Scaling Smarter with AI: Zack Urlocker on Company Growth and Cutting Through the Hype

On this episode of the AI & Data Driven Leadership Podcast, host Dean Guida welcomes Zack Urlocker, Chief Operating Officer at Crescendo.ai, for an honest, grounded conversation on what it really takes to scale a company in today’s AI-driven environment. With leadership experience at high-growth companies like Zendesk, MySQL, and Duo Security, Zack brings a pragmatic lens to the promises—and pitfalls—of AI. This episode is a must-listen for founders, operators, and product leaders who want to use AI to create meaningful, scalable outcomes without getting swept up in the hype.

Where AI Adds Value—and Where It Doesn’t

Zack breaks down the difference between traditional customer service models and newer outcome-based approaches, like those being pioneered at Crescendo. He explains how most companies still rely on legacy platforms and labor-heavy support teams—often scaling headcount instead of impact. By shifting to an outcome-based model powered by AI and automation, companies can deliver faster, more consistent service without relying on over-hiring, especially during high-demand cycles.

That said, Zack doesn’t sugarcoat the limitations. He discusses the real-world friction around data privacy, model training, and the need for continuous tuning. AI isn’t plug-and-play—it’s a system that needs constant attention and skilled oversight. Leaders who want to succeed with AI must either upskill internal teams or bring in external expertise to keep models aligned with changing policies, products, and customer expectations.

Most importantly, Zack pushes back against the notion that AI will replace entire teams—especially in creative or strategic roles. He sees it more as an amplifier than a substitute. From content creation to sales strategy, the companies that will win are those that use AI to empower people—not sideline them.

About Zack Urlocker

Zack Urlocker is a veteran technology leader and growth-stage executive. He’s held C-level roles at industry-defining companies including Zendesk, MySQL, and Duo Security, and is currently the COO at Crescendo.ai. He’s also the author of the blog Build to Scale, where he shares insights on startup leadership, scaling strategies, and organizational culture.

About Crescendo.ai

Crescendo.ai delivers outcome-based customer support solutions that blend AI and human expertise to help companies scale service efficiently. Their platform is designed to handle complexity without sacrificing quality—allowing fast-growing teams to stay responsive without ballooning overhead.

Links Mentioned in This Episode

• Crescendo.ai

• Zack Urlocker on LinkedIn

• Build to Scale Blog

Conclusion

This conversation with Zack Urlocker cuts through the noise around AI and reveals what actually works when scaling tech companies today. From managing expectations to designing smarter customer experiences, Zack reminds us that it’s not about replacing humans—it’s about building systems where AI and people work better together. The key is culture, clarity, and continuous improvement.

Key Highlights from This Episode

• The shift from traditional to outcome-based customer support models

• How to use AI without losing the human element in service and sales

• Practical advice for training and tuning AI systems over time

• Where AI-generated content falls short—and how to fix it

• Why open communication and cultural transparency matter more than ever

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