Top CEOs have coaches behind the scenes.
Executives Unplugged takes you into those rooms for candid conversations with leaders about how they find clarity in the chaos. We distill the systems and mindsets required to navigate high-stakes decisions and build world-class companies.
The hardest part of an AI transformation has nothing to do with the tech. It's breaking the human silos and learning to manage your agents like employees.
Akshit Kandi has mentored over 100 startups and built agents inside Salesforce's Agentforce platform. Now, as CEO of SkySync, he helps companies deploy and manage AI agents. In this episode he walks through the four moves that separate the teams getting real returns from the 90% stuck experimenting. Along the way he unpacks a client that grew new business 300% with a single marketing agent, why fear drives the worst decisions in a transformation, and how to measure ROI with a master dashboard.
00:00 Intro: Akshit Kandi and SkySync
00:48 Why 90% of AI projects are stuck in a pilot
02:22 Manage AI agents like employees
03:45 Inside a 300% growth story
06:55 Why change management is the real bottleneck
09:30 Offense vs. defense: the exec mindset
12:26 The tech decisions behind a true 360° view
15:12 Governance before you scale: CISOs, GDPR, data residency
21:03 Codifying workflows and keeping humans in the loop
23:50 Where to start: internal agents first
26:52 Mining meeting transcripts and existing systems
29:42 ROI dashboards: token measuring, not maxing
30:13 Why Akshit’s building in NYC
Follow Akshit on LinkedIn: https://www.linkedin.com/in/akandi6/ (https://www.linkedin.com/in/akandi6/)
SkySync: https://www.skysync.nyc/ (https://www.skysync.nyc/)
Follow Keith on LinkedIn: https://linkedin.com/in/keithcowing (https://linkedin.com/in/keithcowing)
Join Keith's Inner Circle: https://execs.tv (https://execs.tv)
Subscribe to Executives Unplugged:
YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM (https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM)
Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN (https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN)
Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263 (https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263)
21 Apr 2026
10 Rules for Building AI Agents That Actually Work
I've spent the last year building AI agents and working with CEOs doing the same. Most of what I built, I threw out. Here are the 10 rules that survived.
I've been building agents across my coaching practice, content production, and business operations — and the biggest lesson is that the hard part isn't the AI. It's codifying what actually matters in your work and organizing it so agents can use it. In this episode, I break down 10 rules for building agents that are genuinely useful — from structuring your data and building context that compounds, to choosing the right model for the right job, mixing deterministic software with LLMs, and managing agents the way you'd manage a high-performing team. No hype, no theory — just what I've learned from doing it every day. If you've been curious about agents but haven't started yet, this is your playbook.
Chapters
00:00 Introduction
00:44 Rule 1: Put All Your Data in One Place
02:00 Rule 2: Build Context That Compounds
03:28 Rule 3: Design for Rapidly Swapping Models
05:03 Rule 4: Use the Right Model for the Right Problem
06:55 Rule 5: Mix Deterministic Software with LLMs
08:21 Rule 6: Orchestrate Based on Frequency and Value
10:44 Rule 7: Keep Agents Narrowly Focused
12:04 Rule 8: Get Ready to Iterate
12:52 Rule 9: Managing Agents Is a New Skill
15:00 Rule 10: Half of What You Build Is Disposable
17:11 Your Next Steps: Just Start Building
Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing (https://linkedin.com/in/keithcowing)
Join the Inner Circle: https://execs.tv (https://execs.tv)
Subscribe
YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM (https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM)
Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN (https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN)
Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263 (https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263)
7 Apr 2026
The Truth About Hiring Your First Head of Product
Three top executive recruiters and Foursquare founder Dennis Crowley reveal why the candidate with the perfect resume is usually the wrong hire — and how to find the right one.
Most CEO-CPO relationships fail within the first 18 months and a lot of that pain starts with how the hire was made in the first place.
In this episode, I sat down with three of the best executive recruiters in the business — Chris Running, Jodi Jefferson, and Michael Cullen — plus Dennis Crowley, founder of Foursquare and Hopscotch Labs, to unpack the biggest mistakes founders and CEOs make when hiring their first VP of Product or CPO at Series A through Series C companies.
We cover: why many searches derail, the logo trap that seduces hiring managers into picking the wrong candidate, why you should look for trajectory over altitude, the management answer that's a complete red flag, how AI fluency is reshaping what "great" looks like in a product leader, and what it actually takes to close top talent in a market that's shifting fast.
Whether you're a founder about to make this hire or a product leader evaluating your next opportunity, this episode gives you the playbook from both sides of the table.
Chapters
01:13 Start With Why
03:10 Avoid Logo Trap
04:28 Real Search Example
07:50 Trajectory Not Altitude
08:48 Assess Judgment & Speed
10:52 Culture Fit Walkthrough
12:28 Management In Details
13:59 AI Native Leaders
17:15 Hiring With Conviction
19:23 Candidate Due Diligence
20:48 Align Expectations
23:19 Close The Candidate
25:13 The Market Shift
26:14 Five Takeaways
Find the guests on LinkedIn:
Jodi Jefferson: https://www.linkedin.com/in/jodijefferson/ (https://www.linkedin.com/in/jodijefferson/)
Michael Cullen: https://www.linkedin.com/in/cullenmm/ (https://www.linkedin.com/in/cullenmm/)
Chris Running: https://www.linkedin.com/in/chris-running-a94a8025/ (https://www.linkedin.com/in/chris-running-a94a8025/)
Dennis Crowley: https://www.linkedin.com/in/dpstyles/ (https://www.linkedin.com/in/dpstyles/)
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Perry Steinberg
Natasha Jaffe
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