Greg Shove is a veteran entrepreneur and the CEO of Section, an AI-focused education platform dedicated to transforming the global workforce into "AI maximalists." A six-time CEO with a track record of high-value exits, he previously co-founded and led First Up (formerly SocialChorus), a pioneer in employee communication software that redefined how major corporations engage with their frontline workers. Greg is a vocal advocate for "bottom-up" AI transformation, arguing that leaders have a moral and strategic obligation to upskill their entire staff rather than relying on top-down consulting. Known for his candid "lead or retire" philosophy, he combines decades of leadership experience with a gritty, hands-on approach to modern technology, helping organizations move past "busy work" to focus on high-value human judgment.
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Empowering the Underdog: Building a "Super Company" From the Ground Up
The AI Pyramid: Bottom-Up Transformation
Greg introduces a "mental model" for companies: a pyramid where the current workforce is the foundation.
The Strategy: Instead of hiring expensive consultants (like McKinsey) to dictate an AI plan from the top down, companies should train every single employee to use AI daily.
The Logic: Employees know their own workflows better than anyone. They are the best people to identify which tasks are boring, repetitive, or ready for automation.
The Goal: By making the entire staff "AI-enabled," a company creates a solid base upon which they can eventually build complex automations and new products.
A More Humane Approach to Layoffs
The speakers address the "elephant in the room": job security. Shove pushes back against the trend of massive, immediate layoffs.
Upskilling as an Obligation: He believes leaders have a duty to train their staff in AI.
Future-Proofing: Even if a team eventually needs to shrink, an "AI-enabled" worker is much more employable in the outside market than someone who was simply let out the door without new skills.
The Contractor Shift: Some employees might even choose to leave and return as AI-powered specialized contractors, or start their own ventures.
The Explosion of "Knowledge Work" Entrepreneurship
One of the most exciting takeaways is the idea that AI lowers the barrier to entry for starting a business.
No Technical Degree Needed: Much like "Main Street" businesses (restaurants or shops), Greg believes AI will allow people to start white-collar businesses without needing a huge team of programmers or massive amounts of capital.
Economic Growth: This could lead to a massive wave of new small businesses in the U.S., helping to offset the jobs lost to automation in larger corporations.
Why the Employee Matters Most
Drawing from his experience at his previous company, First Up, Greg emphasizes his "rooting for the underdog" philosophy. He notes that:
Employees are often "in the dark" about company strategy.
AI shouldn't be another way to keep workers sidelined; it should be the tool that turns them into the architects of their own future.
If you’re closer to 60 and you’re resistant [to AI], please don’t stay in the seat. You’re doing a huge disservice to your team... You’re better off to go to the golf course. (Greg Shove)
From FOMO to Flow: How Leaders Can Master the AI Age
Stop "Playing" and Start Producing
The most common mistake leaders make is using AI for home life (like parenting advice) but ignoring it at the office. Shove’s advice is blunt: You cannot lead a transformation you don't understand.
The Action: Get a paid account (ChatGPT, Claude, or Gemini) and put the app on your phone.
The Goal: Don't just "play around" for two hours on a Tuesday. Use it to complete actual work tasks or improve the quality of your decisions.
Hire an AI "Thought Partner"
Shove suggests that every leader now has access to a consultant that is "smarter than them" for $20 a month, available 24/7.
Roleplay: Use AI to simulate a difficult board meeting or a sensitive employee conversation.
Strategic Pressure-Testing: Ask the AI to poke holes in your latest business strategy. A 10–15 minute daily "chat" with AI as a thought partner is more valuable than hours of aimless browsing.
Build an AI Chief of Staff
If you don't have a human assistant, you can now build a digital one. By using features like "GPTs" or "Claude Projects," leaders can feed the AI their specific context, data, and preferences.
The Benefit: This "Chief of Staff" can summarize long reports, draft communications in your voice, and keep you organized, giving you back precious hours of your day.
Empathy Through Usage
Perhaps the most important point Shove makes is about employee anxiety. The media often paints a black-and-white picture: either a "world of abundance" or "mass unemployment." This creates a "freaky" environment for workers, especially software engineers who are seeing AI write 100% of certain codebases.
The Leader's Duty: By using the tools themselves, leaders can feel exactly what their employees feel—the moment where the AI is actually better at a task than they are.
The Reality Check: Understanding the technology helps a leader explain to their team that while their tasks are changing (moving from coding to architecture or design), their value isn't necessarily disappearing.
The early adopters... their work week now ends Thursday night. They’re just not telling their boss. (Greg Shove)
Beyond the Newsletter: How to Build a Real "AI Vibe" at Work
The "Software Update" Trap
Greg warns that many CEOs think AI is like installing Microsoft Office: you do one training session, put a video in the learning portal, and you're "done."
The Reality: AI transformation is a constant, evolving process that will take years, not months.
The "Newsletter" Mistake: Simply putting a "Success Story" in the company newsletter is "naive and stupid" if leadership isn't actually using the tools themselves.
Five Ways to Create a Real AI Culture
If you want your team to actually embrace the change, Greg suggests a mix of high-energy events and daily habits:
1. The All-Hands Hackathon (or Sprint) Don't just leave hackathons to the engineers. Greg suggests shutting down normal operations for a few days to let everyone—sales, HR, marketing—play with AI. The goal isn't necessarily to build software; it’s to build confidence and see what’s possible.
2. AI Shout-Outs At Greg’s company, they give public shout-outs to AI tools (like Claude or ChatGPT) during team meetings. While it sounds "weird" because the AI isn't a person, it highlights specific wins and shows the rest of the team how others are saving time.
3. Centralize the Knowledge Don't let everyone work in silos. Create one Slack or Teams channel where every "win" and every "fail" is documented. This keeps the learning curve steep for everyone.
4. Hire a "Head of AI" (Even if you’re small) Greg reveals that even his 40-person company is hiring a Head of AI. Why? Because business leaders are busy, and even in an AI-first company, people get stuck in their old ways. You need someone whose entire job is to push the boundaries of what the tech can do for the business.
5. Leading with a Growth Mindset Greg emphasizes that being "AI Native" is a mindset, not an age. He jokes that he’s "old" and not technical, yet he figured it out years ago. It’s about the willingness to be a "canary in the coal mine" and try things that might not work.
The Competitive Edge
Greg shares a striking stat: his team of 40 people is currently doing the work of 60 people because of their AI integration. This isn't about working more hours; it's about being more effective with the hours they have.
AI transformation needs to start at the bottom of the pyramid. The workforce is the foundation on which you’ll build the rest. (Greg Shove)
Cut the Busy Work, Create the Future: The New ROI of Leadership
The "Inference" Bill: AI is Your New Second-Biggest Expense
Greg shares a startling insight from his own company's balance sheet. In most software companies, the biggest expense is people, and the second is software (like Salesforce or HubSpot).
The Shift: Very soon, Greg expects "Inference"—the actual cost of running AI models—to become his second-largest expense.
The Leadership Challenge: As a CEO, Greg is looking for managers who can prove they are getting a high return on that investment. If the company is paying for "tokens" and AI processing, he needs leaders who know how to turn that tech spend into real revenue and happy customers.
Standing Out in a World of Automated Spam
We’ve all seen it: our inboxes are flooded with "personalized" AI emails that feel fake. Greg argues that as AI makes marketing noisier, the "human touch" becomes a premium product.
The Return to Human: Because digital space is getting crowded with AI-generated noise, Greg is investing more in in-person and virtual conferences. * Trust as a Product: Success in the future will belong to the "Humanizers"—those who use AI to handle the back-end while they focus on persuasion, trust, and high-quality human interactions.
The "Cut and Create" Strategy
When asked what leaders should stop doing, Greg introduces a simple mental model: Cut and Create.
Cut the "Shit Work": AI has exposed that a massive amount of knowledge work is actually just "busy work." Leaders must aggressively move to hand off repetitive, low-value tasks to AI.
Create the Roadmap: This is the most critical step. If a leader tells their team, "AI will save us 10 hours a week," the team’s first thought is, "They’re going to lay us off."
The Fix: Leaders must immediately tell their team what they are going to do with that saved time. Use it to tackle the big "someday" projects, invent new products, or focus on higher-value services.
Moving Past Anxiety
The goal for any modern leader is to move through the "Cut" phase as fast as possible. The longer a team sits in the "efficiency" phase, the more anxious they get about their jobs. By quickly pivoting to the "Create" phase, leaders can raise their team's horizons and get them excited about building the future.
You have a thought partner available now, 24/7 for 20 bucks a month, who’s smarter than you. Why would you not do that? (Greg Shove)
Check the episode's Transcript (AI-generated) HERE.
To continue the conversation with Greg Shove, connect with him via his LinkedIn.
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