-grade AI without enterprise-grade headaches

Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Val on LinkedIn: https://www.linkedin.com/in/valerie-riley-marketer/

Explore Unbounce: https://unbounce.com/

Explore Insightly: https://www.insightly.com/

Explore LeadsRX: https://leadsrx.com/

Explore Closing Time: https://www.insightly.com/closing-time/

Read the report: https://app.thejuicehq.com/content/TBtyYfywtWN9NQ8T3MCzBbag

Timestamps:

(00:00) Intro

(00:54) Meet Val Riley

(04:19) The importance of conversion and connection

(09:28) Aligning sales and marketing teams

(11:21) Right-sized CRM solutions

(14:50) AI in CRM: opportunities for challenger brands

(18:55) Unpopular opinions in B2B marketing

“Buyers want fast answers and ROI, not a song and dance. But once they’re in, education builds the relationship,” says Cruz Daddario, Customer Education Manager at Seamless.AI.

In this episode of The Content Cocktail Hour, Jonathan Gandolf chats with Cruz Daddario and fellow Customer Education Manager Victoria Meyer about how customer education can be the secret weapon for both onboarding and retention. The duo shares how their backgrounds in teaching and customer success inform their approach to helping users find value quickly, especially in a world where AI can overwhelm as much as it enables. They dig into the importance of foundational education, the rising demand for human connection in a tech-heavy landscape, and why internal teams need to be trained just like customers to deliver consistent, effective experiences.

In this episode, you’ll learn:

1. How customer education builds trust, confidence, and long-term product adoption
2. The role of human connection in an AI-driven world
3. Why today’s B2B buyers care more about immediate value and ROI than relationship-building upfront

Resources:

Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

Explore AudiencePlus: https://audienceplus.com

Connect with Cruz on LinkedIn: https://www.linkedin.com/in/cruz-daddario-a97111184/

Connect with Victoria on LinkedIn: https://www.linkedin.com/in/victoria-meyer17/

Explore Seamless.AI: https://seamless.ai/

Timestamps:

(00:00) Intro

(01:05) Victoria's background and role

(02:22) Cruz's background and role

(07:12) Balancing proactive and reactive training

(11:39) Internal and external enablement

(15:20) AI's impact on customer education

(16:57) The human touch in an AI-driven world

(20:26) Unpopular opinions in B2B marketing