
273 : Lead Forward: AI, Leadership, and the Future of Work with Jack Jendo
What does it actually take to lead in an era where artificial intelligence is reshaping every industry, every role, and every assumption about how work gets done? On this episode of Navigating the Customer Experience, Yanique Grant sits down with Jack Jendo, founder of BrainDigits, AI strategist, and author of Lead Forward, to explore what the future workplace really looks like and why leadership is the most important skill you can develop right now.
Jack brings a perspective shaped by years of working across the Middle East, Europe, and Australia, building AI-powered programs for governments, corporations, and startups. His message is clear: AI is not just a tool. It is a mindset shift, and leaders who understand this will be the ones who define what comes next.
WHAT YOU WILL LEARN IN THIS EPISODE
Jack shares the journey that took him from juggling three jobs during university to running agencies across multiple continents and founding BrainDigits. He talks about why he wrote Lead Forward, a book designed for three types of people he encounters every day: entrepreneurs who are just getting started, senior professionals who feel like their career is winding down when it does not have to be, and leaders in the middle who feel pressure but lack clarity.
Jack also introduces a concept that reframes how leaders can use AI: the Digital Twin. Rather than using AI as a general assistant, Jack trains specialized AI versions of himself, one for brainstorming, one for financial strategy, one for business development. He has been building and refining these tools for years, and the result is a thinking partner that reflects his values, his frameworks, and his way of approaching problems.
THE FUTURE WORKPLACE: AI FIRST OR AI ENABLED?
Jack places AI in the same category as transformative inventions like the printing press and the internet. Each of those disrupted every industry it touched. AI is doing the same. But the change is not primarily about tools. It is about mindset and clarity.
He describes two futures emerging for organizations. The first is a company that adopts AI aggressively without understanding what it is doing, relying on automation without the human judgment to direct it. That organization will struggle. The second is a company led by people who know exactly what they need, who operate with ownership and freedom, and who use AI to remove friction and accelerate execution. That is the organization every leader should be building toward.
AI IS THE NEW LEADERSHIP SKILL
Jack and Yanique explore what it means to treat AI as a leadership skill rather than a software category. His view is that every task with a clear process can now be handled by AI. What cannot be automated is knowing what needs to be done, deciding the direction, and leading people through change.
The leaders who will thrive are those who invest in training their AI tools the same way they would develop a trusted assistant. Not with generic prompts, but with context, values, goals, and frameworks. That investment is what turns a general tool into something genuinely useful.
Jack shares that his two primary tools are ChatGPT, where he has trained a custom model called TwinJack over four years for brainstorming and strategic thinking, and Claude, which he has used for automation over the past year. He describes them as complementary, each with a distinct role, and both trained with the same foundation.
KEY INSIGHTS FROM THIS EPISODE
Experience compounds. Working across multiple roles and industries, especially early in a career, creates a foundation that multiplies future opportunity.
Retirement is not an endpoint. Jack pushes back on the idea that experienced professionals should wind down. Their knowledge, relationships, and judgment are among the most valuable assets available to any organization.
Scaling happens during crisis. When others pull back, Jack leans in. His approach is to build capacity, strengthen teams, and expand during periods of pressure because that is when the real growth happens.
The guiding question Jack returns to during adversity is simple: remember why you started. It is not about nostalgia. It is about using original purpose as an anchor when clarity is hard to find.
BOOKS MENTIONED IN THIS EPISODE
Lead Forward by Jack Jendo https://www.amazon.com/s?k=lead+forward+jack+jendo
Start with Why by Simon Sinek https://www.amazon.com/s?k=start+with+why+simon+sinek
Rich Dad Poor Dad by Robert Kiyosaki https://www.amazon.com/s?k=rich+dad+poor+dad
The Richest Man in Babylon by George S. Clason https://www.amazon.com/s?k=richest+man+in+babylon
TOOLS MENTIONED
ChatGPT (Custom GPT / TwinJack): https://chatgpt.com Claude (AI): https://claude.ai BrainDigits: https://braindigits.com
CONNECT WITH JACK JENDO
LinkedIn: https://www.linkedin.com/search/results/all/?keywords=jack+jendo Instagram: Search Jack Jendo
Jack responds personally to every message.
FOLLOW NAVIGATING THE CUSTOMER EXPERIENCE
X (Twitter): https://x.com/navigatingCX Facebook Community: https://www.facebook.com/groups/NavigatingtheCustomerExperience LinkedIn: https://www.linkedin.com/in/yaniquewagrantcx/ Website: https://yaniquegrant.com/podcasts/
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