Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sits down with Jascha Kaykas-Wolff, CEO and President of Visiting Media, an immersive media and hospitality sales enablement company serving thousands of properties globally. Jascha previously served as CMO at Mozilla and BitTorrent, President at Lytics, and held foundational roles at Microsoft and Yahoo!. He is the author of Growing Up Fast: Agile Business Management and has spent nearly three decades applying lean and agile systems thinking across organizations of every size.
This conversation covers why CEOs must be personally out front on AI adoption rather than delegating it, how Jascha built a three-tiered agent operating system he runs daily, and why the same curiosity that drives great CMOs and COOs is the defining characteristic of great CEOs.
This episode is for C-suite executives who want a concrete model for personal AI experimentation and a philosophy for bringing their organizations along rather than simply mandating adoption from a distance.
Key Takeaways
- Jascha Kaykas-Wolff says AI adoption is an imperative for every C-level leader, and that imperative requires personal experimentation well ahead of the organization, not delegation to a team or vendor.
- Kaykas-Wolff has personally built a three-tiered agent operating system he runs daily, with fifteen subagents handling communications, reporting, development, and code review across his organization, and he credits that personal investment as the source of the organizational change it enabled.
- Glenn Gow observes that Jascha is operating further ahead on personal AI adoption than any other CEO he has interviewed, and frames that lead as both a competitive signal and a model for what executive-level AI literacy actually looks like in practice.
- Jascha Kaykas-Wolff argues that the distinction between a CMO, COO, and CEO role is not a difference in thinking style but a difference in how resource allocation is applied, and that curiosity is the one constant that must hold across all three.
- Kaykas-Wolff sees AI in hospitality not as a replacement for human experience but as a tool for mass personalization at the individual level, delivering the customized experience the industry has aspired to for thirty years but only now has the technology to actually execute.
CEOs Must Be Personally Ahead of Their Organization on AI, Not Just Supportive of It
Jascha Kaykas-Wolff’s position on CEO-level AI adoption is unambiguous. Understanding how AI can exist inside a business is not a nice-to-have. It is an imperative. And the way that imperative is fulfilled is not by sponsoring an initiative, assigning a task force, or hiring an AI lead. It is by personally experimenting, building, and deploying AI systems before asking anyone else in the organization to do the same.
“If you’re sitting in a role like a CEO role, COO role, CMO role, any C-level role, like you need to be so far out front learning and experimenting that you’re able to bring back to your team the theoretical applications of how these tools and systems can relate to your business and then do it with the team. You have to be so far up front. You have to help the organization move along.”
The phrase “with the team” is doing significant work in Jascha’s framing. The CEO’s personal experimentation is not the end state. It is the source of credibility that makes organizational adoption possible. A leader who has personally built agents, run them daily, hit constraints, and solved them is a fundamentally different teacher than one who has read about the technology or watched demos.
Jascha made this visible inside Visiting Media two weeks before this recording. He called a meeting with product managers, set up screen sharing, and walked through agent check-ins live, including making mistakes in real time in front of the team.
“You’ve got the CEO sitting in a meeting with a bunch of the product managers and we’re sharing each other’s screens and talking about: am I checking this incorrectly? Do I need to be thinking about this differently? You have to be so far up front. You have to help the organization move along.”
His argument for why this matters extends beyond business performance. Every person on his team needs to develop genuine AI proficiency not just to help Visiting Media grow, but to remain competitive throughout the rest of their careers. Jascha frames that as a leadership obligation, not a business strategy.
“It is an imperative for us to make sure that every single person that we work with inside of every organization we’re part of adapts, learns, becomes not just proficient, but an expert as much as possible, so that they’ve got the ability to be successful in the rest of their career, not just help the business that we’re in.”
Jascha Kaykas-Wolff Built a Three-Tiered Agent System He Runs Every Day
The distance between Jascha’s stated philosophy and his actual practice is zero. For nine months, he has been running a personal agent operating system daily that now forms the substrate for how Visiting Media operates internally.
The architecture has three layers. The first is an infrastructure and learning layer built on the Noyce MIT Hermes project, accessible via Telegram. It monitors the effectiveness of the broader system, learns from what has and has not worked, and shares a nightly summary that Jascha reviews to determine the next day’s priorities.
The second layer is an operating partner named Mira, built on a combined Claude and OpenAI infrastructure. Mira runs fifteen subagents and handles communications across the organization, manages reporting infrastructure, and coordinates with developers, engineers, and product team members through shared Slack channels. It maintains what Jascha calls an HTML brain: a structured view of pending work, completed runs, and who is waiting for what across the organization.
The third layer is a development partner named Nova, built as a LaunchD wrapper around Claude Code. Nova handles principal development work alongside Jascha and a set of subagents that manage testing, code validation, and delivery.
“I’ve personally built out a relatively interesting fleet of agents that I’ve been working with for the last about nine months pretty consistently on a daily basis.”
The system has since been extended to Visiting Media’s engineering and product teams. Each engineer works with a dedicated set of agents that handle code check-ins, PR reviews, and bug fixes. The CTO extended the model to bring the product team directly into the development workflow, with product managers now pulling work from backlogs, doing their own check-ins into code repositories, and running testing in coordination with the agent layer.
The result is a delivery model where the traditional constraint, engineering bandwidth, no longer defines what is possible. Product managers ship code. Developers move faster. The CEO operates with a real-time organizational intelligence layer that most companies are only beginning to consider.
The One Thing That Must Hold Across CMO, COO, and CEO Is Curiosity
Jascha Kaykas-Wolff has held three distinct C-suite roles across his career: CMO, COO, and now CEO. His answer to what changes between them is simpler than most executives would admit: primarily, the frame around resource allocation.
“The reality is that you’re really thinking about how do you apply resources in a way that is most impactful to try and drive the goals that you have for the specific role that you have. I don’t think that it has to be more difficult than that.”
What he explicitly did not shed moving from CMO to COO to CEO was the way he thinks about go-to-market, ICP, buying committees, and product value proposition. Those mental models travel intact across roles. The lens that focuses them shifts as the resource set broadens, but the underlying analytical framework does not.
The one constant Jascha identifies as non-negotiable across every role is curiosity, not in a general sense but as an active practice of seeking out what he does not know and treating that gap as something to close personally.
“The thing that always has to hold in every role that you’re in is the curiosity that is a driver for you personally and professionally. The reality is that I don’t know all the things that I need to know all the time. And anybody that pretends in the role that I sit in that they do, like they’re making it up.”
This framing has direct implications for how he thinks about the CEO role and AI. A CEO who claims to understand AI well enough to direct others without personally operating in it is, by Jascha’s standard, making something up. Curiosity means going into the uncertainty yourself, building something, failing at it, learning from it, and then teaching from that experience.
Agile Organizational Design Has Become More Relevant, Not Less, as AI Changes the Resource Constraint
Jascha published Growing Up Fast: Agile Business Management roughly twelve years ago. The core thesis was that organizations must be designed for adaptation rather than built on the assumption that leadership knows the correct answer in advance. That argument came from his time at Microsoft, where he watched agile and lean practices transform software development teams and began applying the same principles to marketing and product organizations.
In 2025, he does not think the thesis needs revision. He thinks it needs a new chapter.
“The kind of constraints that I think we’ve thought about historically, which are you and I are on a team, and maybe there’s one or two other people on a team, and our constraint, the throughput which creates constraint for us, doesn’t exist in the same way that it did six months ago.”
The constraint that has defined organizational design for decades, the finite number of people available to execute against a strategy, is being restructured by AI agents. A product manager who can now do their own code check-ins is no longer constrained by engineering availability. An agent that reviews PRs and runs dark factory code operations expands the throughput of a development team without adding headcount.
Jascha’s updated argument is that the organizational structures companies need now must be even more malleable than what lean and agile originally called for, because the resource inputs themselves are changing in real time. A company that builds rigid structures around today’s AI capabilities will be wrong within months. The design principle that holds is adaptation itself.
“The constraint I think that we have to consider is: are we creating systems and harnesses that allow for the AIs that we work with to be able to partner with us well? And do we have financial constraints that we need to be mindful of and how do we design a system to think about financial constraints?”
AI in Hospitality Makes Mass Personalization at the Individual Level Finally Achievable
Visiting Media serves thousands of hospitality properties globally, from management companies to individual hotel brands operating under flags like Marriott and St. Regis. Jascha’s view of AI’s role in that industry starts from the foundational principle that hospitality is built on human care and experience, and any AI application must be additive to that principle, not a replacement for it.
The two specific applications he sees defining the near-term transformation of the industry are discovery and personalization at scale.
On discovery: properties hold rich, specific information about their facilities, their capabilities, and what makes them uniquely suited to a particular type of customer or event. That information is currently hard to surface. AI, combined with answer engine optimization, gives properties the ability to make that specificity accessible to the right customer at the right moment.
On personalization: the hospitality industry has aspired to individualized customer experience for decades. The technology to deliver it at scale did not exist until now.
“There are only a certain number of people that you can hire, and there’s an infinite number of people who can use your services and book at your properties. How do you extend what that group of people at a property want that experience to be to the consumer, to every single person who deserves to have a great experience? Thinking about mass customization, thinking about personalization in a way that truthfully we’ve been talking about for thirty years with the internet. I think we just have the ability to really, really tune it at the individual level.”
The frame Jascha applies to AI in hospitality is the same one he applies to AI inside his company: the technology expands what humans can deliver, it does not substitute for what makes the human element valuable in the first place.
What Jascha Kaykas-Wolff Builds and Applies at Visiting Media
| Principle | What it means in practice | Named evidence from this interview |
| CEOs must personally experiment with AI before leading organizational adoption | A leader who has not personally built and operated AI systems cannot teach from experience, and teaching from experience is what makes organizational adoption credible and effective | Jascha built a three-tiered personal agent system over nine months, ran it daily, then extended the architecture to his engineering and product teams, using live screen-sharing sessions with product managers to demonstrate the workflow in real time |
| Curiosity is the only constant that must travel across every executive role | The resource allocation frame shifts as roles change from CMO to COO to CEO. The analytical models, go-to-market thinking, ICP understanding, buying committee mapping, do not. The one non-negotiable that holds all of it together is personal curiosity about what you do not yet know. | Jascha describes himself as the curious person in the room who has the privilege of asking the team to try something with him, and credits that posture rather than authority as the driver of Visiting Media’s AI transformation |
| Organizational structure must be designed for adaptation, not built on a presumed correct answer | Lean and agile principles produce organizations capable of adjusting as inputs change. Fixed hierarchical structures assume leadership knows the answer in advance, which is increasingly untrue as AI rewrites the resource constraint in real time. | Jascha’s book thesis from twelve years ago holds, with one update: the resource constraints that defined organizational design are now malleable in ways they never were, requiring even more adaptive structures than lean originally called for |
| Extend the development constraint by partnering engineers with agents, then extend that model to product | Engineering bandwidth has historically defined how fast a company can deliver value to customers. Agent-augmented engineering removes that ceiling, and the next step is bringing product managers into direct code contribution alongside agents. | Visiting Media’s product managers now pull work from backlogs, do their own repository check-ins, and run testing in coordination with the agent layer, with Mira’s fifteen subagents coordinating across teams in Slack |
| In human-centered industries, AI must amplify the human experience, not replace it | Industries built on care, service, and relationship require AI that extends the reach and personalization of human service rather than removing the human element. The AI application that adds is durable; the one that replaces risks the core value proposition. | Jascha’s hospitality AI vision centers on surfacing property-specific discovery information and delivering mass personalization at the individual level, both of which extend what human hospitality professionals can offer rather than substituting for them |
Quotes from This Episode
- “If you’re sitting in a role like a CEO role, COO role, CMO role, any C-level role, like you need to be so far out front learning and experimenting that you’re able to bring back to your team the theoretical applications of how these tools and systems can relate to your business and then do it with the team. You have to be so far up front. You have to help the organization move along.” — Jascha Kaykas-Wolff, CEO and President, Visiting Media
- “The thing that always has to hold in every role that you’re in is the curiosity that is a driver for you personally and professionally. The reality is that I don’t know all the things that I need to know all the time. And anybody that pretends in the role that I sit in that they do, like they’re making it up.” — Jascha Kaykas-Wolff, CEO and President, Visiting Media
- “We now don’t have the same kind of resource constraints, not the way that we thought about them traditionally. And that asks for us in an organization to consider even more malleable structures to be able to accelerate the kind of growth that we should expect.” — Jascha Kaykas-Wolff, CEO and President, Visiting Media
- “It is an imperative for us to make sure that every single person that we work with inside of every organization we’re part of adapts, learns, becomes not just proficient, but an expert as much as possible, so that they’ve got the ability to be successful in the rest of their career, not just help the business that we’re in.” — Jascha Kaykas-Wolff, CEO and President, Visiting Media
- “There are only a certain number of people that you can hire, and there’s an infinite number of people who can use your services and book at your properties. How do you extend what that group of people at a property want that experience to be to the consumer, to every single person who deserves to have a great experience?” — Jascha Kaykas-Wolff, CEO and President, Visiting Media
Frequently Asked Questions
What does it actually mean for a CEO to lead AI adoption rather than just support it?
Jascha Kaykas-Wolff draws a sharp distinction between sponsoring AI initiatives and personally leading AI adoption. Leading means experimenting with the technology yourself, far ahead of your organization, until you have built something real, hit constraints, solved them, and accumulated the practical knowledge needed to teach from experience. At Visiting Media, Jascha built a three-tiered personal agent operating system over nine months, running it daily before extending any part of it to his team. When he brought product managers into the development workflow two weeks before this recording, he did it in a live screen-sharing session where he made mistakes in front of the team. That vulnerability, grounded in genuine personal competence, is what organizational AI adoption actually requires from a CEO.
How does agile and lean thinking apply to the way a CEO leads an organization in 2025?
Jascha Kaykas-Wolff argues that the core agile principle, designing organizations for adaptation rather than building them on the assumption that leadership knows the correct answer, is more relevant today than when he wrote about it twelve years ago. The reason is that AI has fundamentally changed the resource constraint that organizational design has historically been built around. When product managers can do code check-ins and agents can review PRs, the throughput ceiling that defined how fast an organization could move no longer exists in the same form. The organizational design implication is that structures must be even more malleable than lean originally called for, because the inputs themselves, the tools, the capabilities, the workflows, are changing faster than any fixed structure can accommodate.
How will AI change the customer experience in the hospitality industry?
Jascha Kaykas-Wolff sees two primary AI-driven transformations in hospitality. The first is discovery: properties hold rich, specific information about their facilities and capabilities that is currently hard to surface to the right buyer at the right moment. AI and answer engine optimization give properties the ability to make that specificity accessible in ways traditional search cannot. The second is personalization: the hospitality industry has aspired to individualized customer experience for decades, but has been constrained by the finite number of people it can employ relative to the infinite number of guests it serves. AI makes mass personalization at the individual level genuinely achievable for the first time, extending what human hospitality professionals can offer rather than replacing the human element that defines the industry’s value.
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Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
