Best Manager Ever: Charlie Coglianese - The Struggle is Real, But So is the Growth

Charlie Coglianese is the Chief Technology Officer at Paloma Learning, a VC-backed edtech startup using AI to improve student learning outcomes. Charlie started his career in finance, before making the leap into startups. He was the Founder & CEO of a startup called Schoolrunner, which was acquired by SchoolMint. Charlie served as the CTO at SchoolMint post-acquisition before returning to early-stage building in his current role

Charlie's direct reports describe him as a leader who invests deeply in the growth of his team. He’s recognized for his ability to spot potential, provide the right level of challenge, and create an environment where people feel trusted to take ownership, try new things, and grow. The most common theme in their feedback is that Charlie empowers his team—he’s known for his intellectual honesty, willingness to jump in alongside his team, and his focus on building trust and clarity.

In this episode, show creator and Fort Light founder Annie Riley sits down with Charlie, and they discuss:

• How to spot talent through trajectory, instead of outcomes
• The concept of “productive struggle” and how to balance challenge and support
• Advice for working with founders and navigating the founder-executive relationship
• Strategies for retaining top performers and keeping them engaged
• The importance of clear goals and mission in motivating teams

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