Why Old Leadership Playbooks Fail in the AI Era With Pantheon
Tech Talks DailyOctober 14, 2026
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25:0422.94 MB

Why Old Leadership Playbooks Fail in the AI Era With Pantheon

How much damage can a proven leadership playbook cause when it is applied to the wrong company? Experience can give executives confidence, but Sameer Kazi argues that confidence becomes dangerous when it replaces diagnosis.

In this episode of Tech Talks Daily, I welcome Sameer Kazi, CEO of the Pantheon Platform, back to the show to talk about copy-and-paste management, first-principles thinking, AI adoption, and the value of listening before making changes. Pantheon supports major websites and provides DevOps tools for agencies and enterprise web teams, putting Sameer at the center of the changing relationship between SaaS, web development, and agentic website creation.

Sameer describes a familiar mistake in technology companies. A new executive arrives with a formula that worked elsewhere, hires people from a previous team, and assumes the same inputs will produce the same growth. In the early SaaS era, for example, a company might have treated its sales efficiency ratio as a direct signal to hire another quota-bearing sales representative.

Product-led growth, changing buying behavior, and different forms of product-market fit have weakened that assumption. Adding salespeople does not automatically create demand.

His alternative starts with product-market fit and how buyers discover, evaluate, and purchase a product. From there, leaders can study the mechanics across marketing, sales, customer success, support, and product development.

Sameer argues that rapidly growing AI businesses don't come with a settled operating manual, so executives need curiosity and evidence rather than a formula copied from the past.

Customer feedback provides one source of that evidence. Pantheon runs a public Slack channel where customers and partners speak directly with the company. Sameer says those conversations can reveal customer experience problems and, in some cases, signal a platform slowdown before observability tools detect it.

A small piece of feedback may not represent every customer, but it can give an experienced leader a reason to investigate immediately.

We also discuss AI return on investment and the growing cost of adding token consumption to an organization's existing workforce and infrastructure. Sameer does not claim a single universal metric. Instead, he recommends looking at customer reactions to AI across sales, support, and internal processes. If AI makes a process faster for the company but worse for the buyer, customer evidence should reveal the problem.

The conversation then turns to data ownership. Sameer compares the hesitation companies once felt about moving data into the cloud with the speed at which some now provide business data to frontier AI labs. He expects small language models and open-weight models to give companies more choices, including running systems on their own hardware and isolating proprietary information where appropriate.

One of the strongest leadership examples comes from Sameer's arrival at Pantheon. He promised to speak with every employee and spent four months holding small roundtables. The format began with introductions and favorite movies, then moved to a direct invitation: tell me what works, what needs attention, and what to address first.

Sameer describes the result as a treasure trove of information from people closest to customers, prospects, products, and daily operations.

That approach also challenged the lazy assumption that long-serving employees represent outdated thinking. Sameer found experienced practitioners who had built agencies, developed large fleets of websites, and worked directly with customers.

Recognizing that knowledge can strengthen commitment, while dismissing it can leave employees disconnected and encourage quiet quitting. Can leaders keep the principles that made them successful while treating every familiar method as a hypothesis to be tested?

Listen to the episode and share how your organization balances executive experience with customer evidence and employee knowledge.

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[00:00:23] What happens when a successful leader brings a proven playbook into a company where the customers, the culture and buying behavior and technology are all completely different? Yep, the experience might look reassuring on paper, but it could quickly become a substitute for understanding the business right in front of them.

[00:00:49] So today, I'm welcoming back the CEO of Pantheon onto the podcast. We're going to discuss why copy and paste management fails, particularly as SaaS matures and AI is changing how companies grow. And also look into why leaders should begin with product market fit, customer evidence and first principle analysis.

[00:01:13] And he'll also share what he learned after speaking with every Pantheon employee and listening to customers through the public Slack channel. This is a conversation, really, about curiosity, diagnosis and resisting the temptation to confuse familiarity with good judgment. Great tech story, this one. So buckle up and hold on tight as I beam your ears all the way to the US,

[00:01:40] where you can sit down with myself and today's guest. But let me introduce you to him now. So a massive warm welcome back to the show. It's great to have you back on. But can you remind everyone listening with a little about who you are and what you do? Neil, it is my pleasure to be back here with you. Thank you for giving us the opportunity to speak to you and your listeners. My name is Samir Kazi. I am CEO at a wonderful company called Pantheon.

[00:02:09] And Pantheon is the platform for agentic website creation, management and governance. What we do is we host and support many of the most important websites on the planet. And we offer a set of DevOps tools to accelerate and streamline the work that's being done by agencies and enterprise web development teams. Well, it's a pleasure to have you join me again today. And I've been following things from afar. And one of the things that stood out to me is you've been warning against copy and paste management.

[00:02:39] So important right now. But can you tell me, maybe bring that to life? Share a decision where a familiar playbook failed because the context was completely different. Because I think that word context is so important, especially in this AI world we now find ourselves. Neil, I don't know if you could have asked or started with a more loaded question for me.

[00:03:02] You know, I think context is the right way to think about it because there's so many different dimensions to being at a company. But what we are, the place in time we find ourselves is one where I feel as if the world of SaaS has reached an inflection point, arguably is on the downturn. And the world of AI is just starting to take off.

[00:03:29] But at a pace that I don't think you or I have seen in our careers, it is incredible how fast things are moving. And I suppose for me, the context that's relevant is what kind of work do I do in particular. And the work that I've done in the past three or four companies I've been at has primarily been what one would call turnaround work.

[00:03:50] Although Pantheon isn't necessarily a turnaround company, but it is a company that requires evolution and matulation from an operating standpoint as it scales past. Where it is today. And what I found is that if I could offer a simple example, it would be one that many go-to-market executives do when they come into a new company.

[00:04:17] They apply a known framework for go-to-market scaling to most companies, which in the early days of SaaS, what was set up was if your quote unquote magic number, which is an equation that determines whether or not you should hire the next QBSR or quota-bearing sales rep. If that ratio shows that you're above one, yes, you should go hire the next quota-bearing sales rep.

[00:04:46] And that's been the rule of thumb in SaaS in the entirety of the history of SaaS. Many executives are locked into that point of view. But what's changed dramatically over the last five or six years, I would say, is that initially with the rise of product-led growth, and then secondarily, just product market fit and how people make decisions about buying products has changed.

[00:05:11] It doesn't necessarily always hold true that you have to hire the next account executive or the next salesperson, and that will automatically drive growth in a business. There's so much context and analysis that needs to be done to understand what metrics move go-to-market in a business. And I think this is primarily a mistake that people make coming into a new business.

[00:05:36] Let's hire a bunch of salespeople and let's get this company moving again when what is actually requires a deeper diagnostic in the business. And I suspect that we've both worked in organizations in our career where a new leader will roll into town. They slowly start replacing people with former colleagues and strategies that delivered huge success in previous careers. But, of course, now the world has changed so much, and even processes and strategies,

[00:06:03] they were all built and successful in a time that is very different to where we are now, especially with AI and agentic AI, etc. So what do you think leaders should study now about a new company before they start importing methods that just work simply somewhere else in a very different time? It is such an important question to think about.

[00:06:27] For the most part, I believe that the first question that all leaders should ask is about product market fit and then go examine the methods by which buyers become aware of your product and then make a decision about the product that they want to purchase. And that's one example primarily on the new business side, but you can extend that on the customer success side. You can extend that on the support side.

[00:06:57] What we're what my my feeling about leaders that come in and try to stamp in a decision from the past is that's what they're comfortable with and they believe that can work. I think you're right in this, not just in the age of AI, but in the age of companies that just operate differently than they've operated in the past. You look at some of the most successful companies in AI and there's they're growing at 150, 200 percent every six months.

[00:07:26] They're driving from zero to 200 million dollars in revenue in 18 months. There are no playbooks to understand how these businesses work and how to keep them on the rails. I think there ultimately is no substitute for the curiosity to try to understand a business, to really use first principles thinking, to understand the mechanics, the levers that move things on the new business side, on the marketing side, on the existing business side, on the product development side.

[00:07:56] No substitute for that level of deep thinking and analysis, in my opinion. Yeah, I completely agree. And at a time where there is a huge focus on return on investment, on just about everything, especially tech projects. And when you don't have that familiar playbook that we were talking about there, it can be difficult knowing what to measure, what metrics to add, etc.

[00:08:20] So what are you finding or what measures are you finding are helping leaders connect those AI infrastructure spending to a very real business result, generating business value, making a big difference?

[00:09:02] Yeah. I think that's a big difference.

[00:09:15] I think that's a big difference. I think that's a big difference.

[00:09:44] And if you're looking at it.

[00:10:16] There's gold in them, there's gold in their hills, as they say. And if you're looking at it.

[00:10:27] There's gold in them, there's gold in their sales process. And if you're looking at it.

[00:10:56] And if you're looking at it, it's a big difference. And if you're looking at it, it can be incredibly difficult for them to tell the difference between experience, judgment, and attachment to old answers. I would imagine bringing this Slack channel. And then listening to customer conversation can quickly make things clear. Is that what you're looking at it. We see it 100%. We see it 100%. We see it every single day. We see it 100%.

[00:11:25] We see it 100%.

[00:11:44] And I think that this idea of boards and even executive teams being able to tell the difference between real-time judgment and something that you bring from your past is so relevant. And because invariably, if you have a point of view about what should be done, it's wrong if you haven't gone and gotten the context of what it is that needs attention.

[00:12:13] And then, and I hate to keep repeating myself, using first principles thinking to really go solve that problem. It's very difficult for boards to know that. The most experienced executives, I feel, have an instinct about feedback from customers, even if it's small, to go derive an expedition to figure out what is happening inside of the company.

[00:12:38] And, of course, speed now is rewarded in tech companies. But when does moving too fast become an excuse for skipping diagnosis? Do you see anyone tripping up here in that almost, you said a few moments ago, there's gold in their hills. And it's very similar. It's like this California gold rush of sorts where everyone's just rushing forward. But are you seeing any major mistakes being made here in the process?

[00:13:03] I mean, the debate about the use of AI is the topic du jour this week. And it feels like it is changing on a week-to-week basis. My point of view is that in the early days of SaaS, companies were so reticent to move their data into the cloud.

[00:13:25] The amount of pushback that you got from potential customers about there's no way that I would take my data that sits in my data center and move it to the cloud. And what we're seeing today is the exact opposite of that. On the words of Frontier Labs that we are not using your data for training, companies have ceded so much of their data to the Frontier Labs that, for me, that feels a little concerning.

[00:13:51] I have a strong sense that with the rise of small language models and open-weight models, that there'll be an opportunity for customers or companies to really think deeply about what parts of their framework they would want to partner with at Frontier Lab with.

[00:14:08] And what are the proprietary things in their business where they would host their own either small or large language models on their own hardware, train them themselves based on what is important in the context of their own business, and then air gap that from the rest of the world so that they're able to protect their own company data. And if we look at everything from startups to Fortune 500 companies, investors and shareholders, they all prefer leaders with a repeatable formula.

[00:14:37] And of course, the world has changed somewhat as well. So what is the strongest case for that view, for playing it safe, playing that repeatable formula? Or where does that break down in this world now? I think when I think about the repeatable formula, I think about executives at large, large or very fast-growing companies that have grown up in the Salesforce ecosystem or the ServiceNow ecosystem, the Oracle ecosystem.

[00:15:06] Executives that grew up in those worlds have learned playbooks to allow things to scale very, very quickly. They have hiring methodologies, management methodologies, etc. And when they go from a large company to another large company, those things do translate over and they are able to drive scaling the way that company might need.

[00:15:27] Where I find that this does not work typically is when you have a much smaller company that is much more proprietary in the set of products that it produces and the kinds of services that it offers and the types of challenges that it might be facing. There, you really need a forensic approach to what's happening in the business before you can diagnose what's happening and then figure out a fix. Those two types of companies, I believe, are very different. Yeah, completely agree.

[00:15:56] And for any leaders listening, any advice on how they should adapt maybe a proven practice that they have without losing the principles that have not only made it effective, but made their leadership effective and getting that right balance? Any tips or advice there? I would offer the same thing that I thought about myself as I was coming into Pantheon.

[00:16:17] And I did a very rigorous due diligence with our board about the company, both on the financial side, on the product market fit side and on the go to market side. And the first thing that I did coming into the business was. I made a promise to the employees at the company that I would speak to every single employee at the company. And what I started doing was hosting roundtables with groups of employees between 8 and 15.

[00:16:45] And there were a lot of roundtables that we did over the period of the next four months. And the format was very light. It was, hey, let's get to know each other. Tell me who you are, what you do, what you did before you got to Pantheon. And tell me what your favorite movie is. And then that was fun for folks. And we had a nice discussion about films. And I would share the same thing. And at the end of that sort of getting to know you process, the real question was, this is your time.

[00:17:14] Please tell me what's going on at the business and things that you feel are working that need attention and the things that you think I should prioritize immediately. It was a treasure trove of information from the most important people in the business, the folks that are closest to the ground, closest to prospects and customers and building product, who have strong points of view about things that the company should do.

[00:17:40] That listening allowed me and others on the executive team to shape how we go about working through some of the challenges in the business. Wow. Again, absolutely love that approach. Speaking to every person, not only finding out their favorite movie, but unlocking the ideas and the knowledge that they've been carrying around in their heads. I've seen far too often in organizations a new technology thrown at our individuals. And those teams are thinking, well, people don't know how we work.

[00:18:09] This is just adding friction and frustration. It's not making a life easier. It's not improving the business. So taking that time to speak with people is so important. And I'm glad you've brought people into this because in our conversation today, we've talked about the impacts on technology, on leaders and on the organization. But it's people on the front line that employees often get impacted the most.

[00:18:33] So what have you seen happen to employees when maybe a new executive imposes a borrowed playbook without understanding the culture of the organization or the customers that they're speaking to every day? I mean, the simplest way to think about that. And again, it's a topic that's very much in vogue is this idea of quiet quitting. I think it is a tenuous job market. The opportunities are few and far between.

[00:19:00] And for folks who are in a job, they're reticent to create waves, but they might just get a little bit disconnected from what they're doing on a day-to-day basis. One of the things that I found when I was doing the roundtables with our team members at Pantheon was how many people at the business were true practitioners of the work that we did in the market.

[00:19:28] They were sleeves rolled up, working with customers or in the past had owned agencies, had done direct web development work for large-scale fleets of websites. And I found that it was really beneficial to lean into that, to really value that. Because people care when your executive recognizes what you're good at and helps to amplify that. I found that to be really unique at Pantheon and I'm super grateful for that.

[00:19:57] I think the opposite is also true. If you just see folks who have been around the business for a long time, if your mindset is their legacy or they've not evolved or they don't know what's happening, I think that would be a giant mistake that folks make. In an attempt to open up seats for folks that they know, I reject the thesis of doing that.

[00:20:22] I think really getting to know people and then being able to harness them to do the best work that they can do is the most important thing a leader can do. Well, you're talking to me today from Chicago. I'm here in the UK where it's very wet and windy and miserable. Summer feels like a long time ago already. But of course, I cannot thank you enough for joining me on the podcast today because I know you've got bigger fish to fry.

[00:20:45] You're right in the heart of organizing Pantheon Go Live, which will be in Miami, I think on October the 6th and the 7th. Tell me more about the event. What can we expect from that? Thank you for bringing that up, Neil. Go Live is Pantheon's very first user conference in our 16-year history.

[00:21:04] We've played a very active role in our community, in the open source CMS community, in hosting really excellent parties at other people's events. Some folks have called us the best T-shirts that have ever been provided at any corporate event. We sort of have this punk rock attitude to what the after party should be.

[00:21:26] What we found is that we now have this body of work that we've done over the last 24 months that we're ready to reveal to the world. We've got two very exciting product launches that we'll be announcing on October 6th in Miami at our conference Go Live.

[00:21:44] And I encourage anybody that's listening, if you have any interest in web development, open source, or Miami for that matter, come and join us at Go Live. We look forward and we welcome you to our first ever user conference. Well, I will be monitoring from afar exactly what those announcements are going to be. I do love a good teaser. I know I've got no chance. You're going to be locked down. I've got no chance of getting any information out of you. Everything will be embargoed.

[00:22:14] But I'm going to try and push you on one thing. This year's T-shirts, do they live up to expectation? Are the designs ready for that T-shirt for people from your community listening? The swag is going to be mind-blowing. I will tease one thing out. In our common areas, we're going to have video games for our attendees. Man, you had me at cool T-shirts and video games. Sounds good to me. So for anybody listening, whether it's the event, whether it's anything we talked about,

[00:22:43] today, I'll include links to your LinkedIn, et cetera. Anywhere else you'd like me to point, everyone? Neil, you can learn a lot more about Pantheon at pantheon.io, P-A-N-T-H-E-O-N.io. And if you have any interest in learning about my background, you can find me on LinkedIn at Samir Qazi. Awesome. Well, I'll be adding links to everything that you mentioned there. I'll also be keeping an eye on the announcements as they come out.

[00:23:11] I'll update the blog posts as they do arrive. But more than anything, thank you for sharing your story today, what you've been up to. We've just got to promise ourselves we don't leave it three years until we speak again. But thanks so much. You've got a deal there, Neil. Thanks for being a wonderful host and the work that you do. I enjoy coming on and chatting with you. I think Samir's advice today offers a very useful test for any leader arriving at a new company.

[00:23:37] Before importing a team metric technology or growth formula, maybe ask whether it fits the business that exists today. It's a very different world right now. And I think his decision to hear from every employee created a direct view of the company's strengths and its problems. And when accompanied by Pantheon's customer Slack channel, that provided evidence that can challenge executive assumptions in almost real time.

[00:24:05] Because some practices transfer well between similar businesses, but equally smaller or highly specialized companies might require somewhat of a forensic diagnosis before diving into action. So thanks to Samir and Pantheon for sharing such an open conversation today. But now it's your turn. When you join a new organization, how do you separate useful experience that you've gained in your career

[00:24:32] from attachment to an answer that works somewhere else and a very different time? Let me know. TechTalksNetwork.com. You can leave me an audio message there. You can connect with me on LinkedIn. Browse through 4,000 other interviews. Lots for you over there. But I'd love to hear from you. But that's it for today. Thanks for listening as always. Bye for now.