Opt In: A CEO’s Take on Becoming AI Native with Milin Desai (3/3)

Nerd Journey: Career Advice for the Technology Professional

What does it mean to become AI native? It’s not about using every AI tool on the market. For Milin Desai, the CEO of Sentry, it’s about becoming familiar with the tools and opting in to use the capabilities that deliver practical value. This mindset was born while Milin was the general manager of a business unit at a software company. In this role, he had to manage a profit and loss statement, learning the art of constrained resource planning and organizational adaptability.

In episode 351, our final installment of the conversation, listen as Milin describes both the gravity and different intensity of the CEO’s role compared to past roles. You’ll get insight into the strategy behind enabling an entire organization to shift and become AI native, how this translates into value for customers and employees, and how the individual contributor can be a better contextual communicator when speaking to busy leaders.

Stick with us until the end to understand how a set of first principles can guide our career progression if we choose to actively participate in it.

Original Recording Date: 09-29-2025

Milin Desai is currently the CEO of Sentry. If you missed parts 1 and 2 of our discussion with Milin, check out Episode 349 – Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3) and Episode 350 – Scope and Upside: The Importance of Contextual Communication with Milin Desai (2/3).

Topics – Contrasting the Role of General Manager with CEO, Embrace Practicality with New Technology, Junior Personnel and a Return to First Principles, Shifting Organizational Focus to Becoming AI Native, Contextual Communication to Leaders and Parting Thoughts

2:41 – Contrasting the Role of General Manager with CEO

• General managers usually own a profit and loss statement (or PNL statement). How was this different than the things Milin had previously gone through?
  • Milin says you do have to prepare yourself for it, and his experience as part of product teams was very helpful to gain familiarity with many of the elements of the general manager role (i.e. revenue protections, investing resources in specific efforts, etc.).
  • Things get very interesting when you are managing PNL in a constrained environment. Milin gives some insight into annual planning and the behaviors he has observed during these times.
    • “Very rarely do people come back and say, ‘I’ve got the same org. I’m going to reshape the org, move things around, and I’m going to do these new things with the same number of people.’ I think most leaders are not very good with that philosophy.” – Milin Desai
  • In this role Milin tells us he learned how to do planning with specific constraints in mind (i.e. stress testing as if no resources / extra people could be added), and this idea of keeping teams lean taught him about the adaptability of an organization.
  • “I really think every organization should do that, and then, you always have the ability to go add more people…. Structurally say, ‘is this how we still want to operate?’ And we rarely do that…. I knew the numbers, the resources, and everything else. We did a lot of planning. But what I learned I needed to get better at is this constrained planning…” – Milin Desai
  • Milin loved working as a general manager and thinking through how to optimize even if the organization didn’t get everything it wanted.
  • “What is the hardest thing to do? To say no. What is the hardest thing for a product manager to do? Shut down a feature. What is the hardest thing for a VP of engineering to do? To shut down a product…. I’m lucky enough to have a leadership team that…thinks along those lines. We are unconstrained, but we kind of try to make sure…let’s put some artificial constraints and see what we would do different.” – Milin Desai
    • Nick mentions this is analogous to the employee who is no longer a fit and having to say no to that person moving on with the company.
• What is the contrast between being a general manager of a business unit and being the CEO of an entire organization?
  • Milin remembers some of the conversations when he was considering becoming a CEO.
  • “Milin, are you sure you want to do this? And it was not a capability question. It was, ‘do you understand what you are signing up for?’ …It is very different. You are responsible for everything. There is no other person. There is no other excuse. There is no other system I can blame. Something goes wrong at Sentry…I am it. And I have to go to sleep every day thinking about it. I wake up every day thinking about it.” – Milin Desai, quoting a question from former boss John Martin and speaking to the contrast of being CEO compared to general manager
  • You have to know you want to be CEO. Many people think they want to do it until they are doing it and realize how difficult it is.
  • Milin admits being CEO has been difficult, but having a great team has been very helpful.
  • Before taking the role, Milin spoke to his wife about it. He describes the role as “a very different intensity.”
  • Three months into Milin being CEO of Sentry, COVID showed up. That is a challenge he never would have expected.
  • “It’s very different to be a GM versus being a CEO. You’re using your same skills, but it’s a completely different magnitude of responsibility and impact.” – Milin Desai
    • As a general manager of a business unit, Milin could change the trajectory of his business unit. As CEO, mistakes are much more costly. But you cannot do it in fear. In fact, for Milin, the larger impact of his role is exciting.
    • The right partners and team around you as CEO are very important as are taking and applying lessons you previously learned. Milin continues to push himself to improve over time even after reaching the CEO level.

9:22 – Embrace Practicality with New Technology

• John cites technology waves like virtualization, cloud, mobile, and generative AI. With generative AI, many of us get value from it. But many people are unconvinced of the value and are even fearful it will turn into something like Skynet (a reference from the movie Terminator 2). How does Milin approach people with this mindset?
  • Milin is practical with his approach to technology.
  • “The unconstrained view of what AI could do…we have seen it in movies already. So, I think the unconstrained aspect of this is what we can imagine or maybe even worse…. You can almost think about that and worry and not participate and be on the other side if that happens…. Or, just practically, on a day-to-day basis, figure out what aspects you want to opt in. So, I’m more in that camp…. On the AI front, just think about how it could practically help you on a day-to-day basis versus trying to worry too much about all the aspects, some of which you absolutely don’t even control…. I think it will bring productivity in ways that we don’t even know.” – Milin Desai
  • For example, Milin doesn’t have a voice assistant, didn’t find them useful, and did not opt in.
  • If you’re worried about supporting a bigger cause, Milin tells us that bigger cause is going to happen irrespective of us supporting it. Instead, we should think about how to practically use AI tools and become an active voice in it.
  • Milin tells us his wife just started using ChatGPT and loves it. He asked her the value question on whether it was worth paying for it vs. staying on the free tier after she talked about how much it helped. She agreed that it was worth the money.
  • Milin cites the potential for productivity gains we don’t even know or understand yet. For example, imagine a robot doing laundry for you so you can do something else.
    • Milin thinks there will be some significant value points with robotics and AI. He’s excited at the potential for optimizing daily tasks that this could bring.
  • “Just be practical in how you’re using it and how it will bring value to your life, and the ones that you don’t find valuable, don’t do it. I don’t try every AI tool…. But the things I care about, I lean in.” – Milin Desai
  • We don’t control the unconstrained and should not worry about it according to Milin, but we can be a positive participant in this (AI) by participating in communities that serve the greater good in this area.
  • Milin says the idea of an AI bubble bursting will be determined over time, but transformation is happening.
    • There are business use cases in vertical industries for AI (i.e. for medical transcribing). It’s not just people doing personal research at home, for example.
    • The intersection of AI and robots will be an exceptional thing.
    • We have to figure out our place in all of this, which is a harder question.
  • “I fundamentally believe you will still need engineers. You will still need certain things. But certain functions are getting automated…. You’re going to have to figure out where is the new value being created and how…you participate in the new value system.” – Milin Desai
    • This comes back to curiosity, asking good questions, listening, watching for where things are moving, etc. We can apply those same principles to the field of AI.
    • Milin tells us almost every company out there is willing to let you explore and learn when it comes to AI (which means. At Sentry, people are encouraged to use the tools they want to become “AI native.”
    • “Leverage that. Lean into it. Don’t shy away from it.” – Milin Desai, on utilizing your job role and resources to learn AI tooling and the value it can provide

15:07 – Junior Personnel and a Return to First Principles

• Nick wonders how junior technology personnel can develop the expertise of someone who is more senior when the senior folks developed their expertise before AI existed? Can giving a junior employee AI tooling help them gain that same level of expertise?
  • Milin says this is about getting more “at bats.” Someone could read all about running a company or working with top leaders, but until they have done it, they cannot really understand what it is like.
  • For senior personnel, using AI tools will remove some of the tedious tasks and be more of an accelerant.
  • Junior personnel do need to become AI native, but in addition to this, Milin recommends spending your time thinking through failure modes and other fundamentals.
  • “If something breaks, will I be able to debug it? What are the failure modes for a user that is accessing the system? At what point in time will we have to look at scale aspects of the system…both just scaling versus architecturally? And then you start asking those questions and putting those pieces as learning building blocks…. I think you have to think again at first level principles, system level thinking.” – Milin Desai
  • In addition to the above questions, think about the following:
    • Is the user’s experience intact?
    • Does good design documentation exist?
  • Milin says these “first principles of system thinking” develop from writing, deep thinking, thinking through things from a user’s perspective, considering failure and scaling modes, etc.
    • “And so you build those habits, even as a young engineer…. When you get to a point, you will start asking the right questions, and AI or no AI, you’re going to be successful and valued because you’re thinking in first principles. You have to develop that, but you can develop that with AI and with the folks around you.” – Milin Desai

17:47 – Shifting Organizational Focus to Becoming AI Native

• With Milin’s view on AI as not pure hype, how are organizations reorganizing priorities around how products get developed, tested, and shipped?
  • Milin tells us over 150,000 organizations use Sentry from the smallest startups to the largest organizations. The customer base scale is massive, and the feedback is constant, fast, and iterative.
  • “We have basically told the entire company, ‘You must become AI native….’ The number one thing we did was we unconstrained everyone to say, ‘go figure out how to become AI native.’ Whether you’re at Sentry or otherwise, this is a skill you are going to need. So, participate in it.” – Milin Desai
    • Milin says employees were encouraged to initially choose the tools necessary to become AI native, and corporate constraints would come into play a little bit later after personnel had built a skill base.
  • The Sentry team also had a set of people building AI-specific capabilities, but the intention was not to have a single, centralized AI team.
    • “There is a set of people who are experts at fine-tuning…the models and how everything works. But, if you want to be the company of the future, it’s not an AI team. It’s everything in terms of what you’re building has a perspective of participating in an AI native world. It cannot be that…30% of the team that is working on AI stuff, and the others are not….” – Milin Desai
    • AI is a tailwind for Sentry according to Milin. It was a goal to take some of the things the team was already doing (i.e. products they were building) and look for ways to make those products AI native.
    • Milin spoke to some of the work new graduates at Sentry did to build session replay summarization. This was their chance to take a project from 0 to 1.
    • Having an AI-themed “hack week” inside the company created a new energy and air of excitement.
  • “And so where are we right now? We basically are like, ‘what does it mean for Sentry to exploit all the opportunity it is in software?’ …It’s not constrained to a team. It’s organization wide…. Pretty much across the board, every team is going to look at what they do and say, ‘Is it a version that brings the experience forward because we now have LLMs and AI and all this new tech?’ That’s the question you have to answer.” – Milin Desai
    • The individual teams also have to think about where the experience in their product gets enhanced with these new technologies. It might be in the front end, back end, or something invisible to the user entirely.
    • Milin also mentions there is an internal team that owns building the core AI and infrastructure elements separate and apart from their product enhancement focus.
    • While everyone is moving in the same direction now, this shift Milin describes came in phases. It was introduced with a little guidance and happened over a period of 3-4 months.
    • “But you have to bring people along for the ride versus… ‘here’s what you’re going to do.’ That doesn’t work.” – Milin Desai
• John says at first these steps sound like ways to modernize an organization, but in this case, it’s more to keep up with current trends and new ways to provide value. Milin says it is to stay relevant.
  • “It’s to stay relevant. That’s why I made the statement – with or without Sentry, every employee has to become AI native…. What we did was let folks opt in into kind of new areas of the product, and now everybody’s opting in.” – Milin Desai
  • Milin says they did not need to do unnatural things to leverage AI as a tailwind. If you are in a situation where a new trend like AI has come out of nowhere to impact what you do or threaten your relevance, it might require a pause and reset.
• John speaks to the technology adoption lifecycle. There are bleeding edge use cases that apply to only the innovators. Next comes the use cases for innovators and early adopters. John says we can be the late majority to some of the things happening and gives the example of e-mail summaries from AI being an extremely useful of a late majority feature.
  • We can opt into late majority features without opting into everything or opting into the worst possible outcomes of using AI.
  • Milin gives the example of Sentry shipping a grouping feature powered by AI that resulted in big efficiency increases for customers. Most people would not know it’s powered by AI, and it was one of the first capabilities they shipped after implementing some of the internal changes Milin described earlier.
  • Milin says our attention spans are getting shorter and shorter, and some of the capabilities AI can bring are going to help with this.

25:35 – Contextual Communication to Leaders and Parting Thoughts

• We spoke about the importance of contextual communication from management down to employees at lower levels and even about how important this is when using generative AI tools. Where Nick sees a lot of people struggle is when they are an individual contributor trying to be a contextual communicator upward to leaders. How can we do this well when working with busy leaders in a world where attention spans are getting shorter?

  • Milin says we don’t really think about this. We don’t think about the potential for running into a senior leader at a company and what we would do if they asked us a question.
  • “What tends to happen is you run into somebody who is maybe 1 or 2 levels of ownership higher than you. They ask you a question. You are deep in the weeds of solving a problem, and so you’re so lost in that problem that when you speak to that person…you may miss an opportunity to talk about why you’re solving that problem…. Always remember and always ask early on in your career…why are we doing this? How does this help? Who does it help? Just knowing that and starting to believe in that is helpful.” – Milin Desai
  • Milin says he’s had 1-1s with people who have told him something isn’t going to work. He would prefer them to speak up and question why something is being built if it’s not going to work based on those questions above.
  • “What is the job of somebody two levels up? They are just asking the right questions. What do you think? Is it going to solve the problem?” – Milin Desai
    • Knowing the fundamentals as Milin outlined above (why, how / who something helps) allows you to have a conversation with a leader on the topic, and you can bring a point of view. It helps with what he calls “asynchronous communication” where you end up getting those unexpected questions about how things are going.
    • “Just always ask this – ‘why am I doing this? Who am I doing it for? And then as a result you’ll know the value, you’ll know the persona, and how does it fit in. Those questions then contextualize everything. It doesn’t matter level 1 or level N at that point in time.” – Milin Desai

• Milin hopes listeners can parse out the value from this conversation.

  • "Just come back to first principles of all the things we talked about. Be insanely curious. Be insanely active. Participate. And then everything kind of flows from there…. At the end of the day, we are only as good as the people around us. And whether you’re a manager listening, you’re an IC…remember, it’s about the humans…. Those people can only help you if you want to be helped. So, you need to take charge and ask and drive the conversation. And there will be a point where you may not be satisfied. We all are impatient. We all want to reach the summit on the very next day. Sometimes it takes time, so you have to understand what level of patience you have. But you own your path, your narrative, your direction…and you need to make sure that you get the most of an organization. I think people tend to forget that. Organizations sometimes get busy. I am not making excuses for people like me and others, but what I am trying to get at is I didn’t get here by waiting for people to give me what I believe was mine…. I actively participated in that conversation. Of course, I then had great mentors who then helped me with it. It did not come right away. I had to wait, be patient. But I’ll tell you, for the most part if you work hard, you’re an active contributor, you’re curious, you have good people you’re working for…things come along. And that formula is going to work. " – Milin Desai

• We cannot assume an organization is going to do wonders but should be active in the story. Milin is living proof of this.

• To follow up with Milin on this conversation:

  • Follow him on X – @virtualmilin
  • Follow Milin on LinkedIn
  • Follow what is happening with Sentry:
    • Sentry Blog

Mentioned in the Outro

• There are layers of opting in throughout this discussion:
  • Opting in to use and learn about AI tools is one aspect, and opting in to leverage the tools for the use cases that provide value is another.
  • Milin had to opt in when he moved into the CEO role, and he has created an environment at Sentry that has enabled people within his organization to opt in for leveraging AI to provide more value to customers.
• Remember those 3 questions Milin mentioned:
  • Why are we doing this?
  • How does it help?
  • Who does it help?
• Due to life circumstances, our show is moving from a weekly release to releasing every 2 weeks for the time being. We want to make it on a schedule that is sustainable and at the quality we want.
  • When you don’t see a release next Tuesday, it’s because of this change.

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