In this episode, Mehmet sits down with Art Rivilis, CTO of Augment, to explore how AI is moving beyond copilots and into the era of AI teammates — intelligent agents that think, act, and collaborate like humans.
Art shares his journey from immigrant engineer to CTO, the lessons learned through two major acquisitions (Shopify and Flexport), and what it really takes to lead engineering teams through hypergrowth and M&A.
From redefining logistics through AI to tackling the hard problems of workflow automation and prompt design, this conversation unpacks how today’s CTOs can build systems — and teams — that scale with intelligence, not just speed.
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👤 About the Guest
Art Rivilis is the Chief Technology Officer at Augment, a pioneering AI company building intelligent teammates for the logistics and freight industry.
With 20 years of experience in engineering and product leadership, Art has held pivotal roles at VMware, Flixster, Symphony, Deliver (acquired by Shopify), and Flexport.
His expertise spans distributed systems, startup scaling, and AI-driven automation.
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🚀 Key Takeaways
• From Code to Leadership: How a lifelong engineer transitions from building software to building teams.
• Leading Through Acquisitions: Lessons from being acquired twice and integrating engineering cultures.
• Beyond Copilots: Why the next wave of AI isn’t about assistance, but collaboration.
• AI in Logistics: How Augment is using agentic AI to revolutionize freight and supply chain operations.
• Prompting for Precision: Why writing great prompts may be the hardest skill in the age of AI.
• Scaling Teams, Scaling Trust: The organizational inflection points at 100+ engineers — and how to maintain clarity and culture.
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🎓 What You’ll Learn
• What it takes to lead a startup through two acquisitions and come out stronger.
• How AI teammates differ from copilots — and why that matters for the future of work.
• The real-world challenges of integrating AI into legacy industries like logistics.
• Why prompt engineering and human context remain essential in building reliable AI systems.
• How CTOs can prepare for the agentic AI revolution — where systems act, not just assist.
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🕒 Episode Highlights (Timestamps for YouTube & Spotify)
00:00 – Intro & what to expect in this episode
02:00 – Art’s early passion for tech and first steps as an engineer
09:00 – From engineer to leader: why he became a CTO
17:00 – The challenges of being on the “acquired” side of M&A
25:00 – Integrating engineering teams and maintaining trust
33:00 – The 100-person rule: when to scale and when to delegate
37:00 – What Augment is building and why logistics is ripe for AI
45:00 – How the logistics industry is responding to AI adoption
53:00 – Can agentic AI transform other verticals?
57:00 – The next frontier: prompts, reasoning, and superintelligence
1:04:00 – Final reflections and where to find Art
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🔗 Resources Mentioned
• Augment – Official Website: https://www.goaugment.com/
• The Innovator’s Dilemma by Clayton Christensen
• Art Rivilis on LinkedIn: https://www.linkedin.com/in/arturrivilis/
