Troubleshooting Enablement

devon mcdermott
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Troubleshooting Enablement is the podcast for enablers who keep it real. Hosted by Devon McDermott, each monthly episode tackles the messy, complex, and sometimes unspoken challenges facing enablement professionals today. From deploying AI strategies and thriving as a team of one, to surviving toxic work environments and revamping your resume we dig into the real talk behind the buzzwords. No fluff. Just sharp advice, hard-earned lessons, and the occasional karaoke reference. Each episode features expert guests helping you troubleshoot one listener-submitted question at a time. Think of it as an anonymous advice line, minus the judgment. Got a burning question? Send it to: devon@troubleshootingenablement.com

Episodes

  1. JAN 14

    Troubleshooting Enablement: Surviving Your First RKO: Callan Coles & Ali Smith

    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 Enablement Leader at Branch) to break down how to take control of an RKO or SKO when you have influence but limited authority. They share hard-earned lessons from running in-person, hybrid, and virtual kickoffs on small teams, including: how to align leadersset boundarieslock decisionsand design an event that actually changes rep behavior If you are eight weeks out (or LESS), drowning in opinions, and worried enablement will take the blame, this episode gives you a practical path forward!

    51 min

  2. 12/16/2025

    Troubleshooting Enablement: Michelle Pietsch - Is This Company Ready for Enablement?

    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 means when a founder says they “believe in enablement.” Question: How do I know if a company is truly ready for enablement? Guest: Michelle Pietsch, GTM leader BeaconGTM Topics: - Red & green flags in CROs and founders - Interview questions that reveal true buy-in - The tipping point for bringing in enablement - Shifting from reactive to strategic work Resources & Links: Follow Michelle on LinkedIn

    29 min

  3. 11/19/2025

    Troubleshooting Enablement: Lauren Brownstone - How to Stay Grounded in a Toxic Work Environment

    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. Question: How do I survive a toxic work environment when I can’t leave yet? Guest: Lauren Brownstone author of Enabling Enablement Topics: - Responding vs reacting in high-stress environments - Gaslighting, bullying, and burnout at work - How enablement influences culture and behavior change - Practical habits to protect your energy and sense of self Resources & Links: - Follow Lauren on LinkedIn - Learn more about Heartwise Self-Leadership - Buy Enabling Enablement

    37 min

  4. 10/19/2025

    Troubleshooting Enablement: Samantha Thompson - How to Break Through the Enablement Job Hunt Wall

    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 wrong? Guest: Samantha Thompson, SEC One to Watch, founder of the enblr Topics: - Resume mistakes that cost you the interview - Crafting compelling enablement impact stories - Red flags in interview processes - Assets worth bringing (and when to protect your time) Resources & Links: Follow Samantha on LinkedIn Explore https://www.theenblr.com/

    36 min
  • 4 Episodes

About

Troubleshooting Enablement is the podcast for enablers who keep it real. Hosted by Devon McDermott, each monthly episode tackles the messy, complex, and sometimes unspoken challenges facing enablement professionals today. From deploying AI strategies and thriving as a team of one, to surviving toxic work environments and revamping your resume we dig into the real talk behind the buzzwords. No fluff. Just sharp advice, hard-earned lessons, and the occasional karaoke reference. Each episode features expert guests helping you troubleshoot one listener-submitted question at a time. Think of it as an anonymous advice line, minus the judgment. Got a burning question? Send it to: devon@troubleshootingenablement.com

Information

  • Creator
    devon mcdermott
  • Years Active
    2025 - 2026
  • Episodes
    4
  • Rating
    Clean
  • Copyright
    © 2025 devon mcdermott
  • Show Website
    Troubleshooting Enablement