Getting Candid with Anneka Gupta

Thrilled to share this week’s interview with Anneka Gupta, Chief Product Officer at Rubrik, Inc. , also a lecturer in Product Management at Stanford University Graduate School of Business.

Anneka brings more than a decade of product and SaaS expertise with a track record of driving revenue growth, navigating expansions to new markets, and overseeing diversity, inclusion, and belonging initiatives. She joins Rubrik from LiveRamp where she was the President and Head of Product and Platforms leading product development and go-to-market operations and strategy. Anneka also sits on the board of directors for Tinuiti.

In this interview, Anneka talks about her strategies to create product roadmaps and ensure it’s execution, her ideas of the skills a PM of a tech-oriented product organization should have, how she manages her time and tasks and what she does outside of work.

Along with being a CPO at Rubrik, you are also a Lecturer at Stanford University Graduate School of Business, how did you find this calling (of also teaching) and how do you manage both roles?

I started teaching at Stanford last year in September and it was my first time doing it. I’ve been associated with the business school, I’ve done Executive Education at Stanford Business School and I’ve also been a guest in some of the classes, but I never had formally taught a class before. I knew when I signed up to do this that it was going to be a big commitment to create the content for the class and also teach it. I had taken this up with another professor, and we decided to teach a class together on product management because we felt that there was a gap in education, especially the hands-on experience that students were getting for Product Management. Given that so many students want to go into product management after business school, we wanted to figure out a way to accelerate their path into these roles. That was the goal of the class and I got very excited about helping with it.

As with anything, when you’re trying to balance a full-time job and doing any kind of hobby on the side or raising a family on the side, it’s all about how you prioritize your time, such that you can do all of these things. My basic approach to it has been to be very clear with myself on any day in any given week, what is the highest priority things that need to get done, because it’s very easy to fill your time with stuff that’s urgent, but not necessarily important. And it’s really important to know that the balance of how I spend my time every day is going to shift.

I was teaching three days a week for 10 weeks, each class being 90minutes long. When I was teaching, I had to go block that time to go to class and teach. So those days, I was more heavily focused on teaching. Of course, I couldn’t spend the same amount of time working every day without burning myself out. So I would have to be really intentional about what do I need to get done this week and planning my week out such that I was setting these blocks of time aside to focus on teaching when I needed to do that and setting the blocks of time to focus on my full-time job when I need to do that. And if I had other personal stuff going on, being able to focus on that too.

I really emphasize having clarity for myself and for the people that I’m working with on what’s most important and that helps me make sure that I get done all the things that I need to get done in a given day or week.

What is the strategy you follow to create product roadmaps and how do you ensure its execution and handle prioritizations?

It comes back to time management in some ways. I feel like every problem that I have in my life, whether it’s professional or personal, I can fall back on the same concepts that I use in product management.

It all comes down to what’s most important for driving impact for the business? At Rubrik, I manage a portfolio of products. When you have one product, it’s a lot easier. But when you start getting into a portfolio of products and you have a portfolio of tasks that you’re working on, it becomes really important to get clarity on the strategic priorities for the business. These strategies might look different for the different products in your portfolio.

Say for your core product, maybe you’ve gotten to a place where it’s growing well, but you also need to get more operational efficiency out of it and you have to focus on what is the North Star for that product. You can decide how much time and resources you’re going to spend and prioritize based on that North Star goal.

For more innovative products, where you’re still trying to find product-market fit, the goal might be to learn about the market, test whether your ideas are resonating with customers and solve an important and urgent problem that your customers are willing to pay money for. So you might have to do a bunch of trials to figure that out. You might have a fuzzy direction in mind strategically, but you need to figure out where in that fuzzy area are you going to focus, what is the entry point going to be and be really disciplined about that. And that means a different set of priorities and roadmap. A lot of this comes down to allocating time — you might want to allocate 20% of your time to new pursuits and 80% of the time to your core pursuits. You have to also make sure that every person knows what is North Star you’re trying to work towards and this is how we measure the success of the product and give them the freedom to prioritize within their bucket.

What do you believe are the vital skills a PM should have to make and lead a tech-oriented product organization?

A lot of people think that in order to lead a technology organization, you have to be a technical person yourself. I don’t subscribe to that fact. I think it’s definitely helpful because you inherently have more empathy for what does it take to build products. If you have an engineering background, it’s easier for you to empathize with engineering, the kinds of challenges that the engineering team faces and you already know the kinds of problems that occur when you’re trying to build a product like where the roadblocks come up. But that doesn’t mean that you need to have a technical background to lead a technical team. I think the biggest skill that you need is the ability to ask the right questions. It is really important to be able to ask the right questions to get to the root of what a problem is so that you can put together from all the signals that you’re getting across your organization about what is actually happening on the ground? Are things going well, are they not? And where are they going? Well, where are they not? And then also asking the right questions to be able to get your team to come up with the solutions because when I’m trying to solve a problem, the solution isn’t going to come from me, it’s going to come from someone who is closer to the work that they’re doing. But the value I can add is I can ask someone a question that makes them think about a problem in a very different way than they otherwise would have because sometimes people get so locked into their own way of thinking about things that they don’t explore the broader universe. This is just a human condition that happens to me too.

A lot of times when I think about myself as a leader of a technology organization, I think of building the connections and that empathy. I do have a technical background so it’s easier for me to do that. And what makes other leaders on my team successful is when they can ask those questions and help broaden the universe of opportunities and exploration that we’re doing as well as using those questions to then hone down into what’s the specific root cause of a challenge or what is the specific way that we’re going to go tackle an opportunity?

How do you ensure that you’re always on top of the technological business and product advancements happening in the industry?

This is a good question. It’s not always easy. There are a lot of things happening around you, especially if you’re working on data security like I am. Before Rubrik, I was in a company that worked in the marketing and advertising space, both of these spaces are going through a high degree of change where there’s rapid innovation happening — both on the technical side and also in the external market forces of what are other big companies doing in this space.

In data security, it is important to know what does the regulation look like, what are the hackers doing, where are the biggest threats coming from — and that’s changing rapidly all the time. So trying to keep on top of all this stuff is not easy, you’re never going to be on top of everything. My one approach is crowdsourcing it from my team. When I see an article or when I see something that comes across my screen, any external resource, I share it with my team, so that they see it, and then I encourage people to do the same. I am with the leadership team, who’s also doing that all the time. And like this, we build a collective understanding of what’s going on.

When I joined Rubrik, which was about seven months ago, I was entering a totally new industry. So I did a lot of research where I just read whatever I could find on the internet, I went to resources like Gartner to look at what they had and what they were seeing as trends, in the IT and security space. That was helpful. The other avenue I find is always helpful is talking to customers. Being able to talk to our customers. And not just customers, but also people that are experts and are doing a CIO role or a CISO role and understanding from them, what do they see changing in the industry? Where things are going? And exploring that thread further.

These are the kinds of things that I do, it’s not easy, because there’s always more research you could be doing. I always feel like maybe I should be spending an hour more reading every day because I’m going to get smarter if I do that, and then I don’t always prioritize that in my time. Then there are times when I need to burst and learn more about a subject because it becomes a more urgent priority for the business and we need to figure out our strategy for XYZ and then I can go into bursts and do a couple of weeks of research and understand what’s going on and come back and share those learnings and brainstorm with others and get a couple of people doing that first with me so that we start learning together and figuring out what’s changing and what we need to do about it.

What are the certain activities you do or priorities you have when it comes to things outside of work?

In the past couple of years, there are two things that I was really focusing on. One was, how do I expand what I’m learning professionally, outside of my primary job, which is what led me to teach at Stanford, do mentorship and advisory work for companies and for people. I want my professional self to be more than just my primary job. That’s something that’s brought me a lot of fulfilment. It’s helped me be a better leader, and do better at my primary job because I’m getting different kinds of experiences, that may not always feel like they’re totally 100% relevant, but there’s always something that you can take from those experiences back into your job.

The other thing has been to cultivate my life outside of work because I think it’s really important to not just have a professional self, but be more than that. And that has taken many forms. Obviously, the pandemic changed the kinds of activities I could do. I used to travel a lot, I used to eat out at new restaurants in San Francisco all the time, but all that changed. So I started to find new hobbies, I got into baking, I was doing more arts and crafts, and I got into crocheting for a while. I was making little animals for all my friends’ kids, which was fun.

Quite recently, my husband and I decided to move out of San Francisco, we decided to buy a house, we’re going to do a big remodel project. So that’s going to be really fun and artistic outlet. I’m also pregnant, we’re having a baby in June, and that is also a new thing that we are so excited about. And since we moved to the suburbs, we’ve been doing a lot more hiking and just going outside, which I’ve always loved — being outside in nature helps me recharge. So between all of these things, I get a lot of energy from having a lot of variety in my life.

What steps do you take to plan out your day and make sure that you address all of it?

I do a lot of calendar management, I have a wonderful assistant, she’s really helped me plan out my time. We spend a lot of time looking at my calendar every Friday and checking all my personal and professional stuff and just trying to make sure that my time is being spent in a way that aligns with my priorities. I also keep track of if I am taking on too much? If I can scale some stuff back if some things can be pushed out for later that don’t need to be done right now

So every Friday we look at my calendar and sort things out, there are things that come up during the week, so it becomes important to constantly be in communication about what’s happening, what are the highest priority items, what needs to get done today versus what doesn’t. And then I make sure that I am on top of my to-do list as much as possible.

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