The Navya Rehani Gupta Hypothesis: CPOs Should Measure Product ROI in Business Outcomes

Navya is the Chief Product Officer at Peek.com, responsible for scaling the industry-leading Peek Pro platform, known as "Shopify for the Experiences economy" with $2B+ bookings. Peek.com helps consumers book fun activities (such as boat rentals and cooking classes), and provides experience operators with powerful software tools to grow their businesses. Prior to Peek, Navya built new business lines at StyleSeat, the world’s largest marketplace for beauty services that has fueled billions of dollars in beauty services. She has also managed large-scale products at Uber, Disney and Goldman Sachs. Navya holds an Electronics Engineering degree from University of Sheffield, UK, a Masters in Computer Science from Stanford and a MBA from NYU Stern.

In this episode of the Product Science Podcast, we cover the major inflection points in Navya’s journey to CPO, how Navya talks about the ROI of product investments, and how she chooses the key KPIs and assumptions that she uses to model ROI.

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Questions we explore in this episode

What were the major inflection points in Navya’s journey to CPO?

• She started as a software engineer but found herself always wanting to be closer to the users.
• She worked in product in a variety of industries, including finance, entertainment, beauty, and travel.
• To go from product leadership to executive leadership, she became really interested in the executives and what challenges they faced.
• She saw that Peak was ready for a CPO and advocated for the role with the founder's.

How does Navya talk about the ROI of product investments?

• She wanted to make the case to the board that the product investment would lead to certain returns in the future.
• She learned to talk the language of the board, the CFO, and the CEO by understanding the financial model and the KPIs that the board monitors in various parts of the business.
• She saw that across departments, KPIs were both short and long term, and that the board was used to seeing long term goals that aren't quantified.
• She broke the product work into categories that she could independently analyze and model.
• In her models she used assumptions that were fact checked with the numbers the board would see from other departments.
• She then shared both an investment number and a return number for each of the areas she analyzed, as well as a list of assumptions.

How did Navya choose KPIs, make assumptions, and build a model for forecasting the product investment for one of her key areas, scalability?

• She looked for initiatives where they created automation and used technology to drive cost savings.
• Looking at the example of building a design system, she calculated how the team would be more productive without adding as much more headcount. They found that work after the design system was in place went about 30% faster.
• She looked at how the higher productivity would drive OpEx cost savings for future development work.

Quotes from Navya Rehani Gupti in this episode

The key difference between a VP of product and a CPO is that as a CPO, you're making decisions at a company level, not just at the product level. So you really need to understand the end-to-end business. So you're no longer responsible for your product KPIs, you're saying, "How can I make the entire business successful?"

We're definitely living through interesting times to say the least. And especially in tech, every company is understanding how to drive profitable revenue growth, and we're at this time where CPOs should be thinking about that. They should be thinking about how to make their team productive and also how to be building a culture where every person in the company is taking ownership of driving profitable revenue growth.

One of the things that was inevitably a learning, even as we looked at the first few weeks of doing this was setting up mutual goals in the company. So if you think about a product led growth company, product can drive the revenue targets directly, but when you're in a company where you have the sales motions, you're actually dependent on sales to sell the product that you're building and you need marketing support. So it is really a whole company rallying around driving revenue.

I set goals and strategic initiatives that I take on every quarter, and those are things that I drive independently to drive impact throughout the company. I'm pretty transparent about my priorities. So I would spread the word in my team and talk about like, "Hey, these are the side projects that I'm taking on, so please loop me in, please send me your ideas." And then I continue to do 30, 60, 90 check-ins, which is when I'm about 30% done, I would share with my team my early thinking and then again at 60 and again at 90. So it gives regular checkpoints for people to be able to contribute to the direction that I'm working on.

Transcription

Holly Hester-Reilly:Hey, Holly here. Before we dive into this week's episode, I wanted to share some information with you about some workshops that we're running. Here at H2R Product Science, we love to teach workshops, both public workshops, private workshops at companies, and even an online workshop for people who can't come to see us in person. If you're interested in learning how to identify the right products and features to build and how to develop the support to do so with the Product Science method, come and join us. You can learn more at h2rproductscience.com/workshops.Hi and welcome to the Product Science Podcast where we're helping startup founders and product leaders build high growth products, teams, and companies through real conversations with the people who have tried it and aren't afraid to share lessons learned from their failures along the way. I'm your host, Holly Hester-Reilly, founder and CEO of H2R Product Science.This week on the Product Science Podcast, I'm excited to share a conversation with Navya Rehani Gupta. Navya is the chief product officer at Peek.com, responsible for scaling the industry-leading Peek Pro platform, known as Shopify for the experiences economy with two billion plus in bookings. Peek.com helps consumers book fun activities such as boat rentals and cooking classes, and provides experience operators with powerful software tools to grow their business. Prior to Peek, Navya built new business lines at StyleSeat, the world's largest marketplace for beauty services that has fueled billions of dollars in beauty services. She has also managed large scale products at Uber, Disney, and Goldman Sachs. Navya holds an Electronics Engineering Degree from the University of Sheffield in the UK and a Master's in Computer Science from Stanford and an MBA from NYU Stern. Welcome, Navya.

Navya Rehani Gupta:Thank you, Holly. Thanks for having me here.

Holly Hester-Reilly:Yeah, I'm excited to have you. That's a lot of degrees. How did do end up going for those different types of degrees along the way?

Navya Rehani Gupta:Short story, I'm a nerd, and longer story, I would say that I always had a passion for technology. When I was 15 years old, my dad got us our first computer and I started programming quite early and I knew that I was interested both in the hardware and the software side of technology. So I figured I should go first figure out how things work and get an electronic degree, electronic engineering degree, but I knew that I wanted to get master's in computer science. So that was pretty clear to me upfront. But as I took my first role and started to work on Wall Street, at that time, I knew that I wanted to understand the business side of things better, and that inspired me to get an MBA, which there are lots of mixed thoughts about whether you should get an MBA or not. Definitely benefited from that experience, especially doing that part time while working for Goldman Sachs. So it was pretty intense to work on Wall Street and get an MBA in the evenings, but definitely learned a lot that I still continue to use in my day-to-day.

Holly Hester-Reilly:Yeah, and I actually teach at NYU Stern, so I have a lot of students who are doing that sort of thing as well. It seems like a lot of people go through that when they're looking to grow out of just finance roles into tech roles. At the time that you were there, was that the case as well, or is that sort of a shift?

Navya Rehani Gupta:For sure. I would say the MBA has been, generally speaking, very helpful when you're trying to navigate to a different career. So definitely all my peers at Goldman Sachs had similar intentions. But outside of understanding more about the business and getting more into tech, I really benefited from creating a network of people that I still stay in touch with and that's the huge, huge plus for getting a business degree.

Holly Hester-Reilly:Yeah, absolutely. That's one of the big things they say is that that network that you build is really strong. So tell me more about how you came to this chief product officer role. What are some of the steps along your journey?

Navya Rehani Gupta:Yeah, so I'd say the big inflection points were, first of all, knowing that I wanted to get into product. So at that time while I was working on Wall Street, I started off as an engineer, but I knew that I liked product. Even though product wasn't a career, I knew that I wanted to sit down with customers. I used to work in the Jersey City office and constantly want to get on the ferry and get to New York to sit next to my customers who were in the New York office. Also, when I was working on initiatives, I knew that I enjoyed the discovery process a lot better than actually doing the coding myself.So I almost created a product role for myself on Wall Street at that time, not knowing that I was doing product. Obviously, there was a lot for me to still learn. As I transitioned into the tech side of things, I truly started to appreciate what product means and the value that product brings to the company and the business. So it has definitely been an evolution of me getting to know product as I've navigated different industries.After Wall Street, I worked at Disney. So very different world to work for Mickey Mouse than Wall Street, and then worked at Uber for a while and then in beauty, and now travel. So the next inflection point was definitely getting from product leadership to product executive leadership, and that came when I was a director and I started to really understand what VPs do and the C-suite does. I was just intellectually very curious about how decisions are made at the C-suite. So I have to say again, I created the CPO role by working very closely with the founders at Peek, knowing that that would be something that was aligned with my career goals, but also something that the company was ready for as they were seeing the growth in the business.

Holly Hester-Reilly:How did you identify that the company was ready for that role?

Navya Rehani Gupta:Yes. I started with research of understanding what a CPO does. So I had to educate myself, did a lot of reading, started with research to understand what a CPO does and what does a CPO bring to the C-suite table. So spend some time doing that, talking to CPOs, following CPOs. They're not that many in the world. So really following them and understanding myself what I could bring to the company. And then secondly was educating the founders. Typically, they would say when you're in double digit million dollars of revenue, that's typically the time when you would start to bring in the C-suite. Ultimately I had to show that I was ready for the role, but also train the company on what the power of having a CPO would mean for the business.

Holly Hester-Reilly:Yeah. And what are the key powers that having a CPO means for the business that you see?

Navya Rehani Gupta:Yeah, so the key difference between a VP of product and a CPO is that as a CPO, you're making decisions at a company level, not just at the product level. So you really need to understand the end-to-end business. So you're talking way beyond product, you're really understanding what each executive brings to the table, what keeps them up at night, how are you looking at productivity, accountability, and metrics through the entire business, and then being that person at the table who says, "How can product help?" So you're no longer responsible for your product KPIs, you're saying, "How can I make the entire business successful?" Which means, what is the work that the product team can do to drive more sales, to drive more retention, to actually understand what keeps a CFO up at night? So that's been the transition and I've really enjoyed it. I've really enjoyed the learning experience of going beyond product and taking the entire C-suite team and making that my team as opposed to the product team being considered as my team.

Holly Hester-Reilly:Yeah. It reminds me a lot, a previous guest was Tommy Forstrom and he was talking about product executives being executives first and product leaders second. That once you make that shift, you're really up at the executive level before you're a product person. Has that been true for you?

Navya Rehani Gupta:Totally. It is your first team as your C-suite, definitely.

Holly Hester-Reilly:Yeah. So one of the things that we talked about is that you have had a really great experience recently talking about the ROI of product initiatives at the board meetings. So I'd love to hear more about that. What was sort of the situation that led to this conversation and how did you navigate it?

Navya Rehani Gupta:Yeah, so we're definitely living through interesting times to say the least. And especially in tech, every company is understanding how to drive profitable revenue growth, and we're at this time where CPOs should be thinking about that. They should be thinking about how to make their team productive and also how to be building a culture where every person in the company is taking ownership of driving profitable revenue growth. So that's something that's been top of mind for several months, but we had a board meeting coming up and I knew at that time what I would be answering for the product team isn't just, "Hey, this is what product did relative to what we were expecting to do." But really explaining the story around this is the investment that we're making within product right now, and when do we expect to see the returns. So it wasn't very difficult question to answer.I looked around for frameworks and in fact found tons of great articles about why you shouldn't measure product ROI. Because product is long term and in many ways, it's the qualitative side of product that actually makes the role special. You're making decisions based on truly, truly understanding the customers. So you have to stay qualitative for a long time while maintaining that long-term vision. So it was a very tough question for me to answer, but I knew that it was also important for me to get there. So I definitely did not sleep for a week.

Holly Hester-Reilly:First off, what you did not do. There's the ante goal, yep.

Navya Rehani Gupta:Definitely I lost a lot of brain cells that I would love to share so that other CPOs who are listening to this, other founders who are listening to this podcast can benefit from the experience. So I took a step back and I said, "Hey, you know, there is tons of great stuff." I have full confidence that whatever we are working on is going to maximize the impact for the company. I know that, but how do I make it so that I'm talking the language of the board and talking the language of our CFO, our CEO, everybody who's been used to seeing ROI as it comes to other functions. It's very easy in sales or in marketing to be able to see a funnel and understand what an ROI is, but product has always been different.So the first thing I did was I said, "Hey, this is not been done in product before, so what can I learn from other functions?" So I sat down, understood our financial model, understood all the KPIs that we're presenting for in the different parts of the org. The key takeaway there was every function actually has short-term and long-term investments. So the board is used to seeing the long-term investments play out, but there are ways that you can quantify the work that you're doing to see the short-term impact. So that was number one. The number one takeaway was, okay, Navya, you need to be able to be okay that not all the long-term investments will play out in the next year, two years. Write disclaimers, explain to the board that some of these investments are just must have for the business. So that was takeaway number one.The second thing I did was I started to create categories of work. So the three categories that I landed with, I wanted to make the categories so that they fully capture the work that we're doing, but also were understandable to the board. The categories that I created were around scalability. The second one was retention and LTV, and then the third one was around expansion. So I'll talk about all three of those.Scalability is everything that the business needs to do to scale efficiently. And the KPI that I created there was around OpEx savings. Again, not everything that you do to scale efficiently will lead to OpEx savings in year one, year two. An example there would be anything that the product team does to reduce risk in the business is not captured there, but that's okay. It goes back to my takeaway number one, which is not everything will be quantifiable. So created that category and labeled that around OpEx savings and then forced myself to put numbers around OpEx savings for everything that we are working on around scalability.The second one was around retention and LTV. As product people, we want to make our customers happy and build a delightful experience. But then again, I forced myself to put a number. So I created assumptions around the work that we're doing today that helps to minimize bad experiences, minimize churn. What is the dollar number that I could create for that? The second category on LTV is everything that the product team is doing to drive value for our customers. And I forced myself to come up with assumptions and put that in the model even that wasn't our retention and LTV.And then the third one is expansion. So everything that the product team does to get to newer verticals, helps drive the sales productivity, how do we quantify that? Again, I came up with assumptions with everything that the product team is doing that is making our sales team more productive and what that impact would be as it comes to the sales goals that the board was seeing for year one and year two.So it was all assumption space, but it was fact-checked with the numbers that the board would be seeing in other parts of the presentation. So that's really the entire process, which is again, understanding short-term versus long-term, being okay that the long-term investments can't be quantified. And then secondly, taking all the work that we're doing and then breaking it into categories, but creating assumptions so that I could put an investment number, but also a return number. And the return number could either come in OpEx savings, it could come in revenue retention or in revenue growth.

Holly Hester-Reilly:Could you pick one of the areas that you came up with this number in and dive a little deeper into what were some of the assumptions that you made and how that played out?

Navya Rehani Gupta:Yeah, let's see. I'll actually talk about scalability because that was the hardest one. It's the hardest thing to quantify for reasons that I mentioned. So there are must haves for the business. You absolutely need to keep the company secure, safe, and reliable. So it was the hardest part of my job there. The way I went about it is I looked for initiatives where we created automation and use technology to drive cost savings. So if there's work that you are doing, that would mean that we don't have to add headcount. What is that? If it's making a team 5x more efficient, let's put numbers around that. So look for categories there.The second thing was, what are the things that the product team does every day to drive productivities? We're used to looking at engineering velocity and something that most engineering teams do, but there is work that product teams constantly do to drive up our velocity. What we don't do is quantify the impact of that. An example would be our team launched our first design systems, which means that engineer doesn't need to create a piece of code to build a button or a dropdown every time they're adding a new page to the product. So that can be quantified by saying, "Okay, so we put in this investment, obviously, it took us longer to ship out the particular product, but the next time around we do this, what is the savings that we're going to get?" So we agreed and we had done a few of these iterations. We knew that the first time was harder, but then the second time and the third time, we actually saw 30% more productivity in the engineering team because of that investment.So that's the number that I used to say, "Hey, we know that the work that we're doing is to help us scale efficiently, which means we're going to make our engineering team more productive, which means we need to hire 30% fewer engineers next year. It definitely took a while to make that connection, to understand what you just simply do because it's right for the business. It can be translated to a number, but the message was received very well.

Holly Hester-Reilly:Excellent. Maybe it's interesting, or maybe it's from my own background, I have spent a good amount of time working with dev tools, so I feel like I've often been in that calculation. I'm curious to hear about some of the other ones as well. So maybe you could share, what was the first category?

Navya Rehani Gupta:Scalability, retention, and expansion.

Holly Hester-Reilly:Yeah, I'd love to hear more about the expansion one, because I think that's a really interesting area where people are always putting numbers on how they think expansion is going to go, but how do you actually come up with the right numbers?

Navya Rehani Gupta:Yeah, definitely. So that was again a challenge because ultimately product is building for the long term. So we're building the product so that the customer's problems are being solved the right way and then the sales team is continuing to benefit from that. So how can you quantify the work that you're doing this year, this quarter as it comes to dollars gained in the following quarter or the following year? What I went about doing was we did an exercise to say, "Hey, sales team, let's sit down and talk about all the features that we have launched in the last year. And we know that a subset of them helped you get more efficient, helped you drive productivity, and let's start to ballpark and say how many extra deals did each salesperson close specifically because of this new functionality?"So we went back and looked at our data, came up with numbers. Obviously, we had to scrape a number of calls to gut check how often the features were coming up on the conversations, but then use those assumptions to say, "Hey, we know that we launched 10 features and that led to increased productivity by 20%." So that was a baseline that we created. But then looking ahead, we are obviously very excited about everything we're working on as it comes to future growth. Let's actually come up with a number on what the 20% would look like in the next year and the following year based on the product roadmap. So you know our product roadmap, let's actually come up with assumptions. And we were easily able to come up with assumptions that meant that the sales team's productivity would continue to double because of our upcoming initiatives.Those were the assumptions that led to creating the model. And then again, it had to tie exactly to the financial projections that the board was seeing. So taking the numbers and saying, "This is the revenue growth that we're planning to see. Out of that 20%, 40% or 60% of them can be attributed because of the product investments."

Holly Hester-Reilly:Yeah. One of the things that you said in there that I guess caught my attention was scraping calls to figure out which ones had talked about certain features and benefits. How did you mobilize to do that? Is that a thing that's just normally a part of the process in your team or was that a special effort in order to come up with the ROIs?

Navya Rehani Gupta:Yeah, I would say that it wasn't. It took us this exercise to get there. And since then, now, we have actually made it a regular practice. So we use Gong for all our sales calls, and Gong has super capabilities that we weren't actually using in advance where you could search by keywords and then set trackers to understand how often things are coming up. So definitely something that we hadn't been using before this exercise. But now having been through this exercise, what we are doing is setting mutual goals for the entire company for a product and for sales to say, "Hey, this is the new, shiny thing we're working on. Let's actually understand how often it's going to be coming up." And also tying it out with sales enablement and training. So if we are investing in training the sales team on an underutilized capability, we should see those numbers going up. So as a product person, it was like hitting a gold mine when you find that you have data that you haven't been using. But it was definitely that kind of moment. But now we've been very excited to use that.

Holly Hester-Reilly:Yeah, I'm so excited to hear that because I love when teams add new ongoing practices wherein it's like, "Okay, and now we're also going to be gathering this and seeing this and incorporating this into what we're doing." So are there other aspects of developing the ROI or how you presented that at the board meeting? Maybe some aspects around storytelling or things like that, that you'd like to share?

Navya Rehani Gupta:Yeah. As I mentioned, the big thing around here was creating a story myself before I could go and talk to anybody about it. I started by creating those right buckets, but then through the board presentation, it wasn't just at the time where I talk about ROI, my entire executive summary, my entire look backs, were all using consistently the three categories so that the board is used to seeing the three categories as it comes to doing the recap of the year, but also our upcoming roadmap.So that was number one, which is figure out your categories and create a consistent story. And then secondly, it was the presentation around the model. So I created a very simple view that just puts numbers because that's what the board members are typically used to seeing. The reaction that I got was, "Whoa! We've never seen anybody put numbers on product." It was very simple as this is the investment and this is the return that we're going to get in 2023, and this is the return you're going to get in 2024 and a disclaimer on everything that's not being quantified, but then definitely got everybody's attention there. But I had a very simple one-slide view that went into documenting all the assumptions that went behind those numbers, and there was tremendous amount of interest to understand how those numbers were created and what those assumptions meant. And it was really a collaboration exercise.So the feedback that I got from one of our board members later was that they loved that I wasn't pitching this ROI model because I started the conversation by saying, "Hey, nobody's done this so I took a step. If you have other examples of other companies that have done this, please actually stop me, tell me I want to improve it so that it actually makes sense and we all agree on it." But then it felt more of a collaboration exercise, which was very well received across the board.

Holly Hester-Reilly:Yeah, that's awesome. I think it's not that often that I hear about conversations with the board feeling like collaborative exercises. So I think that's awesome when that is the case. So what are some of the outcomes that you expect from having done this analysis and sharing it with the board? Where do you think that's going to go in the future?

Navya Rehani Gupta:Yeah, so the big aha for me and for everybody was, hey, we have now created this model, how do we change the thinking on a day-to-day, week-to-week basis so that we're actually going back and making sure that we are still in line with the assumptions, understanding if those assumptions were the right assumptions or not? So an exercise that we started to do in our team is we have an end of week ritual where everybody in the team figures out what they did and then shares and writes an email update to the rest of the org to talk about all the activities. Because on a week by week, it's a lot of activities and less outcomes.And now what we've started to do is we've started to map all the activities to those three categories so that we can see that the work that we had planned to do is still broken down in terms of the investments the same way. But we also now for our roadmap, we have targets for every single team, every single feature that maps to that ROI model. So working on that very closely. I would love to do a follow-up in three or six months and tell you how bad my assumptions were, lessons learned along the way. But definitely it's helped change the thinking to an ROI mindset, especially something that's so important at this time.

Holly Hester-Reilly:Yeah, especially right now, I think just in case anyone's listening to this at a different time, like listening to an older episode or something, we're speaking in late 2022 and the economy is not looking great for tech industries right now. And I think people are really interested in ROI in actual business outcomes from the work that we do, which should have always been the case. But obviously in certain times in the cycles, things get away from that a little bit.

Navya Rehani Gupta:Yeah. I would love to have this conversation in two years and then look back and say what we thought would happen.

Holly Hester-Reilly:Yes.

Navya Rehani Gupta:And the predictions on when things will be better than they are today, but definitely it's a state of the world at this time.

Holly Hester-Reilly:Yeah, yeah, absolutely. So how do you see this affecting the way that your teams do their work? You mentioned that they're tying things back to the three areas that you outlined. What do you envision for tracking and looking at... I guess the big question that comes to mind is, what happens when something doesn't go as planned? In some area, you don't hit the ROI targets, what do you expect? How will that be managed?

Navya Rehani Gupta:As we expect in product teams, we are constantly doing retrospectives and constantly understanding what we could improve as we learn more. One of the things that was inevitably a learning, even as we looked at the first few weeks of doing this was setting up mutual goals in the company. So if you think about a product led growth company, product can drive the revenue targets directly, but when you're in a company where you have the sales motions, you're actually dependent on sales to sell the product that you're building and you need marketing support. So it is really a whole company rallying around driving revenue. So what we've started to do now is we are already setting roadmap targets for the product team, but also the sales team. An example would be product would build three features and that would immediately, not in the long term, immediately drive this much revenue.That was the key learning that has come from even a few weeks of doing this and something that will continue to run into retros. The other big thing I should call out is it would be very, very shortsighted for any company to try to do this and not maintain the long-term vision. So I should clarify here that everything that we're working on, we're tying ROI next to it, but we are continuing to invest in what I'd mentioned as long-term initiatives, knowing that we won't be able to quantify or realize the returns in year one or sometimes even year two or three. So I don't want the takeaway here to be only built for the short term because that's not what product people should be doing. But yeah, there'll be a lot of retrospectives I'm sure.

Holly Hester-Reilly:Yeah, absolutely. Do you have any different formats or practices that you use for retrospectives at that level as opposed to the standard sort of scrum agile retrospective?

Navya Rehani Gupta:We've tried, they're all pretty much the same. The agile retrospective works. Sometimes we switch it out by talking about the good, bad, ugly and just what was good, what was bad, what was ugly. We've also tried a new one because people sometimes don't want to call things ugly. We would call rose, bud, and a thorn.

Holly Hester-Reilly:Yes. I do that with my children. Did you get that from the Obamas?

Navya Rehani Gupta:It was from a new leader that came to the team. I don't know the origin of that, but it's definitely more well received than good, bad, ugly, but it does go back to the agile retrospectives. It's really about understanding what's working and what we should start doing, what we should continue and what we should stop. So pretty much the same format.

Holly Hester-Reilly:Yeah. We started doing that in my family after I read about it in, I think in Michelle Obama's book, Becoming, or maybe in listening to her talk somewhere. But it was a practice that I guess the Obamas did at their dining table with their kids. So I'm like, "Oh yeah, Rose, bud, and thorn, that's like a family thing to me."

Navya Rehani Gupta:Been helpful for your family?

Holly Hester-Reilly:Yeah, it's been fun. It gives us a way to hear a little tidbit about what the kids are excited about and what they're not happy about, and just a different spin on the how was your day question that's so commonly gets discussed.

Navya Rehani Gupta:Yeah. I'm going to try that. That's a great idea.

Holly Hester-Reilly:Yeah, and on that note, I see behind you, our listeners obviously can't see, but you have a lot of pictures that look like children's art. Who is the artist?

Navya Rehani Gupta:I have two kids. Zoya is five years old, and my little son Zuben is two and a half. They definitely love to produce art for their mom's office. It creates a changing new virtual background for me, which is always fun at work.

Holly Hester-Reilly:Yes. Yeah, that is fun. What has your experience been like going on this journey of a product executive while you've got young kids?

Navya Rehani Gupta:Definitely been a journey. I think journey is a great word to use in this context, but it's forced me to more ruthlessly prioritize my time. So definitely, definitely a positive. But I also realized that I've come a long way since I started this journey in five years. So just like product, understanding what your challenges are, seeing around what's working for other people, but then determining what works best for you. So creating your own vision and your own roadmap has been the story through all of this, but can't say enough about how the product thinking has helped me become a better mom.Many times I say the product management is a way of life, it's not a career, but there are many things in your day that you can now bring to your personal life. An example would be, I run planning exercises with my daughter to help prioritize what we are going to do on the weekends. So we'll take Post-it notes and we will create chart and say, "Hey, what do we want to do on a Saturday morning? Saturday afternoon?" And it forces her to think about trade-offs and prioritization. So I can't say enough about product being the winner here.

Holly Hester-Reilly:Yeah, that's fun. Okay, so the thing that's making me think of is I've run retrospectives with my family and my kids and we tried doing it once when my kids couldn't write yet. And so we had them draw pictures. And so I'm curious, how are you doing that prioritization with a five-year-old? Because she might not be writing much.

Navya Rehani Gupta:Yeah, it's definitely with pictures with my really, really bad drawings, I'm not as creative [inaudible 00:28:32]. Definitely with drawings or with, even now, she started to identify characters. So we would say something like Christmas tree and then we would put a C there and then she would know that's what we're talking about, going and seeing dancing Christmas trees, which we're actually going to go check out tonight. Really excited.

Holly Hester-Reilly:Dancing Christmas trees?

Navya Rehani Gupta:Yeah.

Holly Hester-Reilly:What?

Navya Rehani Gupta:I will know more today, but it's a special event in San Francisco tonight.

Holly Hester-Reilly:Oh, okay. Interesting. That sounds fun. I hope you have a great time. So what are some other lessons that you think our listeners would be interested in? In particular, I'm interested in anybody who's looking to make the transition into chief product officer position. What are some of the lessons that have helped you along that journey?

Navya Rehani Gupta:The key one would be around curiosity around every person in the company, understanding how performance is measured for a support rep, how performance is measured for somebody in marketing, and having that curiosity around what could make their jobs easier. And that's something that comes very naturally to product people. We're used to working with different teams, we're used to speaking their languages. But again, it was that transition around how can I help? Which I had to learn. I would typically show up to a meeting and give my updates. And now, I definitely listen more to what people are doing and then always thinking about how can product help. So that would be my lesson, that would be the tip that I would love to share with people who are trying to get to the C-suite. In addition, try to spend more time really understanding what the CFO, the CEO, the CRO, the CMO are actually talking about. Because a lot of times when you start to understand their day-to-day, you'll be in a much better position to be able to be an ally for them.

Holly Hester-Reilly:How does a person in that position learn more about the interests and challenges and outcomes that the people like the CFO care about?

Navya Rehani Gupta:Yeah. I mean, every company is different with different rituals. So at our company we definitely do monthly reviews with the entire company where each function will talk about their goals, their KPIs, their highlights and lowlights. So if you have avenues to get into either through a company meeting, but even shadowing the meetings of other teams. So product, in many ways, because of their cross-functional nature is pretty much welcomed by the rest of the company. So if you're able to go into the monthly sales meeting and just listen to understand what are we talking about, what is the CRO actually trying to get across to the entire team, what is the CMO trying to do. So more shadowing, more active listening would be the way to go here.

Holly Hester-Reilly:Yeah, it's a lot about listening and actually paying attention, right?

Navya Rehani Gupta:Yeah. I actually read this book recently [inaudible 00:31:14], Listen Like It Matters, and that's been a game changer for me.

Holly Hester-Reilly:Oh, cool. Tell me more about the book. What does it cover?

Navya Rehani Gupta:Yeah. This one actually helped me become a better listener both on a professional level and at a personal level with my kids as well. It goes through talking about active listening versus passive listening and things that we could do, even reminders that you can set for yourself. Every time that you're trying to listen, just so that you can make a point, stop yourself, stop yourself, and then think about what else is the person trying to say. It's about more about the discipline around learning to listen more actively as opposed to passively to see how you can interrupt and make your point.

Holly Hester-Reilly:Yeah, I think it's a much more modern book, but reminds me of one of my favorite books, which is How to Win Friends and Influence People, which I think the general message is actually care, which I think is so valuable. Sometimes in the business world, we don't always feel like that's what we're hearing from people around us.

Navya Rehani Gupta:Yeah, it's actually, Listen Like You Mean It. Sorry, I got the name slightly wrong.

Holly Hester-Reilly:Okay, got it. Listen Like You Mean It. Awesome. Well, I'm also curious to hear a little more about just like what stage is the company you're at at because we'd like to tell stories for our listeners about different stages of growth and things like that. So how big is the product team? Can you give us some sense of size?

Navya Rehani Gupta:Yeah, so we're a series C company. We've raised over $100 million. The last round was from Goldman Sachs and WestCap, and we have about 100 people in total in product and engineering and my org is about 25.

Holly Hester-Reilly:Awesome. How long have you been in the CPO role there?

Navya Rehani Gupta:I've been at the company six years now, time flies, and as a CPO for the last two years.

Holly Hester-Reilly:Awesome. And so how big was the company when you joined?

Navya Rehani Gupta:The company was about 50 people when I started and now it's north of 300.

Holly Hester-Reilly:Awesome. So you've seen a good chunk of the growth journey?

Navya Rehani Gupta:Yeah, it's been really fun to see the product side of things in addition to the business. So the product has evolved in these years from a product that was used by small businesses like walking tour in San Francisco and now we're seeing not only mid-market but enterprise level success. So top museums would be using our product on a day-to-day basis to run and grow their business.

Holly Hester-Reilly:Oh, very cool. And how have you been involved in or leading setting the product vision for the future?

Navya Rehani Gupta:That's a podcast on its own.

Holly Hester-Reilly:Yeah.

Navya Rehani Gupta:Let's say that I actually gave a talk around zooming out and zooming in and how product leaders can stay adaptable as they are thinking about two years ahead, but also at a sprint level because ultimately you're being asked to talk about where things are at today, but also have a long-term vision. So the way I've been able to do that is I've been very, very disciplined around where I spend my time. So I carve out time to four strategic thinking and I know that if I don't do that, I would be sucked into the day-to-day.So I carve about 30% of my time around strategic thinking. Another 30% is around driving alignment in the company, seeing how I can unblock my team. And then the remaining is around entering people management and hiring. So I would say that 30%, and again, I can't be like, "Oh, okay, now is my strategic thinking time, what do I want to think about?" I do upfront planning, similar to a roadmap planning process. So I set goals and strategic initiatives that I take on every quarter, and those are things that I drive independently to drive impact throughout the company.

Holly Hester-Reilly:Got it. And how do your team members contribute to those efforts?

Navya Rehani Gupta:Yeah. So I'm pretty transparent about my priorities. So I would spread the word in my team and talk about like, "Hey, these are the side projects that I'm taking on, so please loop me in, please send me your ideas." And then I continue to do 30, 60, 90 check-ins, which is when I'm about 30% done, I would share with my team my early thinking and then again at 60 and again at 90. So it gives regular checkpoints for people to be able to contribute to the direction that I'm working on.

Holly Hester-Reilly:Very cool. And what are some of your goals for the future?

Navya Rehani Gupta:Personal, professional, both?

Holly Hester-Reilly:Professional to start.

Navya Rehani Gupta:To my 30% time, I definitely want to find ways to drive greater impact. So I have some initiatives that I have mapped out, but I also want to get back to doing more of the listening tours in the company. That's something that I used to do quite regularly. So it was a quarterly cadence where I pick 25 people in the company, meet with them, hear about their challenges, but something that I've lost the discipline in the last year. So definitely want to continue focusing on the strategic side of things, but also to my point about listening, resuming my listening tours next year.

Holly Hester-Reilly:Yeah, that's awesome. I think listening is so valuable. What about personal goals?

Navya Rehani Gupta:Personal goals, I want to teach my daughter to write and it's such a struggle. I have the worst handwriting in the world and I want to make sure that she is writing better and she's not landing up like her mom. So that's an immediate Q1 goal for me.

Holly Hester-Reilly:Yeah, we always have some things that we hope our kids won't follow in our footsteps on, right?

Navya Rehani Gupta:Totally.

Holly Hester-Reilly:Yeah. Well, this has been really fun. It's been great talking to you. Do you have any other things that you feel like you wish you'd gotten a chance to say that we haven't covered?

Navya Rehani Gupta:No, this was actually, we covered a lot surprisingly. I'm available if anybody who's listening wants to dig in further to understand how the ROI model was built, how to work with the board members. I've definitely focused on that over the last few years, what it means to be a CPO. If there are topics that resonated that people want to dig deeper into, I would be happy to have a conversation. I can be reached via LinkedIn.

Holly Hester-Reilly:Okay, great. And is there anywhere else people can find you or just LinkedIn?

Navya Rehani Gupta:LinkedIn. I'm pretty good at it responding to LinkedIn messages.

Holly Hester-Reilly:Okay. You got it. Sounds great. We'll make sure that's in the show notes as well, so listeners can just click on that if they want to find you. Thank you so much for your time today, Navya. It's been a pleasure talking to you.

Navya Rehani Gupta:Thank you, Holly. Thanks for having me.

Holly Hester-Reilly:Hey, Holly here. I hope you enjoyed listening to this new episode as much as I enjoyed making it. I wanted to share with you that at H2R Product Science, we run lots of workshops and we'd love to have you join us. We teach the Product Science method, a step-by-step process for evaluating product opportunities and laying the foundations for high growth product development. We help product leaders and startup founders identify the right products and features to build and develop the support to do so. We do this at private workshops. We also do it at public workshops, both in person and online. If you'd like to learn more, check it out at h2rproductscience.com/workshops.The Product Science podcast is brought to you by H2R Product Science. We teach startup founders and product leaders how to use the Product Science method to discover the strongest product opportunities and lay the foundations for high growth products, teams, and businesses. Learn more at h2rproductscience.com. Enjoying this episode? Don't forget to subscribe so you don't miss next week's episode. I also encourage you to visit us at productsciencepodcast.com to sign up for more information and resources from me and our guests. If you like the show, a rating and review would be greatly appreciated. Thank you.

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