In today's episode, Grant Duncan speaks with Navya Rehani Gupta, the Chief Product Officer at Peek, a Series C startup offering booking software for experiences. She has worked in Product at Uber, Disney, Goldman Sachs, and StyleSeat. She also has Masters degrees from Stanford and NYU. Her answer to the toughest product decision is one of our favorites yet! Let’s jump into it.



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Grant Duncan (00:05):

This is the Product Management Leaders Podcast in which you hear from some of the top PM leaders about their real world strategies and tactics for building world class products. It's sponsored by Voximplant, the leading serverless communications platform and no-code drag and drop contact center solution. Voximplant enables product leaders and developers to integrate communications into their products such as embedding voice, video, SMS, in-app chat and natural language processing. Join over 30,000 businesses trusting Voximplant. Now, let's jump into the show.

Grant Duncan (00:41):

Hey, there. It's Grant Duncan. I spoke with Navya Rehani Gupta, the Chief Product Officer at Peek, a Series C startup offering booking software for experiences. She has worked in Product at Uber, Disney, Goldman Sachs, and StyleSeat. She also has Masters degrees from Stanford and NYU. Her answer to the toughest product decision is one of our favorites yet! So, let's jump into it.

Hi, Navya. Great to have you on the Product Management Leaders Podcast today. To start, can you give a quick intro to everyone about yourself?

Navya Rehani (01:19):

Yeah, thanks for having me. I'm Navya. I'm the Chief Product Officer at Peek helps you connect the world through experiences. We have a marketplace to help people like you and me find fun things to do. And our primary focus is our business software that helps tours and activity operators run and grow their business. My background is in engineering and I moved very, very quickly to the product side and have done product for about 15 years in big companies, small companies, Wall Street. I worked for Mickey Mouse for a bit. That was a lot of fun. And then across different verticals like transportation at Uber and then beauty at StyleSeat and now in travel.

Grant Duncan (02:06):

Awesome. Thanks for sharing that background about yourself. And can you tell about your team structure and size at Peek?

Navya Rehani (02:14):

Yeah. So I'm currently responsible for product management, design and product analytics. My team is about 15 people. We're adding about 10 more, as we speak, so continuing to grow. The structure, we used to have a fairly lean team and work as... it's a couple of engineers, so it's working very closely with a couple of designers and PMs, but very, very recently we introduced pods. So, we have three pods right now. One that's very much focused on the sales side. The other one is on the retention side. And then the third one is around payments and expansion.

Grant Duncan (02:52):

So, I think pods are becoming much more popular in product management now. Can you talk about why you made that change?

Navya Rehani (02:59):

Yeah. So, having worked in many different companies, I actually had a very positive experience working with pods. I remember when I was at Uber, when I was there, that was the time that pods were actually getting introduced for the first time at Uber and it was a game changer to have cross-functional team members all focused on a primary mission. It changed how we operated, it elevated all our processes. I've seen that work in many other companies as well, but I've also seen pods not work when the teams are too small. So, we are finally at that stage, at Peek, where we felt like we had enough bodies to actually drive focus in the team, and that's why we chose the pod model.

Grant Duncan (03:44):

What do you feel like is that switch? Is it around that 10 or 15-person level that's worth switching to pods?

Navya Rehani (03:52):

It is definitely the team size, but it also has to do with the business priorities. So, ultimately, do you want multiple lanes of work to happen at the same time or is everybody just focused on one thing? So, it has to start from the business goals. Then, of course, you have to think about the team size and then you have to think about specialization as well, right? You have to think about how you can minimize the overlap between the various pods so that they can actually be independent.

Grant Duncan (04:27):

And how did you decide the grouping for the pods and their focus?

Navya Rehani (04:30):

Again, it was driven through the business. So, ultimately, we raised our Series C last year, $80 million. And coming out of that exercise, we planned for the business, everything we want to achieve in the next two years. So looking first at the business goals, I came up with product goals and rough product areas of focus, and that helped me decide those specific three pods.

Grant Duncan (04:55):

So, can you talk a little bit more about the business behind the build?

Navya Rehani (05:01):

Yeah. So that's a topic I feel very passionate about because as product management, product managers, there's so much good material about perfecting your product management skills, on the execution side, how to be more strategic. But there's not a lot of good material around developing that business acumen. So, for me, especially as becoming a Chief Product Officer, that switch from VP to CPO was very much driven around building my business acumen. And what that meant was being at the executive table and actually understanding my peers, what are they accountable for? What keeps them up at night? How are they making their decisions? And that has helped me inform my product management team on how to build, maximize their impact and make the right business calls as part of all the build decisions.

Grant Duncan (05:57):

That's very cool. And was going from VP of product to CPO something that you advocated for? How did that go about?

Navya Rehani (06:07):

Yeah, I'd say that it was definitely aligned with my career goals and where I wanted to take my career. CPO is a fairly new role in the industry. So, after I developed the understanding of a CPO role, I knew that's something that I wanted. But, having said that, the company has to be ready for that transition as well. The company should be at a scale to be able to bring in C-level executives. So, the timing worked out both from my interest and the company being ready and all the stars aligned last year.

Grant Duncan (06:42):

Do you feel like there's a difference in how you interact with peers or your team based on that?

Navya Rehani (06:50):

So, in many ways, you have to be doing the job already before you get the promotion. So, has anything changed in the last year? Probably not. But leading up to it, I would say the last two, three years, I've been focusing more and more on the business side and having that holistic view of the entire company. And even from a customer perspective, understanding their business models, understanding what drives growth and profitability for our customers. And I would say that's definitely been a switch of thinking and a mindset over the last three years.

Grant Duncan (07:28):

How do you encourage your team to develop that kind of business acumen as well?

Navya Rehani (07:34):

Yeah. So one thing I religiously do is, as part of any executive conversation, I'm always thinking about, how can product help? And then also how to bring this right context to the product management team. So, I religiously share with the PMs, overshare on all the executive level conversations, because they're so cross-functional. They're working with my peers directly and they need to understand what's keeping my peers up at night as well. So, the answer to your question is oversharing and providing as much perspective as possible. And that goes a long way, because then my PMs are able to drive bottom-up recommendations thoughtfully because they have the full picture on the business and are not just constrained from the knowledge that's buttoned down to them.

Grant Duncan (08:29):

Yeah, I think that's so true. And I think when you share frequently or even overshare, I think it also builds trust within your team that you are their advocate when they're not around and that you're helping keep them informed, so that's great. You mentioned having recently raised a Series C round. When you're at that point and even before and after, growth and speed is so important in startups, how do you think about moving quickly and making decisions while still having confidence about them?

Navya Rehani (09:08):

Yeah. So moving fast with confidence and making fast decisions is something that we talk about quite a bit in our team. We are a high-growth startup and are looking at new obstacles every day just like any other high-growth startup would. So, for that, what's most important is to have frameworks around decision making. So, what we religiously use is a framework that we call RAPIDs. For every big decision, we determine who is the person who's actually driving the recommendation because if you're not clear as to who's the one person responsible for it, then you have too many cooks without one person being the advocate. So, it's really, really important to know who's driving the recommendation, who actually is responsible for providing input and who is an approver. And it's quite different there.

Navya Rehani (10:06):

So, many a times, people think that they have the approval authority, but it's sometimes not true, right? So, you have to limit the number of approvers to move fast, get inputs from the right people at the right time. And then there has to be one decision maker and somebody who has the veto power if the approvers don't agree. So, defining, upfront, who is the decision maker, and then, finally, who are we sharing this information with? After you've made the decision, let's, upfront, think about who could be impacted and would need to know. So, it goes a long way and before making any decision, defining all the RAPIDs, and it helps us to move effectively and with confidence.

Grant Duncan (10:54):

Yeah. That's great. It reminds me of the RACI framework.

Navya Rehani (10:58):

Yeah. Every new person that we bring in, they bring up RACI and we talk about how RAPIDs has been adapted by Peek.

Grant Duncan (11:08):

Okay. And when you're thinking about your product investments, how do you balance investing in new innovation and maybe even a new TAM to go after versus incremental improvements on existing products for, let's say, your existing TAM?

Navya Rehani (11:29):

Yeah. It's actually top of mind for us right now. We're planning or doing a quarterly roadmap planning for Q2 and exactly thinking through that question, which is new TAM or existing TAM and the trade-offs involved. So, the framework that I use here is I sit down with our ELT, the executive team, and determine what that split of investments should be for the R&D team and come up with high-level, top-down goals that my product managers can use. So, with that split, it is very clear then with the executive team where we should focus on. And depending on our business goals, that split could be 80/20 or 50/50.

Navya Rehani (12:15):

So, getting that alignment upfront with the executive team is really important. Having said that, on a day-to-day basis, as we're making decisions, we do always prioritize our existing customers over a new sales opportunity because you've already invested in bringing a customer. Retention is cheaper than acquisition. So, on a day-to-day, as we are doing our ROI calculations, we always put a higher multiplier for an existing customer.

Grant Duncan (12:47):

Yeah. Retention is so key and, I think, often forgotten, so that's super good. What metrics are you looking at and tracking most?

Navya Rehani (12:59):

Yeah, there are tons of them, but if I had to pick one that I hold our teams accountable to, the one that I talk to the boards about is how it's the overall revenue impact that product is driving. And it's a very, very hard question to fully answer, because, ultimately, product is building for the long-term. And it's hard to know what's actually driving revenue, if the product is selling itself, how much of that is because of new innovation versus the innovation that's happened over the last 10 years. But still maintaining that discipline around measuring revenue impact as it comes to all our features that are being adopted, new features that are being built, has kept us all focused on the metric that matters for the company.

Grant Duncan (13:48):

And when requests come in from customers, are you tagging that in some way so that you could say like, "Building this will bring us X revenue," and combine those?

Navya Rehani (14:04):

Exactly. Yeah. So, every single request gets tagged in our internal system so that we can tie revenue with every feature. And that applies to every conversation that our sales rep could be having. So, we're able to measure if we're losing a deal because of a feature, we're able to measure what actually helped us close the deal. We also measure what our current partners are asking for, customers are asking for. And we also know the severity of their ask, so we know whether it's a really important request, it's a blocker, a want or a need.

Grant Duncan (14:41):

And, let's say you have 20, well, you probably have a lot more of those to evaluate at once, who gets to vote on the priority there and decide which to do? Is it primarily the product team or are other teams vocalizing their top request as well?

Navya Rehani (15:07):

It's very much a collaboration. So, the product management team works with every other team in the company to align on their product needs, right. And we do it both in a quantitative manner where we're able to say, "Here's what the product team has heard from our feedback repository." And then we have that qualitative conversation where each team gets to talk about their top 10 strategic priorities. So, it's very much a collaboration that happens with every single team and that all comes together as part of the roadmap planning process. Of course, a big part of that puzzle is engineering feasibility, right? And so something could be really high up on the list, which is why the partnership with engineering is really important to understand what we can deliver and the time that we have, and can we really be time driven or can we be scope driven in every sprint?

Grant Duncan (16:06):

Yeah. Tell me more about how you partner with engineering. You were starting to mention it there.

Navya Rehani (16:11):

Yeah. So, Peek's really interesting, and I can't take credit for this because this was something our CTO did from day one, is we called the product team as product management, design, analytics, and engineering. So, engineers are actually part of the product team. I don't meet with just the PMs. We actually meet all together, once a week, where we talk about everything that's important for the product. And that could be technical demos, it could be customer insights, it could be big strategic decisions that we're making as a business. But the reason why I've held off in making a PM meeting is because our engineers are so product minded and they are part of the product team. So, every time I want to share something with the PMs, it actually seems redundant because it should be something that engineers should also hear about.

Navya Rehani (17:08):

So, that's kind of a long way and having a very strong partnership. So to answer the question, how do you develop that partnership? It's basically partner, partner, partner, and we're all the product team. Having said that, a few other tactics are always thinking about how to drive engineering productivity, not setting up meetings for no reason, really working and adapting your style to make the engineers most productive. And then the second tip there would be to always share customer insights and to bring those wins to the engineering team. Everybody works really, really hard to launch features and it's the product management team's responsibility to come back and actually share the impact that we're making to the business.

Grant Duncan (17:59):

Yeah, that's great. And, I think, having engineers caring about the products goes a long way and is even motivating for them in their work.

Navya Rehani (18:12):

Totally. Feel quite fortunate to have that in our team.

Grant Duncan (18:18):

Yeah, that's great. So, can you share about one of the hardest product decisions you've had to make in your career?

Navya Rehani (18:25):

Yeah. So, this one was really tough, probably far more gray hairs than I would've liked. So, this one was a few years ago at Peek as we were evolving a software from an SMB focus to mid-market, so what that means is bigger customers who are not just walking tours. So, SMB could be a simple walking tour that sees 10 or 20 clients versus a mid-market would be a complex operation like a state park that is getting thousands and thousands of customers on a weekend. So, as we were making that switch, what became very clear as a business, but also as a product, is that we weren't ready until we completely rearchitected our entire product. So, we made a very bold decision to go get into that journey and it's almost because we didn't have a choice. We had to. We knew it's going to be hard, but it turned out to be even harder than expected.

Navya Rehani (19:29):

We initially thought, "This is going to take us something like four to six months." And it ended up taking us two or two and a half years. So, it was a massive investment and it was a hard decision to continue on that path. So, once we started developing, the more we looked, the more bodies we found and ended up redoing every single feature from the ground up. And then it didn't end there. What we found was that the go-to market is not going to be really simple. So, we had to migrate every single customer one by one to the new system, educate them on the new offering. So, it took two and a half years, but it has positioned us in a way that we have the best in-class product in the industry. As we continue to grow our business and expand internationally, we have the infrastructure that is scaling with the business.

Grant Duncan (20:33):

Yeah. That is definitely a tough journey to go on. I've been through a similar one and it is a grueling process. When you were in the midst of that, were you still building new features on the new product or platform or was it fully focused on just the upgrade and migration?

Navya Rehani (20:58):

Primary, so 80% focus was on the new software and then the remaining was to keep the lights on. So, we tried not to build redundant features that wouldn't make any sense in the new system, which made the product management job really, really hard. So, for about two years, we said, "No." Everything, just the answer was a default, "No." It made it hard for the product management team. It made it hard for our support, our success, our sales teams as well, because, ultimately, they were on the front lines with customers selling this vision of how amazing the new software would be. So, definitely, definitely a tough journey for everybody involved, but we got there.

Grant Duncan (21:44):

Yeah. It's very nice to be on the other side, I'm sure.

Navya Rehani (21:48):


Grant Duncan (21:49):

How long did the migration process take or is that part of the two years you were talking about?

Navya Rehani (21:56):

It's part of the two and a half. So, roughly about, actually more than a year. Yeah.

Grant Duncan (22:03):

Got it. Yeah. I'm sure all those snowflakes, as well, made it even tougher to migrate, at least that was the case for me in the past.

Navya Rehani (22:12):

Got it. No, our problems were created by our own selves, so can't blame anybody else.

Grant Duncan (22:21):

That's funny. And did you have support for doing this, it sounds like probably all the way up to the board?

Navya Rehani (22:31):

Yeah, definitely. And we, as a business, were aligned on the direction and we, upfront, talked about it. At the executive level, what was obviously hard was explaining why something is not taking the time that we expected it to. So, it was constant communication on the executive level and to the board about our low lights in that process, but constantly also selling the vision of what the new software would enable for the business.

Grant Duncan (23:02):

Do you have any advice for people in presenting to the board, in general?

Navya Rehani (23:08):

Yes, definitely. I have a good blog that I can share. It's by Shelley Perry. She wrote this blog called How Can Product Leaders Wow Board Members, and that was a game changer for me. I implemented what I found in the blog and went from a board meeting that was very, very raw and dry to starting to have meetings where there was active interest from the investors. So, some of the key takeaways from that blog were around not getting too deep into features, but giving a very high level overview on what we're doing and why that matters, because from an investor point of view, what they want to know is, is there more product to be built or can the engineers go home? So they want to know, can we just add sales people and do we actually need to continue investing in the product? They want to know about new TAM versus existing TAM.

Navya Rehani (24:09):

They want to know how much we're investing on the infrastructure side. Are we constantly fighting fires and just keeping the lights on? So that kind of split, upfront, in a board conversation has been exceptionally helpful, so focusing on that. And then I try to always do a demo, if possible, because it's always nice for the board to actually see the entire experience, the customer experience, our software experience, so that's always made it fun and it's changed how those meetings happen, so now they're very, very collaborative. And over the last few years it's been, we go into these conversations, our board is always coming in prepared with ideas to help us, which has been instrumental to work in.

Grant Duncan (24:52):

That's huge.

Navya Rehani (24:53):


Grant Duncan (24:55):

That's great. I think a lot of people will probably be looking at that article.

Navya Rehani (25:01):

I highly recommend it.

Grant Duncan (25:03):

So what's the pie chart of your time or your day look like on an average day or week?

Navya Rehani (25:12):

Yeah. So, I do have a color coded calendar and I measure the split of my time. I set goals for that split, upfront, as well as part of my own roadmap planning, my personal roadmap planning as well. So, it's typically around 30% on strategic initiatives that I can drive myself. So, not my team, not the engineering team, but what I individually can do. I come up with those upfront. I ensure there's alignment, that, that's actually a good focus of my time.

Navya Rehani (25:46):

So, I work with the executive team on that. I set those goals for the quarterly level and actually make time for that investment, so that's about 30%. 30% is around alignment and the product roadmap, product strategy, constantly working with my peers and cross functionally. 30% is the team. Coaching my team, helping them achieve their career milestones, unblocking them. And then 10% is typically the hot topic for the week. It could be anywhere I could zoom in, whether it's looking at metrics, whether it's doing deep dives. But there's typically a 10-person scenario where it's a new story every week.

Grant Duncan (26:35):

Yeah. Great. And how did you come up with those percentages, just trial and error?

Navya Rehani (26:36):

No. As product people, we can get very, very execution oriented and it's easy for us to just constantly zoom in, and it was one of my personal goals to change that. So, I wanted to make time to zoom out and when I started on this journey, I did my analysis and found that I just didn't have room for strategic initiatives and that became a goal for myself. So, that's how I set the goal where I knew that I wanted to spend at least 30%. And by trial and error, I would say that I got to 30% and then I realized that it's something that I need to sustain, right. So, it became important for me to constantly keep that. And I say, "Are you running your life or is the life running you?" It's actually quite true because you have to make time and the right time investment can be game changing for yourself and for the company.

Grant Duncan (27:39):

Yeah. I think that's totally true. And the discipline part is important there to actually keep it up.

Navya Rehani (27:45):

That's right.

Grant Duncan (27:47):

Do you block times that can't have meetings?

Navya Rehani (27:51):

I do. Yeah. And I am very transparent, my calendar is available to everybody in the company. They can see where I'm spending my time. So, I specifically mark out those blocks, but I also call out the initiative. So, when my team needs me, they can make a decision to interrupt me or book over that time because they can decide themselves if what they need me for is more important.

Grant Duncan (29:31):

Yeah. Great insights. What sources or communities do you use to continue learning?

Navya Rehani (29:38):

I love LinkedIn. I have, over the last year, I have been expanding my network. So, I used to only connect with people that I knew, but I've changed that and now I follow thought leaders, I connect with fellow executives. And that has changed, the content that I get is now dramatically different. So, it's become my source to learn because of the thought leadership that I follow.

Grant Duncan (30:07):

Yeah. That's a great insight. I actually made that shift as well in allowing people that I don't personally know to be connected with and I've found value from it as well. So, if I gave you a magic wand and you could change one product management problem, what would you do?

Navya Rehani (30:26):

What would I do? So, I think about this quite a lot. I don't have a good solution, so a magic wand would be great for this. So, we know that product managers want to keep continuing to get better, evolving their own skills, evolving the processes. But what we don't have is an easy way to look at learnings across the various PM teams, right. There isn't an easy... If you know of a product called BetterApp, it's a coaching product. But we don't have a BetterApp for product management. And if there was an easy way, so that my magic wand would be, an easy way to say, "Here is the best way to expedite your discovery. Here is the best tool that actually drives value." There's so many product management tools out there and an easy way to be able to know the opportunities, to optimize your processes, these are all the things that... I don't think it's a solved problem, so if you have a solution, I would love to know about that.

Grant Duncan (31:37):

Well, a very small effort is this podcast and trying to collate those insights, but I definitely don't think we're going to solve it completely with this.

Navya Rehani (31:48):

Yeah. This is a great start.

Grant Duncan (32:56):

Very cool. Is there anything else that you'd like to share with listeners before we wrap up here?

Navya Rehani (33:03):

I would love to go back to your magic wand problem and say, "Let's continue to solve that." Product management is obviously at the forefront of the future, and with great power, comes great responsibility. So, let's continue to elevate each other through this process while we continue to change the world for the better.

Grant Duncan (33:26):

Awesome. Well, thanks for coming on, Navya. I appreciate it. Have a good day.

Navya Rehani (33:30):

Yeah. Thank you for your time.

Grant Duncan (33:33):

Thanks for listening to today's podcast, and thanks to our sponsor, Voximplant, as well. If you are looking into how to improve your communication and customer engagement, check them out. Lastly, if you enjoyed this episode, please leave us a review and tell your friends so that others can find it more easily. Have a great day and feel free to reach out to me, Grant Duncan, if you have any questions you want asked in our next episode.