Genevieve Hayes Consulting

Curiosity may have killed the cat, but for data scientists, it can open doors to leadership opportunities.

In this episode, technology leader Andrei Oprisan joins Dr Genevieve Hayes to share how his habit of asking deeper questions about the business transformed him from software engineer #30 at Wayfair to a seasoned technology executive and MIT Sloan MBA candidate.

You’ll discover:

1. The critical business questions most technical experts never think to ask [02:21]
2. Why understanding business context makes you better at technical work (not worse) [14:10]
3. How to turn natural curiosity into career opportunities without losing your technical edge [09:19]
4. The simple mindset shift that helps you spot business impact others miss [21:05]

Andrei Oprisan is a technology leader with over 15 years of experience in software engineering, specializing in product development, machine learning, and scaling high-performance teams. He is the founding Engineering Lead at Agent.ai and is also currently completing an Executive MBA through MIT’s Sloan School of Management.

• Connect with Andre on LinkedIn
• Andrei’s website
• Agent.ai website

• Connect with Genevieve on LinkedIn
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[00:00:00] Dr Genevieve Hayes: Hello, and welcome to Value Driven Data Science, the podcast that helps data scientists transform their technical expertise into tangible business value, career autonomy, and financial reward. I’m Dr. Genevieve Hayes, and today I’m joined by Andrei Oprisan. Andrei is a technology leader with over 15 years of experience in software engineering.

[00:00:24] Specializing in product development, machine learning, and scaling high performance teams. He is the founding engineering lead at Agent. ai, and is also currently completing an executive MBA through MIT’s Sloan School of Management. In this episode, we’ll be discussing how data scientists can grow into business leadership roles by exploring Andre’s own career evolution from technology specialist to seasoned technology leader.

[00:00:55] And more importantly, we’ll be sharing specific steps that you can take to follow his path. So get ready to boost your impact, earn what you’re worth, and rewrite your career algorithm. Andre, welcome to the show.

[00:01:09] Andrei Oprisan: Thank you. Great to be here. Great

[00:01:11] Dr Genevieve Hayes: We’re at the dawn of the AI revolution with everyone wanting to get in on the act and many organizations terrified of being left behind.

[00:01:21] As a result, there are more technical data science and AI centric roles being advertised now than ever before. However, this also brings with it unprecedented opportunities for data scientists to make the leap into business leadership, if they’re willing and if they know how. And those are two very big ifs, because in my experience, Many data scientists either don’t know how to successfully make this transition, or write off the possibility of doing so entirely for fear that it’ll take them too far away from the tools.

[00:01:55] Now, Andre you started your career as a software engineer, but have since held a number of technology leadership roles, including VP of Engineering at Liberty Mutual Insurance, Chief Technology Officer at OneScreen. ai, And your current role is head of engineering at agent. ai. What is it that first started you on the path from technical specialist to business leader?

[00:02:21] Andrei Oprisan: question. So for me, it was all about asking deeper questions as to the why and that led me to ask them more questions, you know, but why and why again, why are we doing this? Why are we prioritizing this kind of work? What makes us believe this is the right kind of feature, to work on as a developer which inevitably leads to some kind of business questions some questions about. Who the customer is and why we’re serving those customers are those customers, right? Kinds of customers. To serve in the 1st place, or, should we be thinking about different kinds of customer personas?

[00:02:56] And what does that mean? All the way to, how do you actually make money as a business? Why are we doing this? Is it to drive efficiency? Is it to serve a new, on top market potentially? And so. As you mentioned, I started as a developer, I started my career at Wayfair back in the early days when they were, I think it was engineer number 30 company of 100 or so people back in the early 2000s.

[00:03:20] And we were. Developing big features. I remember I own a big part of baby and wedding registries and checkout and customer reviews. And I was building more and more features and I was sitting and also in more meetings with product managers who are usually the kind of the interface right in a tech world to sort of the business.

[00:03:42] And I kept asking more and more questions around it. Hey, but why are we doing this? Why are we solving for baby registries? Why are we solving for wedding registries?

[00:03:51] So again. For me, it really started from early days of my career, all the way through later stages, where I was always asking more questions about, is it the right thing?

[00:03:59] The highest value thing that we can work on as engineers, as developers, as technical folks, or is there something more valuable that we should be working on that we should be aware of? That we should be asking deeper questions about. And it really started with that kind of inquisitive nature, always asking, why are we doing this?

[00:04:16] You know, I’m here as part of this team, and I want to understand why we’re doing these things. So I can be more effective. So I can make sure that, I. Do as much as possible to make a successful

[00:04:27] Dr Genevieve Hayes: That approach of asking all those why questions, that’s what they recommend to people in pretty much every management consulting advice book. The three. of Management Consulting. Why this? Why now? Why me? Did you pick that up from reading some sort of Management Consulting book or do you just have an naturally inquisitive nature?

[00:04:48] Andrei Oprisan: now for me it was more natural, maybe a bit stubborn, maybe depending on what you ask, maybe a bit , irreverent just to sort of asking the question. So, , why are we doing this? But as a developer, as you’re building out features, you can build a very simple version of an ask or you can build something very complex that needs to scale. That needs to take into account a number of different kinds of factors. And so we really started with. Trying to understand, okay, what is the actual technical requirement and why do we think that is

[00:05:16] and that’s usually defined by some kind of either tech lead and a team or a product manager or some combination thereof. And I found that to be very helpful, both for me and those non technical counterparts to ask those why questions because it really revealed a lot of the assumptions that went into the road map that went into even the business thinking there’s obviously some assumption that.

[00:05:41] For instance, we’re going to invest in scale from a dev ops standpoint, for example to make sure these servers don’t tip over. We’ll be able to handle more traffic because we expect growth. Okay. But when is that? Why is that?

[00:05:53] And it started from me, just not really understanding the business and wanting to learn and more wanting to learn on a deeper level to say, okay. I can understand. I became an expert in baby and wedding registries and all the competitors and I think that that’s part of what’s necessary to be able to build.

[00:06:12] Good products that kind of obsession, with the product and , asking questions until you really understand the landscape and what you should and shouldn’t be building. I think those are critical aspects of knowing what to build and not to build to be able to.

[00:06:26] And get some better outcomes.

[00:06:28] Dr Genevieve Hayes: And so by asking these questions, did senior leadership see that as a sign that you had management or leadership potential and then did you naturally get promoted or did you actively seek out those business leadership roles?

[00:06:44] Andrei Oprisan: I think a little bit of both, but more likely in the beginning. It was more the former, so I was asking. More of the questions for the sake of the questions and really wanting. To build a better product, which then led to just more responsibilities. And it was clear to me that I wanted.

[00:07:02] Those kinds of questions to be asked and answered. And many times they want, many of those sort of technical conversations they were having, those kinds of questions weren’t really asked by the technical folks. And so I became the kind of person that would always ask those questions and always.

[00:07:19] Push us to get good answers to those questions and really test those assumptions over time, as I became more senior in my roles building more complex systems that led to more complex questions that needed answers and increasingly got in front of more senior folks.

[00:07:37] So what became conversations Within a team with a product manager or a junior product manager talking to junior engineers became conversations, between senior engineers. And directors of thought up and things like that. And so, I just became part of. In those rooms where those conversations were happening at a higher level that led me to ask more important white questions more around.

[00:08:01] The business strategy, why do we think this is the right segment to tackle? Why do we think we’re going to build technology that is really differentiated, that is not just another solution that we could have just bought off the shelf.

[00:08:13] And those are very interesting conversations to have. And I think that the kinds of conversations that we don’t get to really have, we’re not really focused on both the technical, but not technical just for the sake of technical sort of solutioning, but technology in the service of the business and the service of a business that is, wanting to grow and stay competitive and and be able to win at whatever the business is trying to do,

[00:08:40] Dr Genevieve Hayes: It sounds like your nature made you very well suited to a business leadership role, even though you started off as a technical specialist. But I’ve met a lot of data scientists over the years who are very adamant that they don’t want to move away from purely technical roles and into leadership roles.

[00:09:01] For example, I’ve been in teams where the team leader role has It’s been advertised and every single technical person in that team has refused to apply for it because they don’t want to move away from the tools. Is this something that you experienced early in your career?

[00:09:19] Andrei Oprisan: definitely, and that’s part of every individuals journey as we’re moving through those individual contributor ranks. There are levels to the individual contributor roles, you can go from junior to very senior, to principal or staff or a member of technical staff and different companies have the sort of laddering that can even go up to the equivalent on the sort of management side, all the way to VP levels Microsoft is famous for, their laddering where you can have Distinguished engineers that are the equivalent of VPs will have hundreds of people who are reporting to them and have similar compensation structures.

[00:09:55] So, again, it is possible. Not every organization is set up for that. And so I think part of this has to 1st, start with the right level of research and say, okay. If I’m the kind of person that wants to do only technical work. Will the career progression and this organization really support my objective,

[00:10:14] if the most senior level that you can go to might be just a senior engineer level, that might be okay. And that might be the right place for you. But if you want me more responsible and we want to be more of an architect or someone who. Is coordinating, larger, project deployments across multiple divisions,

[00:10:37] I would say, figure out if the organization. As those kinds of opportunities, and in many cases, they don’t, because they don’t know that I need, it hasn’t been proven as an actual need. So, part of it is, how comfortable are you? And being that sort of trailblazer and taking some risks and, of crafting your own role versus, working within the existing bounds where you may have a well defined ladder.

[00:11:03] And, in other cases, it might be that, no, there is a ceiling and in many organizations, that is the case, especially in a non technology companies, and companies that certainly have a technology or it department and some fashion. But they might not have, the same level that you can go to.

[00:11:21] Compared to in a potential business role and that needs to be a decision that is that made to say, okay, is this the right kind of place for me? Can I grow and learn? To the level that I’m looking to grow and learn to and then figure out, if you can sort of.

[00:11:36] Move beyond some of those limitations, what are they and what are you comfortable with?

[00:11:41] Dr Genevieve Hayes: Early in my career, it was the case that basically in Australia, if you wanted to get beyond a very moderate salary, you had to go into management if you’re a technical person. But. In recent years there are an increasing number of companies and organizations that are building in that technical stream.

[00:12:03] I think Deloitte in Australia now does have a technical stream where you can get quite senior. And I know of some government organizations that also do. I’m not quite sure how well that works in practice, but it’s a move in the right direction.

[00:12:20] Andrei Oprisan: Right, and I think that’s that’s only increased over time. I’ve only seen companies create more opportunities for those very senior technical folks, not fewer. So, again, I think it is encouraging, but I’d also say, you’re not going to find the same.

[00:12:36] Leveling across the board for technical folks as you would, let’s say for management oriented and at a certain point, need to make the decision in terms of. Do you want to stay as an individual and the whole contributor, or are you open to management?

[00:12:51] It doesn’t mean from a management standpoint, you’re not technical or, you’re not needing to your technical skills, but it may mean that, yes, you’re no longer coding every day. Right, you are maybe at best reviewing architecture documents and really pressure testing the way the systems are designed and having bigger conversations around, cost optimization and.

[00:13:14] Privacy and security implications of the work that is being done and making sure that then those are addressed. Which again, there are different kinds of challenges. They’re still technically challenging. And you’re going to need good advice from additional folks, individual contributors on the teams, but they are different.

[00:13:32] Dr Genevieve Hayes: The other thing I’d add to all this is, even if you choose to remain in that individual contributor stream, as you move up the ranks, you are still going to be associating more and more with senior leadership and having to think about things from a business point of view. It doesn’t matter whether you’re managing staff or not.

[00:13:51] You need to become more business centric. And that idea that a lot of very technical data scientists have of just being left alone in a room to code all day. That’s not going to happen once you get above a certain level regardless of if you’re technical or a leader.

[00:14:10] Andrei Oprisan: That’s right, and I think it’s. Figuring out the right balance of enough technical work, and that can mean different things over time with enough. Organizational impact, which is another way to look at the business elements of. You know, we’re doing a bunch of work, but again, is it making money?

[00:14:29] Is it helping our customers get more of what they need? Is it improving some kind of output that the organization is measuring. If we can’t answer any of those questions , to some level of sophistication, then, if we’re working on the right thing or not, would we even know,

[00:14:45] and would it even about it may be a very interesting technical problem, of course, but does it matter at all? will anyone even see it when you care? I think by, understanding the business understanding, maybe how many eyeballs. The product is going to get in front of and what the assumptions are and even, coming up with some of those numbers is going to really affect what you’re thinking about what you’re building and why you’re building.

[00:15:09] Dr Genevieve Hayes: It sounds like you making that transition from being a technical expert to being a business leader was very organic for you, but was there ever a point in time where you actually consciously thought, okay, I’m actually focusing on this business leadership thing. I’m no longer a technical specialist.

[00:15:28] I am a data science or engineering leader.

[00:15:32] Andrei Oprisan: Yes, when I transitioned from Wayfair I work for an eCommerce consulting shop. So there is where I learned a lot of my sort of consulting skills and really understand how to talk to. Chief marketing officers and CEO. So understand, what exactly are you trying to accomplish?

[00:15:48] But in those conversations, it became very clear to me that I needed to understand more about the business, not less, even as I was very technical, I was a tech lead, I was running the technology team, in charge with the recruiting with defining the staffing plans and also architecting some of the solutions.

[00:16:10] And so it became very clear that I needed to understand even more. About what the actual goals were of the organization, because the very first iteration of the project we came in with the wrong assumptions completely, and we came up with some technical solutions that made no sense for where they were trying to go.

[00:16:30] 2, 3, 5 years later we came up with something that made sense for a proof of concept and sort to get to an initial contract. But actually, we were setting them up for failure in 4 to 5 years were actually the solution that we were proposing wouldn’t be able to support the kinds of customization as they would need when they moved to 20 different supply chain partners and just having those conversations at a, higher level

[00:16:57] It was very eye-opening when I walked out of a few of those meetings. Understanding that 90 percent of our assumptions were just incorrect. It’s like, Oh my God, what are we doing? And why are we having this entire team of engineers building these features for, I think it was Portugal and Spain stores where, we were just expected to lift and shift that for Japan, and that we’re just not going to be possible said, okay,

[00:17:22] This made absolutely no sense. Let’s have deeper conversations about. The business what their goals are and how the technology is going to support that both now in the very short term, and we’re applying a very short term kind of mentality. But also long term also in 4 to 5 years, assuming the business is successful and they meet their objectives.

[00:17:44] How can we make sure we’re enabling their long term growth?

[00:17:48] Dr Genevieve Hayes: So it sounds like if one of our listeners wanted to follow your lead and move from technical specialist into a business leadership role, one of the first steps that they should take is to understand the objectives and goals of their organization and how their work can feed into achieving those goals and objectives.

[00:18:09] Andrei Oprisan: Absolutely. I think it’s just having those simple questions answered around. What is the business? What is it doing? Why is it doing it? Why are they in this specific sector now? How has this evolved? And then being able to answer, how are they actually able to do that? Is it people?

[00:18:28] Is it process? Is that technology is probably a combination of all of those different factors, but technology can have a multiplying effect, right? And I think it’s asking those questions in terms of where they are now and looking at different ways of expanding different ways of providing. Goods and services and using technology to more efficient.

[00:18:49] And , it’s just looking at the business, but I would call it. A common sense approach and asking the kinds of questions. Okay. Someone in on the business side, if they can’t answer things in a simple. Way ask more questions if you can understand them in the terms that.

[00:19:08] They’re giving back to you then then ask more clarifying questions. Don’t just assume. Right and it’s okay to not be an expert in those things. The challenge that I had in the beginning was getting frustrated with. My blind spots and my lack of really understanding I think it was.

[00:19:24] You know, 1 of the early examples was this around tax treatments and, how obviously. Different territories have different rules for when and how you collect taxes.

[00:19:34] It gets into a lot of complexity, but, it was very eyeopening. To ask more of those questions and to understand just how complex of an environment the business operates in, which allowed me to be a better developer, which allowed me to be a better team lead, which allowed me to then be a better partner, frankly, to those business folks who, you know, they have the same goals for the organization that we should have.

[00:19:59] The company is going to grow. And if the company grows and it does well, then it means good things for everybody on the team. And if they don’t, that’s going to lead to equally bad things for everybody on the team. And so I think part of it is having that ownership mindset of it’s not someone else’s problem.

[00:20:16] If we don’t understand this, it’s my problem. It’s my problem that we don’t understand how we’re going to need to customize this types engine. Because we might get hit with fines and we might need to retroactively as a severity one drop everything now. Anyways, kind of issue later than the line,

[00:20:34] Dr Genevieve Hayes: So what is the single most important change our listeners could make tomorrow, regardless of whether their role is purely technical or not, to accelerate their data science impact and results and increase their business exposure?

[00:20:47] Andrei Oprisan: I would say, ask, those deeper questions and figure out exactly the kind of work that they’re doing, how it’s having an impact on the bottom line. Whether it does or not, I think, understanding that very well understanding whether or not, the group that you’re in and the division is seen as a cost center or not or revenue center.

[00:21:05] I think that’s the biggest sort of eye opening question that you can get answered and figure out, what are the broader objectives? Well, there are technical objectives. That the team has or business objectives that the whole division has and figuring out, okay, am I playing a part in that today or not?

[00:21:26] Are we directly or indirectly? And how are my bosses or my bosses, bosses seeing the impact of the work that I’m doing in relation to the business success? And if there is no pathway for that, I think it’s the wrong kind of role in terms of long term growth. So again, if the work that you’re doing doesn’t have a measurable impact on that bottom line or on the growth of the organization, I think it’s worth asking deeper questions as to why that is or why it’s seen that way and how you can get into the kind of role that can help it.

[00:22:03] With the growth and resiliency of the business.

[00:22:06] Dr Genevieve Hayes: For listeners who want to get in contact with you, Andre, what can they do?

[00:22:10] Andrei Oprisan: Sure. Can email me at Andre at agent.ai. Can find me on the web at oprisan.com. My blog is linked there as well. I’m on LinkedIn and x and. All the social networks with the same handles but more importantly, just, find me on agent. ai where I spend most of my time building AI agents helping out in the community giving folks feedback on how to build better agents.

[00:22:35] And ultimately aiming to democratize AI and make it more accessible.

[00:22:40] Dr Genevieve Hayes: And there you have it, another value packed episode to help turn your data skills into serious clout, cash, and career freedom. If you enjoyed this episode, why not make it a double? Next week, catch Andre’s value boost, a five minute episode where he shares one powerful tip for getting real results real fast.

[00:23:01] Make sure you’re subscribed so you don’t miss it. Thank you for joining me today, Andre.

[00:23:05] Andrei Oprisan: Thank you. Great to be here.

[00:23:07] Dr Genevieve Hayes: And for those in the audience, thanks for listening. I’m Dr. Genevieve Hayes, and this has been Value Driven Data Science.

The post Episode 58: Why Great Data Scientists Ask ‘Why?’ (And How It Can Transform Your Career) first appeared on Genevieve Hayes Consulting and is written by Dr Genevieve Hayes.