Expand Your Curiosity: Build, Own, and Maintain Relevance with Milin Desai (1/3)

Nerd Journey: Career Advice for the Technology Professional

How curious do you think you are at work? Take a second to rate yourself. After today’s conversation with guest Milin Desai, you’re going to want to dial that curiosity up a notch.

Milin is currently the CEO of Sentry, and one of the keys to his success from the very beginning was allowing the scope of his curiosity to expand over time…beyond specific projects and even beyond his job role. Perhaps without realizing it, Milin was doing the work to build and maintain professional relevance.

Listen closely in episode 349 as we follow Milin from his early days as a computer science student through roles as a QA tester and software developer all the way into technical marketing. You’ll hear advice for expanding your own curiosity inside your current company, ways you can provide value to a mentor, and an empathetic approach to customer conversations that can help you build relevance and develop a strong reputation.

Original Recording Date: 09-29-2025

Topics – Meet Milin Desai, A Unique Trait, Internships and Job Interviews, Curiosity and the Importance of Control, Mentorship as a Stream of Active Conversations, Beyond the Scope, Becoming Relevant in Something Different

2:40 – Meet Milin Desai

• Milin Desai is currently the CEO of Sentry.
  • Sentry helps teams find where code is broken in production and helps them fix it fast, and with AI, fixing it faster is greatly accelerated.

3:15 – A Unique Trait

• Around 7th or 8th grade Milin recognized how much he enjoyed math and science in school. Milin had an affinity for STEM (Science, Technology, Engineering, and Mathematics).
• Milin cites his dad, a mechanical and electrical engineer, as a big influence. Going into 10th grade, Milin thought he would pursue mechanical engineering.
• Milin’s cousin Rajiv (who had worked for NASA) would come visit and began showing Milin some of the work he was doing. This is the point at which “everything changed” for Milin, and he decided to pursue computer engineering / computer science.
  • Milin also tells us he built hundreds of websites in India during the time of dial up modems.
• Milin pursued an undergraduate degree at a school in Mumbai, but his family knew he wanted to come to the United States.
  • Milin came to the United States in 1999 and attended USC (University of Southern California) to purse a master’s degree.
  • The potential for opportunity and the vastness of the United States captivated Milin.
• Did Milin ever ask Rajiv what he should study, or did he naturally gravitate toward those areas?
  • Rajiv would have conversations with Milina and show him the work he was doing.
  • Milin started working for Rajiv while pursuing his undergraduate degree. He was building websites for companies in India.
  • The building of the websites was interesting to Milin, but he was also doing the selling part. Milin had to make a pitch to companies explaining what a website could do for them, share the price, and collect the check if they said yes.
  • “Not only did he influence me in kind of figuring out…this is where the opportunity is and inspire me…but he also went on to tell me that I have a unique trait where I can talk business tech selling, and I know the technology part. And I can bridge the two worlds. He was one of the early people to recommend that in the long run I may want to think about the business side or…the entrepreneurship side of things when it comes to tech, not just the programming or the systems side of things. And he in fact felt my combo made me more relevant…in that lane versus just staying a programmer.” – Milin Desai
  • Rajiv gave Milin these cues early on in addition to inspiring him to do the work.
  • As people who work in sales engineering today, John and Nick agree that the combination of technology and business value is very valuable.

7:49 – Internships and Job Interviews

• Milin began working for Veritas after he finished his master’s program as an entry-level software engineer.
  • Pursuing an advanced degree can give you the chance to pursue internships, and Milin had a family friend working at Veritas who introduced him to the hiring manager for a quality assurance (or QA) internship.
  • After successfully getting the internship at Veritas, Milin was doing QA for software-defined storage volume management.
  • Milin’s work during the internship led to a full-time offer from Veritas upon his graduation.
  • “The first break is always hard, by the way, to get. I see it even to this day with folks coming out of school. Not everyone…lands in the perfect opportunity right away, and the dots need to be connected. I’ve been fortunate enough to have people open doors and open opportunities…. But I remember being rejected a lot.” – Milin Desai
  • Milin tells us he struggled in job interviews as a new graduate. Many of his friends from school had multiple job offers from these conversations, and compared to them, Milin had much less success getting offers outside of the one from Veritas.
  • From a timing perspective, this was around the time of the market crash following the events of September 11, 2001.
    • “Even timing-wise, the difference between graduating with your master’s degree a year and a half versus 2 years. That six months made all the difference. A little luck, a little timing, and a lot of support.” – Milin Desai
• Did the degree program Milin pursued prepare students for job interviews at all?
  • Milin tells us that a school doesn’t really prepare you for the conversation you have in an interview. While you do learn deep systems concepts in school, for example, the interview questions are often situational.
    • “You definitely use those concepts, but you’re never in that setup until you go through that process. And I think interviewing is a little bit of an art form. Some folks are really good at it, and some folks even study it. There is some element of that. But I think the school prepares you with fundamentals. It doesn’t necessarily prepare you for that interview per se, and you have to kind of connect the dots…. You can prepare for it. Some people are just naturally good at it, and some people like me just suck at it.” – Milin Desai
    • Milin feels interviewing is sort of an art form. You can work to prepare yourself
• Did Milin think of interviews as somewhat similar to pitching a company on a website?
  • The selling part is easy according to Milin. In this motion you are telling a story, bringing a problem statement, and delivering value. It’s less about solving some kind of algorithm but rather trying to figure out if what you have to offer will address someone’s pain point.
  • Milin emphasizes the storytelling element of the sales process and the collaborative problem solving you’re doing with someone. It’s more of a conversation.
  • Selling is not about getting into an extreme level of detail like a technical interview can be. Someone could easily make a mistake in a technical interview when describing a specific step in the process and get off track. People can feel a great deal of pressure when in a job interview.
  • Milin feels job interviews are much more difficult than a business conversation. The latter is about human connection and building rapport with the other person.
    • Milin tells us his interview style is more about building human connections than testing the limits of a person’s technical depth.
• John mentions the difficulty in choosing a technical interview style that is well suited for effectively evaluating multiple job candidates. Does having a portfolio of code that is applicable to the role help with this?
  • John also brings up LeetCode style interviews if you’d like to read more about them.
  • Milin says quickly assessing a fit can be a challenge. It can be a combination of skills and experiences with other things layered on top.
    • Milin says the first interview might be more focused on solving some basic elements. But it’s helpful if a candidate can talk about and contextualize other work they have done (like working on an open-source project, for example).
    • "But to get in, there has to be a common baseline, a language, a form…. " – Milin Desai, on early round interviews
    • If interviews are challenging for you as they have been for Milin, you have to work through them over time.
    • “In the later stages what I would tell you is what is most attractive is people who have been from what I call 0 to 1 project where they start something are through the end. The end is not shipping actually. Shipping is just an intermediate point. End is adoption and the scaling and all of those elements. And to be through that journey 1, 2, 3 times is interesting to almost every organization out there…because through that you learn a sense of people, ownership, outcomes.” – Milin Desai
    • Early on the baseline is some kind of entry test. When looking for people with more experience, interviewers will ask about projects people have written about on their resume or elsewhere and how they solved problems within those projects. At this point, the portfolio becomes more interesting and can help you get an opportunity.
  • We emphasize the importance of a portfolio of projects and not just a portfolio of code.

16:16 – Curiosity and the Importance of Control

• How did the role Milin had at Veritas shape the rest of his career?
  • Milin says this was his first job and was an amazing experience that has filled him with fond memories of that time.
  • Milin emphasizes the importance of help from others during the course of his career.
  • The Veritas experience gave Milin the chance to work with great people, but he also found mentors within his area at the time (software volume management).
    • Milin mentions a mentor named Mark who remains a dear friend to this day.
    • “He kind of took me under his wing and explained stuff and was just there. And he didn’t need to do that…. Please, when somebody…experienced takes the time to go that extra mile you make sure you better jump on and do what’s needed. That was a friendship and mentorship I would say on a regular basis that really helped shaped my system thinking…. It was just the way we would talk about systems and concepts, and it really kind of expanded my mind…. The discussions are not always about this piece of code as much as how does this work with this part of the system…?” – Milin Desai
    • Mark was in a leadership role at the company and understood other projects that were in the works. Milin really enjoyed learning about those things even though they were outside his area.
    • Milin emphasizes the importance of curiosity that extends beyond what we own and even what others own. This ever-expanding curiosity was one of the most helpful things in addition to mentors early in Milin’s career.
    • We should also be willing to raise our hands to volunteer to solve a problem or work on something extra. This quality, in conjunction with being curious and having effective mentors, was essential to Milin’s success.
• After completing his first year at Veritas and getting a great review, Milin’s manager told him he needed to find a different role. This was not about job performance.
  • “I’ll tell you the positive out of it. It basically made me realize that I need to control my destiny. I need to keep working at it, not assume anything. It was the best thing that happened to me…. At that point in time, I found a different role. I found another set of great mentors. And things just took off because my mindset shifted from not just being curious and raising my hand. It changed into…I’ve got to take care of myself. No one else will. It was a healthy sense of paranoia of constantly wanting to prove myself. Again, not lack of confidence, impostor syndrome…none of that stuff. It was just about ‘am I doing everything absolutely possible that I become unshakeable?’ That was the most helpful thing that person did for me, but it changed everything.” – Milin Desai
• Did the manager who mentioned Milin would need to find a different role tell him he needed to search inside the company or externally?
  • Milin had to go do the homework to assess his options for new roles. It was up to him to make it happen.
  • “Being curious means you work beyond your project scope, you talk to other people, you get to know other teams. They get to know you. So, when something like this happens it is not like you just showed up at their door. It’s all connected in a way when you are part of something bigger than your project, your team. You take interest. You have conversations. You have lunch with people beyond your team. You do things kind of outside just general scope.” – Milin Desai, on curiosity as a network builder
  • When a job loss type of situation happens and people know you, it is a jumpstart on internal opportunities. A mentor, for example, might vouch for you as well when trying for a new role.
  • “At the end of the day there are humans involved in the process, and that’s where the first connection happens.” – Milin Desai

22:43 – Mentorship as a Stream of Active Conversations

• As Milin looks back, how would he describe ways we can be an effective mentee to a mentor?
  • It’s not about showing up unprepared and expecting magical wisdom to come from a mentor.
  • It’s also not about taking a wide set of problems.
  • “It’s an active conversation. It’s a relationship. And the relationship is not transactional…. It’s a constant stream of active conversations….” – Milin Desai
  • We should go into a meeting with our mentor prepared just like a board meeting. Take with you a set of 1-3 things the mentor could help you with.
  • Milin suggests we figure out how the mentor operates, and figure out how to leverage this. It’s about reverse engineering what a mentor brings to see if they can bring value to you.
  • “And it’s not like they are going to help you suddenly go from point A to point B. I think that’s another big misnomer around this. It’s just somebody as a guide point, as a reference point of…additional data.” – Milin Desai
  • When Milin looks back at the people who have helped him, most mentors were within the same company, but there were external mentors as well.
  • People tend to think a mentor only helps them (a unidirectional relationship). Throughout Milin’s career, he tried to find ways to help his mentors (i.e. taking something off the mentor’s plate).
  • “It became a mutually beneficial thing where they were being successful as well in spending time with someone like me…. It’s various phases, but I always tell people there is no professional mentor. There are professional coaches. That’s different.” – Milin Desai
  • Milin says active mentorship on scenarios or career things requires someone be in the business with you (in the same company), and it also benefits the mentor.
  • People confuse mentors and coaches, but any given person may need both an external coach and internal support systems (like symbiotic relationships with mentors).
• Was it the series of active conversations with mentors that pushed Milin in the direction of product management?
  • Milin encourages us to think back to his time focusing on storytelling and selling before graduating and put it together with his curiosity during his first year at Veritas.
    • Milin mentions spending time with leaders who worked across different functions of the company and how interesting it was to learn about interconnected projects across the company.
  • Now we fast forward to the time after Milin needed to find a new role.
  • “By the way, I was an average coder, but I made up for it with a lot of testing – making sure that it worked, it worked in different scenarios, the UX, the experience…. That’s where I learned…everything is about the user, not about me writing code.” – Milin Desai
  • Milin would send e-mails to product leaders inside the company asking if they had explored specific problem domains. He would make these messages thoughtful and include research. He would also ask questions offline after all-hands calls.
    • Milin mentions names like Jeremy Burton and Mike Spicer as leaders who took the time to respond to his messages.
    • The continued dialogue with product leaders helped Milin realize he wanted to try something different.
    • “I wanted to kind of go to the product definition side because I was really enjoying it, but it was a series of all of these coming together to that culmination. That encouragement, that active encouragement from the folks I just mentioned definitely also helped….” – Milin Desai

29:52 – Beyond the Scope

• Did Milin have any conversations with his manager at the time about pursuing product management before he made the move?
  • Milin feels he may have been operating like a product manager in some form by asking the right questions and being a little disruptive. He thinks people started to see this.
  • Milin’s next role was a technical marketing engineer at Riverbed. He did have the option to become a product manager under Symantec but chose to go to Riverbed.
  • “I made the shift first to a technical marketing engineer, and within a year they said…move over to product management…. I think people realized my aptitude, the way I was spending time, the contributions I was bringing…. I think I had to just make up my mind and start making that choice, which is what I did in 2006.” – Milin Desai
• John emphasizes that we do not always know how the puzzle pieces of experience will fit together later. Without exposure to different things, there is no way to put these together when it’s needed.
  • Milin says many people want to join startups because it will allow them to do many different things in an organization with fewer people. While this is true, not everyone takes advantage of everything a startup can offer in this regard.
  • While it is likely harder in a large organization to do this (do many different things to gain different experience), it is not impossible according to Milin. In fact, he’s changed roles within large organizations to do different things over the course of his career.
  • “There is so much you can learn by just inherently listening for the signals, being curious about it, having lunch with different folks.” – Milin Desai
  • Milin tells us that having lunch with different people or participating in extracurricular activities with your team can be a great time for networking. It’s something that takes you outside the scope of your role, and when you do it, you do not know where it might take you.
    • Milin used to play soccer during lunch, for example, which gave him the chance to network with people in the bay area.
  • Milin says we do not need to be extroverts and should do what is most comfortable for us.
  • "If you’re a curious person and you want to learn a little bit about marketing, you can just ask. And most organizations have good people. They will respond, which is what I was telling you about when I was talking to…all these people who were like 7 levels above me in the larger organization…. They chose to take the time to respond, which created encouragement…. " – Milin Desai
  • John says these are practical tips in going from 0 to 1 in one’s own career management.

33:40 – Becoming Relevant in Something Different

• What led Milin to apply for the technical marketing engineer role?
  • It started by being ready to do something different.
  • “I don’t even remember how I applied for it, but all I can tell you is when I spoke to the team and the people I was like, ‘wow. This is going to be so much fun.’” – Milin Desai
  • The role as a technical marketing engineer was really about telling people how to use a Riverbed product focused on WAN optimization. We might call it developer experience or developer advocacy today.
  • In the job interview, there were no questions about coding because this was a technical marketing job. But they gave Milin a homework assignment as part of the interview to share how he would test something.
    • According to the hiring manager at the time, (Phil), Milin went above and beyond for this assignment. In addition to explaining how he would do the testing, Milin built a PowerPoint representing the story he would use to educate people on this scenario complete with preconditions, advantages, etc.
    • It was the extra push on this exercise that got Milin the job.
  • At the time, Milin didn’t understand what it meant to work for a pre-IPO company (which Riverbed was at the time).
    • “But I didn’t even think about all this stuff. I just literally loved the people and the scope of the role, and I felt like this would be exciting. And I took it…. There will be a point in time in your career where you can choose the people you work for and choose the people you work with, and there is nothing more important than those two things in my opinion when thinking of what you want to do next. Where do you want to spend your time? And most people don’t optimize for that. They optimize for everything else…. Day to day, you’re going to spend more time with these people. As soon as I got to know this group I am like, ‘man, I want to be with this group.’ …It was the people. Just like everywhere else…it starts with people.” – Milin Desai
• John mentions part of technical marketing roles as well as developer relations roles is being what he likes to call “nerd famous.” You have to be a little bit of a draw for attendees. Does this align with Milin’s experience in technical marketing?
  • Milin says yes and no. He feels the people who succeed in these roles are there because they have depth.
  • “That, I think, should not be lost. There have been a lot of people who have come and gone if you notice in that…what people call devrel or whatever…. The ones who have survived and thrived and continue to be respected are the ones with depth.” – Milin Desai
  • Whether it’s writing a product design document or an engineering design document, Milin tells us it is a story very much like a movie script with a beginning, middle, and end. Great storytellers who can simplify things will do well in a technical marketing or similar role.
  • Another thing to consider is whether you are bringing value. If someone comes to talk to you about cooking and you love eating but not cooking, the conversation is kind of pointless.
  • “When you are not famous, the way you become relevant is you bring relevance to the other person in terms of what they care about and then to be able to help solve their problem.” – Milin Desai
  • Milin says when it comes to people in customer facing roles (product managers and many others), it is easy to get into “the diarrhea of our mindset.”
    • People get into the mindset that they are building a feature and need to tell the customer everything about it. And sometimes customers will just let you tell them.
    • “If you pause a little bit, understand what the other side wants, do the storytelling from that standpoint…highly, highly transformational.” – Milin Desai
  • Milin also tells us that keeping our word helps build our professional brand. Are we doing what we say we will do?
    • Getting someone an answer because you said you would, even if the answer is no, build rapport and relationship.
  • The personality aspect is needed to get the best opportunities according to Milin.
    • Milin gives the example of posting some information on bulletin boards about using Riverbed and NetApp together. People got to know him through the content he had shared and the value it brought them. Listen to the specifics of what happened when people would meet him in person.
    • “I feel like if you do it right, you do it for your audience, you know your audience…day in the life of…be in their shoes. I think that’s super important in that TME role, in the product manager role versus the internal, inside view of…we are building something. Nobody cares about your algorithm if it doesn’t work. So, tell me how I am going to use it. If it breaks, tell me when it’s broken…all of that fun stuff. Live in the life, live in the shoes of your customer. Understand what they want, empathize with that, and from there, magic will happen.” – Milin Desai

Mentioned in the Outro

• There is a slow build of through Milin’s experience of developing that relevance. Examples would be:
  • Discussions with early mentors to understand systems and how projects within the company were connected
    • It takes curiosity to understand these things, and we need to have that same kind of curiosity when we help our co-workers or external customers with technical problems.
  • The questions Milin would ask and suggestions he would make to senior product leaders
    • Taking the time to put together thoughtful questions and suggestions made Milin relevant to those leaders, and they took the time to respond to his messages. That kind of thing does not happen unless you are bringing something relevant.
  • Creating the content at Riverbed
    • Milin was relevant to others because of the content he created. We can build relevance through content we create as part of our portfolio of work / public proof of work.
  • Much of Milin’s relevance came after he listened well or listened actively to be thoughtful in his responses.
    • This is what we should be doing in any role that has customers (externally facing or internal customers). If you’re in IT, your customers are the people whose problems you are trying to solve or those for whom you are trying to provide a technical solution.
  • Optimizing who we work for and who we work with is another way to remain relevant.
    • If we like who we work for and with we will want to provide value to them and therefore remain relevant as a member of that team.
• We talked about mentorship in Milin’s career and the bidirectional value flow between mentor and mentee, emphasizing that the mentee should try to bring value to a mentor.
  • For more discussions about mentoring, check out episodes under the mentoring tag on our website.
  • We would also point you to 2 specific episodes that represent a masterclass in mentoring:
    • Episode 288 – Guardrails for Growth: A Mentor’s Experience with Dale McKay (1/2)
    • Episode 289 – Enhance Your Personal Brand: Feedback as a Catalyst for Change with Dale McKay (2/2)

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