How They Lead – S02 Ep 02 | Matt Bennett sits w/ Jenna Eichberg, CPO at AlertMedia

In this energizing and insightful episode, Matt Bennett sits down with Jenna Eichberg to explore what it really means to lead with heart, strategy, and adaptability in today’s world of work.

3 Key Themes:

1. Leadership Without the Title – Jenna shares how early initiative and curiosity shaped her ability to lead long before the job title said so.

2. Culture as a Strategic Advantage – From winning Best Place to Work in Austin to navigating crisis with care, Jenna unpacks how culture, trust, and mission alignment fuel AlertMedia’s success.

3. The Human Side of AI – With AI transforming the workplace, Jenna talks about building psychological safety, learning pathways, and anthropomorphizing tools (hello, Charlie the chatbot) to make tech adoption human-first.

3 Powerful Takeaways from Jenna:

· “Any idea not put on the table is an idea lost.” Create environments where everyone’s voice contributes.

· “You don’t need a title to lead, just the willingness to solve real problems.” Leadership starts with curiosity and initiative.

· “The softer skills are what will define great leaders in an AI-driven world.” Trust, authenticity, and vulnerability aren’t nice-to-haves, they’re the differentiators.

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