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Mental wellness platform Headspace raises $93M Series C



Headspace will use the funding to build out its B2B program, which now works with 600 companies

As the conversation around mental health and wellness has evolved over the last few years, leading to more acceptance and destigmatization, many, many startups have come along to try to take advantage of these trends, to the point where there are nearly 1,000 of them now to choose from.

Of course, a few companies are bound to rise to the top and one that has emerged as a leader is Headspace, a digital health platform that provides its users with guided meditation sessions and mindfulness training. On Wednesday, the company announced new funding that should help solidify its position in the space.

The $93 million Series C round was led by blisce/, with participation from Waverley Capital and Times Bridge, the global investments and partnerships arm of The Times Group of India. ERisting investors, including the Chernin Group, Spectrum Equity and Advancit Capital, also participated. Of the total round, $53 million came from participating investors, while the other $40 million came in the form of debt capital from Pacific Western Bank.

To date, Headspace has raised a total of $163.7 million, including $36.7 million in June 2017 as part of Series B, and $34 million in September 2015.

The Headspace platform contains hundreds of hours of content on topics that range from stress to movement to sleep, which can be accessed online, or via the Headspace mobile app. It also provides services like Headspace SOS, which are two-minute long exercises to help users feel calm and Headspace On the Go, which helps users meditate during daily activities. 

Since being founded in 2010, Headspace has seen over 62 million downloads in 190 countries. It now has over 2 million paid subscribers.

“We believe that mindfulness should encompass every aspect of life, not just when you’re sitting to meditate. So, in addition to guided meditations, members have access to eyes-open exercises, such as mindful walks and runs, breathing and wind-down exercises, sleepcasts, soundscapes and more,” Megan Jones Bell, Chief Science Officer at Headspace, told VatorNews.

(Note: Bell will be a speaker at the Future of Behavior and Mental Health salon, held by Vator, HP and UCSF Health Hub, in March. Get tickets here)

Part of the funding will go toward building out some of Headspace’s product segments, including Headspace for Work, its B2B business.

The program uses admins, who are typically benefits or people leaders within the company, who are provided with a suite of products, including a provisioning portal, resource toolkit, qualitative and quantitative measurement tools. Those admins then make those products available to eligible employees. In addition, Headspace for Work members also get access to features and content that are specifically designed for that program, including in-app team challenges. 

Headspace works closely with the admins to create a mental health strategy for the company and its employees.  

“Our Customer Success Team partners closely with each company to build unique implementation and engagement plans. Our dedicated team of experts travel around the globe to deliver immersive live, or virtual, educational experiences for teams to help them integrate mindfulness into their routines,” Bell said.

The goal of the program, she told me, is to “help companies build healthier, more productive cultures and higher performing organizations,” and so Headspace is “constantly looking for new ways to bring more value to our members.”

“At the end of the day we want to ensure we’re helping our members create healthy routines, whether that’s through our app, the work we do with hundreds of employers or through partnering with healthcare providers as we work to deliver better access.”

Headspace for Work now has more than 600 corporate customers, including Starbucks, Adobe, Hyatt and GE. The company works with 15 percent of Fortune 100 and 20 percent of Fortune 50 companies. The Headspace for Work segment saw its revenue double year-to-year in 2017, 2018 and 2019; the company is expecting to see the same growth in 2020.

In addition to investing in Headspace for Work, the company will also continue to put money into Headspace Health, the company’s program where it integrates mindfulness into healthcare.

“Headspace Health takes a human-centered design approach in which we put patients and healthcare professionals at the center of our design process,” said Bell.

“We are focused on driving meaningful clinical outcomes and helping patients create healthy routines. We are keenly aware of the need to look at the patient in a holistic way. Our programs are specifically designed for those suffering from a broad range of stress­-related chronic diseases, furthering Headspace’s commitment to improving the health and happiness of the world.”

Headspace Health is a relatively new segment for the company, having only been unveiled in June of 2018, so the company is still undergoing clinical testing and finding processes that will allow it bring a product to market that meets the needs of its customers.

“Headspace is a global leader in mindfulness created with one mission in mind: to improve the health and happiness of the world. And in order to do that, we need to reach as many people as possible. One route to accomplishing this has been working within the healthcare system –  partnering with insurance companies, healthcare professionals, and centers of care,” said Bell.

“As we’ve grown these partnerships, we’ve learned firsthand how our existing consumer app is both recommended by physicians and used by patients as a helping hand in a variety of mental as well as physical conditions. We’re excited to double down on our investment in healthcare by setting out to create new digital therapeutic products to help patients manage illnesses.”

Finally, the money will go towards Headspace’s international expansion. Last year, the company launched localized versions of the app in French and German, and also hired former Apple executive Renate Nyborg as Head of Europe to lead that expansion in. The company also launched Latin American Spanish and Brazilian Portuguese.

The investment from The Times of India will help Headspace continue its expansion in Asia going forward.

(Image source: 



SaaStr Podcasts for the Week with Lucidchart and Wrike — February 28, 2020



Ep. 311: Karl Sun is the Founder & CEO @ Lucidchart, a visual workspace that combines diagramming, data visualization, and collaboration to accelerate understanding and drive innovation. To date, Karl has raised $114M with Lucidchart from some of the best in the business including K9 Ventures, Meritech, Iconiq, GV and Kickstart in Utah. As for Karl, prior to founding the company he spent 6 years at Google in some fascinating roles including Head of Patents, Head of Business Development in China and running Google’s energy investments. As a result of his success, Karl was recently announced as EY’s Entrepreneur of the Year.

Pssst 🗣 Loving our podcast content? Listen to the start of the episode for a promo code to our upcoming events!

In Today’s Episode We Discuss:

* How Karl made his way into the world of SaaS with the founding of Lucidchart having been Head of Business Development for Google in China and Head of Patents.
* How does one know when we need to hire generalists vs specialists? How does this requirement change as the company scales? How does Karl fundamentally think about finding great talent and keeping top of funnel full? How does Karl think about working with recruiters? What works? What does not work?
* Karl has been in every interview for every new hire for the first 6 years of the business, why? How does Karl think about doing this at scale? How does Karl structure the hiring process today? Why do they have a hiring committee? What does the process look like? How do they assess and test for culture?
* How does Karl think about retaining agility and flexibility with scale? How does Karl maintain employee empowerment with the implementation of process? How does Karl think about the balance between creating accountability without a fear of failure? What are the challenges of this?

Ep. 312: Starting a company can be daunting, exhausting, and expensive, but with the right focus and idea – extremely rewarding; take it from Andrew Filev, Founder and CEO of Wrike. In this session, he will outline the do’s and dont’s that he learned bootstrapping Wrike. Where it makes sense to invest your precious resources when to outsource, and how to save yourself money without cutting corners.

This episode is sponsored by Owl Labs.

SaaStr’s Founder’s Favorites Series features one of SaaStr’s best of the best sessions that you might have missed.

This podcast is an excerpt from Andrew’s session at SaaStr Europa 2019.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Harry Stebbings
Karl Sun
Andrew Filev

Below, we’ve shared the transcript of Harry’s interview with Karl.

Harry Stebbings: We are back for another week in the world of SaaStr with me, Harry Stebbings, @HStebbings1996 with two Bs on Instagram, and my word, I’m excited for the show today. This company and founder are just incredible and what I love even more, not Valley based, but based in Utah. So with that, I’m thrilled to welcome Karl Sun, founder and CEO at Lucidchart, a visual workspace that combines diagramming, data visualization, and collaboration to accelerate understanding and drive innovation. To date, Karl’s raised $114 million with Lucidchart from some of the best in the business, including Manu at K9, Meritech, Iconic, GV, and Kickstart in Utah. As for Karl, prior to founding the company, he spent six years at Google in some fascinating roles including head of patents, head of business development in China and running Google’s energy investments. As a result of his success with Lucidchart, Karl was recently announced as EY’s entrepreneur of the year award.

Harry Stebbings: I do also want to say huge thank you though to George at Meritech, Gavin at Kickstart, and Ben at Bamboo HR for some fantastic question suggestions today. I really do so appreciate that. 

Harry Stebbings: But that’s enough from me. So now I’m very excited to hand over to Karl Sun, founder and CEO at Lucidchart.

Harry Stebbings: Karl, it’s absolutely fantastic to have you on the show. As I said, I heard so many great things from George, from Brian, from Gavin, so thank you so much for joining me today.

Karl Sun: Well, thank you for having me, Harry.

Harry Stebbings: I’ve been excited for this one for a long time. I’ve actually been a fanboy of the company and the story for a while as well, which I didn’t think you knew that before, but I do want to ask you now, it’s a wonderful world, the world of SaaS, but how did you make your way in and how did you come to found Lucidchart?

Karl Sun: Oh, that’s a great question. It was a pretty circuitous route, quite frankly. I started my training on the technical side, thinking I wanted to be a scientist or engineer, in particular, thinking I wanted to do research. When it came down to it, I realized there was no one area I was so passionate about, that I wanted to spend at least six to seven years or maybe my whole life diving deep and becoming the world’s expert. But I did love technology and I wanted to work in technology, so I thought technology policy might be the area for me. That took me to studying law and policy, which landed me ultimately, in Silicon Valley, where I was practicing law for several years. Then I got a call from a friend who actually was the first lawyer at Google and he was looking for someone to start the patent team there.

Karl Sun: Back in that day, people had started to hear about Google. They were already powering AOL and Yahoo, but it was just another search engine and search engines were sort of a dime a dozen. There was AltaVista, Lycos, Inktomi, and all those. But I went and talked to them, interviewed there and was just super impressed with the people I met and thought this would be fun and just jumped on board at that point. I had the opportunity to run the patent team for a few years and then had the chance to move to China to help start Google’s China office, leading business development. During this time, I sort of drank the Koolaid about how software could be delivered online with instant updates and features pushed out to users every day as opposed to these release cycles of every one or two years.

Karl Sun: Also, Google had pushed out Google docs and what is now Google Sheets back in the day. Those products have certainly gotten a lot better, but I think I saw the promise of those. So when I moved back to the states, moved to Utah, and actually met my cofounder who was still a student at the time, and Ben had built the first version of Lucidchart because he needed the product at his previous startup. He had worked as a CTO at a startup when he dropped out of school. I was just amazed at how smoothly and seamlessly this graphical application operated in the browser when the tech space applications that I was used to working with, like Google Docs and Google Sheets were actually pretty clunky and cloogy back in the day. So loved what Ben had built, got to know him, was super impressed with him as an individual, as well and decided to jump on board. That was the story. It was not planned, but just being in the right place at the right time.

Harry Stebbings: And the rest is history and what a journey it’s been since then. But I do have to ask, it’s such a unique and diverse background as you said, from the patent practice at Google and opening that, to opening Google’s China office. With that, a kind of incredible experience in mind, question from George at Meritech, who asked, “How did your broader journey help prepare you for your current position and what were some of the key learnings and takeaways for you?”

Karl Sun: As I look back, I think, and it’s really only with retrospect that I realize this, I think the background I had brought me two things. So the first is maybe confidence. Growing up and early in my career, even though I think I was fairly good at the things I was doing, I’d say I didn’t have a lot of confidence in myself. I think I probably suffered from a fair amount of imposter syndrome. I think most of us do. So I think having that broad background in realizing that I was developing a little bit of expertise in many areas, I think that brought a confidence that maybe there are other things that I could try and be successful at as well. I’d say that’s the mindset piece.

Karl Sun: The key takeaway, I would say, is people, and that is something that I saw directly at Google. I think the quality and caliber of the people that I was surrounded by there was just amazing and that is something that I took away and realized that if I were to ever do something, I wanted to have that kind of an environment where I was just surrounded by people who are just awesome and fantastic and better than you are at everything that they do.

Harry Stebbings: Incredibly hard of me to go off schedule, but you said there about the imposter syndrome. Honestly, Karl, it’s somebody that I actually struggle with a lot. I use the show ruthlessly for my own self advancement. Karl, what would you advise me in terms of embracing it, getting over it, kind of really dealing with it, in many ways? How do you think about that and what would you advise someone who is struggling maybe with that imposter syndrome and self doubt?

Karl Sun: Well, I think your record already speaks for itself, Harry. So I think that’s a big part of it. But I think it’s just overcoming that fear. I think for a long time, I feared failure and I think probably most of us do. Failure is not necessarily fun, but the first few times you go through it and you get through it, you realize that there’s actually something good that comes out of it. You come out of it sort of stronger and wiser. So trying to overcome that fear of failure and being willing to take some chances and push yourself, I think that’s the advice I would have for anyone.

Harry Stebbings: I think so many of the industry has it and I think it’s a lot of confidence on the front end, which seems to mask it. It’s certainly how I manage to deal with it. I do want to discuss, though, the team and talent itself. I think we forget just how essential talent is to any scaling organization. When I spoke to many of the people that we know and have in common, especially George at Meritech and Gavin and Brian, they all spoke about your ability to assess talent, scale it, but also to sustain it. So I do want to kind of double click on some of these elements. Start me at the very beginning, say at this talent funnel when we’re identifying what we need. How does one know when to hire generalists versus when to hire specialists? Let’s start on that.

Karl Sun: Yeah, I think that it’s an evolution. So in the early days, we hired almost all generalists. Over time, I think we’ve realized that we need to hire specialists. Here in the states, we just had the Superbowl and I read something that David Satterwhite, who’s now the CRO at User Testing, wrote a while back that really resonates with me and I think addresses this question well. So he used this sports analogy around scaling a high tech startup and compared basketball to American football.

Karl Sun: In basketball, you have five people on the court on the team, so a small number. While there are positions and there are plays, in general, you really have general skills. Everyone can dribble, they can shoot, they can pass. So in the early days of a startup, you’re playing basketball. You can have more generalists because you’re playing a bit more positionless. You can ad lib a lot. In fact, if something breaks down, you want people who have all of those skills and can just riff and sort of play backyard ball and figure things out. You sort of also have that natural chemistry by virtue of the small team and by spending a lot of time together.

Karl Sun: Now in American football, by contrast, you’ve got 11 people from each team on the field at one time and each person has a very specific job. For each play, they have a very specific discrete task. Maybe you have to block this particular person on the other team or you need to run this particular route. You need to run in this direction, not because you’re going to get the ball, but because that will draw the defense in that direction, so it opens up opportunities for someone else on your team. As a company scales, you really start to play football and when you do that, you need more specialization. If a play breaks down, like I said, you can riff when you’re playing basketball. But in football, if people don’t do their particular job, everything blows up and you get tackled for a loss and you go backwards. So in football you have to get many more people on the same page in order to execute.

Karl Sun: It seems like this happens certainly when you get to a couple of hundred people, that’s when we started to feel it. I think it can also depend on the distribution of your team. I think we’ve been fortunate because we’ve mainly been co-located, but we really felt this when we moved to two buildings because we overflowed and even though it was a building just across the street, just having those people in separate locations just meant really it became an order of magnitude harder to coordinate and understand what other people were doing.

Harry Stebbings: Totally. It’s always challenging when you get even across the street, that kind of split in teams. I do have to ask you, again off schedule. I had an angel investment of mine in the other day. They’ve raised about $6 million in financing and they found this person who is incredibly talented generally, but they didn’t need a role specifically. Also, the person doesn’t really fit into a specific role. So it’s not even that that they’re generalists or specialists, they’re kind of this kind of special projects person who is kind of plastic enough to do many roles. How would you think about hiring for that sort of position in the early days? Do you think that’s a luxury that maybe only larger companies with more elastic budgets should engage with, advice wise?

Karl Sun: No, I don’t think so. I think if that’s someone who can take on different things… When you were saying that, it reminded me of we hired someone that we called our, “director of special projects,” sort of a similar role and he was fantastic and he was great. One of the things that we asked him to do… Well, the first thing we asked him to do was to build some reporting and dashboards. He likes to say that he did such a poor job at that, that we quickly turned him to a second job, which was, “Hey, we didn’t have a sales organization at all at the time and should we? Do we need a sales org?” We didn’t talk to our customers at all. They all came online.

Karl Sun: So he was tasked with figuring out whether it made sense for us to have some kind of a sales organization to engage with our customers more. That was five and a half years ago and he is now our chief revenue officer. He’s grown in that role tremendously and he’s been awesome at it. There’s a situation where he was a generalist and I think over time, he’s become quite the specialist, but with generalized capabilities too. So if it’s the right person, I would see if there’s something that you can test that personnel on and hopefully, make that work out. That would be my suggestion.

Harry Stebbings: I think that’s great advice. What a journey to CRO. I didn’t actually know that. I do want to ask though, because now we’ve identified the sport that we’re playing, basketball or American football say, and we know the type of person or the type of talent we need. Now, I heard from Brian Pugh, you’ve had candidates that accepted roles on plane rides, in grocery stores, and in many more weird and wonderful locations. How do you fundamentally find great talent? Was Brian’s first question.

Karl Sun: I would say the key is always be looking. To me, that means realizing that great people can come from anywhere, right? All of your interactions, I think, we’ve probably all been in situations where we’ve interacted with someone, maybe it’s at the Kinkos or somewhere, and we just think, “Wow, that person is just amazing at what they do,” whether it’s from a customer interaction perspective or whether someone we meet and just introduced by a friend and have random conversations with. So I think always be looking. I think it also means looking for people who may be working outside of the role that you think you’re hiring for. Sometimes, some people would be willing to make the jump into a different career track or role and some people aren’t, but I think about our head of people and I remember looking for this role and thinking about this role and reading something that she had written and seeing her background and she was a lawyer.

Karl Sun: Usually when you think of lawyers, I don’t think you necessarily think of people-person and someone who would lead your people organization. I can say that, being a lawyer myself. But I could just tell from reading what she had wrote in this interview that she was the kind of person that was fantastic and really cared about people. She worked in employment law, so it wasn’t completely separated from we’re looking for, and so just grabbed lunch with her under the auspices of perhaps pretending to hire her for some of our legal needs and people needs, but really to feel out whether she’d be interested in a career switch. It took a little bit of time, but she did come and it’s been fantastic on both sides. I think she would agree.

Harry Stebbings: I love the always looking and I also love the kind of open-mindedness to bring in someone who maybe isn’t currently doing that role. Can I ask, does that change if it’s maybe a C-suite role or a head of sales, a VP of marketing? Does that willingness to take someone from an outside role, that’s not in that role currently, does that change if it’s a C-suite role where you need to lead a team around it?

Karl Sun: Yeah. I think it probably does, especially once you get later stage. Once you start to get later where you need more specialists and specialization and a little bit of experience, I think that does matter. But I think early on, it’s easier to do that and part of it is getting to know the person and understanding whether that you think they’re going to be a right fit and successful in that role. So I think there’s a part of that process which is mainly getting to know the person, what makes them tick and it’s almost nothing to do with the job. It’s more about getting to know them individually, personally. Do you feel like they’re the person with the right kind of values that would fit with your company’s values? And also, whether you think they’re looking for that challenge to do something a little bit different.

Harry Stebbings: Speaking of that kind of dating pair, so to speak, while you’re already getting to know each other and it’s really kind of the chase for talent. But I heard from a lot of the people that we spoke to and we both know that you really engage heavily in the interview process. I know you interviewed every candidate for the first six years at the company. So why were you so engaged for so long? I guess, first. Let’s start with that.

Karl Sun: Well, I believe that hiring is the most important part of what I do. I don’t want to micromanage people. I want them to have the autonomy to work on the projects that they know will move the business forward. But that’s really a theory that only works well if we hire individuals who we can trust to tackle the problems that we face. So it comes down to finding the right people and putting them in the right role.

Karl Sun: Quite frankly, it’s a little bit of self preservation, right? If you can hire great people, that makes your job and your life easier. You can give away more parts of your responsibilities. So like I said, it’s sort of self preservation. I think I stayed involved and I do still stay involved as much as I can because every time you delegate a task, you become a little bit more removed from things. The person my COO thinks is perfect might be different from the person that I think is perfect. Similarly, with my VP of sales. Of course, I’m not going to veto or rarely will I veto a person that everyone else likes. But I think I like to check in to understand if we’re all staying synced on the same page in terms of the kinds of people, the kinds of skills, the kind of experience, the kind of passion and drive that we’re looking for in people we bring on board.

Harry Stebbings: Can I ask? So I love that as a perspective in terms of really not owning that, but being part of that process and kind of the importance of it. When does it become unscalable, do you think, and how did you manage to scale it for so long?

Karl Sun: In terms of how I was able to scale it for so long, I think it was just, again, trying to set aside the time, realizing that this is one of the most important things I do. But as we grow, of course it’s become harder for me to be in every interview, so we’ve put in place different mechanisms. I still certainly try to be involved when my schedule permits and for certain roles, but we’ve also implemented a hiring committee so that it’s not just me, but other people, other executives as well. We all meet together and we go through each person that we’re trying to hire into the company and we talk about why this person is the right fit. In terms of what I look for, I think there’s something that I often do when I’m meeting someone that I think gets at what I look for. One of our core values is this idea of passion and excellence in everything we do. So I’m looking for that passion.

Karl Sun: I will sometimes ask people to teach me about something and it can be anything that they want. It can be business related, job related, or it can be something that they’re interested in personally, a hobby, but I want it to be something that they’re really passionate about and that they feel they understand and know really, really well. I think I do that for two reasons. One, as I mentioned, we want to hire people who are just very curious, very passionate about what they do. I’ve found that people who have passion in one area tend to be passionate about many other things as well. It’s somewhat counter intuitive, quite frankly, you would think that people who are passionate about one thing to put all of their time to it, but I’ve found that people who are excellent and passionate in one area tend to be the ones who excel across the spectrum. Then secondly, I think you can just really learn a lot about a person when you hear them talk and describe something they truly care about.

Harry Stebbings: I totally agree. I haven’t actually heard that in terms of kind of teaching something and really kind of revealing that passion. I guess my subsequent question is, when we think about bringing in those excellent people, the biggest challenge or thought that I have is when you’re bringing in incredible talent and there’s internal candidates who think that they’re ready for that particular promotion, say, how do you voice it to them and how do you think about bringing in external talent, but without demotivating or disincentivizing internal talent if they’re maybe not getting the promotion that they thought?

Karl Sun: Yeah, I think that’s a great question. I think our goal is always to grow the people we have. We believe that we’ve hired a great group of people, some of them early in their careers. The reason that they came here and took a chance with us is because they saw that opportunity to develop and grow themselves quickly. So we always want to give them that opportunity. I think all things being equal, we would love to have people internally step up into those roles and I think we go out of our way to make sure that they’re given the opportunity to do that. At the same time, I think we have to be realistic and sometimes people just aren’t ready for that next role. I think it’s key to bring in those people who are here internally, those more junior people respect and feel that they can learn from.

Karl Sun: It’s important to bring people in who care about mentoring and working with a great team and not just telling these people what to do but getting their buy in, getting their feedback. That’s part of the culture within the company. I think in situations where we’ve done that, we found that even though people could have viewed themselves as, “passed over,” for a position, they’ve really appreciated the fact that we brought in someone that they can learn from and can mentor them and they’ve been excited about it. So I think done well, there’s that possibility of making a win-win.

Harry Stebbings: Can I ask, how do you do it well? Is it taking them aside, being very compassionate, being very empathetic? Is it by bringing them into the process itself? How do you think about making that process as kind of successful and effective as possible?

Karl Sun: Yeah, I think you definitely want to bring them into the process. No one, I think,, is fond of showing up one day and being told that they have a new boss if they haven’t been engaged in that process. So I think as much as possible, bring people into the process. But yes, talking with people realistically and saying, “Hey, we know you’re interested in this role and we’ve talked to you about this role. We don’t think you’re quite ready for it yet, but we think that with the coaching and mentoring that you can get from this new person that will open up new opportunities for you and we think that’s going to be here with our company. But if not, it will certainly prepare you for wherever you might want to go next, as well.” And of course, we want those people to stay and typically that has worked out.

Harry Stebbings: No, absolutely. I’m sure it has. As I said, I heard many great things also about kind of internal upskilling that you’ve done at Lucidchart. I do want to ask, though, because this additional layers of management and with this scaling that we talked about, there often comes these kind of incumbent processes, which prevent a little bit of agility, maybe. How do you think about allowing for agility as you grow and scale headcount?

Karl Sun: Yeah. This is something I’ve been thinking a lot about relatively recently. I’ve come to believe that taking time to establish processes can sometimes initially slow things down, but it’s actually essential for a larger team to maintain that agility that you talk about throughout scaling. To be clear, this is not something I’ve always believed. It’s something I’ve sort of grudgingly come to realize. I’ll go back to the sports analogy because I think this transition has a lot to do with that shift from generalist to specialists. In football, you need to have a playbook and it’s not just one or two plays, it’s a whole binder full of plays because you need to coordinate a lot better. You have to have known set plays so that each specialized position knows what they’re responsible for in order to make the play successful. Everyone can’t just go off and do their own thing.

Karl Sun: I think we’ve been in this process of making the shift from sports, from playing basketball to playing football for the last couple of years. Last year, we added almost 200 new people. Without having the right processes in place, it’s hard to understand whether the people you’re hiring can even be productive in their role. Because we’ve hired such great people, I think we’re probably a bit late to the game on process. We were sort of so good at playing basketball for so long that we need to slow down now to understand how to play football in order to go faster together as a team. This really takes a shift from the leadership perspective as well. It’s a shift towards sort of systematization and maybe let me give you an example.

Karl Sun: When we were smaller, the right people to make a decision would meet and talk and make a decision, and then everyone knew you made the decision and you’d go out and you’d execute. But now, we run into questions about, how does the organization even know when the decision has been made? Is it when someone says something to their team or is it when there’s a formal email or a Slack message that goes out announcing this change? Or is there some other mechanism just to communicate what has been decided? Even things as simple as that require just a much more coordination, and that’s not something that I necessarily realized earlier on. So I think you have to be explicit about why we have to make these shifts. We’re not being Machiavellian. It’s just the reality of being at scale and there’s too many pieces to wing it. So not everyone can be in the conversations. I think we’ve probably all been in that situation where you are in the meeting and there’s 14 people in the meeting and you wonder, do most of the people need to be here?

Karl Sun: But they’re used to being there because they’re used to being part of every single conversation and decision. We just had a meeting with sales leadership yesterday and the feedback that they heard was they’re not spending enough time with their teams, and that’s because they’re getting pulled into meetings all the time. So we’re trying to put together some formalization about, well, who should be in these meetings? And then how do those people communicate the information to the two other people who need to know, so that information can get disseminated? As you scale, not everyone can have the combination of context and expertise and the personal relationships that you used to have when you were smaller. So you need some process in order to help bridge everything together.

Harry Stebbings: Can I ask you a very tough one? I didn’t quite know 200 people joined last year. That’s incredible. That’s like one every other day, more than that. As I said, unfair of me to ask, but what’s the most challenging thing that comes with scale at that level?

Karl Sun: I think it’s a little bit to the previous point about making the people who come in feel like they are a true owner of their area and not just their area, but hopefully of the company as a whole as well. So we tell people that, “Yes, we’re hiring you into this particular role and there are things we want accomplished, but we want to give you the authority and autonomy to be innovative and to experiment and to knock it out of the park in that area. In fact, what comes with that autonomy is the expectation that you’re going to own the area. You’re not just going to expect someone to tell you what to do, but you’re going to spend all of your time and talent and energy figuring out what the right thing is to do and we really want you to feel that ownership because it’s only by pushing that ownership down to everyone where we can really excel.”

Karl Sun: I think if you have a bunch of people who just want to do the task that they’ve been asked, then I think you don’t scale very well. That comes to a grinding halt pretty quickly.

Harry Stebbings: The final one, but you said that about not feeding kind of ownership. How do you create that ownership, one, and then how do you sustain it, literally?

Karl Sun: Yeah, that’s a great question. I think if you’ve been part of a company that’s grown in scale, you’ve probably heard people talk about the good old days and how they feel disconnected. I mentioned earlier that I sort of very begrudgingly came to my current point of view because I myself felt that sort of longing for the way things used to be where we could move faster, where you could just know what was going on. I think the key is this, if you can map out for each person, each employee, how it is that what they do, their role and their contribution, how that supports the bigger initiatives at their department level and even at the company level, I think they’re much more likely to be innovative and to feel ownership in that role. So I think where we fail is when employees don’t understand their, “why?” And how that applies to the bigger goal and the bigger picture.

Karl Sun: So when there isn’t that shared understanding of the bigger mission and then people end up either innovating in their silos or just worried about their immediate KPIs and their metrics and their team, then when you start to aggregate that up, the risk is everything doesn’t get pulled together. It doesn’t actually fit together or it doesn’t end up benefiting the company by moving in the same direction. Or we realize that multiple people and multiple groups have been working on the same thing and we’ve doubled the work and no one even knew that. So I think understanding our internal operations and how everything works together can not only create sort of cohesion throughout the company, but it ultimately results in sort of a better product and a better experience for our customers as well.

Harry Stebbings: Yeah, absolutely it does, having that kind of extreme cohesion and alignments around the org. I do want to move though, Karl, into my favorite element of any episode, that being the quick fire round. So I say a short statement and then you hit me with your immediate thoughts. Are you ready to dive in?

Karl Sun: Ready. Let’s go.

Harry Stebbings: We spoke about scaling the team there, what’s the hardest role to hire for today, and why do you think that is?

Karl Sun: Probably the role we’re trying to hire now is always the hardest, but probably someone great on the product side. I think it’s a blend of so many things. It’s a blend of vision, but also empathy, and also being strategic, but also being able to execute tactically and operationally. So I think that’s really a hard one to find.

Harry Stebbings: Tell me a moment in your life that’s maybe served as an inflection point and changed the way you think.

Karl Sun: I think by nature, I’m always the kind who thinks about what could be better? What’s next? So you’re always not satisfied. I think there are points in life, for example, when you have someone close to you who gets sick or goes through a difficult time and you realize that to be grateful and thankful for the things that we have and overall things are so good. I think just that perspective and outlook. Of course, you still want to be driven and push forward and be aggressive, but also realizing how fortunate that most of us in tech have it in terms of [crosstalk 00:27:06]

Harry Stebbings: Totally. No, I do agree with that. Now, a little birdie tells me that you’re an amazing father, husband, and even skier. How do you make the work life balance work so well?

Karl Sun: I think work life balance is an elusive concept without a clear definition. For me personally, I really can’t compartmentalize and break them up. So for me, it’s much about work life integration. That means maybe I’m taking a few calls between my daughter’s performances or the occasional call or meeting while I’m on vacation. But that also means that I can break away from work if there’s something important that’s going on. So to me, it’s really about making those two integrated and fit together. I found that’s what works best for me. I also recognize that doesn’t work for everyone, so I’ve tried really hard to provide an atmosphere where everyone is able to create their own definition.

Harry Stebbings: What do you believe that most around you disbelieve?

Karl Sun: I believe there is a right way to load the dishwasher.

Harry Stebbings: What is that way called? Come on, educate me. My mother will love you for this one.

Karl Sun: Well, it’s like a big game of Tetris. I think fitting in the right things in the right order, forks tines up as well as tines down because you can get twice as much into the dishwasher, making sure that things are not haphazard, but in parallel rows. I think you can just fit a lot more. That’s my goal is to fit as much into the dishwasher in one load as possible.

Harry Stebbings: The biggest bugbear for me is people that put knives, forks, and all other utensils in the same compartment in the dishwasher. It just makes taking them out and unpacking a nightmare. So totally align to you there. What a passion we both share. [crosstalk 00:28:31] Gosh, I wonder why I’m still single. At least you’re married. Tell me, what do you know now that you wish you’d known at the beginning of your time with Lucidchart?

Karl Sun: Figure out what you love doing, what you’re really passionate about, and get to doing that as soon as possible rather than feeling like you need to go through the five or eight steps in between that you think you need to or that other people think you need to or that typically happens between where you are now and where you want to get to be. So I would say find what to love and get to that in the fewest steps possible. I think you’re the perfect example of that, Harry. I think that’s a great example to all of us.

Harry Stebbings: That is very, very kind of you. Very lucky to have the time and the support of people like you. So listen, I really appreciate you coming on the show. As I said, I heard so many good things from George at Meritech. I was super excited for this one. It’s been fantastic to have you on, so thank you so much for joining me.

Karl Sun: Thank you, Harry. It’s been a pleasure.

Harry Stebbings: Such an awesome guest to have on the show and I really couldn’t be more excited for the exciting times ahead with Lucidchart. If you’d like to see more from us, you can find us on Instagram behind the scenes @HStebbings1996 with two Bs. I would love to see you there. 

Harry Stebbings: As always, I so appreciate all your support and I can’t wait to bring you a fantastic episode next week.

Published on February 28, 2020


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To Have Great Support — All Of It Has to Be Great



The other day I had a whiplash moment as a customer of a Unicorn SaaS company.  I had a large problem with a piece of software with a lot of integrations in it, and it really wasn’t clear whose problem it was.  But one of the vendors stepped up and said they’d solve the problem.  They worked over the weekend and fixed it!  Beyond above and beyond.

I became the world’s biggest super fan of this vendor.  I said put me on the website, make me a reference account, anything.  I became Mr NPS 100.

And then something happen.  The fix … broke.  And things were sort of bad again.

Under the adage of No Good Deed Goes Unpunished, I went back to the vendor that did the fix and told them the fix didn’t work anymore.  After some research, they said I’d have to go to a third party to fix the problem.  That it wasn’t their problem, it was another vendor, and that they would no longer be able to help me.

Perhaps that was all it was fair to ask of them.  Still, I then became NPS 0.  I no longer had a solution.  After an initial heroic effort.

Then again, the other day, I had another NPS-destroying interaction.  Another vendor that I loved asked me to do a case study.  It was a busy time with Annual coming up, but I loved the product, so not only did I carve out a full hour for the case study, but I had to rearrange my whole afternoon.  So I really lost a half day to do this case study.

I prepped.  I shared fun stories.  I made them look great.  And then, at the very end, the marketer doing the case study told me, “I will let you know if we decide to use any part of it.”

Dude.  I basically gave up half a day to help a junior marketer with a case study that didn’t remotely benefit me at all — and maybe you’ll use it?

NPS from 70 to 0, once again.

OK one more :)  Over the holidays I found a new vendor for SaaStr.  I spent days trying and deploying the app.  And then I ran into a wall.  A feature didn’t scale as expected.  So I hit chat.  It was the holidays, so their Intercom said don’t expect an answer for a week.  A week?? Yes, the app is very easy to use.  But I dedicated days of my time.  Now I need to wait a week for help?  NPS 70 to 0, once again.

My point is great support is far more than solving a problem here or there.  And importantly, even if you do a lot of things well — one bad piece of the customer experience can ruin even the best elements of support:

  • The experience as a prospect and with sales should be great.  No break-up emails, no pricing games, no drama with sales.  A bit more on that here.
  • The onboarding experience should be great.  Don’t fall down here.  It doesn’t matter if your product is so easy to use, almost everyone needs some onboarding.  How good is yours?  What % of your customers are 100% deployed at the time they paid?  Or within some short period?
  • The chat has to be fast and effective.  Bots are fine.  But chat has to solve my problem — fast.  A wiki and a bot are not enough in many cases.
  • Pricing can’t randomly go up.  That just breaks the relationship.  Don’t make me loathe that renewal email.
  • If a customer does you a favor, they deserve 5-star treatment for life.  Don’t forget the folks that joined your webinar, did a case study for you, etc.  Don’t forget because they won’t.
  • Customers should know who their CS rep is immediately.  And always have someone there to help.  If you don’t get CS help on Day 1, it’s not really there.
  • Don’t hide downtime or bugs from customers.  Especially when they see them.  Don’t claim it’s “lag” or “a few customers may be impacted”.  Customers know.  Especially the ones that have built software.  Lying about issues and downtime is another form of bad customer support and experience.
  • You may actually need to answer the phone.  Yes, some customers just want to pick up the phone for help.  It’s frustrating when you can’t get a hold of anyone.

Map your customer journey from first contact through year 10.  Map out each possible interaction.  And see what you can do to improve all of them.

And make sure when you reach out, do NPS surverys, etc. … you ask which part is weakest.  It probably will surprise you.

One weak link can undertime even the best sales, support, onboarding, or success teams.

Published on February 28, 2020


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J&J and Apple team up for heart study, Best Buy debuts wearable for seniors, Molekule raises $58M



In-home devices, week of 2/28/20

In a strange way, healthcare seems to be reverting back to a style that had gone out of fashion many years ago, with an increased amount of health taking place in the home. There are now around 12 million people who are now getting in-home care, from more than 33,000 providers, and last year the annual expenditures for home health care were projected to be over $72 billion.

This is thanks, in large part, to technology and, more specifically, to connected in-home devices that can easily collect and send data to a physicians in real-time. This allows patients to be monitored remotely, without constant trips to the doctor, and for physicians to do more timely interventions based on patterns picked up by AI and machine learning.

In June, Vator, HP and UCSF Health Hub will be holding an event centered around these devices, and how they are affecting the healthtech space. Every week until then we will be doing a roundup of some of the news around in-home devices and what some of the major tech companies are up to in this space.

Molekule raises $58 million

Molekule, which has developed an air purification device that doesn’t just collect pollutants, like traditional filters do, but actually works on a molecular level to get rid of them, raised $58 million in a Series C funding round, bringing its total funding to nearly $100 million.

The company sells two consumer devices: the Molekule Air, a standalone device that launched in 2017, which covers about 600 square feet in the home; and the Molekule Air Mini, a smaller device that covers 250 square feet, which the company launched in October.

Molekule’s patented air purification technology is called PECO, which is able to destroy pollutants 1,000 times smaller than what high-efficiency particulate air (HEPA) was designed to capture, including VOCs, mold, viruses and bacteria. When light shines on the PECO filter, which is produced by LED inside the device, it generates a chemical reaction that breaks down the pollutants.

In addition to the new funding, Molekule also announced a new partnership with Lawrence Berkeley National Laboratory, in which the lab studied the effectiveness of the device on eliminating pollutants. Molekule was able to reduce these by 95 percent and 94 percent, respectively, while also removing more than 50 percent of formaldehyde from the air. On top of that, the tests also showed that Molekule’s device did not generate any ozone by product, a harmful chemical that other air purifiers have shown to emit in the past. 

“One of the reasons why investors have been interested in our company is that this a space where new technology hasn’t emerged in decades. The dominant technology that’s out there today has been around since the 40s, and it’s becoming a major problem around the world,” Dilip Goswami, CEO and co-founder of Molekule, told VatorNews.

“Some of the things that we’ve seen of late, everything from huge amounts of smoke being produced by wildfires to  global pandemics like Coronavirus, which can be spread by airborne droplets, are all set against the backdrop of the larger fight against global air pollution and climate change. That has really brought air quality to the forefront of the mind not just investors but also consumers. The gap that we’re looking to fill is to actually help address all those different pollutants that are there in the air and get rid of them.”

Nemaura Medical puts its sugarBEAT wearable up against the incumbents

Nemaura Medical, a medical technology company that focuses on diabetes, announced it’s planning to initiate a user study comparing its continuous glucose monitor sugarBEAT against a “highly successful major incumbent” sensor. The goal is for the company to position sugarBEAT as an alternative to traditional CGMs.

“Our decision to go head-to-head vs. a hugely successful CGM sensor was based on positive feedback we received from recent meetings with public health insurers in key territories in Europe,” Dr. Faz Chowdhury, CEO of Nemaura, said in a statement.

“We believe that most people with diabetes do not currently use any continuous glucose monitoring system due to the high costs and the invasiveness of current products. We believe that sugarBEAT® changes this paradigm and is the first non-invasive CGM to provide the [masses] an option for daily monitoring whenever they choose at an affordable price point. We believe that this level of flexibility is a better option than any alternative CGM devices with either 7 day, 10 day, or 14 day sensor wear time currently available.”

Several similar studies are planned over the course of this year.

In addition to its wearable, Nemaura is also developing BEAT®diabetes, a planned health subscription service designed to help people with Type 2 diabetes and prediabetes through personalized lifestyle coaching.

Best Buy launches wearable for seniors 

Best Buy and GreatCall, a provider of health and safety solutions for older adults and their family caregivers, launched a new Lively App and Lively Wearable2 medical alert device.

The Lively App and Lively Wearable2 pair together, giving users access to agents 24/7 who can provide immediate responses and dispatch emergency personnel when the users presses a button on the device, or when a fall is detected. The wearable also provides a step count, health tips and it’s integrated with the Lively App to keep track of activity on a daily and monthly basis.

The Lively Wearable2 device will now be available at, in Best Buy stores and on

In addition, GreatCall also teamed up with AARP to offer AARP members exclusive prices on Lively service plans.

About Hero

Johnson & Johnson teams up with Apple for Heartline study

The Janssen Pharmaceutical Companies of Johnson & Johnson, in collaboration with Apple, opened enrollment for the Heartline Study, which is designed to explore if the Heartline Study app on iPhone and heart health features on Apple Watch can improve health outcomes. That includes reducing the risk of stroke, with earlier detection of atrial fibrillation (AFib), a leading cause of stroke in the U.S.

“Heartline is a study that has the potential to fundamentally change our understanding of how digital health tools, like the ECG app and irregular rhythm notification feature on Apple Watch, could lead to earlier detection of AFib, helping patients understand and directly engage in their heart health, prompting potentially life-saving conversations with their doctors, and improving health outcomes,” Dr. C. Michael Gibson, Co-Chair of the Heartline Executive Committee, said in a statement.

To enroll in the Heartline Study, individuals must be age 65 or older, be a U.S. resident, have Original (traditional) Medicare, own an iPhone 6s or a later model, and agree to provide access to their Medicare claims data. Eligible participants will be randomized to one of two possible groups, one of which will participate by only using the Heartline Study app on their iPhone, while the other will participate by using the study app on their iPhone in addition to obtaining an Apple Watch to use the ECG app and irregular rhythm notification feature.

Participation in the study will span a total of three years with two years of active engagement, followed by one year of additional data collection. During the active engagement period, participants will receive heart health education, wellness tips, surveys, and questionnaires across multiple topics related to overall heart health in the app each week.

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