Troubleshooting Enablement

You're using AI every day. But when leadership asks for your strategy, you freeze. This month, Melina Giakas, Head of Enablement at Clay, joins me to break down how to stop operating in piecemeal mode and start connecting your AI work to real business outcomes. We dig into: Why AI ownership is one of the biggest opportunities for enablement right now Building a custom GPT for real-time coaching wh...

Planning a sales or revenue kickoff with a tiny enablement team and massive expectations can feel impossible: Leaders want a world-class experience. No one wants to make decisions. Everything funnels back to enablement. In this episode of Troubleshooting Enablement, Devon McDermott is joined by Ali Smith (Senior Manager of Customer Success Enablement at Recharge) and Callan Coles (Global Sales Ena...

This week, we’re diving into a deceptively tricky question: How do you know when a company is actually ready for enablement… and when they’re just looking for someone to clean up the mess?! Joining Devon is GTM powerhouse Michelle Pietsch, who’s built and scaled revenue teams at Datadog, Drift, and Dooly. Michelle shares real talk from the other side of the hiring table, including what it really m...

When your workplace turns toxic but you can’t afford to leave, how do you protect your mental health, show up for your team, and avoid losing yourself in the process? Author and behavior change expert Lauren Brownstone joins Troubleshooting Enablement to explore self-regulation, gaslighting, burnout, and how enablement can challenge harmful dynamics and shape healthier cultures from within. Questi...

You’ve done great work. You’ve applied everywhere. You’re still not landing the job. What gives? In this episode, Samantha Thompson, award-winning enablement leader and founder of the enblr, breaks down how to navigate the job search slump, tell better impact stories, and rebuild confidence when the rejections keep coming! Question: I keep getting rejected for enablement jobs. What am I doing wron...