CIO Classified

Andy Boettcher has spent 33 years in tech, 13 of them in the Salesforce ecosystem, and his advice to CIOs can sound like heresy: stop waiting for perfect data. He compares the classic MDM project to an eclipse. You watch it coming for months, and then it’s gone. Today's transformation happens in weeks, and the competition is moving at that pace too, so a year spent planning is a year spent losing.
In this episode, Andy explains how DoubleTrack maps every organization’s systems into eight core data domains before any technology enters the picture, and why “good enough” has to rest on fact rather than gut. He makes the case for managing AI like a new hire who needs ongoing oversight, calls out human-in-the-loop programs that amount to someone skimming logs, and gives a candid read on where Salesforce’s governance model has made Agentforce harder.
Listen or subscribe wherever you get your podcasts. Visit ciopod.com for more episodes.
3 Takeaways:
Andy starts every engagement by reducing a company’s systems to eight data domains and mapping how that data feeds and consumes itself, then treats technology as the activator.
“Good enough” data has to be grounded in fact rather than gut, and it gets re-earned every week as new tools arrive.
Generative AI is built never to answer the same question the same way twice, so it needs oversight like a new employee, and human in the loop has to mean more than someone glancing at logs.
Chapters:
(00:00) Introduction
(01:19) What DoubleTrack Does
(02:42) Data-First Clarity
(04:24) The Real Cost of Bad Data
(06:07) What "Good Enough" Looks Like in Practice
(09:18) Why AI Still Needs Guardrails
(11:06) Salesforce Agents & Governance
(13:54) Security & Identity Risks
(16:52) The Founder Journey & How Innovation Really Happens
(21:25) Lightning Round
(22:29) Final Advice for CIOs
About Andy:
A data futurist and tech entrepreneur at heart, Andy Boettcher has spent three decades bridging engineering grit and business agility. From bootstrapping 7-figure IT startups and becoming a Salesforce Hall of Famer to advising Fortune 500s on AI strategy, his superpower is simplifying the complex. Sometimes this means architecting enterprise data systems, and sometimes it means explaining them to CEOs over bourbon. He’s great with both. Today, as Chief Innovation Officer of DoubleTrack, he leverages all he’s learned throughout his dynamic career to help organizations unlock hidden value in their data ecosystems, turning sprawl into strategy.
Off the clock, he’s a proud dad, grandpa, and Jeep enthusiast (ask him about river-swapped engines), and living proof that the best career paths are built by following curiosity, not roadmaps.
Guest Highlights:
“It’s okay to be good enough. Because next week you’ll be good enough again, and the week after that you’ll be good enough, but you’ll have new tools.”
“You would never hire an employee and just set them at their desk and never talk to them again and assume that they’re gonna do the same thing over and over.”
“They have tools to help the crazy chaotic human brain express ideas that got muted for years, or died in committee.”
Get Connected:
Yousuf Khan: https://www.linkedin.com/in/yousufakhan/
Andy Boettcher: https://www.linkedin.com/in/andyboettcher/
Learn more about DoubleTrack: https://www.doubletrack.com/
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Dilip Venkatachari came to banking from Google and PayPal, where moving fast was the default and scaling meant adding servers. As SEVP and Chief Information and Technology Officer at U.S. Bank, he now runs technology for an institution built on decades-old core systems where the data is people's money, and his team is moving agentic AI out of the experimentation phase and into how the bank actually operates.
Dilip explains why he held off on productivity metrics during the bank's AI rollout and let teams run their own experiments first, why the real work of scaling AI turned out to be data, identity, security, and observability rather than model selection, and how he modernizes legacy systems by hollowing out the core in business-driven chunks instead of attempting a risky rip-and-replace. He also makes the case that banking's heavily codified procedures, from KYC to disputes, are unusually well suited to agents.
Listen or subscribe wherever you get your podcasts. Visit ciopod.com for more episodes.
3 Takeaways:
Why Dilip's team launched "Let a Thousand Flowers Bloom" and deliberately skipped productivity metrics early, to avoid rewarding behaviors nobody understood yet.
How U.S. Bank treats data, identity, integration, and observability as the real bottleneck to scaling AI, with the goal of making each new use case cheaper than the last.
Why Dilip argues banking's codified procedures, from customer onboarding and fraud checks to dispute management, give agentic AI clear control points and a clear definition of what good looks like.
Chapters:
(00:00) Introduction
(02:09) Dilip's Career Path
(03:34) Tech Scale vs. Bank Scale
(05:39) Innovation With Control
(08:24) What CIOs Actually Prioritize
(10:44) Scaling AI Use Cases
(11:42) Agentic AI in Banking
(14:13) Managing the Human Side of AI Adoption
(16:10) Evangelize, Then Experiment
(17:58) AI Plumbing & Security
(18:43) Cybersecurity Group Therapy
(22:59) Modernizing Legacy Systems
(27:47) Leadership Lessons at Scale
About Dilip:
Dilip Venkatachari is Senior Executive Vice President and Chief Information and Technology Officer at U.S. Bank, where he is responsible for global technology infrastructure, security, products and services, and digital and technology transformation. He also serves on the board of U.S. Bank Europe. Dilip joined U.S. Bancorp in 2018 and joined the company's executive leadership team in 2023. In 2026, he was named one of American Banker's Most Innovative People in Finance for his work developing agentic AI and digital-asset infrastructure across the bank.
Before U.S. Bank, Dilip held senior executive roles at Google and PayPal/eBay, and spent time at McKinsey & Company helping large U.S. and international banks accelerate their digital transformations. He also co-founded and led three startups — Compass Labs, CashEdge, and CommerceSoft. Dilip holds an MBA from Harvard Business School and master's and bachelor's degrees in electrical engineering from Rice University and the Indian Institute of Technology, respectively. He holds more than a dozen U.S. patents.
Guest Highlights:
"The hardest part here isn't proving that it works. The hardest part is how do you scale it? How do you industrialize it?"
"If we put productivity metrics, speed metrics right now, there's a risk we are creating incentives for behaviors which we don't quite understand."
"AI for us is not just another technology program. It's a new way of building and running the bank."
Get Connected:
Yousuf Khan: https://www.linkedin.com/in/yousufakhan/
Dilip Venkatachari: https://www.linkedin.com/in/dilipvenkatachari/
Our Sponsor:
Want to accelerate software development by 500%? Meet Blitzy, the only autonomous code generation platform with infinite code context, purpose-built for large, complex enterprise-scale codebases.
While other AI coding tools provide snippets of code and struggle with context, Blitzy ingests millions of lines of code and orchestrates thousands of agents that reason for hours to map every line-level dependency.
With a complete contextual understanding of your codebase, Blitzy is ready to be deployed at the beginning of every sprint. Blitzy handles the heavy lifting, delivering over 80% of the work autonomously. The platform plans, builds, and validates premium-quality code at the speed of compute, turning months of engineering into a matter of days.
It’s the secret weapon for Fortune 500 companies globally. To hear how engineering leaders are transforming the way they deliver software, visit blitzy.com. Schedule a meeting with their consultants to enable an AI-Native SDLC in your organization today.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Ashwin Ballal trained as a materials scientist, then worked his way through marketing, product, and engineering roles at KLA-Tencor before the CEO asked him to run IT. Three CIO jobs later, now at Freshworks, he's become the company's single most important customer, shaping its product roadmap from inside the org he runs.
In this conversation, Ashwin explains why AI-generated code needs more human verification, not less, why counting token usage tells you nothing about whether AI is actually working, and how Freshworks tore apart a "Frankenstack" of roughly 400 disconnected systems by refusing to customize its own workflows. He also gets candid about what worries him most heading into the next phase of enterprise AI: agents running with privileged access and few real guardrails. Listen in for an unfiltered read on where AI is actually delivering, and where it's just noise.
Listen or subscribe wherever you get your podcasts. Visit ciopod.com for more episodes.
3 Takeaways:
Ashwin argues AI-generated code needs more engineers, not fewer, because someone still has to verify what the model produces before it reaches production.
He says most companies are tracking the wrong AI metric, counting token usage instead of asking what revenue or savings actually resulted.
Freshworks cut a "Frankenstack" of roughly 400 disconnected systems down by implementing tools out of the box instead of customizing them.
Chapters:
(00:00) Introduction
(03:16) Early Life & What Drives Ashwin
(05:06) From PhD to CIO
(07:51) Career Lessons & Leadership Style
(10:56) Why Freshworks, Why Now
(13:57) The CIO as Product Customer
(17:05) AI Adoption & Rethinking Workflows
(22:24) Killing the Frankenstack
(25:30) Agent Risk & Guardrails
(27:20) Lightning Round
About Ashwin:
Ashwin Ballal joined Freshworks in May 2024 as Chief Information Officer. His significant leadership experience of over 30 years in technology and business strategy will now be channeled to spearhead all facets of IT infrastructure, systems, and operations within Freshworks. Prior to this new responsibility, Ballal served as the Senior Vice President and Chief Information Officer at Medallia. He successfully led and revamped the IT and security, workplace services, corporate procurement, and travel divisions during his tenure there. His preceding role was as the Chief Information, Intelligence, and Data Officer of KLA Corp.
Guest Highlights:
"Oh, 90% of my code is written by AI. How do you know if it's right? Who verified it, right?"
"Let's count token usage. I mean, that's not a behavior you want. What outcomes change?"
"If you thought the SaaS crawl was the Wild Wild West, Yousuf, you ain't seen anything yet."
Get Connected:
Yousuf Khan: https://www.linkedin.com/in/yousufakhan/
Ashwin Ballal: https://www.linkedin.com/in/ashwin-ballal-9a89961/
Our Sponsor:
Want to accelerate software development by 500%? Meet Blitzy, the only autonomous code generation platform with infinite code context, purpose-built for large, complex enterprise-scale codebases.
While other AI coding tools provide snippets of code and struggle with context, Blitzy ingests millions of lines of code and orchestrates thousands of agents that reason for hours to map every line-level dependency.
With a complete contextual understanding of your codebase, Blitzy is ready to be deployed at the beginning of every sprint. Blitzy handles the heavy lifting, delivering over 80% of the work autonomously. The platform plans, builds, and validates premium-quality code at the speed of compute, turning months of engineering into a matter of days.
It’s the secret weapon for Fortune 500 companies globally. To hear how engineering leaders are transforming the way they deliver software, visit blitzy.com. Schedule a meeting with their consultants to enable an AI-Native SDLC in your organization today.



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Trevor Schulze has spent over a decade running AI transformations, going back to early work in visual computing and machine learning in the semiconductor industry. So when he says AI broke his old operating rhythm as CIO, it's not a hot take — it's a confession. A year into using GPT-era tools, he realized his old pace of decision-making, and his old definition of what a change agent does, no longer applied. If he's overwhelmed, he says, he can't imagine how the rest of the C-suite is holding up.
In this conversation, Trevor lays out why he now treats his CHRO and general counsel as closer partners than ever, breaks down the 20/60/20 split he sees in how employees are actually adopting agentic tools, and explains "Genesys on Genesys" — his push to apply the same customer-experience thinking his platform gives to customers to Genesys's own employees. Listen for a clear-eyed look at what it actually takes to lead IT through this moment, not just talk about it.
Listen or subscribe wherever you get your podcasts. Visit ciopod.com for more episodes.
3 Takeaways:
Why Trevor believes every CIO has to reallocate their own time and speed of working now that AI's pace has outstripped the old CIO playbook.
Trevor's read on adoption inside his own company: roughly 20% of employees are already all in on agentic tools, 60% just need examples, and 20% won't touch it at all.
Why Trevor started applying Genesys's own customer experience platform to the employee experience, once he realized employees deserve the same proactive attention as customers.
Chapters:
(00:00) Introduction
(02:47) Genesys Cloud Explained
(04:38) The CIO as AI Leader
(05:56) AI Is a Team Sport
(08:35) Why CIOs Need to Partner With CHROs
(10:16) Transforming How IT Delivers
(12:04) Keeping Up With the AI Pace
(16:15) The Future of Customer Experience
(18:00) Genesys Running on Genesys
(19:51) Data, Scale & Privacy
(21:14) Career Advice for CIOs
(25:42) Lightning Round
About Trevor:
Trevor Schulze is the Chief Information Officer at Genesys, where he leads the global information technology organization and is responsible for driving the company’s AI and cloud strategy to support innovation and growth.
Trevor brings more than 30 years of experience in enterprise technology and digital transformation. Prior to joining Genesys in 2025, he served as Senior Vice President and Chief Digital and Information Officer at Alteryx, where he led enterprise AI initiatives and digital modernization. He has also held CIO and senior IT leadership roles at RingCentral, Micron Technology, Broadcom, AMD, and Cisco Systems, with a focus on aligning technology with business outcomes.
Guest Highlights:
"I have to rethink my role as a CIO. I no longer can continue to function as a change agent in a company with my old behaviors or my old speed of working."
"AI is a team sport."
"What if attention is free? What if attention to your customer no longer is a cost structure you need to worry about?"
Get Connected:
Yousuf Khan: https://www.linkedin.com/in/yousufakhan/
Trevor Schulze: https://www.linkedin.com/in/tschulze/
Our Sponsor:
Want to accelerate software development by 500%? Meet Blitzy, the only autonomous code generation platform with infinite code context, purpose-built for large, complex enterprise-scale codebases.
While other AI coding tools provide snippets of code and struggle with context, Blitzy ingests millions of lines of code and orchestrates thousands of agents that reason for hours to map every line-level dependency.
With a complete contextual understanding of your codebase, Blitzy is ready to be deployed at the beginning of every sprint. Blitzy handles the heavy lifting, delivering over 80% of the work autonomously. The platform plans, builds, and validates premium-quality code at the speed of compute, turning months of engineering into a matter of days.
It’s the secret weapon for Fortune 500 companies globally. To hear how engineering leaders are transforming the way they deliver software, visit blitzy.com. Schedule a meeting with their consultants to enable an AI-Native SDLC in your organization today.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Parul Saini has spent enough time in serious IT leadership roles (Splunk, Zuora, Uber) to know the difference between organizations that are genuinely building AI capability and those that are performing it. Her read? The governance assumptions that barely held together in the SaaS era are already being outpaced by agent deployments. The executives making AI strategy calls often haven't built anything themselves. And the boards mandating AI fluency are not getting results.
This episode is a direct conversation about what it actually takes to close that gap — from why Parul believes every executive needs to personally build, break, and debug an agent before making another strategic call, to what responsible AI adoption looks like when the security tooling hasn't caught up with the technology.
Listen or subscribe wherever you get your podcasts. Visit ciopod.com for more episodes.
3 Takeaways:
Every executive needs to personally build an agent, watch it fail, and understand why
The same governance gaps that took years to close in the SaaS era are already compounding in AI agent deployments
The most important thing Parul would do immediately in a new CIO role: rebuild how people experience work, starting with what she calls personalized productivity
Chapters:
[00:00] Introduction
[01:53] Career Journey & Uber Lessons
[04:20] Scaling Trust & Partnerships
[07:20] Founding AI AllyWorks
[11:07] Managing AI Budgets
[16:09] Operationalizing Agents & COE
[21:13] The New CIO Playbook
[23:43] Agent Security & Governance
[25:30] Board Fluency & Leadership
About Parul:
Parul Saini is the Founder of AI Ally Works, where she serves as a fractional AI and technology advisor for small and mid-size businesses navigating the shift to AI-driven operations. She brings deep enterprise experience from leadership roles at Uber, Splunk, and Zuora, where she built IT organizations that moved from reactive support functions to proactive business partners. At Uber, she led technology operations across a 30,000-person global company and drove early AI adoption starting in 2023. After stepping away from full-time executive life to prioritize her health, she recognized that the small businesses forming the backbone of the U.S. economy had no one with real CIO-level expertise in their corner on AI — and built AI Ally Works to change that.
Guest Highlights:
"I always thought my job was to take that cognitive overload that stakeholders have with regards to technology and take that on myself, so they can focus on their primary jobs and be a hundred percent successful."
"The things that will prevent catastrophe are not moving as fast as the technology enabling these agents. Even now when I talk to my peers, I don't think the answer is clear."
"Unless the agent you've built breaks and you have no idea what broke it—unless you understand what your teams are working with—you won't be able to make the right decisions or the right strategic moves. It's absolutely critical for us to have that hands-on experience right now."
Get Connected:
Yousuf Khan: https://www.linkedin.com/in/yousufakhan/
Parul Saini: https://www.linkedin.com/in/parul-saini-it-management-leadership/
Our Sponsor:
Want to accelerate software development by 500%? Meet Blitzy, the only autonomous code generation platform with infinite code context, purpose-built for large, complex enterprise-scale codebases.
While other AI coding tools provide snippets of code and struggle with context, Blitzy ingests millions of lines of code and orchestrates thousands of agents that reason for hours to map every line-level dependency.
With a complete contextual understanding of your codebase, Blitzy is ready to be deployed at the beginning of every sprint. Blitzy handles the heavy lifting, delivering over 80% of the work autonomously. The platform plans, builds, and validates premium-quality code at the speed of compute, turning months of engineering into a matter of days.
It’s the secret weapon for Fortune 500 companies globally. To hear how engineering leaders are transforming the way they deliver software, visit blitzy.com. Schedule a meeting with their consultants to enable an AI-Native SDLC in your organization today.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.