Norwest Webinar: The Path from CPO to CEO

- Thanks to everyone who joined this morning. I think we've just got a fantastic panel. And hopefully, we'll cover a lot of grounds here.

To kick things off, my name is Parker Barrile and I'm a partner at Norwest Venture Partners. We are a big multi-stage investment firm, headquartered in the Bay Area. We invest across all sectors, all stages.

We really love to partner with founders early in their journey. So despite our size, series A are still really our bread and butter. And that's how I connected with Sanish Mondkar and Elliot Shmukler, two amazing founders who are on the call today. And we're also lucky to be joined by Donna Boyer. But Norwest led the series A round for Legion, Sanish's company, and for Anomalo, Elliot's company. And it's just been an amazing experience to work with both of them as a board member.

Both of them obviously, are former product leaders. And Donna is actually still in that role as a product leader at a really important company called Teladoc. So we're just excited to spend some time with them today and talk about the journey from chief product officer to chief executive officer.

So with that, maybe, we'll just start with some intros. I guess, I'll call names so we're organized here. Maybe, Sanish, you could give us just a quick 60 second bio on yourself.

- Sure, yeah. My name is Sanish Mondkar. I'm the Founder and CEO of this company called Legion.

Legion builds labor management solution for labor intensive industries and helps them to manage labor from the perspective of cost and efficiency, but also from the perspective of employee satisfaction and employee engagement. So we operate in and we serve industries like retail and hospitality, and so on and so forth. My background prior to Legion, I was Chief Product Officer at SAP.

I was running there procurement and supply chain innovation areas, both from product and engineer standpoint. And prior to that, I was the Chief Product Officer of a company called Ariba, that was acquired by SAP. And my role was similar there, running products and engineering. Great to be here, Parker. - Yeah.

Awesome. All right. how about you, Elliot? - Thanks, Parker. Thanks for having me. I am Elliot, Co-Founder and CEO of an Anomalo.

And Anomalo helps data teams find and root cause issues with their data. And we do it before anyone else notices. So if you're having problems with your data, Anomalo might be a good product for you. In terms of my background, I started my product career many years ago at a company called Ebay, and then ended up running product teams at LinkedIn. And ultimately, was the Head of product at companies like Wealthfront and Instacart most recently, where I was also the Chief Growth Officer. So excited to talk to everyone today.

- Thank you, Elliot. And Donna, how about you? - Hi, everyone. I'm Donna Boyer. I'm Chief Product Officer of Teladoc Health.

Teladoc leads our virtual first healthcare. We started with general medical which means that 24/7, you can call to get diagnoses, to get help, to get medical consults, and expanded to include primary care, mental health care, chronic conditions, all integrated into one. So you can think about it as a virtual first full medical office buildings skyscraper where you can get all your care connected in one place.

My background is in product, similarly started product way back when, my first role was in a very early stage startup that got acquired, that got acquired, that got acquired, and ended up at Oracle. My journey to Teladoc, it's my first role in healthcare and I returned to B2B prior to Teladoc. My background's mostly consumer product. I led product management and design at Stitch Fix. And before that, led the host side of the platform at Airbnb. - Wow.

Well, we've got some really stellar panelists today. This is gonna be fun. So I guess, maybe, just to kick it off, I think, most great companies have sort of a founding myth. There's some sort of catalyst that led the founder to step away from a big job and venture out, and start a company. So I'd love to hear about that.

And maybe, we'll start with Elliot. What inspired you to start Anomalo? - Yeah, absolutely. Great question, Parker. And I love how you're calling it, the founding myth. 'Cause over time, it takes on grandiose details as it's over and over.

But the impetus was really being in Instacart with my co-founder, Jeremy, who's our CTO. And Instacart, as many of you know, is a grocery delivery company. You know, very popular, very successful, and intensely data driven. You know, everything is powered by data. There's realtime GPS, tracking of every driver that's delivering your groceries coming in. There's inventory feeds coming in from every grocery store in North America, pretty much.

There's of course, product analytics and all those kinds of things. So intensely data driven place. And I was just surprised when I started there at how often issues with the quality of the data were impacting our work. And this is in a sophisticated organization with all the best data people, with all the best tools, right. And one of my favorite stories is coming in one morning, this is pre pandemic.

So coming into the office in San Francisco, one morning, and my entire team was running around, freaking out, because they were looking at the sales that day. And sales from Costco, which is a big partner retailer for Instagram, were down by 50%, right. And everyone was like, what is going on? What is happening? Did we break the site? No, the site still works. Did we break the search experience? There's people reporting that they can't find items. No, the search is, works.

There's nothing wrong with search. Turns out, it was literally just a data quality issue. The way Instacart works is we put items for sale that are actually available at the grocery store. And so that's done through a system of these inventory feeds.

So every day, Costco and other retailers would send us a feed of this is what's in my store today, so we can put those items up for sale and delivery. And that particular morning for reasons unknown, the feed from Costco excluded anything in the meat department. And our code did what it's supposed to do. It said, well, there are no meats in the inventory feed. There must be no meats for sale at Costco today. And it dutifully took down all the meat items from the Instacart site.

And so folks were going in and searching for chicken and salmon, and hotdogs, and whatever they get at Costco, and finding nothing, and abandoning their order as a result. Actually, a great natural experiment. What happens if you take away all the meats from Costco? Turns out you lose 50% of revenue that day. And if you think about it, any reasonable system that was watching these inventory feeds coming in and checking for unusual issues, would've spotted this instantly, right.

Would've been obvious that every day, there's some number of meats. But today, it's zero meats. But we have no such system, despite having all the tools in the world and all the best people.

And so literally, that was one of the big inspirations for Anomalo. And today, Anomalo watching a feed like this for our customers, would instantly spot this issue and would alert them as well as many, many others, but that was one of the inspiration. - Yeah. I mean that resonates with me. Yeah, I've spent 15 years in products before I got into VC and had the opportunity to work with Elliott at LinkedIn back in the day. And we had the same issue there where you'd wake up in the morning to a dashboard on how a certain part of the business performed.

And if something looked off, you spent half your day running around trying to figure out what was going on. And so when Elliot brought me up to speed on Anomalo, it was an easy decision to get excited about it. And then just such a awesome opportunity to invest. So I think empathy for the problem, is a really important theme in a lot of founding myths. But then I'll shift over to Sanish and Donna, I promise, I'll loop you in here too. But Sanish, Legion is a platform for companies that employ hourly workers and it helps them run their businesses more efficiently, but it also gives the workers more say in when and how they work in which is a dimension that is, I think really important and inspiring.

You never worked at a business that employed hourly workers as far as I can tell. And you've never been a blue collar worker as far as I can tell that I don't wanna presuppose, but tell us about the founding myth behind Legion. Like what got you fired up about this problem? - Yeah. So firstly, I agree with Elliot. This starts with like the myth and then it takes its own story over the years. And sometimes you're like, what exactly were the details? So I always have to kind of remember those things pretty well.

After I left SAP, after pretty long stinted enterprise software and building other things, supply chain and stuff like that. And I spent six months, basically doing nothing, which was awesome. And visiting, driving across country, there was a pretty long trip, visiting national parks and going across the country, and things like that, which is again, pretty awesome. One of the things that on that trip I was, just seeing a lot of these small businesses, large businesses like these service industry, whether it's in outside of national parks or hotels where I was staying in, and there were a lot of these four higher signs everywhere. Like everyone seemed to be not having enough workers. And that's still, by the way, the case too.

In fact, it's even more compounded now with after the pandemic and whatnot. And just out of curiosity, I just kept digging in, like what is the problem? And you'll too, you hear simultaneously and you read about, it starts from workers not having enough, they're not making enough pay to have a basic livelihood. So if people are looking for workers all the time, and if workers don't have enough work to do, it's just like there's a broken picture.

Like, why are these two supply and demand signals? Like my supply chain brain goes, why are these things not needing? And it turns out, there are lots of both, technology and human problems that have not been solved. Technology problems are a lot of these businesses, they operate on very, very thin labor, very thin margins, and they don't have the sophistication to do some schedule employees optimally in a way that employees are gonna be happy with the flexibility that's provided to them. And the getting the number of hours they need to work, so that they can make the necessary wages to take care of themselves. And from an employee standpoint, they have no tools at all. Like even today, when look at retail, including large retailers, right. 90 plus percent of retail workforce, they don't even get a company email address, leave on any other tools to help them with their jobs.

So it was very underinvested area. There wasn't anything targeted towards making employees life a little bit better, but also simultaneously making sure that the employees who hire them, they have the tools to do the right thing, to schedule them properly, but also drive their own efficiency and things like that. The other thing I observed was also, these problems existed in all types and sizes of hourly work. It was a horizontal problem. It's not as verticalized as retail problem and this problem. Anybody hiring hourly workers, hospitality and banks, and service industry, and anywhere there's a hourly workforce, this was a problem.

Employees wanted flexibility and better experience. Employers were struggling with efficiency, productivity, and turnover. Same things. So that was very compelling to kind of ask the question for such a large workforce. We are talking about 80 million workers in the US, the largest workforce in the US and by far the largest workforce in the world.

It's way more than the other side of it, which is a salaried workforce. So it was just very compelling that why haven't these problems being solved? And for me it went from this, oh, this is a great idea and technology could be used, and business could be built, and all that stuff. Yes. You kind of layer all those things up. But ultimately, it was like, wow, we could improve a lot of these experience and these lives of these workers.

And that was really kind of the most dominant factor that kinda led to the founding of Legion. - Yeah, I love it. And I love how both of you were really fired up about solving a problem that you perceived. One, you felt it firsthand, the other you sort of perceived from the outside in. And both of those paths led you to starting what have become very successful businesses.

I guess, just to loop in Donna here. Donna, what inspired you to join Teladoc? I mean, chief product officer is an incredibly important role within a company. You are almost sort of the, typically, the CEO or founder's right hand person in sort of executing this strategic vision.

So you have to feel a lot of empathy. Well, I would imagine you have to feel a lot of empathy for the problem. You have to be really inspired by what you're doing everyday. So what led you to Teladoc? - When I joined Teladoc and made the decision to, first of all, look at healthcare and health tech. I live in San Francisco and for people who were here in the summer of 2020, it was a really dark time in the city, quite literally. It was early pandemic, my husband had just gotten into a biking accident and had to deal with sitting in the parking garage while he was in surgery for eight hours.

So that there was nowhere to go. You couldn't go into waiting rooms. The wildfires were raging and the sky was dark. Health equity was a very significant problem.

And you have those moments where I had always wanted to get into healthcare. When I was in college, I thought I was gonna go to medical school. And then I thought like, I have to take too many biology classes. And then after I thought, well, I wanna go back to medical school, but I really loved tech. And I then, I got my EMT license.

And I thought, well, maybe that's close enough, but not really. And I got to the point where if it was like, if not now, when? When am I gonna do this? And I looked at a lot of things, everything from founding a company to joining a larger company, to everything in between. And really made the decision to join Teladoc because healthcare is really complicated. And so, especially given my background in consumer, the natural fit for me, would be to start a DTC company. But I really wanted to make sure that I understood all of the ins and outs that allowed me to have the biggest impact possible.

So I just started, I went from, am I doing, if I'm not founding something because it's scary or am I not founding something because I really wanna learn. And healthcare, I think, I absolutely made the right decision to be able to impact things at scale and to be able to give so many more people access to healthcare and to change the way people are able to get care from their home. And to make access to the system less scary and more accessible, was really what motivated to do it. And I think whether your founding or leading product in a larger company, it's that passion and that curiosity for solving the problem deeply that gets you going through all of the inevitable, best days and worst days that are often in your same day.

- Yeah, that resonates. I mean, I think, one of the common themes here, is that product is a great stepping stone into the role of founder and CEO, I think. That's why most people are here today, attending this panel. And so why don't we just go right after that question. You know, I think, it prepares you extremely well. But at the same time, running a company as founder and CEO is a much broader set of responsibilities.

You know, sales, marketing, legal, HR. So maybe, I'll start with Sanish on this one. How did you learn how to manage all the functions beyond product and kind of what experiences in your prefounder career have been most valuable in being effective in the CEO role where you're responsible for every aspect of what the company does? - I think the keyword is what you just said, which is learn, right.

And it is important to approach this with that mindset, which is there is a lot to learn. And there is a lot that you have to just like, even in the previous career as having product that I think, one thing about product leaders, and I'm sure everybody on this panel here too, can attest to that, is the learning never stops, right. When as a product leader, you are responsible for seeing around the corners, you are responsible for having a point of view on where the world is going and how that translates to innovation within your company.

That is fundamentally the job, right. And then of course, there's execution part of it and things like that. So I think, in my opinion, and I could be biased, but product leaders are already tuned into that, that forward looking learning. And all of that stuff translates, in my opinion, very naturally to these new areas of learning as you found a company or step into a new role, what are new things? It doesn't have to be product related, but has to be, maybe, it's on a scale that is higher, now you're talking about company topics like sales or market strategies or marketing plans and sales compensation, and things like that. So first and foremost, that learning just the ability to learn at that scale, translates really well. And to me personally, what's been and has always been the case with me, is just surrounding myself with people who are great in those things and having the ability to find these people and then trust them with their subject matter expertise, but also partner with them on the product vision, the strategy of the company, and things like that.

I think that's been definitely kind of a pretty big part of Legion's success. - Gotcha. Yeah, Elliot. I mean, maybe, to segue over to you, you spent most of your career in products, working at consumer companies.

And then now Anomalo as a B2B company, which from the outside looking, and seems like a meaningful switch. I mean, how's that going? How have you adapted to having a sales team for example, which isn't something you often think about in a consumer context? - Yeah. There's definitely learning. As Sanish said, you have to continue to learn and you have to surround yourself with great people. What's interesting about my prior roles is, although they were consumer products, they had actually quite a bit of enterprise and B2B sales exposure.

A lot of folks may not know this, I know Parker knows this. But LinkedIn actually, is an enterprise SaaS company, right. That sells a product to businesses that wanna recruit folks. Instacart, little known fact, right.

Most folks know it is as a consumer grocery delivery company. Actually, the people that pay Instacart its revenue for the most part, are the grocery retailers. So there's a sales team inside of Instacart that's on the road, trying to strike massive, massive deals with grocery retailers, all over North America, possibly all over the world this time. And so what's great about being in a product role at a place like Instacart, is you get exposed to that.

I would go on those sales calls to the grocery retailers. I would read the contract, right. That we were about to sign and be on the call with the lawyers analyzing what was going on, because often it had impact on product, right. It was committing us to certain SLAs or committing us to certain feature developments that we needed to do. So I've gotten some great exposure in my roles, largely, because product is so broad, right. It touches so many pieces within our organization too, nearly every function, right, including sales.

Another great example was key goal for Instacart was profitability, right. Making sure we were making money on every order, right, which for delivery, a logistics company is very important. And so literally, I had a part of my team that was working on that.

And we would be in meetings with the CFO, talking about the detailed accounting of our profitability on every order. So it gives you some great exposure for when you have to manage those functions as the CEO. - Gotcha. And maybe, Donna, I've been in a product role before, as I mentioned, and I don't think I was probably deliberate enough about seeking or about learning about the other functions.

I certainly interacted with them and collaborated with them, but I didn't sort of spend extra time with the head of sales that I partnered with to learn more about that function. (dog barking) Do you think about that at all? Do you spend time sort of deliberately seeking functional experience beyond product? Or is that you just don't have the bandwidth for that? I'm curious. - I do.

I think about sales really as another customer. I've oriented my team and restructured my team. So it's about like our members, like our healthcare consumers, our clinicians, like the people who are providing care and our clients, and our sales team. 'Cause it's just a very different, they really are leading innovation and leading new ways of getting care. So I do really try to both connect with customers as well as think about, okay, who am I connecting with to hear what are the gaps, what are the needs on our sales side as well. It's B2B is, it's different, right.

I think about it as when I initially did B2B, one of the things that was hard for me, was that you're a step away from the product, right. Like there's things that are in- (dog barking) Sorry, I might need to get the door in a minute. There are things that are in your, like standing in your way, like the sales team is in the way of whether or not you can close the deal, the database technology.

And it's just not the right way to think about it. Like this is super early in my career. And when you're doing consumer, there's nothing that tells you whether your product is good or not.

Whether it's like the right design, whether you've really got product market fit other than the product. Like you can see the numbers go up into the right and sometimes not go up into the right. And we've all had those days when you're like, what just happened, right? But if you think about, it's a really important source of information. What is making it possible for your sales team to sell? And it really thinking about the product holistically, it's a much broader and easier path to success. So that's been I think, an important learning. Maybe from my 22 year old self to my no longer 22 year old self.

Like fast forward, some decades in there, is really making a very concerted effort to have empathy both for the sales team as well, and really focus on that as a customer. - Got it. Yeah, these are helpful perspectives.

I think there are a lot of product leaders, probably many of the folks on this call who daydream about founding a company. I mean, I think it's natural and to do so. And then at the same time, for Elliot and Sanish at least, you're on the other side of it. And so you've got some scar tissue, you know that it isn't easy.

I mean, I'm curious. Now that you're a couple years into the role of founder CEO, what's been the best part of being a founder and CEO so far, and kind of what has been the worst part or your least favorite part? Maybe Elliot, we'll start with you. - Yeah. so I think my best part or my worst part are the same.

Which is the best part, you get to kind of see everything, right. You get to be a part of everything. That's something that always annoyed me in various product roles, is although my exposure was very broad, I didn't get to make the decisions in other areas.

And sometimes, I disagreed with the decision that was made. So what's great about the CEO role is, if you want to, you can make all the decisions, right. Or you could set up things in a way where you're involved in those things. But that's also the worst part, because if something is broken, well, that's your fault, right.

It's ultimately up to you to fix it. There's no one really to complain to. You can only complain to yourself about things that are not going well. So it kind of puts a lot of bonus on you to really fix things that are broken and keep an eye out for them. - Yeah.

Yeah. And Sanish, how about you? - Yeah. I think, I agree with the best part answer that Elliot just gave. I think for me, as a product leader, there was things that were in my control, but there's also things that I was influencing and there's things that were kind of couple layers away.

As a founder, you are putting it all the pieces together. Like that is, now you finally have that, not just access, but it is actually, as Elliot said, you have to make a lot of decisions, which are historically the product roles, not necessarily being in your decision-making sphere. So, that's great. And I think, it's been very, very satisfying to actually being able to put the picture together the way you think it needs to be.

Of course, the downside to, as sometimes that things do not work out. And obviously, you have to take the blame for it. For me, the thing that I also talked to other, newer founders about is just to, and this is something I personally, thought for challenging early on to me, was just to get my mind oriented about how long these things take, right.

When coming out of a company like SAP or even a rebar to some extent. And there were a lot of resources to do a lot of things that you imagine. And once there is broader alignment, companies of that size can move very, very impactful.

Even if it's not fast, the impact could be at a much larger scale. So losing all of that stuff and then starting from scratch, and then building without having those types of advantages and resources. Of course, there are new advantages of agility and decision-making, and kind of whiteboard thinking, and whatnot. But losing some of the advantage, I think, it's something, especially founders coming out of larger companies would need to, and I think kind of go through some adjustment period, which I had to go through.

And I think that was for a period of time, pretty challenging. But even looking back, I think this would be, I would definite do exactly the same things I did. And overall, it's just more of an awareness rather than kind of a hindrance in any way. - Gotcha, gotcha.

Yeah. I mean, one of the things you kind of hinted at, was talking to other founders. I mean, and one of the commonalities I think, between all C-level roles, whether it's CPO or CEO, is that there's no one else at the company who's an expert in what you do typically.

So even as a CPO, you may report to a CEO who came from the go-to-market side of the house, or maybe they did product a long time ago. But I mean, you are responsible for the function and you can go to them for sort of general advice and coaching and management, but they're not gonna tell you how to run products typically. And same with the CEO, I mean, obviously, you don't have anybody else at the company who's even a peer to you to go to. So Donna, how do you find or what sort of coaching or mentorship do you seek out as CPO? - Like one of the best things about being CPO is I have peers. I don't have as much of the, like it's just me. So part of it, is reaching out to my peers all the time around.

Okay, this, like wheels are coming off the bus over here. And what do we do? So part of it is just, it is product. And I own, and I'm responsible for product. Product is really just part of an overall system too, right.

So there's the parts that are purely product and then it's how does product interact with everything else. And I find that you go through these phases where your next evolution, you almost are sometimes the victim of your own success. Like something works and then, oh, it suddenly stops working, and it stops working fast.

And so really, just making sure that I'm staying connected with my peers, is part of it. And then there's a good network. And I think one of the benefits I've had of growing up in product is that there's a lot of product people that are in similar roles, whether they're CEOs or GMs or chief product officers, just asking for help. Like calling and just being like, okay, this is what I'm experiencing now.

Like, how have you helped with this? How have you dealt with this? Or what's your best resource for this? Or how do you think about training an organization or a team through this? And just really making sure that continuous learning and continuous, not closing off, but really being open to what's this next evolution. Product is, I'd say 80% the same and 20% very different everywhere you are. And so really making sure that being able to reach out all the time, is what's really helped quite a bit for me.

- Got it, got it. All right. Well, we're gonna circle back now to the early days again. Sanish and Elliot, one of the things that I think every aspiring founder thinks about is, I've got this idea and maybe there's someone, I have a co-founder in mind, but I'm only gonna be able to go after it if I can raise money. And that initial round of funding is often a really intimidating proposition for folks. You were both experienced founders, but even in your case, I'd love to hear about that very first round, sort of what was the state of the company when you raised it, how did you get in touch with investors, and what was that fundraising process like.

And again, I'm talking about the seed round, which was before Norwest investors, just how you first got started with some funding. So, maybe, Sanish, we'll start with you. - Sure, yeah.

I had made some progress by that time in terms of just evolution of my own thought process around what I wanna build. And had some slides that I think the most important part of work I've done was talk to a lot of customers by then, talked to a lot of prospects and operators, and employees. So there was a lot of, like in my mind, my conviction level was pretty high, but I didn't build a lot of product and I had just hired couple of people to start building the product. So that was the stage I was at. It was helpful. I mean, I think one advantages that product leaders starting companies have is that, generally, the question is not about whether they can build products or not.

Like they've already established that in the past, it's about all the other things. So that's an advantage. So I didn't have to spend too much time convincing people that I can build products. It wasn't about that, it was all about viability of the idea. Is there a market for it? Is the timing now? All the other very important questions.

So I focused more on that part. And was fortunate enough to have a lot of interest from early stage companies. We ultimately partnered with Ross Fubini from XYZ Ventures and First Round Capital to get the seed round done. But my advice to new founders, sort of, be aware of the situation and like what are your strengths and which objections you're trying to actually mitigate by doing some early work. If you are a non-product founder, non-tech founder, maybe the objection is around building the product and demonstrating some sort of early proof or, so it really depends on the situation, depends on the space, consumer space, where do we space, and things like that.

But generally, doing some work to show that you're committed and to show that you have thought about this problem long enough that you have a perspective that you really believe in. I think at the siege stage is super important. - And quick follow up, Sanish, how do you get in touch with Ross and First Round? - In some cases, I was introduced through some folks.

Every time I would meet someone, I would ask them, who else should I meet? And generally, somebody and folks are very helpful. If I'm meeting- That's how I met my first customers by the way. Philz Coffee was the first customer. And I've met Philz through an investor conversation with Maynard. So it was Maynard at Admin Labs by the way. In the early stages, just building this sort of, this network of either someone's gonna use your product or service or someone's gonna join your company hopefully, or someone who gonna invest in your company and in the middle I think, it's a super productive way to spend your time.

- Yeah, it's interesting. The theme there is, how outbound things are at that early stage. You really have to be out talking to people. - Yes.

- Customers. You know, early employees, but also investors or just really anyone in your network. Sanish and I got connected through a former colleague of ours at- Or a colleague of mine and Elliot's at LinkedIn, who was friends with Sanish and thought what he was working on was interesting, and introduced us, and the rest is history. But I never expected that person to be someone who connected me with an investment.

And so I think it's the network that you build over time, just working in the Valley or virtually in the Valley, is incredibly important, incredibly powerful. But when you first start a company, you kind of gotta get out and pound the pavement, and prime the pump on those introductions, and fire up that network. And Elliot, I'm curious, in your case, what that seed round looked like and how you got in touch with folks.

- Yeah, I mean it was pretty similar to Sanish's story. We had a great conception of the problem, we were trying to solve because we had faced it ourselves, right. And we had a demo of how we were gonna solve it, which mostly worked. (Parker chuckles) And then it was exactly as Sanish described, we went to our network, right.

And so this is why it's actually helpful throughout your career if you're on product or other functions to meet people and to go to events, and to participate in the community because you establish some of that network in addition to the network you're building through just your professional career, right. The people that you work with, like I work with Parker. And so we went to our network and maybe we were very fortunate that we were pretty experienced, but anyone we touched in the VC community through our network took that meeting, right. And they didn't always understand what we were talking about or what our product did, or our problem, but they almost always gave us feedback. Very often, they introduced us to potential customers, right.

That were either portfolio companies or folks they've heard have issues with this. And that gave us an opportunity to kind of refine our pitch, right. Our problem statements stayed the same, but we learned to also answer the question well. Why is this gonna be big? Why is this gonna be a huge company someday? Which was not a question we had in our original pitch. And actually, that's how we got connected to the folks at First Round who also led our seed. And by that time, we weren't even doing the product demo anymore.

The pitch was the problem and why this was gonna be big, right. And that was how we made it happen. - Got it. That's great. Common theme there with First Round.

Great fun by the way. And then, Donna, how do you think about kinda building out your network, so that you would be in a position to start something and raise money or do you not kind of think about it that way? - I think for me, and what both of you have said was really resonates, is that it's really important to be deliberate about it. I am an introvert.

I'm a very loud introvert, but I'm an introvert. And so, going to events and connecting to people, it takes some work, right. And I think, when you think about it more as less about selling, I think for me a change in mindset was less about like selling or networking for some gain and more about there's an amazing community of people who are here to help and innovate, and co-create things. And if you just change your mindset, it became much, much easier.

I approached going to events or I approach now speaking opportunities, is just more opportunities to learn. That's really changed things for me. And so I think having that mindset when you have an idea, knowing that there's people in your network or one hop away who can give you feedback, who can give you money, who can give you advice, it really changes things. - Gotcha. Yeah. Good, good.

Alright. So we'll do a little bit of a seventh inning stretch here, mix things up a little bit. Maybe just quick interlude with story time. Would love to hear from each of you. Just maybe, kind of a day in the life of being CEO of a startup or something meaningful that happened in your role as founder recently.

Could be anything, could be a frustration, could be a triumph, could be a learning. Any stories, Elliot? Anything come to mind? - I don't know if I have anything great. I mean, I feel like, well, I'll say one thing.

I've been really pleased at some of the executive hires we've made recently at the company. That's one of the things you get to do as the CEO, right. Build out the executive team over time. And it's actually amazed me how much of a difference a great executive hire makes in our ability to do stuff. You know, I knew that kind of intellectually, right.

But every day I am experiencing that in a very emotional way where I see how the great executives we hired are just pushing ahead and knocking over obstacles that are making things happen, right. And I compare that to some executives that we may have mis-hire in the past that weren't doing that, where I had to push and I had to kind of get very involved in what they were doing. So that's probably one of the highlights of, we've had some new executive start in the last few months and it's been amazing to see them ramp up, and really push their area forward, right. - I think that's a theme that I've seen in my six and a half years in venture, is the common thread among the companies in our portfolio that are extremely successful, is that the founders are great at attracting talent.

But that's really hard. So any sort of pragmatic words of wisdom or advice on how you are able to source and convince these really talented leaders to join your cause at the early stage? - Yeah. I mean, no silver bullet, right. Again, go to your network. And hopefully, you've built a network over time where folks know other folks.

You know, use referrals. So a recent executive that we hired was referred by a more junior member of our team who had worked with them, right. That's a very powerful signal when someone already on your team is saying, I want this person to be my leader, right. I've worked with them before, they would do great here. That's better than almost any other signal you can get.

So we've done that quite a bit. And some of our strongest executives were referrals from other folks inside the company that I worked with them. And then just meet a lot of people and calibrate, and hold the bar high, right. And find great ways of evaluating candidates that's perhaps another insight.

So we now almost always do case studies and exercises, and all these kinds of things in our executive hiring process. Because interviews alone, any senior executive can present well, can talk a good game as they say, it's hard to cut through that to what will they actually be able to do. But if you give them an actual case study, an exercise, something that shows their work, you learn quite a bit. So, that's been another thing that we're doing heavily. - I love it.

All right. Sanish, not to over-manage, but how about something here. I know Legion has closed some really big impressive multi-year deals over the past year plus. Any stories about kind of going the extra mile to drag one of those deals across the line? Like what does it take to sign a fortune 500 company to a multi-year deal when you're a series B2B, C startup? - Yeah. I think it takes, firstly our advantage is, we compete in those types of deals with companies much, much larger than us who've been around for a very long period of time. So they have their advantages of scale and reputation over a period of time.

Our advantages are we can deploy entire company and really basically product, and engineering, and sales, and marketing can all be super coordinated, are really understanding what our value proposition is, what the customers challenges are, mapping the two. And they really turn these to all hands on deck. So if you have a product that fundamentally you're convinced can work for this companies of these large size, and we are talking about employees over a hundred thousand and so pretty massive scale of organizations. Some of these employers are out there.

If you're convince to build a product that can genuinely add value and support them from a scale standpoint, then the whole go-to-market process, it takes time. You gotta build a reputation, you gotta be invited in many of these cases to RFP. So you need some early wins and early customers who gonna vouch for you. And say, no, this work for me. And if they can scale up to X, Y, Z things.

It may work for larger companies. And you've gotta go through that journey. That's why it takes longer to get there. But once you're there, and if you're able to retain that advantage of all hands on deck for critical deals, because that's the thing that larger companies will not be able to do.

I wouldn't be able to cover an SAP for example. We tend to have success and those successes are pretty impactful for our company's trajectory as you can imagine. So yeah, that's hopefully answered. - But tell me how that manifests.

I mean, any examples where you jumped on a plane at the last minute to just go be at the customer and kind of put the deal on your back and drag it across the line or, I mean, I'm just curious. Any sort of color commentary on that? - Yeah. I mean, enterprise software deals are to require, there is a relationship aspect to it too. And especially companies are sized, like I have to be really making sure that I am providing some level of confidence because customers may have concerns about our long-term viability.

Will we get acquired by somebody else? And those types of things have to be addressed even over and even after they like the product and after they, and we've done a great job with all the other parts of the process. There is that extra mile that you have to go through that say, hey, we are small company, but we are around and our ambition is to grow and leaders in this space. And here's our vision and roadmap, here's what we are ready to do to partner with you and things like, those conversations generally with me, and they've been mean plenty of times. Like we are still a small company, so I'm very involved in every major deal. I have a great team that runs the deal, but it is also my job to help them. So getting on a plane and meeting a prospect or like what we did last week which was by the way, was one of those things that was incredible for us.

Actually, it's been a couple of weeks now, this NRF conference, which was a National Retail Federation conference in New York. This is sort of the retail operators, Woodstock, right. I mean, everybody is there. And we had just a pretty amazing three days. As a company, we felt like we presented ourselves really well. I had over 30 me meetings back to back.

And those are the type of conversations and that's the type of momentum that will be built with. It really translates to a lot of momentum for the company. - Yeah, that's great. I mean, I think, one of the common themes is, whatever it takes. I know going through some of these executive hires with Elliot, we've had to stretch in all sorts of ways, right. You know, many of the candidates have met the board.

Sometimes the board helps sell or close the candidate. Sometimes we have to stretch on comp, but a strong hire can make a huge difference on the company. And then same on sales, right. I mean, it literally requires a ton of just elbow grease, a ton of work from the founder, at least in the early days to close these deals, Anomalo us closed a couple of really big chunky deals.

And Elliot and his co-founder, Jeremy, were extremely hands-on in that process. You can't outsource that to the head of sales. And Sanish, I know you've got a great CRO on your team now.

But I mean, I can't imagine a founder being more hands on with customers than you. So that's definitely a theme and something anybody who starts a company should be ready for. But we'll do this, we'll address the audience question here, and then I kind of wanted to wrap up with one more open-ended question. But maybe Donna, you can take this one. So it's about disagreements between different C-level execs and their ability to influence the CEO, and kind of how the CEO makes decisions when there's dissent among the leadership team. And I'm curious, one, how that, whether you ever experience that at Teladoc, I think it's only natural.

And then two, maybe how your CEO kind of, the degree to which he or she seeks input and kind of makes decisions. - Yeah. I think there's two levels of it. One is, Elliot, what you had said earlier about like, it's just you as CEO, making the decision, right. And people kind of come on board, right. As chief product officer, you've got a way of running product, but then you've got all these other, we should be doing it this way, we should be doing it this way all the time in any company.

Like, that's just kind of, I think in some ways how it is. And one of the most important things, I think, too, is the relationship with your CEO, there's gonna be CEOs that are more product focused, less product focused. And I think that's a really important thing to know going in.

Like, where are you your best and what is the nature of the change that you need to lead? So, I've spent a lot of my career working with founders. And often working with founders, the most important thing is, especially when things start getting to later stages, you get to a whole lot of pressure from your board about like, why can't you be like that company or be like that company. You start losing that sort of initial founder vision. And so I've found that, working as a CPO with a founder is really about how do you carry that vision forward? What is your next horizon of the vision and what does that look like? Your initial product, you're moving beyond that. And so, there's all this pressure to do things that are maybe really great revenue drivers, but not natural emotional fits, right.

So how do you thread the needle and find that to your next horizon? And then sometimes, like at Teladoc, the role is really establishing product. And so when you're establishing product in a company that has not historically high product, that's very different. So it's important to know what are you signing up for? And then modulating for that, right.

And it's not a fit for different phases and different flavors are different fits for different people, right. And so, at Teladoc product is, it's very much an evolution and very much, it's not very hands-on in terms of CEO input, but very much involved in terms of like, hey, are we shipping great products? Are we doing what we need to be doing? You know, I think there's a flavor of it, it's how do you deal with sort of disagreement, right. From other CTO or CEO or other people around that.

And I think part of it, is also sort of seeking the why. Like not just having it stop at, well, we disagree. But like, what are you seeing? Like how and where are we now? And a lot of times, people have said, engineering gets us sometimes too. Like, oh, I could build that like in my garage in a week, right, without understanding like the allegiance of tech debt that you've accumulated or the level of complexity. And product is sort of the same.

Like you've gotta sort of pace how much change can the organization take at a certain time, how much are you reframing where you are to where you need to be. And I think, really understanding and connecting is the best way of dealing with it. One of the things I think is a downfall of product at all levels, and one of the things I think, is maybe the worst thing that ever happened to product was the CEO of the product tag, right. Because it implies two things. One is that everyone is reporting to you, and that's just not the case, right. It's very much an influence role.

But it also implies that, I mean, I don't wanna speak for the CEOs on the panel. But you can't just direct people to do things, right. Like you can do it, but like there has to be a level of buy-in and a level of alignment for those things to be carried out with a level of conviction and commitment that makes it possible. So often what I'll hear a lot of, well, who gets to make the decision or product needs to be CEO of the product.

And if you're doing it well, the decision makes itself, right. If you're bringing in the right data, if you're bringing in the right customer focus, if you're bringing in the perspectives of the people that you are working with, I could count on one hand in 30 something years of how often it's been like, sorry, I gotta make this call, right. Usually, if you do it well, it's not about committee, it's about synthesis. And really good synthesis leads to like great product decisions. - Yeah. That really resonates with me.

The point about influence and in building consensus. I love it. So we are coming up on time here. But just maybe to wrap, we'll go to Elliot and Sanish for final comments on the following. Either, advice you would have for the heads of product on this call that are interested in becoming founders or framing in a different way, the pitch you'd give them to make that leap. Elliot, you wanna start? - Yeah, absolutely.

So very quick advice. If you're listening on this call and you wanna start a company, I would say just do it, right. Especially, if you are kind of in Silicon Valley or connected to the tech community, it's pretty risk-free, right. If it doesn't work out in a couple of years, you can get something like your old job back, right. But meanwhile, you're gonna have a great adventure. You're gonna follow your dream and you're gonna learn a ton.

And if you end up coming back to a regular job, you're gonna come back better. And we're a greater insight of what makes companies successful. And as I think, Donna and Sanish pointed out before, there's such a huge support network in the technology community.

That even if you feel like you don't know something, oh, I wish I knew more about finance or legal. There are people you can find in the tech community that will help you with that, whether that's other founders or experts in those fields. So I would definitely say, if you have an inkling, if you have a dream, just do it. - Love it. Okay.

Sanish, your thoughts. - Of course, these days if you don't know anything, you can ask CatGPT and you get all the answers. So that's- (Parker chuckles) Well, I would completely support what Elliot said. That's my advice. Just taking the first few steps. Don't worry about what comes after that.

Because there isn't, I don't think any founder journey is exactly the same. It's essentially problem solving of certain kind and making progress. That's kind of the only things common, right.

But the problems you get and how you define progress is, and everybody's journey is different. So just getting started, not overthinking that. If you're passionate about something, don't worry that you don't know sales or marketing or any of the things that haven't been part of your job. Just getting started is the most important thing. And there is a lot of support system, a lot of communities, a lot of help out there that can guide you. And I think in the possible scenario where after some time, if you don't like what you're doing, I don't think it's for you.

It's very easy to minimum get back to sort of where you were with a ton of new experience which is, would make you a better product leader. - Thank you. This is great advice. So I think, it's time to wrap up. I'm a stickler for ending on time, and you all have big jobs, and probably need to move on to the next thing. So first of all, thank you so much for spending an hour with us today.

I had a blast having this conversation. I learned a ton. You know, Donna, nice to meet you.

Sanish and Elliot, it's just been a blast working with you. And I'm a huge fan and admirer of yours. The last thing I'll say is, we talked a lot about the path from head of product to founder today, and just to plant the seed for maybe the next webinar. There's also a path from head of product to VC, the path I took.

And I think that is, also worth discussing at some point. So stay tuned for that. But again, thank you to all the panelists. I really appreciate your time. - Thanks, Barrile.

- Thank you all. - Goodbye, everyone.

2023-02-10 06:50

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