Drew Houston on wooing Dropbox’s IPO investors: ‘We don’t fit neatly into any one mold’

Dropbox went public this morning to great fanfare, with the stock shooting up more than 40% in the initial moments of trading as the enterprise-slash-consumer company looked to convince investors that it could be a viable publicly-traded company.

And for one that Steve Jobs famously called a feature, and not a company, it certainly was an uphill battle to convince the world that it was worth even the $10 billion its last private financing round set. It’s now worth more than that, but that follows a long series of events, including an increased focus on enterprise customers and finding ways to make its business more efficient — like installing their own infrastructure. Dropbox CEO Drew Houston acknowledged a lot of this, as well as the fact that it’s going to continue to face the challenge of ensuring that its users and enterprises will trust Dropbox with some of their most sensitive files.

We spoke with Houston on the day of the IPO to talk a little bit about what it took to get here during the road show and even prior. Here’s a lightly-edited transcript of the conversation:

TC: In light of the problems that Facebook has had surrounding user data and user trust, how has that changed how you think about security and privacy as a priority?

DH: Our business is built on our customers’ trust. Whether we’re private or public, that’s super important to us. I think, to our customers, whether we’re private or public doesn’t change their view. I wouldn’t say that our philosophy changes as we get to bigger and bigger scale. As you can imagine we make big investments here. We have an awesome security team, our first cultural principle is be worthy of trust. This is existential for us.

TC: How’s the vibe now that longtime employees are going to have an opportunity to get rewarded for their work now that you’re a public company?

DH: I think everyone’s just really excited. This is the culmination of a lot of hard work by a lot of people. We’re really proud of the business we’ve built. I mean, building a great company or doing anything important takes time.

TC: Was there something that changed that convinced you to go public after more than a decade of going private, and how do you feel about the pop?

DH: We felt that we were ready. Our business was in great shape. We had a good balance of scale and profitability and growth. As a private company, there are a lot of reasons why it’s been easier to stay private for longer. We’re all proud of the business we’ve built. We see the numbers. We think we’re on to not just a great business, but pioneering a whole new model. We’re taking the best of our consumer roots, combining them with the best parts of software as a service, and it was really gratifying to see investors be excited about it and for the rest of the world to catch on.

TC: As you were on your road show, what were some of the big questions investors were asking?

DH: We don’t fit neatly into any one mold. We’re not a consumer company, and we’re not a traditional enterprise company. We’re basically taking that consumer internet playbook and applying it to business software, combining the virality and scale. Over the last couple years, as we’ve been building that engine, investors are starting to understand that we don’t fit into a traditional mold. The numbers speak to themselves, they can appreciate the unusual combination.

TC: What did you tell them to convince them?

DH: We’re just able to get adoption. Just the fact that we have hundreds of millions of users and we’ve found Dropbox is adopted in millions of companies [was enough evidence]. More than 300,000 of those users are Dropbox Business companies. We spend about half on sales of marketing as a percentage of revenue of a typical software as a service company. Efficiency and scale are the distinctive elements, and investors zero in on that. To be able to acquire customers at that scale and also really efficiently, that’s what makes us stand out. They’ve seen Atlassian be successful with self-serve products, but you can layer on top of that leveraging our freemium and viral elements and our focus on design and building great products.

TC: How do you think about deploying the capital you’ve picked up from the IPO?

DH: So, we’re public because they wanted us to be a public company. But our approach is still the same. First, it’s about getting the best talent in the building and making sure we build the best products, and if you do those things, make sure customers are happy, that’s what works.

TC: What about recruiting?

DH: It’s a big day for dropbox. We’re all really excited about it and hopefully a lot of other people are too.

TC: When you look at your customer acquisition ramp, what does that look like?

DH: I mean, we’ve been making a lot of progress in the past couple of years if you look at growth in subscribers. That will continue. We look at numbers, we have 11 million subscribers, 80% use dropbox for work. But at the same time, we look at the world, there’s 1 billion knowledge workers and growing. We’re not gonna run out of people who need Dropbox.

TC: What about convincing investors about the consumer part of the business? How did you do that?

DH: I think, when you explain that our consumer and cloud storage roots have really become a way for us to efficiently acquire business customers at scale, that helps them understand. Second, it’s easy to focus on how in the consumer realm that the business has been commoditized. There’s all this free space and all this competition. On the other hand, we’ve never lowered prices, we’ve never even given more free space, we know that what our customers really value is the sharing and collaboration, not just the storage. It’s been good to move investors beyond the 2010 understanding of our business.

TC: How did creating your own infrastructure play into your readiness to go public?

DH: When I say that today is the culmination of a lot of events, that’s a great example. We made a many-year investment to migrate off the public cloud. Certainly that was one of the more eye-popping investors watching our gross margins literally double over the last couple of years from burning cash to being cash flow positive. We’ll continue reaching larger and larger scale, and those investments will.

TC: Getting a new guitar any time soon?

DH: I probably should.


Dropbox CEO Drew Houston emphasizes user trust on IPO day amid Facebook’s troubles

Dropbox made its public debut today, with the stock soaring nearly 40% on its first day of trading — meaning the company will now be beholden to the same shareholders that sent the company’s valuation well north of $10 billion.

As a file-sharing and collaboration service, Dropbox’s first principle is going to be user trust, CEO Drew Houston told TechCrunch after the company made its debut. This comes amid a tidal wave of information throughout the week indicating that data on 50 million Facebook users ended up in the hands of Cambridge Analytica several years ago through access gained via an app that was on the Facebook platform. While not a direct breach in the core sense of the word, the leaked data was a considerable breach of trust among Facebook’s users — and as Dropbox looks to crack into the enterprise and also continue to win over consumers, it’ll likely continue to have to increasingly emphasize security and privacy going forward.

“Our business is built on our customers’ trust,” Houston said, asked of its security. “Whether we’re private or public, that’s super important to us. I think, to our customers, whether we’re private or public doesn’t change their view. I wouldn’t say that our philosophy changes as we get to bigger and bigger scale. As you can imagine we make big investments here. We have an awesome security team, our first cultural principle is be worthy of trust. This is existential for us.”

Houston, and Dropbox, aren’t unfamiliar with some of the challenges that come into securing a service that has more than 500 million registered users. Dropbox in 2016 disclosed that it discovered a chunk of user credentials obtained in 2012 had been circulating on the Internet after an employee’s password was acquired and used to access user information. Dropbox, clearly, has recovered from that stumble and has pulled off a successful IPO, but it does underscore the challenges of not only maintaining security, but also user trust and political capital to actually get the business going.

In the end, that may come down to the trust of individual users. A large portion of Dropbox’s 11 million paying customers are, or started off as, the typical consumer. Dropbox’s playbook is a familiar one, first getting consumer adoption and using that to slowly creep into teams that use the tool because it’s easier than existing ones. Those teams adopt it, leading to further adoption, to the point that Dropbox in theory locks in a customer without having to pick up those direct partnerships or spend a ton of money on marketing. Should it stumble at step one, it would have a much steeper ramp to start acquiring the kind of enterprise companies that will help it build a much more robust business.

“We have this set of stated values in the company, and the number one value is literally, be worthy of trust,” Dropbox SVP of engineering, product, and design Quentin Clark said. I have observed and experienced that the protection of our users is very deeply woven in to the DNA of our company. This is why we encrypt the data at rest, in transit, and it’s why our user experience is designed to keep people down the path of keeping things secure by default. You see it in the tools we give admins and the events they look through. We’re very deeply committed to their privacy and security. We’ve never sold data, it’s not in our business model, it’s about the value people get in software.”

While Dropbox at its heart was born as a consumer company — and there are, indeed, hundreds of millions of consumers — it’s also morphed over time into one with an arm looking to crack big businesses. And now that it’s a public company, it will have more intense oversight from public investors who will be scrutinizing its every move and calibrating its valuation as a result of those moves. Dropbox, too, is moving onto its own infrastructure in order to improve its margins and show it can be an operationally efficient business. All this means that, if it’s going to be a successful company, it has to ensure the kinds of snafus like Cambridge Analytica, which sent Facebook’s stock off a cliff, don’t happen.


Dropbox finishes up 36% on first day of trading

Dropbox was off to the races on its first day as a public company.

After pricing above the range at $21 per share, raising $756 million, Dropbox kicked off its first day soaring to $31.60, and closing the day at $28.48. This is up almost 36%.

It’s surely a sign of public investor enthusiasm for the cloud storage business, which had initially hoped to price its IPO between $16 and $18 and then raised it from $18 to $20.

It also means that Dropbox closed well above the $10 billion it was valued at its last private round. Its market cap is now above $12 billion, fully diluted.

Dropbox brought in $1.1 billion in revenue for the last year. This compares to $845 million in revenue the year before and $604 million for 2015.

While it’s been cash flow positive since 2016, it is not yet profitable, having lost nearly $112 million last year. But it is significantly improved margins when compared to losses of $210 million for 2016 and $326 million for 2015.

Its average revenue per paying user is $111.91.

There has been a debate about whether to value Dropbox, which has a freemium model, as a consumer company or an enterprise business. It has convinced just 11 million of its 500 million registered customers to pay for its services.

Dropbox “combines the scale and virality of a consumer company with the recurring revenue of a software company,” said Bryan Schreier, a general partner at Sequoia Capital and board member at the company. He said that now was the time for Dropbox to list because “the business had reached a level of scale and also cash flow that warranted a public debut.”

He also talked about the early days of Dropbox pitching at a TechCrunch event in 2008 and how disappointed they were that the slides stopped working during the presentation. We have footage of that here.

Sequoia Capital owned 23.2% of the overall shares outstanding at the time of the IPO. They shared Dropbox’s original seed pitch from 2007. 

Accel was the next largest shareholder, owning 5% overall. Sameer Gandhi made the investment at Sequoia and then invested in Dropbox again when he went over to Accel.

Founder and CEO Drew Houston owned 25.3% of the company.

Greylock Partners also had a small stake. John Lilly, a general partner there, said he “invested in Dropbox because Drew and the team had an exceptionally clear vision of what the future of work would look like and built a product that would that meet the demands of the modern workforce.”

But there are quite a few other businesses with similar products to Dropbox. The prospectus warned of the competitive landscape.

“The market for content collaboration platforms is competitive and rapidly changing. Certain features of our platform compete in the cloud storage market with products offered by Amazon, Apple, Google, and Microsoft, and in the content collaboration market with products offered by Atlassian, Google, and Microsoft. We compete with Box on a more limited basis in the cloud storage market for deployments by large enterprises.”

Note that it downplayed its competition with Box, a company that’s often mentioned in the same sentence as Dropbox. While the products are similar, the two have different business models and Dropbox was hoping that this would be respected with a better revenue multiple. If the first day is any indication, it looks like that strategy worked.

The company listed on the Nasdaq, under the ticker “DBX.”

We talked about Dropbox’s first day and the outlook for upcoming public debuts like Spotify on our “Equity” podcast episode below. We were joined by Eric Kim, managing partner at Goodwater Capital.  He authored a research report here. 


Storytelling for B2B startups: Avoiding ‘buzzword bingo’ to make your wonky enterprise company worth talking about

If there’s one thing I learned from my time as both a journalist at The Wall Street Journal and Forbes and, now, advising a global venture capital firm on communications, it’s that storytelling can make or break a company.

This is especially true the more complicated and arcane a company’s technology is. Stories about online-dating and burrito-delivery apps are easily understood by most people. But if a company specializes in making technology for hybrid-cloud data centers, or parsing specialized IT alerts and cybersecurity warnings, the storytelling task becomes much harder — but, I would argue, even more important.

Sure, a wonky company will still be able to talk easily to its customers and chat up nerdy CIOs at trade shows. But what happens when they raise a Series C or D round of financing and actually need to reach a broader audience — like really big, potential business partners, potential acquirers, public investors or high-level business reporters? Often, they’re stuck.

It can be painful to watch. When I was a reporter, I was amazed at the buzzwords thrown at me by some technology companies trying to get me to write about them. For fun, my colleagues and I would put some of these terms into online “buzzword bingo” websites just to see what indecipherable company descriptions they would spit out. (Example: “An online, cloud-based, open-source hyperconverged Kubernetes solution.”) Often, when pressed, PR representatives couldn’t explain to me what these companies actually did.

These companies obviously never made it into my stories. And I would argue that many of them suffered more broadly from their overall lack of high-profile press coverage; large business publications like the ones for which I worked target the very big-company executives and investors these later-stage startups were trying to reach.

Now, of course, I’m on the other side of that reporter/company equation — and I often feel like a big chunk of my job is working as a technology translator.

A natural-born storyteller

So why is this B2B storytelling problem so common, and arguably getting worse? Lots of reasons. Many of these hard-to-understand companies are founded by highly technical engineers for whom storytelling is (not surprisingly) not a natural skill. In many cases, their marketing departments are purely data-driven, focused on demand generation, ROI and driving prospects to an online sales funnel — not branding and high-level communications. As marketing technology has gotten more and more advanced and specialized, so have marketing departments.

As a result, many B2B and enterprise-IT companies are often laser-focused on talking about their products’ specific bells and whistles, staying in “sell mode” for a technical audience and cranking out wonky whitepapers and often-boring product press releases. They’re less adept at taking a step back to address the actual business benefits their product enables. Increasingly, this tech-talk also plays well with the legions of hyper-specialized, tech-news websites that have proliferated to serve every corner of the technology market, making some executives think there’s no need to target higher-level press.

Everyone has a story to tell. It’s up you to figure out what your company’s is, and how to tell that story in a compelling, understandable fashion.

One prominent marketing and PR consultant I know, who has worked with hundreds of Silicon Valley startups since the 1980s, says she is “shocked” by how poorly many senior tech industry CEOs today communicate their companies’ stories. Many tend to “shun” communications, considering it too “soft” in this new era of data-obsessed marketing, the consultant Jennifer Jones, recently told me. But in the end, poor communications and storytelling can create or exacerbate business problems, and often affect a company’s valuation.

So how do you get to a point where you can talk about your company in plain terms, and reach the high-level audiences you’re targeting?

One tactic, obviously, is to ditch the jargon when you need to. The pitch you use on potential customers — who likely already have an intimate understanding of your market and the specific problems you’re trying to solve — is not as relevant for other audiences.

A big fund manager at Fidelity or T. Rowe Price, or a national business journalist, probably knows, for example, that cloud computing is a big trend now, or that companies are buying more technology to battle complex cybersecurity attacks. But do they really understand the intricacies of “hybrid-cloud” data center setups? Or what a “behavioral attack detection solution” does? Probably not.

The David versus Goliath angle

Another tip is to put your company story in a larger, thematic context. People can better understand what you do if you can explain how you fit into larger technology and societal trends. These might include the rise of free, open-source software, or the growing importance of mobile computing.

It’s also helpful to talk about what you do in relation to larger, more established players. Are you nipping away at the slow-growing, legacy business of Oracle/EMC/Dell/Cisco? As a journalist, I once wrote a story about a small public networking company called F5 Networks that specialized in making “application delivery controllers.” But the story mostly focused on F5’s battle with a much larger competitor; in fact, the editors titled the story “One-Upping Cisco.” That’s the angle most readers were likely to care about. Journalists, particularly, love these David versus Goliath type stories, and national business publications are full of them.

Start focusing on high-level storytelling earlier, not when you’ve already raised $100 million in venture funding and have several hundred employees.

Another key storytelling strategy is leveraging your customers. If your business is boring to the average person, try to get one of your household-name customers to talk publicly about how they use your technology. Does your supply-chain software help L’Oréal sell more lipstick, or UPS make faster package deliveries?

One of our portfolio companies had a nice business-press hit a few years ago by talking about how their software helped HBO stream “Game of Thrones” episodes. (The service had previously crashed because too many people were trying to watch the show.) You can leverage these highly visible customers for case studies on your website. These can be great fodder for your sales team as well as later press interviews, as long as they’re well-written and understandable. Try to get more customers to agree to this type of content when you sign the contract with them.

From “Mad Men” to math men

Finally, there’s the issue of marketing leadership inside tech companies. In my experience, most smaller, B2B or enterprise IT-focused startups have CMOs or VPs of marketing who are more focused on data and analytics than brand communications — more “math men” than “Mad Men.” This isn’t surprising, as these companies often sell data-rich products and have business models where PR and general advertising don’t directly drive sales (unlike, say, a company making a food-delivery app). The CEOs of these companies value data and analytics, too.

I encourage B2B tech CEOs to focus on hiring CMOs with some brand/communications experience, or at least a willingness to outsource it to competent partners who are experts in that area. After a couple of early rounds of funding, you should be outgrowing your highly specialized PR firm (if you even have one) that focuses on a narrow brand of trade publications, for example. These firms usually don’t have contacts at the bigger, national business and technology outlets that are read by big mutual fund managers, and the business development folks at Cisco or Oracle. Hiring ex-journalists — not technical experts — to write content and develop messaging can be a good idea, too.

In other words, start focusing on high-level storytelling earlier, not when you’ve already raised $100 million in venture funding and have several hundred employees. By that point, it can simply be too late: Your company has already been typecast by the trade press and written off by higher-level reporters, and sometimes even potential business partners, as too niche-y and hard to understand.

As a journalist, I learned that everyone has a story to tell. It’s up you to figure out what your company’s is, and how to tell that story in a compelling, understandable fashion. If you do, I’m pretty sure the business benefits will follow.


Y Combinator’s Jessica Livingston on Dropbox IPO: “It was just a dream of ours”

Dropbox, after more than a decade, finally went public this morning — and the stock soared more than 40% in its initial trading, making it a marquee success for one of the original Web 2.0 companies (at least for now).

While we still have to wait for the dust to settle, it’s been a very long road for Dropbox. From starting off as a file-sharing service, to hitting a $10 billion valuation in the middle of a massive hype cycle, to expectations dropping and then the announcement of a $1 billion revenue run rate. Dropbox has been a rollercoaster, but it’s another big moment this afternoon: it’s Y Combinator’s first big IPO. And Y Combinator still has a very deep bench of startups that are, thus far, obvious IPO candidates down the line like Airbnb and Stripe.

That isn’t to take away anything from the work of CEO Drew Houston and the rest of Dropbox’s team, but Y Combinator’s job is to basically take a bunch of shots in the dark based on good ideas and potentially savvy founders. Houston was one of the first of a firm that now takes in a hundred-odd founders per class. Y Combinator Founder and partner Jessica Livingston was there for the start of it, recalling back to the day that Houston rushed to her and Paul Graham to show him his little side project.

We caught up with Livingston this morning ahead of the IPO for a short interview. Here’s the conversation, which was lightly edited for clarity:

TC: Can you tell us a little bit about what it’s like to finally see the first Y Combinator company to go public?

JL: I feel like 13 years ago, it was just this dream of ours. It was this seemingly unattainable dream that goes, ‘maybe one of the startups we fund could go public someday.’ That was the holy grail. It’s an exciting day for Y Combinator. It shows what a long game investing is in early-stage startups. I do feel kind of validated.

TC: How did Y Combinator first end up in touch with Houston?

JL: He applied as a solo founder. We had met Drew the summer before. Back then, we were so small that we always encouraged people to bring friends to a Y Combinator dinner. [Xobni founder Adam Smith] brought [Houston], and we met him then and talked it through. When he applied, we invited him to come to an interview, and Paul [Graham] before the interview reached out to [Houston]. He said, “I see you’re a solo founder, and you should find a cofounder.” Three weeks later Drew showed up with [co-founder Arash Ferdowsi]. It was a great match that worked well.

TC: As Dropbox has grown, what’s stood out to you the most during changes in the market?

JL: They’re a classic example of founders who are programmers who built something to solve their own problem. Clearly, this is a perfect example of that. Drew gets on the bus, he forgets his files, and he can’t work on the whole trip down. He then creates something that will allow him to access files from everywhere. At the time, when he came on the scene with that, there were a lot of companies doing it but none were very good. I feel like Dropbox, regardless of market dynamics, from the very beginning was always dedicated to wanting to do well by building a better solution. They wanted to build one that actually works. I feel like they’ve stuck to that and that’s been driving them since. That’s been their guidepost.

TC: What was your first meeting with Houston like, and do you think he has changed in the past 10 years?

JL: When I first met him, he was young — he was very young — and he was always a good hacker, and very earnest. During Y Combinator he was very focused on building this product and was not distracted by other things. That’s when there were just two people. He’s really evolved over the years as an incredible leader. He’s grown this company and he’s navigated through all different parts of his life cycle. I’ve witnessed his growth as a leader and as a human being. He’s always been a great person. It’s sort of exciting to see where he is now that he’s come a long way, it’s really cool.

TC: Houston and Ferdowsi still own significant portions of the company even after raising a lot of venture capital. Do you think Y Combinator had any effect on companies looking for more founder friendly deals?

JL: I think when Y Combinator started, our goal in many ways was to empower founders. It was to level the playing field. You don’t have to have a connection in Silicon Valley to get funding. You just have to apply on our website. You don’t have to have gone to an Ivy League school. We [try to tell them], don’t let investors take advantage of you because you’re young and have never done this before. In general, times have changed over the past 15 years. Hopefully Y Combinator played a small role in some of those changes in making things a little more found friendly.

TC: What’s one of your favorite stories about Houston?

JL: He was always very calm, cool, and collected under pressure. I remember that was definitely a quality about him. His feathers didn’t get ruffled easily. One of the things I remember most clearly is from that summer when we had demo day. Back then it was, like, 40 people tops. Still, there was a lot of pressure. I remember Paul [Graham] came up with this idea that, ‘hey, Drew, during your demo day you should show people how well Dropbox actually works by deleting your presentation live and restoring it through Dropbox.’ That’s kind of risky, right? To delete your presentation. You’re just standing up there without anything. And he did it and he nailed the presentation. It sounds a little gimmicky, but it really worked and showed his product worked. I remember thinking, like, wow, he’s pretty calm. If it were me I don’t think I could hit the delete button in front of these people. That’s an important quality in someone, not to get flustered.

By the way, we funded them in 2007. If you asked me in 2008 how were they doing, I would say, well, they’re making progress. But it wasn’t like we funded them and we could say, ‘this is gonna be a great one.’ We just knew, yeah they’re making progress, but it’s always hard to know there.

TC: Back then, what were you just expecting? M&A? Did you even anticipate an IPO?

JL:  As we were formulating the idea, the hope was rather than going to work at Microsoft — I use them as an example because that was the company back then — and rather than going to get a job out of college, why not build a company and make Microsoft acquire you to get you to work for them? We had low expectations back then. We were hoping there’d be some small acquisitions. But yes, the hope was always acquisitions, but maybe someday in our wildest dreams there’d be an IPO. We didn’t even think YC would work when we started, people didn’t believe in YC’s models for many years.

TC: Looking back, what would you say is one of the biggest things you’ve learned throughout this experience?

JL: What a long road it is for startups. When we started YC back then, it wasn’t a popular thing to do a startup. Now, thank goodness, more people are starting them, and more types of people are starting them. It’s not just super high-tech companies. That’s exciting, but what I think a lot of people don’t realize is how hard startups are. You say, yeah, I know how hard, but people don’t realize how difficult they are and how long the commitment is. If you’re successful, it takes such a long time. For [someone like Houston] to make it to that point, they’ve committed a lot of their life and energy and all their intellectual capacity to making this work. To me, that’s so exciting, but I think it would surprise people to know realistically how long that could take.

TC: What would you tell startups with the hindsight of what happened with Dropbox’s valuation hype cycle?

JL: I will say, with startups, sometimes you just have to stick to what you’re doing. There’s a lot of stuff going on around you, especially now with social media and things like that. With a startup, you just have to keep moving forward with building a company and building a great product.


Dropbox prices above its original range at $21 as it heads toward an IPO

Dropbox today said it is pricing above the range it originally set ahead of its public listing tomorrow, handing the company a valuation inching ever-closer to its original $10 billion valuation.

Dropbox earlier this week said it would price its initial public offering in a range between $18 and $20 per share, settling on a valuation near $8 billion at the high end of the range (or closer to $8.75 billion, based on its fully-diluted share count). With the new pricing, Dropbox will be valuing itself at around $8.4 billion — or a hair above $9 billion based on its fully-diluted share count. That $18 to $20 range, too, was a step up from its original proposed range, which fell between $16 and $18. Dropbox will be raising more than $700 million in the IPO, in addition to existing shareholders selling more than 9 million shares as part of the process.

What all this means is that Dropbox initially tested the waters to gauge interest, and clearly there was a lot. Companies sometimes set conservative price ranges (though this isn’t always the case) and then revise upwards as they see how much interest there is in potential investors buying shares at that price. Dropbox will make its public debut tomorrow, and the usual process here aims to get as much value for the company as possible while still ensuring the so-called IPO “pop” — usually a jump of around 20%. We’ll probably get the formal price in the form of an SEC filing this evening as it gets ready to list tomorrow.

Should that be successful, Dropbox would fall above the valuation of its last financing round, which gave the company a $10 billion valuation amid a hype wave of consumer startups. Dropbox, one of the original pioneers of online storage, in recent years has found itself looking to slowly scoop up more and more enterprise customers as it tries to create a second lucrative line of business. The company deploys a classic playbook of attracting initial customers within teams and then growing up to the point it reaches the C-Suite of companies, though the reverse is certainly possible as Dropbox matures over time.

CNBC first reported the news.


IBM can’t stop milking the Watson brand

More than seven years after IBM Watson beat a couple of human Jeopardy! champions, the company has continued to make hay with the brand. Watson, at its core, is simply an artificial intelligence engine and while that’s not trivial by any means, neither is it the personified intelligence that their TV commercials would have the less technically savvy believe.

These commercials contribute to this unrealistic idea that humans can talk to machines in this natural fashion. You’ve probably seen some. They show this symbol talking to humans in a robotic voice explaining its capabilities. Some of the humans include Bob Dylan, Serena Williams and Stephen King.

In spite of devices like Alexa and Google Home, we certainly don’t have machines giving us detailed explanations, at least not yet.

IBM would probably be better served aiming its commercials at the enterprises it sells to, rather than the general public, who may be impressed by a talking box having a conversation with a star. However, those of us who have at least some understanding of the capabilities of such tech, and those who buy it, don’t need such bells and whistles. We need much more practical applications. While chatting with Serena Williams about competitiveness may be entertaining, it isn’t really driving home the actual value proposition of this tech for business.

The trouble with using Watson as a catch-all phrase is that it reduces the authenticity of the core technology behind it. It’s not as though IBM is alone in trying to personify its AI though. We’ve seen the same thing from Salesforce with Einstein, Microsoft with Cortana and Adobe with Sensei. It seems that these large companies can’t deliver artificial intelligence without hiding it behind a brand.

The thing is this though, this is not a consumer device like the Amazon Echo or Google Home. It’s a set of technologies like deep learning, computer vision and natural language processing, but that’s hard to sell, so these companies try to put a brand on it like it’s a single entity.

Just this week, at the IBM Think Conference in Las Vegas, we saw a slew of announcements from IBM that took on the Watson brand. That included Watson Studio, Watson Knowledge Catalog, Watson Data Kits and Watson Assistant. While they were at it, they also announced they were beefing up their partnership Apple with — you guessed it — Watson and Apple Core ML. (Do you have anything without quite so much Watson in it?)

Marketers gonna market and there is little we can do, but when you overplay your brand, you may be doing your company more harm than good. IBM has saturated the Watson brand, and might not be reaching the intended audience as a result.


GitLab adds support for GitHub

Here is an interesting twist: GitLab, which in many ways competes with GitHub as a shared code repository service for teams, is bringing its continuous integration and delivery (CI/CD) features to GitHub.

The new service is launching today as part of GitLab’s hosted service. It will remain free to developers until March 22, 2019. After that, it’s moving to’s paid Silver tier.

GitHub itself offers some basic project and task management services on top of its core tools, but for the most part, it leaves the rest of the DevOps lifecycle to partners. GitLab offers a more complete CI/CD solution with integrated code repositories, but while GitLab has grown in popularity, GitHub is surely better known among developers and businesses. With this move, GitLab hopes to gain new users — and especially enterprise users — who are currently storing their code on GitHub but are looking for a CI/CD solution.

The new GitHub integration allows developers to set up their projects in GitLab and connect them to a GitHub repository. So whenever developers push code to their GitHub repository, GitLab will kick off that project’s CI/CD pipeline with automated builds, tests and deployments.

“Continuous integration and deployment form the backbone of modern DevOps,” said Sid Sijbrandij, CEO and co-founder of GitLab. “With this new offering, businesses and open source projects that use GitHub as a code repository will have access to GitLab’s industry leading CI/CD capabilities.”

It’s worth noting that GitLab offers a very similar integration with Atlassian’s BitBucket, too.


Ansarada gets $18M in Series A funding to help companies better prepare for major deals

Australian startup Ansarada, which provides tools for companies preparing for a major transaction, will expand in the United States, Europe, the Middle East and Africa after raising an $18 million Series A. The funding was led by Ellerston Capital, with participation from Tempus Partners, Belay Capital and Australian Ethical Investments. A noteworthy detail about the raise is that all advisory fees from the deal will be donated to Ugandan and Nepalese charities through Ansarada’s partnership with Adara Partners, a corporate advisory firm made up of financial services experts who donate their fees to help women and children living in poverty.

Ansarada provides data rooms, or secure virtual spaces that enable companies about to undergo a complex event or transaction, like a merger or fundraising, gather all relevant data and files in one place. This allows the process of performing due diligence, legal compliance, writing contracts and other tasks to go more smoothly and also lets companies track who accesses which documents. Ansarada’s clients have included some of the biggest names in tech and financial services, including Google, VMWare, Sony, Microsoft, Deloitte, PwC and KPMG. The Sydney-based company, which claims up to 80% of deals in Australia happen through its platform, will use its new funding for sales and marketing in its target countries, especially the United States, and on product development.

Other virtual data room providers include Firmex, Intralinks and Merrill Corporation, but Ansarada chief executive officer Sam Riley says one of its competitive advantages is its recently launched Material Information Platform (MIP), which serves as a complement to its data rooms. MIP uses machine learning and natural language processing algorithms trained with a dataset gathered from more than 20,000 transactions to give companies information that can potentially reduce deal risks and improve their ongoing business operations. These include an algorithm that Riley says is “up to 97% accurate by day 21 into an M&A deal at benchmarking a bidder’s behavior, scoring their engagement levels and predicting their likelihood to submit an offer and win.” It also scores the completeness of material information and tracks if risk and compliance requirements are being met.

“We’ve seen thousands of companies find out their biggest risks and opportunities too late in their life cycle, which prevents them from performing better pre-deal and ultimately getting less-than-ideal outcomes when they sell or raise capital,” Riley told TechCrunch in an email. He added “We define readiness as being able to express the value of your company very well and very fast, especially to an investor, advisor, auditor or any party that’s critical to success in your company’s most important events. Companies get control and visibility over their most important information and ensure improvement by scorecarding and assigning accountability to their management teams.”

As one would expect, Ansarada used its own products while raising its Series A.

“We eat our own ice cream, so even using the product for our own capital raise resulted in less time by our management team to prepare for the deal and more time spent executing our strategy,” said Riley. “We are now using the platform to give our board an objective score over how well our vital information and key risks are being managed. Simultaneously we are now ready for the next event on our calendar, which is likely to be a financial audit.”


Clari raises $35M for its AI-based sales platform, expands into marketing and supply chain management

Clari — a startup that has built a predictive sales tool that provides just-in-time assistance for sales people close deals and for those who work in the bigger chain of command to monitor the progress of the sales operation — is capitalising on the big boom in interest for all things AI in the business world. The company is today announcing that it has closed a Series B round of $35 million, funding that it will be using to build out its own sales and marketing team and expand its platform capabilities.

The round was led by Tenaya Capital, the VC fund that started its life as a part of Lehman Brothers, along with participation from other new investors Thomvest Ventures and Blue Cloud Ventures, and previous investors Sequoia Capital, Bain Capital Ventures and Northgate Capital. It brings the total raised by Clari to $61 million.

Andy Byrne, the founder and CEO who is a repeat entrepreneur and has been involved in several exits, said the funding closed “definitely at an upround, and much bigger than we thought it was going to be,” but declined to give a number. For some context, Clari, according to Pitchbook, had a relatively modest post-money valuation of $83.5 million in its last round in 2014, so my guess is that it’s now comfortably into hundred-million territory, once you add in this latest $35 million.

The funding comes at an interesting time for AI startups, particularly those aimed at enterprise IT.

When Clari first emerged from stealth in April 2014, the idea of applying AI to solve pain points for non-technical people in organizations was a fairly nascent and still-novel concept.

Fast forward to today, things have moved very fast, as is often the case in the tech world. Now, you can’t seem to move for all the enterprise IT startups that are either using or claiming to use AI in their solutions. There are so many startup hopefuls, and so many organizations looking for the best way to use AI to improve their business and operations, that there are even startups being founded to manage that opportunity of connecting the two pieces together, such as Element AI.

“I’m not saying we were clairvoyant for targeting the idea of using AI for sales in 2013,” Byrne said. “There has been a large macro trend and if you happen to be a small company that is along for the ride. When we first launched, we had this thesis about AI for sales. Now it’s not the number three or two priority for sales teams, it’s number one. It’s everywhere. Businesses want to invest and spend more money on AI and making things more efficient.”

Clari says that its customer base has tripled in the last year, with customers including Adobe, Audi, Check Point Software, Equinix, Epicor Software Corporation, GE, and PerkinElmer.

Clari’s approach for using AI for the sales team comes in two main areas. First, the company’s system is aimed to reduce some of the busywork that salespeople have in maintaining and updating files on people, by bringing in a number of different data sources and using them to provide composite pictures of target companies that salespeople might have had to otherwise compile with more manual means. Second, Clari puts a lot of focus on its “Opportunity-to-Close (OTC) solutions” — a type of risk-analysis for salespeople and their managers to help them figure out which leads and strategic directly would be the most likely to produce sales.

“Working with Clari since inception, we have been impressed with its growth and strong execution,” said Aaref Hilaly, Partner at Sequoia Capital, in a statement. “Clari has fast become indispensable to many of the most successful sales teams, giving them visibility into their most important metrics: rep productivity, pipeline health, and forecast accuracy.”

Indeed, risk and outcome is a smart area to be in: using AI to help model this is a key area of focus in enterprise IT at the moment, according to feedback I’ve had from a number of others in the enterprise world.

“If you have 150 opportunities presented to you as a salesperson, how do you choose 10 where you should spend your time?” Byrne asked. “A more traditional CRM platform has never showcased your risk and outcomes.”

While up to now Clari has focused on providing intelligence on what is already in a company’s account database, the next step, Byrne noted, is to draw on data from around the web, providing completely new business leads to the sales team.

When we last covered a funding round for Clari, we noted that the company’s laser focus on sales was something that made the company stand out for investors: nailing one aspect of a business’s operations without distractions from other parts of the organization and what it could be spending time solving elsewhere (in fact, when you think about it, the very goal that Clari has been aiming to achieve for salespeople through its product).

But four years on, the company is now widening that ambition. It’s applying its AI engine now to help marketeers weigh up the best opportunities for reaching out to prospective customers; and interestingly it sounds like it will also be applying its engine to product development and specifically supply chain management.

Byrne described one customer, a medical device maker, that was encountering “inefficiencies” around what they should build and when to meet market demand. “Now that they can predict and forecast order bookings and revenue targets, and what’s happened is that their supply chain has become more efficient,” he said. “It is great example of how our AI is now being expanded.”

“The Clari team has leveraged its deep AI expertise to build a unique platform that surfaces predictive insights for sales reps, managers, and execs during the opportunity-to-close process,” said Brian Paul, MD at Tenaya Capital, in a statement. “We see a massive opportunity for AI to transform how sales teams operate which is clearly validated by Clari’s customers and the impressive growth the team has achieved.”

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