57. Sales Enablement as Force Multiplier

On this episode of Thoughts on Selling, I sit down with Jackie Retig, a passionate sales enablement leader and COO at EnableWorks. Jackie recently made the leap into entrepreneurship after years in the tech space, and she brings a grounded, practical perspective to what it really takes to build consistent, scalable sales teams.

We get into why enablement is more than just onboarding and training—it's about creating the conditions for consistency, repeatability, and predictability in your sales org. Jackie and I talk about the transformation that comes from good enablement, how to help reps lean in and grow, and why the founder-led sales playbook doesn’t scale.

We also dive into:

• Why enablement is finally being seen as a force multiplier by CROs and VPs of Sales

• How tribal knowledge is great—but institutional knowledge wins

• What makes discovery truly impactful (hint: it’s not about checking boxes)

• Why AI is an assist—not a substitute—for great selling

• The power of deliberate practice and role play in building sales muscle

Key takeaways:

• 🎯 Consistency, repeatability, and predictability are the north stars of effective enablement.

• 🔁 Discovery isn’t a stage—it’s a mindset. Great sellers co-create value throughout the sales process.

• ⚙️ AI can streamline the busywork, but insight and connection still require the human touch.

• 💡 Sales enablement isn’t just tactical—it’s transformational when tied to business outcomes and measured impact.

Whether you're in enablement, sales leadership, or building out your first team, Jackie’s insights on modernizing and scaling sales efforts are well worth your time.