Following Curiosity and Learning On-The-Go by Twilio General Manager

In this episode of the Product Podcast, Twilio VP & GM Jodi Alperstein talks about following curiosity and learning on the go.

“How did you get your first PM job?”

That first PM job is so exciting. And how do you get into it? How do you get there?

For me personally, I stumbled into it. I didn’t know what it was at the time I joined E-Trade back in…well, I’m not going to say when, you can find out on LinkedIn. But a while ago. And I came in to do strategic development, actually a mentor of mine brought me in and I was buying companies. I think I had been there for a month and the CEO said, have you bought anything yet? I’m like next week, next week. And you know, did that for about a year. And then we determined that we didn’t really need that department anymore.

So I found myself on a hunt for a job, and I wound up working for the Chief Product Officer kind of almost like a chief of staff, but not quite my role was to put in a product prioritization process for all of E-Trade, because we hadn’t really been doing it formally. It was more who you knew, it’s how you things funded (back then, I’m sure have changed).

And so that’s what I did at first across the entire organization put in this prioritization framework, and then I also worked on the steering committee for a new redesign of the entire website, which was very, very, very large and it involved every single Product Manager and I had never done Product before. I was working with every single one of them.

And that’s when it clicked to me, this is the job I want. All these other things I had to kind of do on in my career, that wasn’t right. And from there I went in and after a year of supporting her, did the Product Management role and rose up through the ranks and ended my career at E-Trade after eight years as a Senior Director and having done quite a few different roles at the time. It was a great experience, great place to learn the craft of Product Management.

“I find that really cool because you didn’t know what Product Management was, you just said yes to a challenge and suddenly you discovered that that was for you.”

Exactly. It was really neat, and I’ve been essentially doing it ever since. So it’s been a while.

“Was there was a Chief Product Officer when you were there?”

That’s right.

“That role is becoming more and more popular these days. I think the last time I checked, it was around one third of the Fortune 500 companies that have that role. And I I’m sure it’s going to become more popular. But how was having a Chief Officer when Product wasn’t cool?”

This was the early two thousands, I think E-Trade was ahead of this head of the game on a lot of different things. They were extremely innovative. She was really responsible for not only product but content as well. And it was pretty critical. It was the digital product.

E-Trade was one of the first financial services companies that really translated their product to the internet, coming out in the early in the nineties with it. They were transformative into what is digital Product Management versus say a financial Product Manager who’s managing the credit or something like that. And it was great. It was a great opportunity.

She was very inspirational and really helped a lot of people understand what the, what the role is and, and what it was we needed to do in order to drive impact for our customers and for the business.

“So I’m looking at your formal education, right? It says you have a BA in Psychology. So how does a psychologist end up leading Product?”

I know, it’s so funny. Things are different today than they were back in the day. There was no Product School. You learned how to do it as you went. And so I had an even more bizarre early career that I won’t get into, but I think for me, it was really about using just my smarts and learning as I went and being willing to follow the curiosity and do what needed to get done. I don’t have formal training in this.

“You’ve been successful in Product across many different industries. Right. Is there any type of connection? How do you go about switching industries?”

Yeah, it’s, it’s, it’s another great question about how to switch industries or how to, how to you is grow. And I, I think it’s about being, being curious, being open to learning. I, I do think one of my personal superpowers is understanding context very broadly and knowing when to go deep. And there are definitely roles where having the at deep domain expertise really matters. But in many cases, the skills of Product Management I think are FA fairly transferable. And so, and certainly when I’m recruiting for people, I am looking at a pretty diverse team that I want to hire Product Management. And from my experience, it is that cross section between the user business and technology. And there’s not one path to get here. And I, I don’t know if you’ve ever seen this diagram. It’s basically just a triangle equilateral triangle, and kind of that perfect Product Manager is so well rounded that they sit right in the middle of that equilateral triangle.

And they have experience from all of those different areas. Most of us come from one or the other me, I’m a little bit more business, user oriented versus technology engineering oriented, but you can come from any angle and you use your strengths to continue to grow and develop lean in. And that’s you, that’s that motivation that you’re going to get better in the things that you’re better at. You should work on the things you need to develop as well. But and I, and I think if you have that curiosity and that willingness to learn, and somebody willing to give you a chance, you can just jump into it and make it happen.

“You’re at Twilio / Segment, a public company. Twilio recently acquired Segment for 3.2 billion. What is your day to day like now with another public company, with a lot of people that are part of your product team?”

Yeah. Yeah. So in terms of a day to day and, and you’re right, it really, there is some differences between being at a public company versus early startups. And, and as you mentioned, you know, E-Trade, I was also at, at, at Moody’s for a long time. And then these last six years at a number of startups, and I, I would say certain things are very much the same, no matter where I’ve worked and that is start your day. Or I start my day with the daily dashboard, I am looking at the numbers. I’d like to be very data driven, customer driven and data driven in understanding what’s what’s happening. So I look at that and make sure things are on track. See if anything’s glitchy and, you know, sometimes things happen. You want to be able to address that right away or there’s any new trends coming up. And then honestly, for me, what I’m doing today, I, I, I say my, my job is meetings most of the time. I’m either meeting with my direct team. I’m meeting with one on ones I’m meeting with other executives. I’m meeting with customers, literally, that’s what I do for a living I meet. So,

“I’m glad you were so upfront with that because it’s true. It’s not for everybody. There are a lot of people who really like to just stay there in the front line and build, which is something that I miss a lot. I also spend a lot of time meeting. In leadership roles, you probably spend more time empowering others who are building.”

Absolutely. Your job as a leader, I think is to empower and you need to set that context. You need to set the vision and you need to then give them that space to go and run. You know, that it’s really, really central. I also think one of the things that’s been really great over the last, I don’t know how many years now, but a trend where there’s not just one way to get ahead in Product Management. It doesn’t just need to be managing others to your point. Not everybody likes that part of the work. Some people want to be a Product Manager, you know, proper at a very, very senior level. And we’re seeing that happen now at the same way that it happens for engineers being able to go the architect route, or, you know, the designers who want to be a chief designer versus managing the entire design org. You can do the same thing in Product Management today and, and decide which, which path you want to be on.

“That is so great. When I started Product School, people would come to us like, I want to be a Product Manager at company. Okay. Imagine if you actually get the job, then what? You’re just starting your journey. It’s good to see that there are so many different options. You can grow as an individual contributor. You can grow as a people manager. There is no right or wrong answer.”

That’s, that’s true. I will say, I do believe in Product Management, maybe, maybe in every roles, but maybe more so than in others in even at the senior levels, you are expected to do more than just manage and mentor, right? The strategy sits with you. The accountability for the execution sits with you. The responsibility for a P and L often sits with you. Not always some, some orgs, the PNL is not in product. And so you need to be enough in the weeds with what’s happening and helping to direct that strategy, but not micromanaging it again, getting to that context and, and setting the open end. So even people who go the management route my, my leaders who report to me in product, they are very much not only managing individual dual Product Managers, they are doing a lot of the strategy work themselves.

“What are the key skills that help you go from being a great individual contributor to being a great VP of Product?”

Yeah. So that’s a great question in terms of the skills that help you go from being great VP or great individual all the way up to a, to a VP. And, and it, it is some of the things we talked about already around setting, making sure you have a really clear vision and strategy and the empowerment of the team, but leadership itself also requires more than that. You, you need to be able to have strong values within your company and ensure that those values are translated into the culture. And for me, I believe in a culture of execution. So ensuring that your teams have the tools that they need necessary in order to execute, being service, driven, to know how to remove obstacles for people without going in and, and solving every problem for them, because they, again, they want to have that agency to be able to do it themselves.

I would also say there’s a lot of empathy that needs to go into it. Not only the empathy that you’re going to have for your custom, but the empathy that you’re going to have for your colleagues, Product Management is such a cross-functional role. Right? And I, I always say the best Product Managers are able to be strong generalists. And I, I mentioned before that you might come from one particular area or another and have a super song strength in there, but they wind up filling in. I, I, I describe it like this, you know, so many different gaps, right? So the Product Managers obviously responsible for the product strategy, but, you know, there are a lot of things that need to happen, whether it be the technical design or the development, or the program management or legal reviews, or go to market strategy and working with marketing and rolling it out and enabling it, there’s just so many things.

And you can, and if the Product Manager doesn’t kind of here, I’m going like this move in a little bit, to be able to do a little bit of every single one of those roles, you have a gap. And when things fall through the cracks and don’t happen, then your product probably is going to fail, right. That’s not going to be a culture of execution. So having, you know, the thing that you’re really good at, but then knowing enough about everything else that you can ensure that things don’t fall through the cracks. I think that’s a really, really important skillset.

“I keep thinking about the T shaped idea, of being crossfunctional, but also at certain areas you can go deep. And one thing that caught my attention is your title, VP and GM. What is the difference between a “VP” and a “VP and GM?””

So, I mean, I think VP is basically the corporate level general manager represents the actual role. So as a GM, I am responsible for more than product. I’m responsible, all the NG nearing rules up to me, as well as product operations, technical operations documentation. And then I have accountability for the PNL for my business unit. And so that is the difference between, I’d say a GM and a, you know, VP of product might just have the Product Managers reporting to them. They may also have some of the other roles in some places we call it, people call it a, a head of product and it includes engineering, but usually head of product doesn’t include engineering.

“The title can cause some confusion. Especially in startups, where in the small team everyone is a VP.”

Yes, yes, yes. This is this is not that situation definitely. Well, at all, I feel very, very fortunate to have this responsibility and, and really it’s, it’s leadership over an incredible team that delivers just an incredible amount of work on the regular basis in terms of understanding what the most important things are for us to do for our customers and problems to solve working through the day to day of execution and being able to ship it, and then working collaboratively with our, our marketing and, and sales teams to, to ensure that our customers get access to it. So it’s I like to say I’m overhead, but they’re the ones doing all the hard work

“I’m grateful that you are here with us, finding time to give back to the community. There wasn’t always so much clarity on how to grow in Product.”

Yeah. I think it’s important. I think you also touched on something that’s really important. It could be titles, but it could also just what is Product Management? It is not the same in every company at all. And there are different methodologies and for the way people do product you know, different approaches, whether you’re talking waterfall or agile whether the Product Manager is super strategic or they’re and really setting the strategy and your engineering team is really figuring out the how of, of what it is. There are other places where product is expected to really articulate every last requirement down to, you know, every single definition of done and user acceptance criteria. Some companies, it it’s much more high level and your product designers and your researchers and your engineers are coming in and really solving the problem that you as a Product Manager has identified as this is the important problem for us to solve. This is our key, you know, metric that we’re going for and team, I want you to figure it out how and any, it’s not the same in every company at all.

“In product leaders, and leaders in general, the curiosity never stops. What are you curious about learning these days and how do you find time for investing in yourself?”

It’s a great, great question in terms of curiosity does never stop that, that, that is true. There’s, there’s two ways I think about this in terms of the problem space that I’m super interested in. It’s of course, what, what we’re focused on and, and solving the, the big data problems for, for our customers. In terms of myself and my own curiosity, I’m thinking more about communication, actually, especially in this new world where we’re all remote and you may never have met anybody I’ve been at, at Twilio for you know, I joined after the pandemic started and we are growing so, oh, fast. That’s the same for over half my team. And we’ve got people who have never met in person. How do you get things done? How do you work collaboratively? How do you build trust? What is the language that you use and the way in which you use it you, whether it’s over video or over slack or, or anything else. And I do think it’s shifting and I, I’m working really hard to be extremely intentional with the way that I communicate. And honestly I don’t always get it right. So I’m, I’m working on it. And that, and I think we all are a little bit in this, in this new format and, and we’re all figuring it out together to some, to some degree,

“In the startup world, there is a famous saying from the founder of Y Combinator which is, “you have to do things that don’t scale.” I found that that can also apply in larger organizations. You have a lot of responsibilities over working with people, but is there anything in particular that you know doesn’t scale, but is so core to your values that you still like to do yourself?”

Oh yes. Actually. So one of the things that I want to always do myself and not, I’m not the only one who’s going to do it. We all have to do it. That is talking to the customer. So it is critical to be in my, in my view, you’re running a business running product. You have got to be customer focused, customer obsessed. You need to understand, and it can’t all just be filtered through your go to market teams. It can all just be filtered either through, even from my product teams up to me, I need to talk to them. I need to understand what’s going on with them. And so I always make time to have those customer conversations, what’s most important to them. What are the problems they’re trying to solve? And how do I ensure that we are aligned towards their big vision? And we’re not going all the way over here in a, in a completely different, different direction. I think that that’s the, where the magic happens when the customer’s problems and the, and your business opportunity completely intersects, like, boom, you’ve hit the nail on the head. And you know that by talking to customers,

“It must be difficult as the company grows. There are more people who are supposed to be doing that, but we can’t forget that this is a team sport. This is for everybody.”

That’s right. That’s right. And, and quite frankly, not this product, I know there’s a lot of places that say, you know, product is customer focused and engineering is over here building some sort of, you know, crazy dark room with never talking to anybody. I, I don’t agree with that either. I have, I’m a big proponent of like business customer focused engineers. And so I want to bring them forward and make sure they get the opportunity to talk to customers as well. Probably not as much as the product people, but learn so much when you’re actually seeing how they use your product day to day.

“I’m glad you brought up that topic. I come from an engineering background, and there was a lot of these stereotypes around, “well, an engineer you’re supposed to receive an instruction code and give it to the business person.” They might, they might know something that the engineers don’t know because the engineers don’t see the sun. But it’s not true. And that applies to many other stereotypes in tech and in Product. I believe in creating this type of representation of the user in your own teams.”

AB absolutely. I, I fully agree with that. And, and again, when you think about empowered product teams, I’m not just talking about Product Management teams as a function for me. And, and I’m, I’m a big fan of Marty Kagan and, and his books inspired and empowered product guru out there. He you know, a product team is a cross-functional team and that includes product engineering, design, research, analytics and others. And it’s that combination that’s going to come up with the best solution and that collaboration that happens, it’s not just everybody doing their one individual thing. Yes, people need. I’m also a big believer of the analogy I use as a soccer field with six shes on it. And you don’t want everybody mobbing the ball. People do need to stay in their positions to some, to some degree, but, you know, there are times when you come in and the, the play shifts a little bit and you switch roles with people. And these things, it requires communication in order to do that elegantly and you know, without all swarming the ball.

“So Jodi, if I had to take a, kind of a snapshot at your calendar for a week and, and think that’s like different blocks, right. One is, as you say, like being with your team, but I can mind there are others that a recruiting or piano responsibilities, executive management, whatever, but maybe like, how do you actually structure your, your week or your math big picture?”

Mm that’s that’s a great question about how to do that. I have to say this is an area for me to continue to, to evolve because I do find that I get a lot of requests coming in. One of the things that we try and do at Twilio is have a no meeting Friday, which is great. It does sometimes get filled up with recruiting. I will say, it’s no meeting Friday, but keep it open for that recruiting opportunity. Again, when you’re growing really fast, you have to be available when your candidates are. So that’s one thing that we do. We have some pretty big block for our executive team that happens every week. And we make sure that we think about the tactical things that we’re reviewing as well as the strategic things. And we separate those out. I make sure that I have a meeting every week with my, with my executive team in order to not only cascade, but make sure that we’re really bringing up the things that are most critical for, for the team as a whole to know about, you know, that break down those silos, not only across function, but across different parts of the product or, or business lines.

I always set aside a decent amount of time for, one-on-ones not only with my direct reports, but I think it’s really important to do skip levels. I do don’t want to just, you know, manage down through them. It’s really important that I’m hearing from the team what’s going well with them, where are their challenges and also just strategizing and, and how do I help them grow their careers maybe from entry level all the way up to where they want to go. And then a pretty big chunk that goes to, like I said, customers and all of the other departments that I need to interact with on a regular basis, finance, marketing, sales and other business units within Twilio. So we’re, we’re real on making sure that we are supporting each other, learning from each other and not just being so myopic about hitting our own goals. We’re all going to rise together if we are, if we are sharing the time and the space and the knowledge,

“One, one thing that I’m, especially when I talk product leaders, work companies, where they can actually use the product, like in this case, TWI, I can imagine obviously your company drinks their own champagne. Right. And I would be using internally. But what is this part of your product stack?”

Yeah. So as, as the GM for, for segment core, I’m really responsible for the overall data pipeline. So for people who don’t know, we are a customer data platform. And so we have a lot of integrations out there that allow people to bring their data, their event, streaming data, their cloud option data in, through our pipeline. We, you know, we cleanse it, we transform it, we process it. We make sure compliant with your governance rules and then we send it along its Merry way where it needs to go. Maybe, you know, to another part of our platform, maybe to one of your downstream destinations in a data warehouse or some other tool that allows you to make it actionable. And so those are the, the types of services that are, are part of my platform. And then of course all the infrastructure that supports it. So

“My last question is always about the younger, your younger self, right? Obviously you’ve, you’ve done a lot of different things. And if you were to give advice to your younger self in order to maybe get to where you are a little bit faster, what, what would it be?”

Yeah, so younger Jodi I think what I would tell myself and, and, and I think I’ve been very lucky. I, I talked about the fact we talked about how did I get here with, you know, a degree in psychology and doing it on my own. I, I would probably learn more about data analysis. I would learned more about engineering early on. I am one of the lucky people. I think that’s able been able to grow my career substantially without having done those things early on, but, you know, the, the market is shifting or has already shifted Product Managers are expected to be even more technical. And I would recommend even if you are not an engineer or data scientist as you’re, you know, starting out point taking a class in that, in that regard, I think if I had done that, I I’d be even do it, you know, maybe moved even faster. Who, who knows.