As a techie in Silicon Valley, you might often hear the line: “Fail fast, and break things.” It’s a common saying that illustrates the tech capital’s hungry lifestyle of “rise and grind,” but Square’s Rohini Pandhi thinks that saying could be decoupled a bit.
At Square, you’re dealing with someone’s money. “You’re dealing with the way that they get paid. Don’t break that. Do not break that for people, that is their lifeblood, the cashflow for their entire business,” Rohini explains. Tech companies nowadays have a lot of responsibility for people’s data and information, so breaking things shouldn’t be a value. Practice responsible innovation: fail fast, and don’t break things.
When I sat down with Rohini earlier this year, we discussed what qualities are important for product managers. Transparency is easily one of the top qualities because transparency breeds trust. Product managers interact with a wide range of people regularly so it’s important to prioritize clear communication about the product process. Otherwise, the job becomes so much more difficult when teamwork and collaboration are off the table.
Documentation is often a process that helps build clear transparency. As companies scale in size or experience rapid growth, documentation often helps the provide information that can be easily shared and consumed. Documentation also democratizes meetings because everyone is given a voice. It also forces people to write well-thought-out and reasoned explanations for their decisions.
In this episode, Rohini talks about Square’s “magic number” metric, time management, and her favorite product, an AI assistant that might help you coordinate your meetings, too.
I am now happy to share a lightly edited transcript of our conversation. Whether you prefer audio, or love reading, I hope you enjoy it!
Eric Boduch: Well, welcome, lovers of product. Today, joining me on the Product Love podcast is Rohini Pandhi. She does product currently at Square. Rohini, why don’t you give us a little bit of your background?
Rohini Pandhi: Sure, yeah. I started my career and kind of in the same way a lot of product people have started I think, as an engineer. And then after school I actually decided to become a tech consultant to get out of the code a little bit. I just really wanted to learn more about client management, business development, project management. I had a lot of fun just traveling all over the world, so consulting would seem like a pretty sweet gig. And then after that, I decided I wanted to go get my MBA, really just kind of learning more about that, “Business knowledge,” and getting classes in like finance and entrepreneurship, and just knowing more about that world was really exciting to me. Afterward, after I graduated from grad school, I then learned about this role called product management. It was this amazing mix of everything that I loved between tech and business, and so I started just dipping my toe into that role and now I’m at Square and I work on our Square Invoices product line.
E: Let’s chat a little bit about your experience in the product at companies of much different sizes. Right? So you’ve worked in your own startups, but you’ve also worked in larger companies. First, let’s talk a little bit about the startups. Talk to me about running product in those cases.
R: Yeah. I feel like a lot of us probably say the same thing as an answer to this of the scale, and I guess there’s a lot of different inputs into what the product role is. Scale is one of them, but it also depends on the industry you’re in, the company and its culture, the impact potential of your role, and then even just what that role needs at that time. There’s like a function of time and where you need to be putting more effort into. And so for me at startups, I think the role was a little bit of everything. It’s very focused on that breadth of what you’re doing, so one day could be into product marketing, one day could be with the sales team, one day could be with engineering trying to figure out a problem.
And as you grow, or as the company scales or you move into a larger company, I think the biggest change for me has been handling the communication as you increase in size. So communication is an N squared problem, right? Making sure everyone is kind of kept aware, aligned, and on track just becomes a more complex problem very quickly as you add more people to the mix. And so at scale or in the growth stage that I think Square is at, we handle that in a very Amazon-esque approach. We are a very documentation heavy culture and that’s really just to provide transparency across the org. It also, it was something new to me and something that I don’t think I really learned in the startup world because at a small company, I could just call in all hands and tell people what was going on. I can’t really do that at the size of Square, and so having documentation that can be easily shared and consumed is really important.
It also forces you as the author to write out well-thought-out, reasoned explanations to things, and this is something that I learned from our VP. It also allows for all voices to be heard, so it almost democratizes meetings in a way. It’s not just the loudest voice in the room or the ones that have the most senior titles. So I really appreciate having a kind of like group documentation that can be commented on and can be discussed by introverts as well as the extroverts and in a way that’s much more community and consensus-driven.
E: Now, are you an introvert or an extrovert?
R: I think I am an introvert in the sense that I do need some downtime to myself in order to recharge.
E: But at the same time you’re up on stage speaking at product conferences.
R: That’s true.
E: How do you reconcile that?
R: I think as a product manager, you almost have to be a little bit of both. Maybe I should say if you are an introvert, you have to almost force the extroversion in some sentences because you do have to have discussions with a broad team. You need to make sure that you can get everyone aligned and in the right direction. And so even though it’s not my nature, it’s still something that you learn how to do, and it’s not … It becomes less and less scary. I still get worried about getting up on stage. I still have those nerves, but the more you do it, the easier it becomes, or I’m hoping.
E: I definitely think that’s true. You talked a little bit about startups and public companies and how that’s affected how you allocate your time. Could you expound on that a little bit?
Where your time gets spent at a startup versus a public company like Square? I imagine it’s very different. I would expect, at least. But you tell me.
R: Yeah. I think the biggest difference is, again, just the size and the sheer number of people that you interact with. And so at a startup, some of my time would be spent actually wireframing and designing things myself, and handing that over and working with engineering, because we didn’t have a design team. At the size and scope of Square, we have specialists now, specialists in marketing, specialists in design, specialists in finance and analytics, and so I’m not writing these finance models anymore in my own spreadsheets, or I’m not doing the algorithms that kind of power any of our products. The specialists are really there because they know a lot more than I do. And so I think a lot of my time is more spent on the kind of working with those teams and ensuring we’re all communicating and heading in the right direction.
E: Do you find that is the challenge for people? Like when they have to move from being involved in a lot of different things to moving into a company now that as specialists for different areas? Is everyone able to make that jump and what should people do and think about to make that jump effectively? I don’t even say jump, but it’s just a big change.
R: Yeah, it is a big change. And I think it’s really about owning something yourself at a very small scale, versus having a broad team that challenges and brings in new ideas and perspectives to building something even better. And so I think it is difficult for some people to go from creating myself to allowing others to create, and influencing that creation but not actually doing it on your own. I think that the product role though is a role of like lifelong learners, and so you have to learn how to do each of those cross-functional roles yourself in some capacity, because otherwise, I wouldn’t be able to speak the same language as design if I’ve never wire-framed or designed something myself.
The same thing with if I’ve never been on the other end of a support call and taking the call, I can’t really talk to my support team in a way that makes sense to their day-to-day. Same thing with sales or business development, but at some point, you need to know that you’re only going to have breadth in those disciplines, and you might have depth in one or two, but you can’t really scale yourself into multiples that will have depth in every single one of those categories.
E: So talk to me about you personally. What did you like or dislike at the different stages?
R: I think at this small stage, it was really fun because you are trying to figure out your product market fit still, and there’s a sense of everyone’s kind of in it together. It’s a very lean and hungry team, and you just are fighting for survival, which is kind of fun at a startup scale of like a zero to one product or innovation needs to have specific types of team members to collaborate, and they all almost have to be breadth types of engineers or project managers or designers. They all need to be able to think about the customer and also the infrastructure, or the customer, and the visual design. The customer and the business metrics that we’re trying to pull together. And so I really love how quickly you can move to a smaller company, and you’re all going towards this goal of just finding that product market fit.
What I love about being at a company the size of Square now is there’s still that hunger and there’s still always this sense of you need to run as fast as you can, but also don’t break things as much. There is this, I guess, line that we tell ourselves in Silicon Valley of like fail fast and break things. I think those should be decoupled a little bit. When you’re a company like Square, you’re dealing with people’s money. You’re dealing with the way that they get paid. Don’t break that. Do not break that for people, that is their lifeblood, the cash flow for their entire business. If your building maybe, I don’t know, a dating app or something, you can break things and no one’s livelihoods will get affected maybe, but it’s a different ballgame almost. You’re really not just building for yourself, but you’ve already found that product market fit and there’s this sense of these customers depend on you now. Still innovate, still challenge, because there’s going to be new incumbents that want your business, but do it in a responsible way.
E: I think that’s a very good point. I mean you often hear the break things mantra in Silicon Valley, and it has to be applied judiciously to disrupting business models, but not breaking people’s financial systems first thing. Let’s chat a little bit about metrics.
E: What metrics are important to you in product and how have those metrics changed as the size of the company changes?
R: We pretty much have like these north star metrics that we keep an eye on at all times. If things start changing or shifting or trending in one direction or another with those metrics, we started digging into it some more. But I think our revenue equation is pretty simple and straightforward. We know what inputs affect our business and then we kind of double-click into each of those inputs in our formula to learn more about what’s going on. And so our process is kind of a series of looking at the very broad, high level, and then cutting into the narrow specifics.
And I’m looking back up again at the broad level to make sure that you’re gut checking and ensuring that you’re not blinding your perspective to some sort of limited view analysis and seeing a local inflection point instead of thinking about global maxima or minima that you’re trying to achieve. And from my experience, I think that kind of framework for metrics doesn’t change that much between company size. You bet high-level view coupled with the detailed granular perspective, but it just at larger companies or companies with multiple product lines, that analysis has a lot more input in things that might influence those numbers.
E: Now, do you have specific metrics you look at?
R: We do. I’m trying to think of what I’m allowed to share. And I think the things that aren’t going to be surprising are going to be the number of monthly active sellers we have on our system. We also look at our, “Magic number,” which is when do people start becoming active sellers on Square or Square invoices? What is it that kind of converts them from, “I’m just checking it out and I might,” to, “I’m going to use you now month over month, and unless something fundamentally changes in my business, this is the product that I want to continue using.”
And so I don’t know if I can share that specific metric, but it is something like Facebook had a blog article about like after you friend seven people, you become much more … The probability of you staying on the Facebook platform is much higher than you just churning and leaving. It’s probably the same with like Pinterest and the number of pins that you make. There’s probably an inflection point of as soon as you hit five or six pins on your local board, you’re going to be pinning as a lifelong Pinterest user. We kind of have the same thing where we’re pretty sure after a certain type of activity, you’re going to be on the product a little bit longer.
E: Yeah, absolutely. There’s like the tipping point in a lot of companies where you do these three things.
E: You know that you’re either going to buy the product or continue using the product or be a monthly user. So I think it’s important for any company to try to identify what those key activities are and then measure against that metric.
E: And that’s a metric that’s really specific company to the company, right?
E: And when you were doing startups, I’m sure you had a different metric for that same thing.
R: Yeah, absolutely. It’s going to change based on the size of your product and the type of product you have.
E: So you had this great example of experimentation metrics and UX analysis from an initiative you did at Square Invoice and you posted about. Can you share the details of that with us?
R: Yeah, yeah, absolutely. I think in the article you’re talking about, we designed an improved organized experience of our product that actually drove growth and conversions and we did nothing else to change like the core functionality of the product. It was simply just kind of reorganizing that user experience for our sellers. And it highlighted the fact that great design hides complexities of something big and confusing. For us, that is the ethos of Square, where we try to make payments and the complexity of payments very simple, elegant, approachable, understandable. And so yeah, it really just highlighted kind of what I was most proud of about that blog post. It really put together how engineering, analytics, design, and product work together, brought each of their strengths to the table in order to solve this problem for our sellers. I’m not sure if you want me to go into kind of the change that we made but if-
E: Sure, sure. That would be great.
R: Sure, so one of our core pieces of the product is when a merchant needs to create an invoice, they go into, if they’re on a desktop or laptop, they go into our web portal, our dashboard, and they can create an invoice by just simply putting in the buyer’s name, email address, what they’re invoicing for, the amount, and then hit send. The way that the form was originally set up was in this two-column design where you put in the name, email address, and then you kind of dart your eyes to the right and put in the additional messages. Then you have to dart your eyes again to the left, put in any items that you wanted, and then go across to the right again, put in your price and then all the way up to send the invoice. And what we realized was there are certain fields that were being used constantly, really just the required pieces of information. Everything else that was kind of optional was still in the form and embedded in this order and structure that we thought made sense, but was never used. Our data and our analytics team just kind of showed us that.
And so we took another look at it from a design perspective and said, “All right, how would we want this to work if we only needed the simplest pieces of information?” And just knowing kind of web design, we looked at like an F shape of you go from top to bottom, left to right, and the middle part of the screen has a little bit less left or right eye movement, and just rejigger the form a little bit from the visual styling, put the most important pieces of information at the top so that our sellers and merchants could look at it from top down to confirm that that invoice looks good to them and then hit send. And that alone just drove new invoices being created and sent and money being paid in a significant way.
E: I think that’s an awesome story about using data to think about visual design, how it affects someone’s job, and how you can make things just much better by optimizing things from a best practice standpoint.
R: Yeah, it was pretty cool. We all saw that there was maybe a problem. Data made it very clear to us. Engineering had some ideas as to how to now use that re-articulated form design to actually make the process even faster and then design worked on the visual elements of it. And it’s kind of the epitome of all of these disciplines coming together to solve this really cool problem.
E: So you talked about communications as companies grow, but even in the early days, calling a town hall when you wanted to talk to a larger group of people about some important issue. So let’s talk about that transparency. Why is that especially important for product managers?
R: Yeah, yeah. Transparency is incredibly important. I think the crux of it is really simple. It’s that transparency breeds trust and everyone on your team needs to be able to trust you. It’s honestly as simple as that. You are, as the product manager, leader, whatever it is, you’re going to be interacting with a huge group of people, people that are on your core team, people that are cross-functional, people outside of your company. And if you aren’t able to communicate clearly or be transparent about your process and where you are in that process, it just makes your job so much more difficult because now people may not trust you, people may go around you. There is just this element of teamwork and collaboration that will go missing.
E: So I think that’s very important. That teamwork and collaboration need to be there, and transparency instills that. Now you’ve been at Square for two-plus years, so a lot of things have changed there over that time. I mean the company has a huge growth rate. What have you learned from seeing that company growth and the change over that time span?
R: Yeah, it’s been a really fun time to be at Square. I think I keep learning from everyone here, honestly. In these two plus years, I feel like I am constantly learning new things. I play a little bit of tennis, and I always make the analogy of you always want to play with someone just a little bit better than you. If I play with Serena, that would be really fun for me. It would not be fun for her, but it wouldn’t be a great game because I would just …It would be a terrible outcome.
E: Yeah, and you probably wouldn’t learn very much from it. I mean it would just be you going and picking up the ball.
R: Exactly. So if you’re playing with somebody just a little bit better, it challenges you to be at that new level. And I feel like that are the type of people that we have at Square. And so they, from any sort of role, any part of the company, it always kind of forces you to be better. And I think the biggest learning that I’ve seen is from our senior leadership and how open they are to getting feedback from the company, how flexible they are in kind of having strong opinions, but being open to changing those opinions if they learn something new, if they see some new direction that we should be going in, and also leading by example. And none of them have offices, they all just sit with us in our open space and we can go up to any one of them, talk to them, ask them questions, and I love the ability to not worry about what’s happening behind closed doors.
E: Great. So talk to me about the direction of the craft of product management.
What trends do you see in the next few years?
R: You know, actually I saw something recently on your blog post that piqued my interest. On Pendo’s blog post, the idea of separating the concept of a product owner and an agile world from the product manager and how those responsibilities are starting to shift and become more specialized I guess as companies grow. So I might even throw this back at you. What I love to kind of hear more about how, since Pendo brought it up, how you’re thinking about the product owner versus product manager debate.
E: I do think that’s interesting. I mean, not just from a Pendo perspective, but in general. There’s oftentimes that people try to push that all together. I was talking with an expert in the field the other day and he was talking about how like some people think of product management as a development manager. And that’s not what a product manager should be. A product manager needs to be that person that’s that communicator between the customer and sales and the development team. It needs to be the person that understands the market, has empathy with the customers.
And I think when you separate those roles out and a product manager and a product owner, you can have more of that internal focus on the product owner’s standpoint, where they’re working more in a detailed fashion with the development team. And then the product manager can be more externally focused too. So he doesn’t get kind of pigeonholed into that, “Oh yeah, I never leave the office because I have to be doing this stuff with the developers on a day in day out basis.” So I mean I would say that’s the short answer to that.
R: Yeah, I agree with you. I think when you’re maybe at the startup, or the smaller scale, you’re doing a little bit of all of that because you don’t have enough people to specialize. But as the product discipline kind of becomes more formulated, and we all agree on what that encompasses in terms of roles and responsibilities, and companies start growing and needing those specializations, to me that is going to be an interesting separation of responsibility.
E: Yeah. And would say at a small company, if they’re separated on your calendar so to speak, like you have to physically change that hat and carve out that time, because otherwise one of the two areas could just subsume all of your time, so it’s hard to get that balance.
R: Yeah, I think that kind of reminds me of like the maker’s schedule, manager’s schedule from Paul Graham of YC. And like you’re wearing both of those hats at all times and so it’s probably not going to work out at scale.
E: Yeah, absolutely. It definitely won’t work out at scale. Let’s turn this back to you a little bit. Talk to me about your favorite software product and why it’s your favorite.
R: So I love this question. I think I asked it almost in every product interview. Whenever I’m talking to a product manager candidate. And whenever I get asked this question, I try to think of something new. So I hope I haven’t said this answer before, but there is this company called X.AI, or the product is X.AI. And what they do is they allow you to carbon copy on emails an AI bot that helps you schedule meetings. And it has been a lifesaver for me. Instead of me going in, you know when you get those emails of, “Can we meet for coffee next week?” Or, “Can I talk to you about this for 30 minutes?” And I have to go through my calendar and say “Okay, here are the things that are open for me. What times fit for you?” And then there’s this series of back and forth email messages. And now, I just CC Andrew, who is my AI assistant, and Andrew now takes all of that back and forth offline, away from me, and then just sends me a calendar invite when we’ve decided on a date that is open on my calendar.
E Awesome, awesome.
R: It’s pretty cool.
E: So talk to me about words of wisdom that you would impart to others in product leadership.
R: That is a great question. I think … I don’t know if I have any words of wisdom. It’s something that I feel like the PMO has always been this balance of art and science, and so the thing that I will say is there’s pieces that you can learn about product management, and that’s more of the science part and how to do the things that we do day to day. But I think the other piece is on the more soft skills and really what I feel like I’ve learned the most is how important the people on your team are. Having a strong team is a rare and crucial advantage. So invest in the people around you, treat them with respect, learn from them, and come in every day as a student. And I think that’s what I try to do every day. And so in terms of, “Words of wisdom,” that’s probably all I can impart.
E: I think that’s great. And so one final question for you, which I ask of all my guests. Three words to describe yourself?
R: Okay. I like these. So I’d say collaborative. I think like we talked about, I’m a bit of an introvert, so I can tell when there are voices in the room that I’m not hearing. And so I try to be as inclusive and ask for feedback directly as possible. Inquisitive because the PM position is a role that requires constant learning and that’s my favorite thing about this job. And the third word is probably flexible. One of my favorite phrases is to have strong beliefs held loosely, so being open to changes in direction as new information comes in, or as situations become more or less ambiguous, it’s a skill that I think I picked up from the startup world, but it’s been incredibly helpful to me when building all sorts of products and working with different teams.
E: Awesome. Well this has been fun. Thank you, Rohini.
R: Thank you. This is fantastic.