AI-Powered Seller How Top SaaS Reps Use AI Digital Teammates to Win More Deals in 2026
Nov 25, 2025
Ryan Staley, Founder and CEO of Whale Boss, shares how AI can transform sales roles into more efficient units. He emphasizes the shift from viewing AI as a simple tool to treating it as a digital teammate that can handle multi-step tasks. Ryan explains the importance of creating tailored AI assistants like deal strategy and account research. He also addresses common barriers to AI adoption and strategies to present AI effectively to drive engagement. Finally, he urges leaders to retrain teams urgently to stay competitive in this evolving landscape.
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AI Matches Deep Sales Intuition Fast
- Ryan realized GPT rapidly matched years of enterprise-sales intuition in minutes.
- That experience reframed AI as a fundamentally different capability, not just another tool.
Personal Wins From Treating AI As A Mind
- Ryan shared personal examples: journaling to coach parenting and using prompts to diagnose a chronic condition.
- He also described executive teams building yearly plans in 45 minutes using AI instead of days.
Start With One Assistant, Then Orchestrate
- Build assistants for single functions, then link them into a multi-step teammate that executes workflows.
- Use orchestration to automate chains like transcript → analysis → Slack → Google Doc outputs.
