Always Be Testing

In this episode of Always Be Testing, host Tye DeGrange sits down with John Toskey, a seasoned marketing leader with over 25 years of experience in global partner and performance marketing. Having held senior roles at eBay, Affirm, and Opera Software, and now running his own consulting practice, John unpacks lessons from decades of leading high-performing global marketing teams. He shares valuable insights on building diverse and sustainable teams, creating a culture of experimentation, and the importance of asking the right questions when testing. The conversation dives into why diversity in location, experience, and seniority strengthens team performance, how to avoid “talent logjams” and keep growth pathways open, and what it takes to scale a test-and-learn culture while ensuring results are properly shared. John and Tye also explore the balance between data, intuition, and executive alignment in decision-making, the evolving future of performance marketing—from BNPL to retail media to influencer backlash—and the promise and risks of AI in marketing, including generational differences in its adoption. Adding a personal touch, John opens up about his passion for cooking, vegan living, and even bird-watching apps, making this conversation both insightful and relatable.

In this episode of Always Be Testing, host Tye DeGrange sits down with Kayla Castro, Senior Manager of Affiliates & Partnerships at Zenni Optical, to talk about the evolving world of affiliate marketing. Kayla shares her experience leading affiliate programs and offers practical insights on how to audit and optimize affiliate strategies for long-term success.The conversation covers common mistakes brands make in affiliate marketing and why internal communication is critical for gaining leadership buy-in. Kayla also dives into the complexities of measurement, breaking down MTA, MMM, incrementality, and attribution models in a way that helps marketers understand how to use the right tool for the right decision.They explore how to balance efficiency, partner diversity, and sustainable growth while leveraging AI as a supportive tool without losing the human touch that drives authentic, trust-based relationships with partners. Beyond marketing, Kayla shares personal perspectives on travel, books, and professional growth, making the discussion both practical and relatable.

In this special episode, Tye DeGrange, CEO of Round Barn Labs and host of Always Be Testing, reflects on his journey in marketing and the timeless principles he calls the Cowboy Code. Drawing from his upbringing on a California ranch and decades of experience leading growth at eBay, StubHub, and beyond, Tye explores what B2B marketers can learn from consumer brands.He highlights why trust and authenticity are more critical than ever in today’s trust-deficit world, and how partner and affiliate marketing can help bridge the gap. From lessons in finishing what you start, keeping promises, and “talking less but saying more,” Tye makes the case that B2B has its moment now—to embrace authenticity, invest in brand, and build lasting trust with buyers.

In this episode of the Always Be Testing podcast, Peter Denton—a seasoned growth and marketing leader with a 25+ year career in startups, product experimentation, and marketing innovation—shares a wealth of insights from his journey through the dot-com boom to leading growth at XMTP and previously Pioneer Square Labs.Peter discusses how to de-risk startups before launch, leverage APIs and data for faster insights, and adapt to changing marketing landscapes driven by AI, privacy, and emerging tech like blockchain and quantum security. From the rise of agents and protocols to the future of messaging platforms, Peter offers a masterclass on building, testing, and scaling products in today’s fast-moving world.

In this episode of Always Be Testing, host Tye DeGrange sits down with Erica Yoon, Director of Marketing at BuildOps, a vertical SaaS platform designed for commercial contractors. With prior experience at companies like Reddit, Erica brings a rich perspective on scaling marketing strategies that go beyond demand generation.

We’re joined by Lucas Beland, Co-Founder & CEO of Goloot, an innovative content platform helping Consumer and B2B brands secure content placements on a performance basis. In this episode, we dive into the evolving world of content and influencer marketing, exploring why it’s time to move past vanity metrics and focus on real business outcomes like customer acquisition cost, ROAS, and lifetime value rather than likes or impressions. We also discuss why authenticity wins—how raw, relatable, and creator-led content resonates more deeply with audiences than overproduced ads, ultimately driving stronger engagement and higher sales.

In this episode of Always Be Testing, host Tye DeGrange sits down with Kevin Weatherman, co-founder of Upscale AI, a performance streaming platform using AI to power connected TV ads for DTC brands. With a rich background that includes being the first business hire at multiple startups, angel investing, and co-founding a global run club, Kevin shares his journey from selling limo rides to Google employees to scaling AI-driven advertising solutions. Their conversation covers Kevin’s approach to identifying market trends, the evolution of A/B testing, connected TV measurement strategies, AI in creative production, the intersection of brand and performance marketing, influencer and affiliate strategies, hiring in the AI era, and personal insights from his journey to sobriety.

Sydney Sloan – CMO of G2, a leading software marketplace for businesses to discover, review, and manage technology solutions. She has extensive experience in customer marketing, community building, and scaling B2B SaaS companies. Formerly at Adobe, SalesLoft, and other high-growth companies, she’s recognized as a champion of customer advocacy.

In this episode, Ben Edelman shares insights from his years studying the intersection of economics, digital marketing, and consumer protection. He and the host dive deep into the evolution of affiliate marketing, the early days of web advertising, and how regulation and business incentives have shaped online behavior—both good and bad. Ben also reflects on ad fraud, deceptive affiliate practices, legal enforcement challenges, and how platforms and advertisers can improve accountability in the digital space.

Bryant Garvin, a 20-year veteran of the digital marketing world, announced his new position as Operator in Residence at Triple Whale. This role leverages Triple Whale's massive data set (35,000+ stores, $55B+ GMP annually) to build better products for marketers and e-commerce operators. Garvin discussed his evolved perspective on attribution, emphasizing Triple Whale's holistic approach using AI and data integration beyond simple dashboards. He highlighted the power of MOBI, Triple Whale's platform, in providing data-driven insights for strategic planning, such as Prime Day optimization. The conversation also touched upon the importance of humanizing data, considering the broader context of marketing beyond immediate clicks, and the crucial role of product quality in marketing success. Garvin shared successful marketing strategies from his past, including adding value instead of discounting and leveraging Kickstarter for product launches. He championed YouTube as an underutilized e-commerce channel and cautioned against relying solely on quick wins, advocating for long-term brand building. Finally, he emphasized the importance of authenticity and human connection in marketing, even in the age of AI, and shared a personal anecdote about his childhood dream of becoming a paleontologist.