Guest: Sam Daish

Chris and Corey are joined by Blackpearl Group’s CTO, Sam Daish. In this episode, he's dousing us with the reality of why most sales AI tools are basically expensive cat toys. Blackpearl has built Bebop.AI, a tool that makes sense as an addition to a sales pro’s tech stack. It could probably replace several nonsensical shiny AI  tools they are currently batting around instead of making calls.
Corey's firing questions about AI fatigue (because let's face it, we all have it), while Chris goes full mathematician on us with this brutal insight: sales reps are like cats chasing laser pointers with AI. Lots of movement, lots of fascination, but nobody's actually catching anything.
You may wonder how this fits in with BeBop.ai. It will make more sense after you hear the origin story - they almost called it "Hot Pipe" until someone pointed out the, uh, alternative interpretations. Instead, they went with a full bebop jazz vibe in the function and tone because they wanted sales to feel like improvisation, not a pile of dated rigid playbooks.
As the real kicker, Chris breaks down why most AI implementations fail: false negatives. You're not just calling the wrong people - you're missing the right ones entirely. And Sam's nodding along because BebopAI tackles this by making the entire Internet your database instead of some limited proprietary dataset.
The feature that gets reps most excited? Not the fancy prospect data. It's the objection handling. Turns out confidence beats information every time.
Join us for this episode, “The Laser Pointer Problem: Why your reps are chasing AI like distracted cats .”
Action Items Suggested in This Episode:
For Sales Leaders/CROs
Audit your AI strategy focus - Are you trying to bring bottom performers up, or amplify your top performers? Chris argues the latter delivers exponentially better ROI
Identify your "Jonti McLarens" - Find your top performers and give them 10% more time/better tools (equivalent to adding 10 middle-tier reps)
Evaluate your current AI tools - Are they creating "laser pointer cat" behavior or getting reps to more conversations?
For Sales Reps
Test BeBop.ai's's dossier approach, with a special focus on the objection handling feature that receives the most positive feedback.
Use AI for discovery prep, not avoidance - Read dossiers in the minutes before scheduled meetings when memory retention is highest.
Ask "why" to AI responses - Sam emphasizes this helps uncover hallucinations and improves reasoning.
For Sales Operations/Enablement
Shift from proprietary databases to "Internet as database" tools - Evaluate platforms that can digest broader data sources
Implement AI that works as "companion, not a replacement" - Focus on tools that enhance human expertise rather than substitute for it
Measure false negatives, not just false positives - Track opportunities missed, not just wrong prospects contacted
For Product/Marketing Teams
Load your website into BebopAI - Sam says this simple step works really well for basic company understanding
Document your go-to-market messaging - Feed it into AI tools for consistent, company-specific responses.
Create objection handling libraries - The most requested feature, according to Sam's feedback.
For Executives/Investors
Recognize top salespeople as an innovation economy constraint - Chris's thesis: Elite sales performance limits how fast innovation spreads
Budget for commission accelerators - Top performers using AI tools may exceed traditional quota expectations
Rethink headcount-based scaling - Focus on amplifying existing top talent vs. adding middle-tier reps
Immediate Next Steps
Try the "Internet as database" approach - Ask AI tools open-ended questions like "find me customers for [your company]"