About the episode:
In this episode, Michael and Kate dive into the realities of implementing AI in sales enablement, from building foundational knowledge before jumping into tools to managing the challenge of reps using their own AI solutions. They explore why starting with education beats rushing into adoption, how to measure real behavior change beyond just usage metrics, and why treating AI implementation like any other sales methodology requires proper change management and integration across the entire organization.
About the guest:
Kate Stringfield is a reformed seller turned enablement expert who spent nine years in sales before discovering her passion for enablement in 2019. At her last position as a Senior Manager of Enablement at Dialpad, she managed six enablers globally and focused on building strategic programs around emerging technologies like agentic AI to help sales teams change behavior and drive revenue outcomes.
Where to find Kate Stringfield:
LinkedIn: https://www.linkedin.com/in/kate-stringfield/
Where to find Michael (Founder & CEO @ SellMeThisPen AI):
Email: michael@sellmethispen.ai
LinkedIn https://www.linkedin.com/in/michaelocean/
Try SellMeThisPen AI @ https://www.sellmethispen.ai/
At SellMeThisPen, we help sales leaders transform team performance without adding headcount or management overhead ✨
Our AI roleplay and coaching platform enables your reps to practice with realistic scenarios tailored to your use case, then receive personalized feedback after every interaction - real client calls or AI simulations.
The result?
👉 Faster onboarding
👉 Consistent methodology adoption
👉 Continuous skill development that scales across your entire team.
Your reps get unlimited practice in a safe environment, real-time call assistance, and objective coaching that reinforces your sales framework. No more “hoping training sticks”, see measurable improvement in deal outcomes.
