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March 5, 2025 13 mins

In this episode, Josh Kail shares insights from his nearly two decades in strategic communications and PR, discussing his "sink or swim" approach to career development, team leadership philosophy, and vision for the PR industry's future. Josh offers a candid look at how early career challenges shaped his management style and why he believes the PR industry needs to refocus on its psychological foundations rather than over-relying on technology.


What You'll Learn in This Episode:

How embracing early career challenges can accelerate professional growth

The importance of balancing professional demands with creative outlets for mental health

Why being challenged by team members leads to stronger strategic outcomes

How to establish professional boundaries with clients while maintaining relationships

Insights into the future of PR and strategic communications in the AI era


Key Quotes:

"I like to look at my career, or my early career in particular, as a series of sink or swim moments."

"I like to have every member of my team input and preferably argue with me... I want outside views at every level to come in and challenge me."

"The foundation of PR is psychological... How does an organization or an individual communicate to individuals? We need to get back to that fundamental."


Meet The Interviewee Josh Kail has nearly 20 years ofexperience in Strategic Communications and PR, with a strong focus on high-tech B2B markets. He has worked with clients in AI, Machine Learning, Data, Blockchain, Ad Tech/Mar Tech, digital transformation, and emerging technologies. Throughout his career, he has represented a diverse range of industries, from consumer products to cutting-edge AI advancements. Josh has held leadership positions including Managing Partner at SamsonPR and Senior Vice President at various firms. Colleagues describe him as calm, strategic, and inclusive. Outside of work, he pursues creative outlets including writing, acrylic painting, woodworking, and coffee roasting.


How to Connect

🔗 LinkedIn: Josh Kail

📧 Email: jkailpr@gmail.com


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With ConnectToWork, we amplify real career stories toinspire and connect professionals. If you or someone you know is navigating a career transition, we'd love to hear your story.


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