What WRITER’s CSO Kevin Chung Has Learned from Hundreds of Enterprise AI Deployments

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Sep 16, 2025

In this engaging discussion, Kevin Chung, Chief Strategy Officer at Writer, shares insights from over 20 years in Silicon Valley. He reveals how Writer transformed from a translation tool to a full-stack AI platform, focusing on the pitfalls of enterprise AI projects. Kevin emphasizes the crucial 'last mile' challenge and why successful deployments involve treating AI as a digital employee. He offers advice for executives on achieving ROI and collaborating with trusted partners, all while dispelling common AI misconceptions and advocating for a hands-on customer approach.

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ANECDOTE

From Translation Tool To Enterprise AI

Writer began as a translation business founded by May Habib and Wasim Al‑Shik and then pivoted into generative AI around 2020.
The founders' early tinkering with transformers set the technical foundation for Writer's enterprise focus.

INSIGHT

High Failure Rate Hides Big Winners

Many enterprise AI projects fail because the problem is hard and organizations are early in the journey.
The winners who persist see massive ROI and expansion after surviving initial failures.

INSIGHT

Last‑Mile Integration Is The Real Barrier

The 'last mile' of deploying AI—accuracy, output, integration—breaks many projects, not model availability.
Large enterprises often think they can build everything in‑house but buying from specialists usually accelerates success.

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Is it possible to drive real businesses transformation with AI amidst reports that 95% of enterprise projects have been failing? On the debut episode of MindMakers, host John Kim is joined by Kevin Chung, Chief Strategy Officer of WRITER, to unpack what it really takes to scale enterprise AI efforts successfully.

Kevin shares how WRITER evolved from a niche translation tool into the full-stack AI agent platform it is today. Together, he and John offer their own insights on the widespread MIT / NANDA report. You’ll hear why so many AI deployments stall in the “last mile” and what the most successful companies do differently. These are the organizations seeing real ROI, launching hundreds of AI agents, and reclaiming tens of thousands of hours in productivity.

Throughout the episode, Kevin and John explore how AI is shifting from tool to teammate, why treating AI like a new hire changes everything, and how WRITER builds trust through a hands-on approach with their partners.

Whether you're building AI tools, leading digital transformation, or just trying to make your org more efficient—this episode is packed with insight on getting real results from AI at scale.

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Guest Bio

Kevin is the Chief Strategy Officer of Writer, the leading generative AI platform for enterprises. He is an accomplished technology leader with over 20 years of experience in Silicon Valley. Kevin has led GTM and product teams through some of the world’s most disruptive digital transformations, including mobile payments (Google), cloud storage (Dropbox), visual collaboration (Miro), and now generative AI (Writer).

Kevin is a recipient of Singapore’s Overseas Networks & Expertise (ONE) Pass, a designation given to the top global talent in business, arts & culture, sports, academia and research. Kev currently splits his time living/working in San Francisco and Singapore.

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Guest Quote

“Number one, you gotta get your people empowered. Number two, you actually have to start promoting the people. And promoting in a sense of [not just] giving them the tools, but actually finding those champions who can be your AI advocates, right? The AI leaders in the organization that are gonna drive forward those initiatives.” – Kevin Chung

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Time Stamps

00:00 Episode Start

02:00 WRITER – From translation tool to AI platform

06:30 Unpacking the MIT Report on AI ROI

10:45 The importance of customization and last-mile AI

15:30 Building enterprise strategy: trade-offs and focus

20:20 Hands-on AI deployment

25:15 AI’s role in upskilling vs. replacing the workforce

30:40 Misconceptions about LLMs and enterprise readiness

34:00 Treating AI as a digital employee, not just a tool

38:30 Measuring real ROI

42:00 The journey from SF to Singapaore

44:05 Kevin Chung’s Human Prompt

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