As you look ahead to 2026, what’s rising to the top of your marketing priorities?

In this special episode of Growth Talks with Krystina Rubino, we highlight our favorite CMO insights on building brands that customers trust and love.

It's packed with insights on subjects all CMOs should be thinking about today, such as brand versus performance marketing, incorporating AI into your marketing strategy, and how to build and enable your team.

🗝️Key Takeaways:

• Tamara Mendelsohn, COO at Overstory and former CMO at Eventbrite, shares why brand and performance aren’t competing priorities and how real growth comes from bringing both teams together.
• Jaleh Bisharat, former fractional CMO at Skillshare, argues that the best CMOs think like CEOs, focusing on what the business truly needs, even if that means reallocating budget away from marketing.
• Katelyn Watson, CMO at Talkspace, recommends that leaders step into an AI-native mindset and rethink how teams create, connect, and scale brands.
• Aaron Magness, CMO at Full Glass Wine Co., highlights why effective marketing leaders should stop obsessing over tactics and instead focus on hiring great talent, setting clear expectations, and deeply understanding the business and its narrative.
• Cate Lochead, CMO at Bentley Systems, shares how leading with empathy creates more authentic campaigns and builds deeper connections with customers.
• Matt Gehring, CMO & Advisor, details how clear data definitions such as clarity around LTR versus LTV keep teams aligned and focused on the metrics that matter.

⏰ Timestamps

• 00:42: Tamara Mendehlson
• 04:21: Jaleh Bisharat
• 06:09: Katelyn Watson
• 08:41: Aaron Magness
• 10:30: Cate Lochead
• 13:09: Matt Gehring

🔗 Mentioned in this episode:

• Eventbrite: https://www.eventbrite.com/
• Skillshare: https://www.skillshare.com
• Talkspace: https://www.talkspace.com/
• Full Glass Co: https://www.fullglass.wine/
• Bentley Systems: https://www.bentley.com/

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The fastest-growing brands treat customer insight like a strategy—not just a survey.

In this week’s episode of Growth Talks, CMO & Advisor, Matt Gehring joins host Tyler Elliston, founder and CEO of Right Side Up, to unpack what it takes to succeed in your first 90 days as a marketing leader.

Drawing from his leadership roles at Dutch Pet, Everlane, and Rothy’s, Matt shares how to map the customer journey, turn post-purchase insights into smart segmentation strategies, and use real-time data to drive repeat purchases.

Find out why acting on customer insights early is key to refining your product, aligning your team, and making informed decisions before you scale.

🗝️ Key Takeaways:

• Start with listening. In your first 90 days as CMO, forget quick wins and shiny tactics. Your real job? Uncover the real issues, gain your team’s trust, and align the org around a shared understanding of success.
• Smart teams adjust early. When customer insights tell a different story about your product, don’t rush to scale. Hit pause, review feedback, and pivot. Sometimes the smartest move is starting over.
• Don’t confuse revenue with value. Always calculate LTV using gross margin—not top-line revenue. It’s the only way to get a true LTV:CAC ratio and avoid scaling based on a false signal.
• Personalization is about context. It’s not about crafting the perfect one-to-one offer—it’s about using what you already know, like ad intent or entry point, to create the customer experience at every touchpoint.
• Post-purchase is a powerful growth lever. Use customer data to track what they bought and when they bought it to inform segmentation. Then test upsells, cross-sells, and timing to drive repeat purchases and increase lifetime value.
• Insights drive action. When Rothy’s opened its first store, it created a direct feedback loop. Store associates captured what drew customers in, offering real-time insights that led to smarter product decisions and more effective marketing.
• Start with why. Focus groups, surveys, and AI all have value—but only when used intentionally. As you scale, tools like AI and surveys can help synthesize insights, but they’re no replacement for talking to real users.

⏰ Timestamps

• 02:52 Navigating the First 90 Days
• 05:45 Building Trust with Teams
• 08:59 Understanding Customer Dynamics
• 11:57 The Importance of Data Definitions
• 18:01 Defining the Customer Journey
• 21:12 Personalization in Marketing
• 27:02 Segmentation and Post-Purchase Strategies
• 32:59 Understanding LTV and CAC Calculations
• 40:32 DefiningCustomer Acquisition Costs
• 44:44 The Importance of Consumer Insights

🔗 Mentioned in this episode:

• Lifeforce: https://www.mylifeforce.com/
• Dutch Pet: https://www.dutch.com/
• Everlane: https://www.everlane.com/
• Rothy’s: https://rothys.com/
• Hims: https://www.hims.com/

👍 Did you enjoy this video? Don’t forget to click the like button! And find more episodes of Growth Talks here: https://bit.ly/3xXGJJc

🤝 Connect with Right Side Up

Right Side Up is a premium growth marketing agency that has helped more than 1,000+ companies hit their growth goals.

‣ Check us out and send us a note at: https://bit.ly/4bfaBQt

‣ Subscribe to our channel: https://bit.ly/3HWiJYD

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Every marketing leader should give their team an AI framework for rethinking how they work.

In this week’s episode of Growth Talks, Vanessa Hope Schneider, Head of Marketing at Decript, joins host Tyler Elliston, Founder and CEO of Right Side Up, to break down how AI is becoming core to every marketer’s role and what that shift means for how modern teams operate.

Drawing on her leadership experience from Airbnb, Eventbrite, and Descript, Vanessa outlines a framework for helping teams adopt AI while preserving the human element that defines great marketing.

Find out why learning AI tools and experimenting with real workflows is key to understanding where AI adds value and setting your team up for success.

🗝️ Key Takeaways:

• Lead with identity. Every disruptive brand starts by tapping into something deeper than function—it connects to pride, purpose, and self-expression. When people see themselves in what you’re building, adoption follows.
• Try out this AI framework. 1) Use AI to research and synthesize insights, 2) automate repeatable workflows, and 3) connect your tools to create smarter systems that improve efficiency and decision-making.
• Turn personas into prompts. Build GPTs trained on real customer research to test messaging and ad creatives to sharpen your GTM strategy. One setup can boost speed and alignment across every campaign.
• Expand your creative options. From early brand concepts to visual patterns, use AI to help your design team explore ideas faster, gather feedback, and make more confident creative decisions.
• From prompt to production. Turn a single video concept into a first draft with scripted scenes and multilingual voiceovers. Use AI in creative ideation so your team spends less time setting up and more time storytelling.
• New AI-native marketing teams need two key roles. AI-native builders who design the workflows, and people with taste who choose the strongest creative direction. Together, they’ll set your team up for future success.
• Take an AI vacation. Block off a week to immerse yourself in the tools. Upload strategy docs, test workflows, and explore new use cases. The best way to lead your team into AI is to experience it yourself.

Timestamps

• 02:51 Balancing Culture and Performance
• 05:09 Disruption and Identity in Marketing
• 08:07 Expanding the Customer Base with AI
• 11.22 User Profiles and Market Education
• 16:51 Practical Frameworks for AI Marketing
• 22.54 AI's Impact on Video and Storytelling
• 31.43 Navigating the Future of Synthetic Media
• 34.28 Inside Airbnb’s Superhost Success
• 43.31 Building AI Marketing Teams

🔗 Mentioned in this episode:

• Descript: https://www.descript.com/
• Airbnb: https://www.airbnb.com/
• Eventbrite: https://www.eventbrite.com/
• Replit: https://replit.com/ai
• Lindy: https://www.lindy.ai/
• Bolt: https://bolt.new/
• ChatGPT: https://chatgpt.com/
• Claude: https://claude.ai/
• Zapier: https://zapier.com/
• Relay: https://www.relay.app/

👍 Did you enjoy this video? Don’t forget to click the like button! And find more episodes of Growth Talks here: https://bit.ly/3xXGJJc

🤝 Connect with Right Side Up

Right Side Up is a premium growth marketing agency that has helped more than 1,000+ companies hit their growth goals.

‣ Check us out and send us a note at: https://bit.ly/4bfaBQt

‣ Subscribe to our channel: https://bit.ly/3HWiJYD

‣ Subscribe to our marketing newsletter: http://bit.ly/44SEjbu

‣ Follow us on Linkedin: https://www.linkedin.com/company/rightsideup/

‣ Follow us on Facebook: https://www.facebook.com/RightSideUpCo/

‣ Follow us on Twitter: https://twitter.com/rightsideupco