Sep 25, 2025 · 32m · big-technology

What’s Holding Back Enterprise AI — With Shiv Ramji

Shiv Ramji · 23m spoken Alex Kantrowitz · 6m spoken
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Host Alex Kantrowitz and Okta President Shiv Ramji discuss why most enterprises struggle to operationalize generative AI profitably, highlighting the critical identity, data governance, and authorization frameworks required to deploy autonomous agents safely into production.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 22.1% of the talking time here. How this is scored →

Alex as informed peer 3.5 Guest teaching 2.2 Guest disagreement 0.7 Alex pushing back 0.8
05100:0010:0020:0030:002:21–8:08 · Alex as informed peer 4/10 Data Security Risks and Identity and Access Management Alex articulates the core issue of probabilistic systems needing access to deep software stacks and references real-world leaks like executive emails. Shiv validates Alex's framing and elaborates on coarse versus fine-grained access control.8:08–13:15 · Alex as informed peer 4/10 The CISO Dilemma and Data Governance Frameworks Alex brings up bottom-up shadow AI adoption and cites a statistic that only 10% of companies have AI governance processes. Shiv reframes AI governance as fundamentally a data governance and endpoint inventory issue.13:15–17:35 · Alex as informed peer 3/10 High-Value Real-World Applications and Agent Productivity Alex steers the conversation constructively toward practical ROI and shares personal context about healthcare data entry burdens. Shiv outlines high-value sectors including software engineering, healthcare, and consumer travel.17:36–25:19 · Alex as informed peer 4/10 Core Characteristics of AI Agents and Auth0 Security Pillars Alex pushes past industry buzzwords by proposing a three-tier AI taxonomy and questioning how software seats handle AI workers. Shiv outlines the core pillars of Auth0's security suite and confirms enterprises now store agents directly in employee directories.25:20–31:47 · Alex as informed peer 5/10 Digital Credentials, Verification, and Content Watermarking Alex brings external domain knowledge citing Ethan Mollick's CAPTCHA testing and tech CEOs deploying avatars for earnings calls. Shiv analyzes the rising need for verifiable digital credentials, in-person identity verification, and cryptographic watermarking.31:47–32:43 · Alex as informed peer 1/10 Conclusion and Enterprise Resources Standard promotional outro where Alex asks for enterprise resources and Shiv directs listeners to Auth0 and Okta portals.2:21–8:08 · Guest teaching 3/10 Data Security Risks and Identity and Access Management Alex articulates the core issue of probabilistic systems needing access to deep software stacks and references real-world leaks like executive emails. Shiv validates Alex's framing and elaborates on coarse versus fine-grained access control.8:08–13:15 · Guest teaching 3/10 The CISO Dilemma and Data Governance Frameworks Alex brings up bottom-up shadow AI adoption and cites a statistic that only 10% of companies have AI governance processes. Shiv reframes AI governance as fundamentally a data governance and endpoint inventory issue.13:15–17:35 · Guest teaching 2/10 High-Value Real-World Applications and Agent Productivity Alex steers the conversation constructively toward practical ROI and shares personal context about healthcare data entry burdens. Shiv outlines high-value sectors including software engineering, healthcare, and consumer travel.17:36–25:19 · Guest teaching 3/10 Core Characteristics of AI Agents and Auth0 Security Pillars Alex pushes past industry buzzwords by proposing a three-tier AI taxonomy and questioning how software seats handle AI workers. Shiv outlines the core pillars of Auth0's security suite and confirms enterprises now store agents directly in employee directories.25:20–31:47 · Guest teaching 2/10 Digital Credentials, Verification, and Content Watermarking Alex brings external domain knowledge citing Ethan Mollick's CAPTCHA testing and tech CEOs deploying avatars for earnings calls. Shiv analyzes the rising need for verifiable digital credentials, in-person identity verification, and cryptographic watermarking.31:47–32:43 · Guest teaching 0/10 Conclusion and Enterprise Resources Standard promotional outro where Alex asks for enterprise resources and Shiv directs listeners to Auth0 and Okta portals.2:21–8:08 · Guest disagreement 1/10 Data Security Risks and Identity and Access Management Alex articulates the core issue of probabilistic systems needing access to deep software stacks and references real-world leaks like executive emails. Shiv validates Alex's framing and elaborates on coarse versus fine-grained access control.8:08–13:15 · Guest disagreement 1/10 The CISO Dilemma and Data Governance Frameworks Alex brings up bottom-up shadow AI adoption and cites a statistic that only 10% of companies have AI governance processes. Shiv reframes AI governance as fundamentally a data governance and endpoint inventory issue.13:15–17:35 · Guest disagreement 0/10 High-Value Real-World Applications and Agent Productivity Alex steers the conversation constructively toward practical ROI and shares personal context about healthcare data entry burdens. Shiv outlines high-value sectors including software engineering, healthcare, and consumer travel.17:36–25:19 · Guest disagreement 1/10 Core Characteristics of AI Agents and Auth0 Security Pillars Alex pushes past industry buzzwords by proposing a three-tier AI taxonomy and questioning how software seats handle AI workers. Shiv outlines the core pillars of Auth0's security suite and confirms enterprises now store agents directly in employee directories.25:20–31:47 · Guest disagreement 1/10 Digital Credentials, Verification, and Content Watermarking Alex brings external domain knowledge citing Ethan Mollick's CAPTCHA testing and tech CEOs deploying avatars for earnings calls. Shiv analyzes the rising need for verifiable digital credentials, in-person identity verification, and cryptographic watermarking.31:47–32:43 · Guest disagreement 0/10 Conclusion and Enterprise Resources Standard promotional outro where Alex asks for enterprise resources and Shiv directs listeners to Auth0 and Okta portals.2:21–8:08 · Alex pushing back 1/10 Data Security Risks and Identity and Access Management Alex articulates the core issue of probabilistic systems needing access to deep software stacks and references real-world leaks like executive emails. Shiv validates Alex's framing and elaborates on coarse versus fine-grained access control.8:08–13:15 · Alex pushing back 1/10 The CISO Dilemma and Data Governance Frameworks Alex brings up bottom-up shadow AI adoption and cites a statistic that only 10% of companies have AI governance processes. Shiv reframes AI governance as fundamentally a data governance and endpoint inventory issue.13:15–17:35 · Alex pushing back 1/10 High-Value Real-World Applications and Agent Productivity Alex steers the conversation constructively toward practical ROI and shares personal context about healthcare data entry burdens. Shiv outlines high-value sectors including software engineering, healthcare, and consumer travel.17:36–25:19 · Alex pushing back 1/10 Core Characteristics of AI Agents and Auth0 Security Pillars Alex pushes past industry buzzwords by proposing a three-tier AI taxonomy and questioning how software seats handle AI workers. Shiv outlines the core pillars of Auth0's security suite and confirms enterprises now store agents directly in employee directories.25:20–31:47 · Alex pushing back 1/10 Digital Credentials, Verification, and Content Watermarking Alex brings external domain knowledge citing Ethan Mollick's CAPTCHA testing and tech CEOs deploying avatars for earnings calls. Shiv analyzes the rising need for verifiable digital credentials, in-person identity verification, and cryptographic watermarking.31:47–32:43 · Alex pushing back 0/10 Conclusion and Enterprise Resources Standard promotional outro where Alex asks for enterprise resources and Shiv directs listeners to Auth0 and Okta portals.

speaking balance: gold is Alex, purple is the guest (3 minute bins)

0:00 · Alex 33.9% · guest 66.1%0:00 · Alex 33.9% · guest 66.1%3:00 · Alex 30.7% · guest 69.3%3:00 · Alex 30.7% · guest 69.3%6:00 · Alex 26% · guest 74%6:00 · Alex 26% · guest 74%9:00 · Alex 13.8% · guest 86.2%9:00 · Alex 13.8% · guest 86.2%12:00 · Alex 11.7% · guest 88.3%12:00 · Alex 11.7% · guest 88.3%15:00 · Alex 23.5% · guest 76.5%15:00 · Alex 23.5% · guest 76.5%18:00 · Alex 18.6% · guest 81.4%18:00 · Alex 18.6% · guest 81.4%21:00 · Alex 14% · guest 86%21:00 · Alex 14% · guest 86%24:00 · Alex 23.7% · guest 76.3%24:00 · Alex 23.7% · guest 76.3%27:00 · Alex 14% · guest 86%27:00 · Alex 14% · guest 86%30:00 · Alex 34.5% · guest 65.5%30:00 · Alex 34.5% · guest 65.5%
Sharpest disagreement ▶ 10:44 Reframing AI governance to data governance

Shiv politely but firmly reframes the host's prompt by stating that the challenge enterprise leaders face is not really AI governance, but foundational data governance.

Hardest push from Alex ▶ 13:51 Skepticism on coding generation claims

Alex pushes back against inflated market claims of 90% AI-written code, anchoring the realistic adoption baseline between 10% and 30%.

Biggest teaching moment ▶ 6:35 Coarse vs. fine-grained authorization breakdown

Shiv breaks down why standard coarse-grained IAM permissions fail with autonomous agents, educating the host on real-time permission requirements.

Alex holds their own ▶ 27:48 Citing Ethan Mollick's CAPTCHA research

Alex demonstrates subject matter expertise by bringing in research from Wharton professor Ethan Mollick showing AI bots cracking complex CAPTCHAs.

the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
Data Security Risks and Identity and Access Management 4311 Alex articulates the core issue of probabilistic systems needing access to deep software stacks and references real-world leaks like executive emails. Shiv validates Alex's framing and elaborates on coarse versus fine-grained access control.
The CISO Dilemma and Data Governance Frameworks 4311 Alex brings up bottom-up shadow AI adoption and cites a statistic that only 10% of companies have AI governance processes. Shiv reframes AI governance as fundamentally a data governance and endpoint inventory issue.
High-Value Real-World Applications and Agent Productivity 3201 Alex steers the conversation constructively toward practical ROI and shares personal context about healthcare data entry burdens. Shiv outlines high-value sectors including software engineering, healthcare, and consumer travel.
Core Characteristics of AI Agents and Auth0 Security Pillars 4311 Alex pushes past industry buzzwords by proposing a three-tier AI taxonomy and questioning how software seats handle AI workers. Shiv outlines the core pillars of Auth0's security suite and confirms enterprises now store agents directly in employee directories.
Digital Credentials, Verification, and Content Watermarking 5211 Alex brings external domain knowledge citing Ethan Mollick's CAPTCHA testing and tech CEOs deploying avatars for earnings calls. Shiv analyzes the rising need for verifiable digital credentials, in-person identity verification, and cryptographic watermarking.
Conclusion and Enterprise Resources 1000 Standard promotional outro where Alex asks for enterprise resources and Shiv directs listeners to Auth0 and Okta portals.

Statements from this episode (10)

Assertion Supported
Kantrowitz: MIT Study Finds 95% of AI Deployments Lack Profitability
“There was an MIT study that 95% Of businesses that are trying to implement AI aren't doing so profitable with profitability.”
Alex Kantrowitz Sep 25, 2025 ▶ 0:25
Assertion Not checkable as stated
Ramji: Room Poll Shows ~80% Prototyping AI but Few in Production
“I polled everybody in the room and said, you know, how many of you are experimenting with AI or prototyping? And you could see like, 80% of the room lit up and hands were up. And I said, now keep your hands up if these experiments or prototypes are in producti…”
Shiv Ramji Sep 25, 2025 ▶ 0:37
Opinion
Ramji: Non-Deterministic AI Agents Scare CIOs Due to Unpredictable System Access
“With AI, what happens is because these AI chatbots or agents that you create are non-deterministic and can really go access any system, I think a lot of CIOs, CTOs are kind of nervous because there is so much of their internal infrastructure that may not be pr…”
Shiv Ramji Sep 25, 2025 ▶ 1:07
Assertion Partly supported
Ramji: McDonald's Chatbot Breach Exposed Internal API and '1234' Password
“I mean, I, you know, one reason when it comes to mind is sometime in the summer, you know, McDonald's had Breach with their chatbot. So the chatbot kind of processing applications for people who want to work at McDonald's. And there were several issues, you kn…”
Shiv Ramji Sep 25, 2025 ▶ 4:06
Assertion Not checkable as stated
Ramji: CISOs Lack Full Inventories of Internal APIs Exposed to AI
“Usually they don't even have the inventory of all the internal APIs that can be exposed, right?”
Shiv Ramji Sep 25, 2025 ▶ 9:08
Assertion Supported
Ramji: Big Tech Claims 10% to 30% of Code Is Agent-Written
“I mean, you've, or you've probably already heard a lot of stats from a lot of the large tech companies where they're claiming anywhere between 10 to 30% of their code is now written by agents.”
Shiv Ramji Sep 25, 2025 ▶ 13:41
Disclosure
Ramji: Okta Customers Use AI Agents to Process Patient Medical Information
“We have customers who are using agents to essentially process medical information for their patients and customers.”
Shiv Ramji Sep 25, 2025 ▶ 15:03
Prediction Held up
Ramji: AI Agents Will Soon Execute Tasks Running for Days or Weeks
“So whether it's minutes, hours, I think there'll be some tasks that will run for days or weeks. Really? Yeah. So we're just gonna, we'll come to that kind of use case soon, and it'll be super interesting, because, you know, all these models are getting large, …”
Shiv Ramji Sep 25, 2025 ▶ 20:09
Assertion Not checkable as stated
Ramji: Enterprises List AI Agents Alongside Human Employees in HR Directories
“I have seen our customers, you know, you probably use some HR or HR system where you have a directory of everybody in your company. Well, I've seen our customers where, you know, you see employees and then you see agents in the same directory. Yeah. So this is…”
Shiv Ramji Sep 25, 2025 ▶ 25:01
Assertion Supported
Ramji: Companies Return to In-Person Interviews to Combat AI Video Cheating
“Well, there are so many tools now you can install on your computer that, that will do a real-time translate, you know, analysis of the question that interview is asking and will give you an answer that you can replay back. So, so you're seeing some companies a…”
Shiv Ramji Sep 25, 2025 ▶ 28:43
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