In this episode, Greg Grand, CEO of G Squared Advisors, shares how he integrates AI into sales leadership, coaching, and business operations. Drawing on more than three decades of sales experience, Greg explains how his approach evolved from chasing new AI tools to focusing on solving specific business problems. The conversation explores practical AI applications in sales training, role play coaching, meeting analysis, hiring, workflow automation, and productivity. Greg also discusses the future of AI in sales, why consultative selling remains irreplaceable, and how sales professionals can start using AI today to save time, improve performance, and stay competitive in a rapidly changing market.

Takeaways

• Greg Grand transitioned into fractional sales leadership after seeing small and mid-sized businesses struggle to scale without experienced sales management.
• His breakthrough with AI came when he stopped chasing tools and started identifying business problems first.
• AI serves as a brainstorming partner, helping solo consultants and business leaders generate new ideas and challenge assumptions.
• Sales role play training powered by AI can provide personalized coaching, grading, and feedback at scale.
• AI-driven interview analysis helps evaluate candidates for cultural fit, sales skills, and role suitability.
• Meeting transcription and automated summaries save significant administrative time for sales leaders and consultants.
• AI is most effective today in preparation, research, training, documentation, and workflow optimization rather than replacing complex sales conversations.
• High-value consultative sales skills remain difficult to automate because trust, relationships, and human judgment drive buying decisions.
• Entry-level sales development and transactional sales roles face greater disruption from AI than senior consultative sales positions.
• The best way to start with AI is to dedicate regular learning time, follow trusted AI educators, and look for opportunities to save time in daily work activities.

Today's guest, Greg Grand, can be found at:

Website: https://gsquaredadvisors.com/

LinkedIn: https://www.linkedin.com/in/greggrand/

Your host, Hunter Jensen, can be found online at:

Website: https://www.barefootsolutions.com/

LinkedIn:https://www.linkedin.com/in/hunterjensen/

Keywords

Artificial Intelligence, AI, Sales Leadership, Fractional CRO, Revenue Growth, Sales Coaching, Sales Training, Role Play Training, Sales Enablement, Business Development, Prospecting, CRM Management, Workflow Automation, Meeting Transcripts, Zoom AI, Custom GPTs, Gemini, Claude, Perplexity, ChatHub, AI Agents, Make Automation, Sales Process, Consultative Selling, Sales Strategy, Candidate Assessment, Hiring, Revenue Operations, Productivity, Knowledge Work, Sales Playbooks, Pipeline Management, Lead Generation, B2B Sales, Sales Technology, Business Scaling, Time Management, AI Adoption, Voice AI, Sales Performance, Customer Discovery, Objection Handling, Coaching Frameworks, Automation Tools, LinkedIn Prospecting, Dux-Soup, Sales Operations, Human Connection, Trust Building, Revenue Leadership, AI Workflows, Digital Transformation