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Harnessing Data for Health | Yasi Baiani (Fitbit, Cleo, Teladoc)

The Seed Stage · 2024-04-16 · 48 min

0:00--:--

Key moments - from our scoring

Substance score

48 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality7 / 20
Guest Caliber13 / 20
Specificity & Evidence11 / 20
Conversational Craft8 / 20

Yasi Baiani reflects on her extensive experience as a product leader across health and wellness platforms. At Fitbit, she built the sleep tracking product - which became the most engaged feature - and expanded into female health, eventually overseeing all software experiences while contributing to over 60 million device sales. Her core insight is that emerging technologies follow predictable cycles: early competitive advantages based on technology fade as capabilities become standardized, making execution and use-case application the differentiator. She advocates for immersing yourself in rising tide industries (wearables, mobile, AI) early to develop genuine expertise before most competitors. At Cleo, she applied a different strategic approach - starting from customer research rather than technology - discovering that her core parenting platform could expand into elder care and family caregiving end-to-end. Her framework for product decisions hinges on three aligned elements: business needs and maturity, customer pain points validated through research, and competitive advantage. For B2B operators, her advice applies directly to product strategy, market timing decisions, and the importance of customer-centric versus technology-first approaches depending on context.

Key takeaways

  • →Immerse yourself early in emerging technology trends before they mature - the people who test products, shape their point of view, and become experts fastest will outperform competitors when that technology scales.
  • →Product expansion decisions should balance three factors: business goals and maturity, validated customer needs discovered through research, and your company's actual competitive advantages.
  • →As technologies mature, competitive advantage shifts from technological capability to execution quality and cost-effective application - utility beats novelty.
  • →Sleep tracking succeeded at Fitbit because it combined an unmet customer need (everyone sleeps but wanted better data), continuous sensor capability competitors lacked (continuous heart rate), and alignment with business growth goals.
  • →Strategic product decisions require alignment across the entire organization toward a clear North Star - everyone must understand the goals, customer needs being solved, and what changes are required to execute.

Guests

Yasi Baiani

Topics in this episode

Apple WatchCustomer research methodologyHardware-software integrationFitbit sleep trackingJawbone wearablesCleo (parenting platform)TeladocWearable technology market cyclesAI adoption and expertiseContinuous heart rate monitoring

Questions this episode answers

How did Fitbit's sleep tracking become the most engaged product feature?

Yasi's team identified that everyone sleeps but wanted to understand and improve their sleep quality, yet few knew how. Fitbit had a technological advantage through continuous heart rate tracking that competitors lacked, and betting on this feature aligned with business goals of increasing device engagement and repeat purchases.

What's the difference between a competitive advantage in emerging tech versus mature markets?

In early markets like wearables, the advantage comes from technological capability and form factor. As markets mature (like mobile today), the technology becomes standard and expected - the real competitive advantage shifts to how effectively and cost-efficiently you apply that technology to solve customer problems.

How should you decide between launching a new product or improving an existing one?

Align three factors: your business goals and maturity stage, validated customer needs discovered through research, and your actual competitive advantages. At Cleo, customers explicitly said they'd buy more products, and research showed parenting extends through teens and elder care - those signals justified expansion.

What's the strategic value of becoming an expert in emerging technologies early?

Early immersion in rising-tide industries (wearables, mobile, AI) lets you develop genuine expertise and shape your point of view before most competitors do. These experts have a temporary advantage in identifying which use cases matter most before the technology commoditizes.

How did Cleo expand from fertility and pregnancy to end-to-end family caregiving?

Customer research revealed Cleo's clients and employees wanted more - parenting doesn't stop at age five, and special needs and elder care support were needed. The brand trust in the core product, combined with explicit customer demand and business expansion goals, justified the product line expansion.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

The episode has pockets of genuine product-strategy insight - particularly the Fitbit sleep bet grounded in a real competitive intelligence finding - but the majority of runtime is biographical narrative, generic leadership philosophy, and motivational filler (growth mindset, dare to fail, Taylor Swift). The insight-to-fluff ratio is poor for a 48-minute runtime.

we knew if we bet on sleep, we will have a significant competitive advantage comparing to some of our competitors who are making false claims at that point
it really becomes in terms of use cases, how do you apply it, how do you utilize it most cost effectively

Originality

7 / 20

The technology-lifecycle parallel (wearables → mobile → AI all follow the same commoditisation curve) is mildly interesting but well-trodden, and most of the episode recycles standard frameworks - growth mindset, customer obsession, connecting the dots (literally citing Steve Jobs). The Taylor Swift inspiration angle has become a podcast cliché, and the M&A commentary adds nothing contrarian.

utilizing AI is not a competitive advantage by any means. Today is right. But it really becomes in terms of use cases
you can only connect them looking backward. And if I had to kind of run a parallel path for me, I don't know what it would look like

Guest Caliber

13 / 20

Baiani is a genuine operator with substantive roles at real scale - head of software/product at Fitbit during its peak growth, SVP at Cleo, and integration leadership at a $18.5B merger at Teladoc. These are credible practitioner credentials, though she is now primarily an advisor/consultant, which distances her from current at-scale operations.

I got, you know, promoted multiple times and overseeing all of our software experiences
I've been part of Teladoc Livongo merger, which, you know, it was huge. It was $18.5 billion merger

Specificity & Evidence

11 / 20

The episode contains a meaningful number of concrete data points - $18.5B merger size, Salesforce/Pepsi/Uber as named Cleo clients, 60M devices and $2B revenue at Fitbit, 2M users for the female health product - but the strategic claims around product expansion, M&A integration, and leadership are consistently left at an abstract, hand-wavy level.

I've been part of Teladoc Livongo merger, which, you know, it was huge. It was $18.5 billion merger
our clients. Salesforce, Pepsi, Uber, you know, some of the biggest companies were our clients

Conversational Craft

8 / 20

The host shows occasional craft - pushing for 'actual practice, actual tips' on Taylor Swift, asking what she would specifically change in past M&A situations - but the episode opens with several minutes of pure fluff (movie titles, Salma Hayek), frequent affirming filler ('that's a great way to think about it'), and no real challenge of any claim made by the guest.

Is there any practice you would bring from Taylor Swift? Actual practice, actual tips to the startup world?
If a movie was made about your life was what will the title be? And who would you want to play? You.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A77%
  • Speaker C21%
  • Speaker B2%

Most-used words

product48different31fitbit24experience23hard20team19products17market16first15point14teams14strategy14important14career13part13love13

Episode notes

️ Join us for an enlightening conversation with Yasi Baiani, former head of software product and experience at Fitbit, as we explore the intersection of product innovation and personal growth in the tech industry. With a diverse background spanning Fitbit, Cleo, and Teladoc, Yasi shares profound insights and strategies from his expansive career. In this episode, we discuss: The significance of integrating customer feedback into product development Strategic decision-making in product launches and acquisitions Harnessing data and technology to enhance user engagement and health outcomes The challenges and triumphs of leading through mergers and acquisitions Personal growth and risk-taking in a fast-evolving industry ...and more! _______________________________________ Where to find Yasi: Linkedin: ⁠⁠⁠ Twitter: Where to find June Twitter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠ Linkedin: ⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠ Website: ⁠⁠⁠ The Seed Stage Podcast is powered by June.so & Point Nine

Full transcript

48 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: I would expect even AI get to that maturity and at one point, like even a few years, like utilizing AI is not a competitive advantage by any means. Today is right. But really becomes in terms of use cases, how do you apply it, how do you utilize it most cost effectively. That becomes really interesting.

Speaker B: Welcome to the seed stage. I'm your host, Enzo, CEO at June. Every week, June and.9 invite the most inspiring product and growth leaders to share their practical advice on how to grow your SaaS. Whether this is a story behind a feature, a marketing framework, or a, uh, risky update made on the pricing, we're digging ideas you and your team can put in place next week. No fuzz, no bs.

Speaker C: Enjoy the show. Hi Yassi and welcome to the podcast.

Speaker A: Hi Enzo. Thanks for having me.

Speaker C: I'm so glad to have you today for this chat. Unique track record. You worked on some of my favorite products. Career is made of really rich moments, so I can't wait to dive in.

Speaker B: Same here.

Speaker A: Thank you for having me.

Speaker C: So I'll try to do a quick summary about your background because you've done so many things. You are an operator, a builder. You've created new markets and categories including when you work as the head of software, product and experience at Fitbit, where you created Fitbit Sleep, which had been the most engaged part of Fitbit for many years. You also worked on the female health product there, which had over 2 million users in the first months. And you contributed to sell over 60 million devices and grew the revenue over $2 billion. I was one of your happy customers, by the way. You also worked at Clio, uh, the global parenting and caregiving platform. You strategized and built Clio teams and Clio elder care products, enabling the company to become, um, the end to end platforms to support families that we know today. And you were the SVP of product and marketing where you led the innovation. So you not only touch on product, but a lot more other things. Today you're the co founder of Raya, where you advise CEOs, founders, executives on their product, on their business strategy, on marketing, and also on recruiting top talents. And you're also an active investor and a public speaker. Did I meet any? Did I miss anything?

Speaker A: You didn't. You did a great job interviewing me. Thank you.

Speaker C: So I, uh, wanted to ask maybe something a bit light to get started. If a movie was made about your life was what will the title be? And who would you want to play? You.

Speaker A: Oh, wow. Uh, that's a good one. That's a good one to get Me warmed up. I, uh, like that. I think that the person who immediately come to mind is Salma Hayek. And don't ask me why. It just is the. Is the first one coming up. I don't know, maybe the combination of being an international player in the field and just her, uh, style and attitude, I think is the first one that pops up. Does that sound reasonable?

Speaker C: It does, yeah. Salma is great. She's been also very engaged with a lot of topics and causes. Right. Is it, uh, is it something also close to your heart or not?

Speaker A: Definitely, yeah. She definitely is the one that pops out. So I think I always feel like the first answer is the right answer. So she'll be the one. And in terms of what the movie will be called will probably be something like live like this is your last day or living your best life full with, you know, love, learning and laughter. Because when I kind of think about myself and how I operate, I live, like, literally every day is so precious and it could be the last day. I have this sense of urgency to live and do things that I love. Uh, so I can totally imagine that will be the theme of my story.

Speaker C: Lovely. Did it come, uh, did you have this, uh, attitude since, uh, many, uh, many years, or did it come one day? And so what, what brought you there?

Speaker A: Yeah, I think it was always part of who I was as. Even as a kid. Like, I remember, like, playing sports. I always was very competitive. I always have to do my best. I have to reach the kind of end goal always. I remember my parents, uh, friends and family always commented about that, uh, about this. Attributes of me to my. To my parents. And I always feel like, you know, my friends always ask me, why do you do so many things and how do you do so many things? You know, I have two little kids. I'm very involved in the community for their, you know, schools and all that, but also in, you know, technology community, investment community. So I do a lot with my time. Part of it is like, I try to be very efficient, but part of it is like, I think that innate, um, drive and sense of urgency that I have for life. And I feel like, you know, I have to live it, live it to the fullest, and I truly fit in 36 hours of stuff in 24 hours. Um, I would say I'm not a big sleeper, so that sometimes helps. But even aside from that, I have this sense of urgency and excitement about do a lot of great things fast.

Speaker C: And that reflects on your, I think, on your track record and things you have Achieved. Ah, at least the one that we can see publicly on your LinkedIn and things like that. So let me dive into one of, uh, these topics. Let's dive a little bit into your experience in some industries. One of the ones I really want to start touching on is your time at Fitbit. So when I was in college, I bought one. I remember installing the app and I was mind blown of the possibilities of the raribles, the wearables. This is a hard word for a French person. And then the industry seems to be suddenly very mature and now very crowded. I wanted to ask you what's a big learning you had from that time around, the cycle of innovations and maybe the market dynamics?

Speaker A: Yeah, absolutely a lot. I probably can write a book one day about that whole experience was first of all one of the best part of my career. The highlight of my career. Learned a lot, a lot of things. I applied as I moved on to other industries and doing other things, but few things that was really fascinating about that kind of wearable movement. Um, I was kind of watching it from early on. I was one of those weird people that had 15 or 10 devices on my hand, like test pretty much all different form factors of wearables. I was really fascinated by the fact that I always been very much into fitness. And then when these things came out, I was very much fascinated by what wearables can do for, you know, your fitness, but more importantly also for healthcare. Because I was like thinking like having all this data 247 versus like going to doctor visit once a year or uh, for most people, more than once a year, how can this change the uh, story? How can that have impact on our health overall? And that's where my fascinated fascination started. I was testing the products and at that point there were not, there were definitely not that many people who were experts in wearables. So soon you could become expert if you were really immersing yourself into that. And that's what I did. I was testing product, I was comparing them. This is like Nike Fuel Band time, Jawbone, a lot of those competitors like went out of business pretty, pretty fast. Even though some of them, including Jawbone, raised a tremendous amount of money multiple times than Fitbit ever did. And kind of watching that industry. And I started writing about them because I was so fascinated. I was like, more people should talk about this. I started writing about that and all of that, uh, first of all gave me the platform to talk about these things and soon became someone that people thought of them as an expert, someone who has a point of view in that, um, industry. Uh, but also ultimately that's how I ended up at Fitbit. And they gave me a big role to help the company expand beyond fitness and step tracking. My mandate was to figure out our wellness strategy, which ultimately we kind of doubled down based on the recommendations myself and my team gave, based on a lot of research and work to invest in sleep as one of our first big kind of areas. And that paid off really well. And ultimately my role got expanded. I got, you know, promoted multiple times and overseeing all of our software experiences. But I think when I always look back at that is a few things to kind of take away. First of all, follow your passion and let your curiosity to kind of go to different directions. I think truly my fascination started with wearables out of curiosity and out of like, you know, passion I had for health and wellness and fitness. But also like immerse yourself in early technologies. Don't be afraid of that. I was an engineer, I wasn't technical, but I was, you know, someone who tear apart some of this product, understand their components, tested various products to have a point of view. And all of that really allowed me to have a great success, um, figuring out what customers want and what these technologies can enable, which I think could be very much applicable to many other kind of similar, I would call them rising tides of industries. Like I feel like in my career I've seen that with wearable, I have seen that with mobile and kind of, I'm sure like you remember the App Store and everyone's trying to build an app and all that experience, like people who immerse themselves have been advantaged for a period of time and then we are now seeing it with AI in my view, it's very similar, probably magnitude of, you know, impact a lot bigger than what we've seen in any technology. But people who immerse themselves today we don't really have experts in AI. There are handful of people across the globe that have been doing research in AI or building products with AI for the last 10, 15 years that they can claim. There are very few people. The remaining of the population and talent are immersing themselves now. And the people who are not afraid test those products, become users, shape their point of view, become the experts faster will be able to really write this tight, uh, much better and see the result of that.

Speaker C: That's a great way to think about it. And it seems like when a new trend happens, people rush into it and then eventually some experts happened to, you know, to take off and then eventually There is like the maturity of that industry and the next thing uh, comes in. Did you see that happening by the way with wearables? Did you see the maturity happening or the concentration because of all you mentioned the fundraisings and these crazy numbers. Is there like some sort of plate something that just was very visible and now you pay attention to these kind of things. For instance, when you apply to AI.

Speaker A: Absolutely. I mean with AI it's a bit I think different. With wearable we've seen that. I think some of these early technology you have technological advantage when it becomes, you know, when it initially started right. Then these things become standard and platform and expectation. Like today if a company is on mobile, it's not a uh, competitive advantage for them. Right. It's expected. But then still it's important to understand how to use, utilize that to then do other things. Right. I would expect even AI get to that maturity and at one point like even a few years like being on, you know, utilizing AI is not a competitive advantage by any means. Today is right. But it really becomes in terms of use cases, how do you apply it, how do you utilize it most cost effectively. That becomes really interesting with variables. We definitely have seen that I think early on was to figure out how to build this technologies, how to get variables to sync with your mobile and the data exchange to happen the most cost effective way, how to collect some of these, this data with different sensors. So it was a lot of kind of early stage and early days went to figure those pieces out just like where we are with AI. Like they're like in that early days of figuring some of those technical aspects out then when you get to a certain point is all about experience and then ultimately it's about how do you scale that business. And I think it's fascinating a lot of investors early on got the competition between Jawbone and Fitbit to some extent. Wrong. Right Everyone. Early on when I got into Fitbit there was a big bet on Jawbone. They got valued for you know, over a billion dollar. So they were named as a, as a unicorn. And of course Nike Fuel band was within a much larger company and that was not like technology and syncing data and all that wasn't just like the bread and butter of Nike. So they didn't go that far with that. So the competition was primarily with ah, between Apple and Jawbone and plus some other smaller players, sorry between Fitbit and Jawbone and then there were some smaller uh, in the market. But ultimately when, when and and Fitbit grew and really became a Kleenex of wearables. Like people knew Fitbit as a wearable. Like that's how they talked about wearable. And I remember a, uh, couple of holiday seasons we were out of stock. Like the, the wearable devices, our, our products were flying off the shelf. Like we had hard time to catching up with the demand. Which was really fascinating to, to see all that type of growth and that type of demand. And we have sold so many devices that for a period of time during the day after Christmas, our site went down because so many people hit our site for syncing their devices and open the box experience that we couldn't really handle the load. Uh, which, that was a fun, fun exercise for our engineering team to get us back on track. But the point is like true demand and growth, you experience that and it's really fascinating. And then on the flip side, as we saw Apple coming to the market, right, Apple is the master building hardware, software, have a lot of cache of brand with the consumer, has a lot of appeal on that side. So they start kind of taking some of that market share. And I think that's where the maturity became that um, in the industry and then more consolidation of smaller companies. And then ultimately Fitbit was acquired by Google. So you definitely see some of those trends in these industries and sometimes you're part of it.

Speaker C: Yeah, you've seen the full cycle. And the interesting thing with Apple, and let me know if I'm mistaken, but it seems that they entered the market with a device that people already had, which is the phone. Right. Is there any learning here that uh, having a best in every product can only last for as long as people will replace it with uh, something more convenient? Especially uh, maybe there is a bridge to be made with currently, you know, the VR space where things seems to move very fast, but it's still very expensive to adopt one of these VR headsets, you know?

Speaker A: Yeah. And tell me a little bit more. Like when you say they come with a product in the market that was uh, like similar to, Is it similar to phone in your mind or because it was like the same operating system, is that what you're alluding to?

Speaker C: No, no, what, what I mean is like uh, for Apple, they came with the phone, right? So they could do some of the things that Fitbit or other companies were doing, but just with a device people had already purchased.

Speaker A: Sure, sure. So that's definitely true. And then the other piece is, you know, there's a lot of competition for this small real estate. It's, you have tourists, you probably Would will wear one wearable. I still wear my Fitbit, which I'm very proud of after many years. Um, but it was a lot of competition for this small piece of, you know, real estate, right. And figuring out who wants to wear that. And there were some event of Apple, you know, again, hardware, software, super smooth user experience. So they brought to the watch even from day one, which was really, you know, interesting but they also got some of the aspects wrong. You know, uh, but ultimately when you have so much money and you have again so much already brand cache and access to the consumer and the operating system, people who bought, you know, Apple phones still want Apple watch and you know, a lot of that, which I think to some extent Fitbit, because we were on, you know, we were compatible both with Android and you know, iOS. That was like an interesting strategic decision and definitely to our advantage. But over time, you know, people who were Apple fans, you know, ultimately decided to move to a more kind of Apple product. And definitely you'll see the kind of pressure in the market from market share and pricing and all those aspects.

Speaker C: 100%. Yeah. It seems like such a long time when I, when I bought my Fitbit and I mean now honestly you guys have opened a huge market because uh, I mean it's with Apple health and all these things, it's become, you know, kind of a norm to have that. That's crazy.

Speaker A: Totally, totally. It's an definitely interesting market to continue to watch but you know, I think the most important part becomes data and how do we utilize that data for then other use cases. And the device could be Apple, could be Aura, it uh, could be, you know, uh, Fitbit, it could be many different devices. But I think there's still a lot of great work can be done in that area just utilizing data and improving sensors that we can have on people and the information we can collect.

Speaker C: 100%. You mentioned the launch of these products and the Christmas, uh, season you worked on other products that you launched, including teens and elder care at Clio. I mean that's going to be a big question, but maybe you can find a short answer. How do you decide when is a good time to launch a new product versus keep an existing one, you know, and keep building on the existing one because you've seen this happening many, many times. So I'd love to hear your thoughts.

Speaker A: Yeah, I think it depends on many different things. Right. At the end of the day you kind of the goal is not just to build something or launch a new product line. It's really to Kind of step back and think about. In my mind, always it comes down to a few things. One is, what are the needs of the business, where we are in the maturity of the business, how do we need to go from here to where we want to go? Right. And each business is different and they have different goals and ambitions and different capabilities and advantages. Um, the other piece is what do the customers in our sector want and how well we know that and how much we can bet on that. And my team, um, both at Clio, Fitbit and other places in particular now that I'm working with a lot of clients, we spend a lot of time really making sure we build a lot of confidence in terms of what the market want, what the customer want, and what are we capable of delivering, um, as our competitive advantage as a company. Because I think all of those come into equation to have a really sound strategy and North Star that you can then drive towards and create millions of dollars of revenue or billions of dollars of revenue. But you need to do your work really well to understand that. And it's an alignment to build among, um, not only just product team, but across the organization because you need to make sure everyone's rolling toward the same direction. It's very clear what's our goals and ambitions as a business, what are the things we can deliver and what do we need to change in order to get to that North Star, um, and also what are the customer needs? Ultimately you need to solve real problems to be able to generate revenue at scale. And it's important to really understand the customer needs. So where we were at, for instance, uh, Fitbit, and ultimately some of the business goals will tie to the key metrics you're trying to move. Right. When we were at Fitbit, the opportunity for us to expand and grow was of course, partially how do we sell more devices, but more importantly, how do we create engaging experiences. So first of all, people continue to wear their devices and then come back for the next generation of the devices. So a lot of my work as a software team was to partner with our hardware team to figure out, first of all, what are the sensor capabilities, what are our advantages as a company Fitbit, and what are the things we can deliver that people really want and care about? And that was, for instance, one of the foundation of betting on sleep, because everyone sleep. When we did user research, everyone was really curious about how they can get more out of their sleep, but they didn't know how a lot of people cut their sleep short. They had really inconsistent, uh, sleep time all of those are terrible for your productivity and for your health benefits. So we see a lot of opportunity for educating a, um, large number of people and our users. And also at that point we were one of the first companies that actually had um, hardware tracking continuously. And some of our competitors were claiming they're doing that, but when we dig deeper in their product, we realized they don't. So they have false claims. And for sleep staging and getting sleep tracking effectively, you need to have continuous heart rate tracking. So we knew that. So based on our competitive advantage from technological perspective, we knew if we bet on sleep, we will have a significant competitive advantage comparing to some of our competitors who are making false claims at that point. Um, so combination of, uh, seeing customer needs, our technological advantages and building confidence around that and uh, where the competitors are, we saw that could be a big category. And when we doubled down on that, it helped with sales of a lot of devices. And even, honestly even today, I think Fitbit has still probably one of the best sleep tracking products. So that's where Fitbit was. The goals and intentions were different with Clio when I joined as a head of product, um, I typically like to get out there and talk to customers and really understand the customer market. And that's what we did. And when we talk with clients, we realized we have amazing group of clients. Salesforce, Pepsi, Uber, you know, some of the biggest companies were our clients. They love our initial product. They said if you sell us more product, we buy it. Our employees love your product and love your support. Uh, which was primarily focused on early stage of fertility and family creation and early stage days of baby life and mom's experience with pregnancy and post pregnancy. We heard from parents that parenting doesn't stop at one, it doesn't stop at five. You know, I have teenagers and still that's challenging to manage that or I have a special need kit and I need support for that. So the combination of hearing that the clients want more from us and the, you know, employees want more from us and we have a love product and brand with our early product, um, and our goal of, you know, expanding our business, we saw a huge opportunity for kind of expansion of the product line. So we, we support caregiving end to end and that's what we ended up doing. So I think you bring all these pieces of puzzle together to make strategic decision and you need to make sure you build alignment across the organization so everyone is moving towards the same direction to execute on that strategy.

Speaker C: Yeah, these are great examples. I think one, you started from the technology and the other and then figure out how this could match the needs. And the other one was more starting from the needs. And it seems like a pretty standard, I would say classic strategy where you expand in the journey of the life of the person. Right. Like try to map more touch points and in this case probably the most natural thing for human, which is growing up with them. Right. Like aging with them.

Speaker A: Uh, totally, totally. And I always believe that's true. Yeah. And I always believe no matter where you start, you need to bring all of these puzzle pieces together in order to have a sound strategy. So you shouldn't just listen to the customer's need. You just shouldn't just follow the market trend. You just like see what your competitors are doing and do something different. But you have to bring all of them together. And it needs to make sense for your company at that stage to be able to execute on that effectively 100%.

Speaker C: And I think something you touch on a little bit is the people you're selling to. Like, do I hear that the great strategy is to expand by trying to sell, I mean the easiest strategy or one of the best strategies to expand by selling to the same people. Is it easier to expand within the same people than to try to target new people?

Speaker A: Typically, I think in general always is better to have, you know, uh, it's easier to upsell probably to your clients if and only if you had already a great product and you have enough engagement and retention. So I think that technically is true. Right. But you shouldn't just stop there because like you need to build a product and if you wanted to scale your business, you need to be able to sell, expand your clientele. So you should think about both. And not only you talk with customers. And that's what we did. But we also got out there and talked with prospects and potential customers and people who decided to say no to us at one point and really understand the whys. So I think it's important to bring both of them together. But if your current customers are not buying your product, that is a very negative thing to focus on and understand the why. It's either your product experience is terrible or, or you are launching a product line that they don't care about. So understanding all of those are important. But sometimes you may decide going from small SMB market to enterprise market, so you're tactically and strategically don't expect your, uh, current clients buy your product. So it's very different if it's intentional and everything end to end makes sense. Yes, great. But most likely you want your existing clients by your new product line. And if they don't and don't care about it, you should really understand the.

Speaker C: Why. You should. You should. Yeah. Uh, you should wait a bit, I think. Brian Chetzkid called that the permission to build. He said that they had the Airbnb experience for a long time as an id, but they waited until people gave them the permission to build something different 100%.

Speaker A: And that's exactly what we heard from clients. Uh, specifically, one of our buyers at Salesforce used the same. Same statement and say, you guys have all the permission from us to expand and, you know, provide us other other types of products. And we love to hear that. You know, it's. It's great.

Speaker C: Sweet. I'd like to touch. Sorry. A little bit on the mergers and acquisitions. So you've been involved in a lot of these situations where basically products were not launched but acquired. So one of these experience was at Teladoc, where you were the head of the mental health products. You worked on integrating another company called Live Longo, if I'm not mistaken. And you know, I mean, merger and acquisition are a bit of a taboo. Sometimes they go. Well, sometimes they go wrong. Sometimes, you know, the founders leave and there's just many situations. But it seems like overall they're pretty complicated.

Speaker B: Right.

Speaker C: They're not just as easy as spinning up a new product or something like that. What is it that doesn't work? And what is the secret of a good acquisition and a good integration?

Speaker A: Yeah, absolutely. My favorite topic, mergers and acquisitions. I'm not sure if I can give you a perfect secret answer. I haven't really figured that out. And, uh, I've been involved in mergers, acquisitions of different sizes. I've been both involved in mergers and acquisitions as an executive and operator and leader, and early in my career as an investment banker. I've also been involved in, you know, doing the financial aspects of mergers and acquisitions. And I will say that I've never seen it being easy or not messy. So it's always messy, it's always complicated. And most of the time it doesn't generate the, you know, financial returns or even experiences that people expect. At least not in the short term. And long term is always debatable. Right. Um, so I've been part of Teladoc Livongo merger, which, you know, it was huge. It was $18.5 billion merger. I've also been part of acquisitions that we acquire a company that had only a few employees. And even that has been hard. I haven't seen Mergers being easy. Um, and I think on the product side, I focus because there are a lot of human aspects and operational aspects and all that, which is, you know, could be a story for another podcast. But for the product aspect, I think the challenges are, um, a lot of times you wanted to bring the product experiences to be smooth and as um, synchronized and coordinated as possible between two companies. Right. And in terms of Teladoc, the challenge we face very quickly, uh, we wanted to make our Livongo mental health product connected with our Teladoc, you know, mental health product. It made sense from strategic perspective because what Teladoc had was really awesome teletherapy kind of experience. What we brought to the table was assessment and triaging. And if someone has low mental health needs, we put them on more digital solutions with low cost. If someone had high acuity and they needed to talk to someone faster, we put them on more of a path to talk with psychologists, psychiatrists. It made strategically sense. But when we start doing that work, uh, a few things became apparent. Uh, first of all, both of these companies had huge book of business, had a lot of complexity already in their way of delivering their products to different types of customers, from health insurances to employers. And Teladoc has been very acquisitive company anyway, so they had a lot of other complexity and smaller companies that. But we need to consider how do we make those product experiences consistent with Livongo. So there's a lot to be kind of considered in these types of product building and experience creation. Even with the smaller companies, I think you experience a lot of similar things. There are many different things you need to consider. It's always more complicated migrating clients and that experience is always disruptive for both clients. But for internal teams, how do you do it to be most smooth? Um, so there's a lot of technical aspect to consider, there's a lot of UI and experience aspect to consider that inherently make it harder. I think what could be interesting is first of all, really focus on not only what's good for the business because it's absolutely important. At the end of the day, we want to make sure business can return their, um, ROI that's required for these types of acquisitions and continue to grow and all that, but also really focus on customer and customer experience. Really try to understand that and build the product around that experience. That's one aspect. And then have rational timelines. Because I think when you have really irrational timelines and expectation on your R and D team, either people have to cut corner from the experience, which Then eventually come back and bite everyone. And you know, customer will not be happy. There will be complaints. You will have customer turns, so you want to prevent that. And also, you know, the teams will get burnout if there's really irrational expectations. So I think having focusing on business strategy, but really importantly, understand the customer and focus on the experience you want to create for them across the multiple companies or two companies and then have rational timelines that teams can execute towards a really good product experience rather than just cobbling a bunch of stuff. I think is going to be really key.

Speaker C: This seems to be the common things, uh, I keep hearing, did you face one of these, did one of these problem happen to you and if you go back in time on one of the merger or acquisition you worked on, what would you change? Maybe it sounds like you're a bit more skeptical that you were right.

Speaker A: Yeah, I think I already shared that I will probably change and try to do different things for pretty much all the acquisitions I've been part of because I feel like in my experience they all have been really disruptive and still, you know, it was hard to see the, the results and um, execute towards that. So I would say I would change things, but would it give us the results we all wanted to? I don't know because I think inherently mergers are very challenging and you know, integrating two companies effectively together is challenging. I can tell you how much, um, you know, how do I think about those. I have been been given offer to join a company as chief product officer, a company that had nearly a hundred million revenue. So it was like a really exciting role. But all they wanted to do was expanding their products with a lot of acquisitions. So a part of a strategy was, you know, very acquisitive company. And I, uh, ultimately thought about that and I'm like, I'm not excited to just integrate different products into our core product. And I said no to the company. It was very hard to say no to a company that's growing, especially in the, you know, this offer came within the last 18 months. So in this market, getting a big role with a big team and, you know, nearly 100 million revenue, and saying no to that wasn't that easy. But I would just wasn't excited about integrating a bunch of products into the core product as my main kind of strategic work. There will be a lot of work still in the acquisition process. As a chief product officer, as an ex, any executive, you evaluate a lot of different things of the company. You have to think about how do you integrate it into the company. So it's interesting work, but the reality of it is very messy and I just wasn't excited about that.

Speaker C: Right. So that was more like a personal decision. Right. Or kind of a judgment you made, uh, thinking that maybe it wasn't the right strategy and so you wouldn't be convinced to drive that strategy if it wasn't the right one.

Speaker A: Yeah, I think it was the right strategy for that company. I think as an innovator and as a builder, doing a lot of acquisition integration is just like a different type of work versus innovating and building and things like that.

Speaker C: Yeah, you touch on one thing that I think is very interesting, which is, uh, I mean, you're clearly like a very product minded person and when you talk about strategy and so on, you really focused on the consequences for humans and all this integration going on. You touched on something very interesting, which is in tech, sometime there are some hard things that required really hard work. Time, um, creates tension, burnout people. And I've seen this thing over and over again. I don't know, do you think they're needed? Do you think it's the, it's like a way companies have to go through and that's just the way tech works? Or do you think some of the amazing companies out there manage to avoid this very hard building integration phase?

Speaker A: Yeah, you know, my general philosophy. I'm giving a talk in UC Berkeley in two days and, um, part of it is like, you know, sharing what's the secret sauce of building a resilient and successful career. And I thought about a lot of these things a lot. Um, and I do think working hard is, you know, part of the process. Like, I personally don't, you know, there are different philosophies. There are people who say you don't need to work hard and you can see great, great results. I truly think that for doing really exceptional things, would it be at the personal level or at the company level? You need to work hard, the teams need to work hard. Do they need to work hard all the time? Do they need to pull all nighter? No, but, um, I generally. General philosophy I have is like, you need to work hard to get to big things. With that in mind, I don't necessarily say thing. You need to drive teams hard all the time. There might be time and point that you need to do that. Like, let's say you have a big milestone, you have a, you, you know, for, for Fitbit, for instance, we had to hit the, you know, holiday season and CES would come up in January. So our big product launches were happening in that kind of September to, you know, January. So if you were behind schedule, we have to catch up as a team and we will rally and do that. Right. So there are times that as a team you need to rally. I think what's important and, and what I have seen with the teams, if you are very rational about it, very open about it, you really explain the whys behind it. Well, the teams are willing to put extra time and effort to get the company to the milestones that is required. But if you have to run the teams hard all the time and it's not rational and it feels like busy work and people are not seeing result, it's really hard to, you know, perform in that, in that type of environment. And I would not at all advocate for that. But there is something magical about rallying about big goal that everyone cares about, hit that goal and see the result and everyone feels that. And I'm really big in celebration at uh, smaller milestones. I always like to kind of cheer up my team members, call them out in uh, larger meetings and celebrate them, appreciate the work that they have done. I do think doing that will really um, buy a lot of good social capital for the leader and allow them to then make the hard ask from the team and still the team willing to do that.

Speaker C: Yeah, cycles, cycles like we're humans after all. And sometimes you can increase uh, your energy level, sometimes you have to rest a bit. I know you're taking a lot of very uh, human approach to things. Uh, I know you also take a lot of uh, inspiration from various sources and I saw recently one of your LinkedIn posts around uh, Taylor Swift, the economy she has created around our tour called the ERAS tour, which is absolutely massive. Everyone is talking about that, that she's projected to generate 5 billion revenue you said, in consumer spending in the US alone. I'm curious about where you're taking inspiration these days and especially when it comes to art or music. Do you think startups have things to learn, more things to learn from art than uh, people would assume?

Speaker A: Yeah, absolutely. I think there is something really powerful about cross pollination across different industries. Um, I truly believe in that and you know, I like to spend time understanding philosophy or understanding art, economic behavior, things like that, because I truly believe those make me a better product person, even though they're in different fields. But uh, they give me inspiration, they allow me to better understand the psychological drivers behind people, um, and how they make decisions. And that's a lot of our work in product and design. And I'm, of course, fascinated by Taylor Swift. I think she's a better business woman than she is a singer and artist, which says a lot about her because she's, of course, a genius artist. Right. We all know that. And she's a genius businesswoman. I am studying her and, uh, learning from her because I think she is fascinating. Like, things she does, like, little things she does. She was one of the only people, I've heard at least that that gave bonuses to all her staff after her performance. And after her really successful tour, she gave $55 million to her staff, which is something we do in companies. Right. So she definitely brought that corporate mindset to her team, and she shared revenue with other people when they did something really big and amazing. She announced her next album at the Grammy, and next thing you know, tomorrow when we all went to order her album, we had to wait 45 minutes. So she used a really big podium and platform launch, something that's coming up. So she's just fascinating in terms of her wittiness and smartness in terms of business, um, decision and acumen. Um, and of course, she's a genius artist. So I think she has learned from the business side and she is applying some of that to her, you know, artistic journey and career. And I think we have to also learn from her and many other industries and many other kind of of personalities in different, um, categories to see how can we bring some of that creativity, how can we bring something that's resonating with people to our work? Like, for instance, in the talk I'm giving at UC Berkeley, I am using Taylor Swift as one of my kind of people and quoter, just because I know that that's a person that audience resonate with. Right. So how can we do these cross pollinations? Um, I think, uh, it's an interesting thing to think about.

Speaker C: Is there any practice you would bring from Taylor Swift? Actual practice, actual tips to the startup world?

Speaker A: Yeah, I think truly, like, one thing I really like about her is, first of all, like, she's an amazing marketer. Right. She's kind of out there being authentic, building her own brand, which I think a lot of artists do. But, like, you'll see her kind of being repeatedly, regularly and consistently to do that. And also, like, the fact that she cares for other people. I appreciated that. And she is keeping her style and her approach in a way that is approachable to people. You know, when we think about her fashion and in super bowl, they were kind of doing some of her analysis of her fashion. And they were saying she's keeping it simple. Even she can do very differently because she want to be approachable and accessible. And I think as a leader, as um, as an executive, we all can learn from that. Like how can we be more accessible? How can we really care about other people? I think is really important.

Speaker C: I love it. Yeah, I remember she was uh, sitting in the, in the stadium with like other people. Right. She didn't have a VIP lodge or whatever. She was just sitting there. Right.

Speaker A: Yeah.

Speaker C: I think that was a great communication move from her. Any other leadership principle you consider very important across your years? I mean again, there must be a lot, but maybe two or three that you constantly remember yourself and you're like, this is important. This I need to tell.

Speaker A: Yeah, I think maybe the one that is leadership, but also, uh, you know, life philosophy and something I really try to pass on to my kids is really treating other the way that you like to be treated. Um, and I'm really trying to build that empathy in my kids and sometimes when they do something, I'm like, would you like someone else do that to you? And they are kind of building that muscle. So I think that's truly important. And I always, you know, do that. Like if I want to do something to any, I don't like to be treated that way. I will not do that to people. Um, that's my first number one principle. The other thing is over time I learned your impact is really amplified to your team. So you're as good as your team. And building great teams and making sure you prioritize their health and their success is really important. Um, I over time learn as an executive particularly my job is to unblock my team and just kind of get out of their way and support them and empower them. Uh, and I fundamentally believe in that. I think some of the best leaders, um, they really care about their teams, uh, rather than caring about themselves. And over time that always shows. Another thing is also like of course being customer obsessed. I think that has been a big principle for me for my product work, but also for building a business and building successful business. I think you always wanted to prioritize your customers and what's best for them. And I also think that will really show long term. Uh, particularly now I'm experiencing it. I'm technically in a service business right now. I'm working with clients and supporting them. Um, and you definitely want to build a long term relationship and you always wanted to prioritize what's good for the customers and that Will, over time, pays off really well. And, uh, I think the other piece, last piece, is that I do that for myself. And again, I try to teach my teams. I emphasize that with my teams a lot and I do that with my kids, is to build a growth mindset. Things are changing so rapidly. I think the AI revolution is the best example. But even other things are moving pretty rapidly and having growth mindset is really important.

Speaker C: Do you tell your kids growth. Do you use the word growth or do you use another word?

Speaker A: I tell them develop the love of learning. Like love learning new things. That's the most important things. And I try to teach them love learning new things, no matter what it is, and challenge yourself.

Speaker C: Did you figure these things out on the way or did you look up to some people and learn from other people? Because, yeah, when I was young, I just assumed leaders knew everything. And then I realized, you know, we all learn, we all have role models. Was it your case?

Speaker A: Absolutely. I think there are a few things. Of course, I have people who at different time of my career have been critical in either growing me or helping me to point me to different things. And not always they said to me, oh, go do this next thing. But it was a process of communication, learning from them. You know, things that, when I look back, they have been critical in my, um, journey, professors, you know, people I work with, people in my network. There have been multiple people I can name. I also read a lot. I care about, you know, self development and growth. Um, so I read about on average 20 books per year. Um, a lot of them are around similar topics. And I try to analyze people that I look up to quite a lot to see what have been their decision, how, what were their key to success. And I try to learn and replicate things that really resonate with me because I also believe in authentic leadership and authentic growth. Um, but I do spend a lot of time and effort on that and try to apply what makes sense for me and try to again, pass on some of that knowledge to my, you know, teams, to people who follow me on LinkedIn and to my kids.

Speaker C: Lovely. Is there one of these learning you would, you would want to share with us? Recent one, maybe?

Speaker A: Recent one, yeah. I think one thing that, you know, more and more became obvious for me, particularly as I'm now landing on my own business, is dare to fail and embrace risk. You know, which is also I'm trying to teach my kids. I have grown up in a very conservative family. My dad was extremely risk averse, diverse, and I had to rewire Myself and reteach myself that how you can take risks. And over time I got more and more comfortable with it. But I do think that the kind of financial, uh, theory of risk reward, it does exist. And if you just do easy things, if you go to Google or Meta and stay there for 20 years, you'll probably have a very different career. You probably make more money than many of us. Uh, but it's a very different career trajectory than going and do different things and take different risks and expose yourself, yourself to different things. Even though you may fail, I think you may have a lot more thriving and fulfilling career. And I got more and more comfortable with that over time. Um, and it's been really fulfilling just kind of watching that. The fact that I get comfortable with it and embrace it and then do things that I, you know, take more risk. And it's amazing to see what the results in terms of returns, financial returns, but more importantly, satisfaction returns.

Speaker C: And keep learning. Like as you're teaching your kids, always be learning, challenging yourself. I love this mindset, the growth mindset.

Speaker A: You said it 100%.

Speaker C: Indeed. In retrospect, is there anything you wish you knew earlier? So you learn a lot? Some things on the spot. Some things. Reading, meeting people, looking up to people. What are the stuff that came, but they came very late or too late?

Speaker A: Yeah, I think that's a really good question. And I've been thinking about this because we've been traveling and in a trip, you know, we've been talking with family that would any of us do things differently, like major decisions in our lives? And initially I thought I would, but then after I really deeply thought about that question, I kind of felt I would live my life the way I lived it, partially because, you know, I'm very happy and content where I am. Um, you know, all the, the kind of combination of decisions I made really made me happy and satisfied. But also, I don't think you can kind of connect, uh, the dots of your career, as Steve Jobs said, really well, uh, looking forward, you can only connect them looking backward. And if I had to kind of run a parallel path for me, I don't know what it would look like. It would have been very interesting. But, uh, it's hard to say what would be my story and who would I be and how do people talk about me if, if I would make one or two decisions differently. So I would probably feel like looking back at my career. I feel really grateful for the decisions I made. Some failed, some miserably failed, and you could technically say I should have not done that. But where I am today, I'm happy I took all those turns and twists because it taught me a lot. And I don't know if I look back, what I would do differently, maybe everything differently. But that would have been another journey, another person.

Speaker C: That would be another person. This is such a great conclusion. Um, I think this is just the perfect way to wrap up this conversation. Thank you so much, Jesse, for coming. It was a great chat.

Speaker A: I appreciate that. Enzo, thanks for having me.

Speaker C: If people want to follow up with you, where should they go?

Speaker A: Yeah, absolutely. They can follow me at, uh, yossibayani on LinkedIn. I'm pretty active a lot to come out there and I'm always pretty responsive to people, so they can definitely be in touch with me. They you are.

Speaker C: That's how we got in touch. I'll make sure I point to your LinkedIn profile. Thank you so much again and have a great day.

Speaker B: Thanks for listening to this episode of the Seedstage. The best way to support us is by leaving a five star review. The team is pushing hard to bring you the best stories and insights and your feedback helps others discover our podcast too. So please, if you haven't done it, take a moment to leave us a review. This means a lot. Until the next episode. Take care.

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