Dropbox to acquire secure document sharing startup DocSend for $165M

Dropbox announced today that it plans to acquire DocSend for $165 million The company helps customers share and track documents by sending a secure link instead of an attachment.

“We’re announcing that we’re acquiring DocSend to help us deliver an even broader set of tools for remote work, and DocSend helps customers securely manage and share their business critical documents, backed by powerful engagement analytics,” Houston told me.

When combined with the electronic signature capability of HelloSign, which Dropbox acquired in 2019, the acquisition gives the company an end-to-end document sharing workflow it had been missing. “Dropbox, DocSend and HelloSign will be able to offer a full suite of self-serve products to help our millions of customers manage the entire critical document workflows and give more control over all aspects of that,” Houston explained.

Houston and DocSend co-founder and CEO Russ Heddleston have known each for other years, and have an established relationship. In fact, Heddleston worked for Dropbox as a summer in intern in 2010. He even ran the idea for the company by Houston prior to launching in 2013, who gave it his seal of approval, and the two companies have been partners for some time.

“We’ve just been following the thread of external sending, which has just kind of evolved and opened up into all these different workflows. And it’s just really interesting that by just being laser focused on that we’ve been able to create a really differentiated product that users love a ton,” Heddleston said.

Those workflows include creative, sales, client services or startups using DocSend to deliver proposals or pitch decks and track engagement. In fact, among the earliest use cases for the company was helping startups track engagement with their pitch decks at VC firms.

The company raised a modest amount of the money along the way, just $15.3 million, according to Crunchbase, but Heddleston says that he wanted to build a company that was self-sufficient and raising more VC dollars was never a priority or necessity. “We had [VCs] chase us to give us more money all the time, and what we would tell our employees is that we don’t keep count based on money raised or headcount. It’s just about building a great company,” he said.

That builder’s attitude was one of the things that attracted Houston to the company. “We’re big believers in the model of product growth and capital efficiency, and building really intuitive products that are viral, and that’s a lot of what what attracted us to DocSend,” Houston said. While DocSend has 17,000 customers, Houston says the acquisition gives the company the opportunity to get in front of a much larger customer base as part of Dropbox.

It’s worth noting that Box offers a similar secure document sharing capability enabling users to share a link instead of using an attachment. It recently bought e-signature startup SignRequest for $55 million with an eye toward building more complex document workflows similar to what Dropbox now has with HelloSign and DocSend. PandaDoc is another competitor in this space.

Both Dropbox and SendDoc participated in the TechCrunch Disrupt Battlefield with Houston debuting Dropbox in 2008 at the TechCrunch 50, the original name of the event. Meanwhile, DocSend participated in 2014 at TechCrunch Disrupt in New York City.

DocSend’s approximately 50 employees will be joining Dropbox when the deal closes, which should happen soon, subject to standard regulatory oversight.


By Ron Miller

Dropbox shifts business product focus to remote work with Spaces update

In a September interview at TechCrunch Disrupt, Dropbox co-founder and CEO Drew Houston talked about how the pandemic had forced the company to rethink what work means, and how his company is shifting with the new requirements of a work-from-home world. Today, the company announced broad changes to Dropbox Spaces, the product introduced last year, to make it a collaboration and project management tool designed with these new requirements in mind.

Dropbox president Timothy Young says that the company has always been about making it easy to access files wherever you happen to be and whatever device you happen to be on, whether that was in a consumer or business context. As the company has built out its business products over the last several years, that involved sharing content internally or externally. Today’s announcement is about helping teams plan and execute around the content you create with a strong project focus.

“Now what we’re basically trying to do is really help distributed teams stay organized, collaborate together and keep moving along, but also do so in a really secure way and support IT, administrators and companies with some features around that as well, while staying true to Dropbox principles,” Young said.

This involves updating Spaces to be a full-fledged project management tool designed with a distributed workforce in mind. Spaces connects to other tools like your calendar, people directory, project management software — and of course files. You can create a project, add people and files, then set up a timeline and assign and track tasks, In addition, you can access meetings directly from Spaces and communicate with team members, who can be inside or outside the company.

Houston suggested a product like this could be coming in his September interview when he said:

“Back in March we started thinking about this, and how [the rapid shift to distributed work] just kind of happened. It wasn’t really designed. What if you did design it? How would you design this experience to be really great? And so starting in March we reoriented our whole product road map around distributed work,” he said.

Along these same lines, Young says the company itself plans to continue to be a remote first company even after the pandemic ends, and will continue to build tools to make it easier to collaborate and share information with that personal experience in mind.

Today’s announcement is a step in that direction. Dropbox Spaces has been in private beta, but will be available in public beta starting today. It should be available publicly at the beginning of next year.


By Ron Miller

Dropbox begins shift to high efficiency Western Digital Shingled Magnetic Recording disks

Last year, Dropbox talked about making a shift to Shingled Magnetic Recording or SMR disks for short because of the efficiency they can give a high volume storage platform like theirs. Today, Western Digital announced that Dropbox was one of the first companies to qualify their Ultrastar® DC HC650 20TB, host-managed SMR hard disks.

Dropbox’s modern infrastructure story goes back to 2017 when it decided to shift most of its business from being hosted on AWS to building their own infrastructure. As they moved through the process of making that transition in the following years, they were looking for new storage technology ideas to help drive down the cost of running their own massive storage system.

As principal engineer James Cowling told TechCrunch last year, one of the ideas that emerged was using SMR:

What emerged was SMR, which has high storage density and a lower price point. Moving to SMR gave Dropbox the ability to do more with less, increasing efficiency and lowering overall costs — an essential step for a company trying to do this on its own. “It required expertise obviously, but it was also exciting to bring a lot of efficiencies in terms of cost and storage efficiency, while pulling down boundaries between software and hardware,” Cowling said.

As it turns out, Dropbox VP of engineering Andrew Fong says that the company has been working with Western Digital for a number of years and the new SMR technology is the latest step in that partnership.

Western Digital says that these drives deliver this cost savings through increased storage density and lower power requirements. “When considering exabyte-scale needs, and associated capital and operating cost of the data center, the long-term value in terms of lower cost-per-TB, higher density, low power and high reliability can help benefit the bottom line,” the company said in a statement.

Time will tell if these disks deliver as promised, but they certainly show a lot of potential for a high volume user like Dropbox.


By Ron Miller

The highest valued company in Bessemer’s annual cloud report has defied convention by staying private

This year’s Bessemer Venture Partners’ annual Cloud 100 Benchmark report was published recently and my colleague Alex Wilhelm looked at some broad trends in the report, but digging into the data, I decided to concentrate on the Top 10 companies by valuation. I found that the top company has defied convention for a couple of reasons.

Bessemer looks at private companies. Once they go public, they lose interest, and that’s why certain startups go in and out of this list each year. As an example, Dropbox was the most highly valued company by far with a valuation in the $10 billion range for 2016 and 2017, the earliest data in the report. It went public in 2018 and therefore disappeared.

While that $10 billion benchmark remains a fairly good measure of a solidly valued cloud company, one company in particular blew away the field in terms of valuation, an outlier so huge, its value dwarfs even the mighty Snowflake, which was valued at over $12 billion before it went public earlier this month.

That company is Stripe, which has an other worldly valuation of $36 billion. Stripe began its ascent to the top of the charts in 2016 and 2017 when it sat behind Dropbox with a $6 billion valuation in 2016 and around $8 billion in 2017. By the time Dropbox left the chart in 2018, Stripe would have likely blown past it when its valuation soared to $20 billion. It zipped up to around $23 billion last year before taking another enormous leap to $36 billion this year.

Stripe remains an outlier not only for its enormous valuation, but also the fact that it hasn’t gone public yet. As TechCrunch’s Ingrid Lunden pointed out in article earlier this year, the company has remained quiet about its intentions, although there has been some speculation lately that an IPO could be coming.

What Stripe has done to earn that crazy valuation is to be the cloud payment API of choice for some of the largest companies on the Internet. Consider that Stripe’s customers include Amazon, Salesforce, Google and Shopify and it’s not hard to see why this company is valued as highly as it is.

Stripe came up with the idea of making it simple to incorporate a payments mechanism into your app or website, something that’s extremely time-consuming to do. Instead of building their own, developers tapped into Stripe’s ready-made variety and Stripe gets a little money every time someone bangs on the payment gateway.

When you’re talking about some of the biggest companies in the world being involved, and many others large and small, all of those payments running through Stripe’s systems add up to a hefty amount of revenue, and that revenue has led to this amazing valuation.

One other company, you might want to pay attention to here, is UIPath, the robotic process automation company, which was sitting just behind Snowflake with a valuation of over $10 billion. While it’s unclear if RPA, the technology that helps automate legacy workflows, will have the lasting power of a payments API, it certainly has come on strong the last couple of years.

Most of the companies in this report appear for a couple of years as they become unicorns, watch their values soar and eventually go public. Stripe up to this point has chosen not to do that, making it a highly unusual company.


By Ron Miller

Dropbox CEO Drew Houston says the pandemic forced the company to reevaluate what work means

Dropbox CEO and co-founder Drew Houston, appearing at TechCrunch Disrupt today, said that COVID has accelerated a shift to distributed work that we have been talking about for some time, and these new ways of working will not simply go away when the pandemic is over.

“When you think more broadly about the effects of the shift to distributed work, it will be felt well beyond when we go back to the office. So we’ve gone through a one way door. This is maybe one of the biggest changes to knowledge work since that term was invented in 1959,” Houston told TechCrunch Editor-In-Chief Matthew Panzarino.

That change has prompted Dropbox to completely rethink the product set over the last six months, as the company has watched the way people work change in such a dramatic way. He said even though Dropbox is a cloud service, no SaaS tool in his view was purpose-built for this new way of working and we have to reevaluate what work means in this new context.

“Back in March we started thinking about this, and how [the rapid shift to distributed work] just kind of happened. It wasn’t really designed. What if you did design it? How would you design this experience to be really great? And so starting in March we reoriented our whole product roadmap around distributed work,” he said.

He also broadly hinted that the fruits of that redesign are coming down the pike. “We’ll have a lot more to share about our upcoming launches in the future,” he said.

Houston said that his company has adjusted well to working from home, but when they had to shut down the office, he was in the same boat as every other CEO when it came to running his company during a pandemic. Nobody had a blueprint on what to do.

“When it first happened, I mean there’s no playbook for running a company during a global pandemic so you have to start with making sure you’re taking care of your customers, taking care of your employees, I mean there’s so many people whose lives have been turned upside down in so many ways,” he said.

But as he checked in on the customers, he saw them asking for new workflows and ways of working, and he recognized there could be an opportunity to design tools to meet these needs.

“I mean this transition was about as abrupt and dramatic and unplanned as you can possibly imagine, and being able to kind of shape it and be intentional is a huge opportunity,” Houston said.

Houston debuted Dropbox in 2008 at the precursor to TechCrunch Disrupt, then called the TechCrunch 50. He mentioned that the Wi-Fi went out during his demo, proving the hazards of live demos, but offered words of encouragement to this week’s TechCrunch Disrupt Battlefield participants.

Although his is a public company on a $1.8 billion run rate, he went through all the stages of a startup, getting funding and eventually going public, and even today as a mature public company, Dropbox still evolving and changing as it adapts to changing requirements in the marketplace.


By Ron Miller

Moving storage in-house helped Dropbox thrive

Back in 2013, Dropbox was scaling fast.

The company had grown quickly by taking advantage of cloud infrastructure from Amazon Web Services (AWS), but when you grow rapidly, infrastructure costs can skyrocket, especially when approaching the scale Dropbox was at the time. The company decided to build its own storage system and network — a move that turned out to be a wise decision.

In a time when going from on-prem to cloud and closing private data centers was typical, Dropbox took a big chance by going the other way. The company still uses AWS for certain services, regional requirements and bursting workloads, but ultimately when it came to the company’s core storage business, it wanted to control its own destiny.

Storage is at the heart of Dropbox’s service, leaving it with scale issues like few other companies, even in an age of massive data storage. With 600 million users and 400,000 teams currently storing more than 3 exabytes of data (and growing) if it hadn’t taken this step, the company might have been squeezed by its growing cloud bills.

Controlling infrastructure helped control costs, which improved the company’s key business metrics. A look at historical performance data tells a story about the impact that taking control of storage costs had on Dropbox.

The numbers

In March of 2016, Dropbox announced that it was “storing and serving” more than 90% of user data on its own infrastructure for the first time, completing a 3-year journey to get to this point. To understand what impact the decision had on the company’s financial performance, you have to examine the numbers from 2016 forward.

There is good financial data from Dropbox going back to the first quarter of 2016 thanks to its IPO filing, but not before. So, the view into the impact of bringing storage in-house begins after the project was initially mostly completed. By examining the company’s 2016 and 2017 financial results, it’s clear that Dropbox’s revenue quality increased dramatically. Even better for the company, its revenue quality improved as its aggregate revenue grew.


By Ron Miller

Why is Dropbox reinventing itself?

According to Dropbox CEO Drew Houston, 80% of the product’s users rely on it, at least partially, for work.

It makes sense, then, that the company is refocusing to try and cement its spot in the workplace; to shed its image as “just” a file storage company (in a time when just about every big company has its own cloud storage offering) and evolve into something more immutably core to daily operations.

Earlier this week, Dropbox announced that the “new Dropbox” would be rolling out to all users. It takes the simple, shared folders that Dropbox is known for and turns them into what the company calls “Spaces” — little mini collaboration hubs for your team, complete with comment streams, AI for highlighting files you might need mid-meeting, and integrations into things like Slack, Trello and G Suite. With an overhauled interface that brings much of Dropbox’s functionality out of the OS and into its own dedicated app, it’s by far the biggest user-facing change the product has seen since launching 12 years ago.

Shortly after the announcement, I sat down with Dropbox VP of Product Adam Nash and CTO Quentin Clark . We chatted about why the company is changing things up, why they’re building this on top of the existing Dropbox product, and the things they know they just can’t change.

You can find these interviews below, edited for brevity and clarity.

Greg Kumparak: Can you explain the new focus a bit?

Adam Nash: Sure! I think you know this already, but I run products and growth, so I’m gonna have a bit of a product bias to this whole thing. But Dropbox… one of its differentiating characteristics is really that when we built this utility, this “magic folder”, it kind of went everywhere.


By Greg Kumparak

Three years after moving off AWS, Dropbox infrastructure continues to evolve

Conventional wisdom would suggest that you close your data centers and move to the cloud, not the other way around, but in 2016 Dropbox undertook the opposite journey. It (mostly) ended its long-time relationship with AWS and built its own data centers.

Of course, that same conventional wisdom would say, it’s going to get prohibitively expensive and more complicated to keep this up. But Dropbox still believes it made the right decision and has found innovative ways to keep costs down.

Akhil Gupta, VP of Engineering at Dropbox, says that when Dropbox decided to build its own data centers, it realized that as a massive file storage service, it needed control over certain aspects of the underlying hardware that was difficult for AWS to provide, especially in 2016 when Dropbox began making the transition.

“Public cloud by design is trying to work with multiple workloads, customers and use cases and it has to optimize for the lowest common denominator. When you have the scale of Dropbox, it was entirely possible to do what we did,” Gupta explained.

Alone again, naturally

One of the key challenges of trying to manage your own data centers, or build a private cloud where you still act like a cloud company in a private context, is that it’s difficult to innovate and scale the way the public cloud companies do, especially AWS. Dropbox looked at the landscape and decided it would be better off doing just that, and Gupta says even with a small team — the original team was just 30 people — it’s been able to keep innovating.


By Ron Miller

On balance, the cloud has been a huge boon to startups

Today’s startups have a distinct advantage when it comes to launching a company because of the public cloud. You don’t have to build infrastructure or worry about what happens when you scale too quickly. The cloud vendors take care of all that for you.

But last month when Pinterest announced its IPO, the company’s cloud spend raised eyebrows. You see, the company is spending $750 million a year on cloud services, more specifically to AWS. When your business is primarily focused on photos and video, and needs to scale at a regular basis, that bill is going to be high.

That price tag prompted Erica Joy, a Microsoft engineer to publish this Tweet and start a little internal debate here at TechCrunch. Startups, after all, have a dog in this fight, and it’s worth exploring if the cloud is helping feed the startup ecosystem, or sending your bills soaring as they have with Pinterest.

For starters, it’s worth pointing out that Ms. Joy works for Microsoft, which just happens to be a primary competitor of Amazon’s in the cloud business. Regardless of her personal feelings on the matter, I’m sure Microsoft would be more than happy to take over that $750 million bill from Amazon. It’s a nice chunk of business, but all that aside, do startups benefit from having access to cloud vendors?


By Ron Miller

How to handle dark data compliance risk at your company

Slack and other consumer-grade productivity tools have been taking off in workplaces large and small — and data governance hasn’t caught up.

Whether it’s litigation, compliance with regulations like GDPR, or concerns about data breaches, legal teams need to account for new types of employee communication. And that’s hard when work is happening across the latest messaging apps and SaaS products, which make data searchability and accessibility more complex.

Here’s a quick look at the problem, followed by our suggestions for best practices at your company.

Problems

The increasing frequency of reported data breaches and expanding jurisdiction of new privacy laws are prompting conversations about dark data and risks at companies of all sizes, even small startups. Data risk discussions necessarily include the risk of a data breach, as well as preservation of data. Just two weeks ago it was reported that Jared Kushner used WhatsApp for official communications and screenshots of those messages for preservation, which commentators say complies with recordkeeping laws but raises questions about potential admissibility as evidence.


By Arman Tabatabai

Dropbox snares HelloSign for $230M, gets workflow and eSignature

Dropbox announced today that it has purchased HelloSign, a company that provides lightweight document workflow and eSignature services. The company paid a hefty $230 million for the privilege.

Dropbox’s SVP of engineering, Quentin Clark, sees this as more than simply bolting on electronic signature functionality to the Dropbox solution. For him, the workflow capabilities that HelloSign added in 2017 were really key to the purchase.

“What is unique about HelloSign is that the investment they’ve made in APIs and the workflow products is really so aligned with our long term direction,” Clark told TechCrunch. “It’s not just a thing to do one more activity with Dropbox, it’s really going to help us pursue that broader vision,” he added. That vision involves extending the storage capabilities that is as the core of the Dropbox solution

This can also been seen in the context of the Extension capability that Dropbox added last year. HelloSign was actually one of the companies involved at launch. While Clark say the company will continue to encourage companies to extend the Dropbox solution, today’s acquisition gives it a capability of its own that doesn’t require a partnership.

HelloSign CEO Joseph Walla says being part of Dropbox gives HelloSign access to resources of a much larger public company, which should allow it to reach a broader market than it could on its own. “We share a design philosophy based on building the best experience for end-users, fueling our efficient business models and sales strategies. Together with Dropbox, we can bring more seamless document workflows to even more customers and dramatically accelerate our impact,”  Walla said in a blog post announcing the deal.

Whitney Bouck, COO at HelloSign, who previous held stints at Box and EMC Documentum, said the company will remain an independent entity. That means it will continue to operate with its current management structure and Clark indicated that all of the employees will be offered employment at Dropbox as part of the deal.

When you consider that HelloSign, a Bay area startup that launched in 2011, raised just $16 million, it appears to be a impressive return for investors.

This is a developing story. More to come.


By Ron Miller

Dropbox expands Paper into planning tool with timelines

Dropbox has been building out Paper, its document-driven collaboration tool since it was first announced in 2015, slowly but surely layering on more functionality. Today, it added a timeline feature, pushing beyond collaboration into a light-weight project planning tool.

Dropbox has been hearing that customers really need a way to plan with Paper that was lacking. “That pain—the pain of coordinating all those moving pieces—is one we’re taking on today with our new timelines feature in Dropbox Paper,” the company wrote in a blog post announcing the new feature.

As you would expect with such a tool, it enables you to build a timeline with milestones, but being built into Paper, you can assign team members to each milestone and add notes with additional information including links to related documents.

You can also embed a To-do lists for the person assigned to a task right in the timeline to help them complete the given task, giving a single point of access for all the people assigned to a project

Gif: Dropbox

“Features like to-dos, @mentions, and due dates give team members easy ways to coordinate projects with each other. Timelines take these capabilities one step further, letting any team member create a clean visual representation of what’s happening when—and who’s responsible,” Dropbox wrote in the blog post announcement.

Dropbox has recognized it cannot live as simply a content storage tool. It needs to expand beyond that into collaboration and coordination around that content, and that’s what Dropbox Paper has been about. By adding timelines, the company is looking to expand that capability even further.

Alan Lepofsky, who covers the “future of work” for Constellation Research sees Paper as part of the changing face of collaboration tools. “I refer to the new breed of content creation tools as digital canvases. These apps simplify the user experience of integrating content from multiple sources. They are evolving the word-processor paradigm,” Lepofsky told TechCrunch.

It’s probably not going to replace a project manager’s full-blown planning tools any time soon, but it at least the potential to be a useful adjunct for the Paper arsenal to allow customers to continue to find ways to extract value from the content they store in Dropbox.


By Ron Miller

Dropbox overhauls internal search to improve speed and accuracy

Over the last several months, Dropbox has been undertaking an overhaul of its internal search engine for the first time since 2015. Today, the company announced that the new version, dubbed Nautilus, is ready for the world. The latest search tool takes advantage of a new architecture powered by machine learning to help pinpoint the exact piece of content a user is looking for.

While an individual user may have a much smaller body of documents to search across than the World Wide Web, the paradox of enterprise search says that the fewer documents you have, the harder it is to locate the correct one. Yet Dropbox faces of a host of additional challenges when it comes to search. It has more than 500 million users and hundreds of billions of documents, making finding the correct piece for a particular user even more difficult. The company had to take all of this into consideration when it was rebuilding its internal search engine.

One way for the search team to attack a problem of this scale was to put machine learning to bear on it, but it required more than an underlying level of intelligence to make this work. It also required completely rethinking the entire search tool from an architectural level.

That meant separating two main pieces of the system, indexing and serving. The indexing piece is crucial of course in any search engine. A system of this size and scope needs a fast indexing engine to cover the number of documents in a whirl of changing content. This is the piece that’s hidden behind the scenes. The serving side of the equation is what end users see when they query the search engine, and the system generates a set of results.

Nautilus Architecture Diagram: Dropbox

Dropbox described the indexing system in a blog post announcing the new search engine: “The role of the indexing pipeline is to process file and user activity, extract content and metadata out of it, and create a search index.” They added that the easiest way to index a corpus of documents would be to just keep checking and iterating, but that couldn’t keep up with a system this large and complex, especially one that is focused on a unique set of content for each user (or group of users in the business tool).

They account for that in a couple of ways. They create offline builds every few days, but they also watch as users interact with their content and try to learn from that. As that happens, Dropbox creates what it calls “index mutations,” which they merge with the running indexes from the offline builds to help provide ever more accurate results.

The indexing process has to take into account the textual content assuming it’s a document, but it also has to look at the underlying metadata as a clue to the content. They use this information to feed a retrieval engine, whose job is to find as many documents as it can, as fast it can and worry about accuracy later.

It has to make sure it checks all of the repositories. For instance, Dropbox Paper is a separate repository, so the answer could be found there. It also has to take into account the access-level security, only displaying content that the person querying has the right to access.

Once it has a set of possible results, it uses machine learning to pinpoint the correct content. “The ranking engine is powered by a [machine learning] model that outputs a score for each document based on a variety of signals. Some signals measure the relevance of the document to the query (e.g., BM25), while others measure the relevance of the document to the user at the current moment in time,” they explained in the blog post.

After the system has a list of potential candidates, it ranks them and displays the results for the end user in the search interface, but a lot of work goes into that from the moment the user types the query until it displays a set of potential files. This new system is designed to make that process as fast and accurate as possible.


By Ron Miller

Dropbox drops some enhancements to Paper collaboration layer

When you’re primarily a storage company with enterprise aspirations, as Dropbox is, you need a layer to to help people use the content in your system beyond simple file sharing. That’s why Dropbox created Paper, to act as that missing collaboration layer. They announced some enhancements to Paper to keep people working in their collaboration tool without having to switch programs.

“Paper is Dropbox’s collaborative workspace for teams. It includes features where users can work together, assign owners to tasks with due dates and embed rich content like video, sound, photos from Youtube, SoundCloud, Pinterest and others,” a Dropbox spokesperson told TechCrunch.

With today’s enhancements you can paste a number of elements into Paper and get live previews. For starters, they are letting you link to a Dropbox folder in Paper, where you can view the files inside the folder, even navigating any sub-folders. When the documents in the folder change, Paper updates the preview automatically because the folder is actually a live link to the Dropbox folder. This one seems like a table stakes feature for a company like Dropbox.

Gif: Dropbox

In addition, Dropbox now supports Airtables, a kind of souped up spreadsheet. With the new enhancement, you just grab an Airtable embed code and drop it into Paper. From there, you can see a preview in whatever Airtable view you’ve saved the table.

Finally, Paper now supports LucidCharts. As with Airtables and folders, you simply paste the link and you can see a live preview inside Paper. If the original chart changes, updates are reflected automatically in the Paper preview.

By now, it’s clear that workers want to maintain focus and not be constantly switching between programs. It’s why Box created the recently announced Activity Stream and Recommended Apps. It’s why Slack has become so popular inside enterprises. These tools provide a way to share content from different enterprise apps without having to open a bunch of tabs or separate apps.

Dropbox Paper is also about giving workers a central place to do their work where you can pull live content previews from different apps without having to work in a bunch of content silos. Dropbox is trying to push that idea along for its enterprise customers with today’s enhancements.


By Ron Miller

Dropbox announces COO Dennis Woodside is leaving as its second quarterly check-in with Wall Street once again outperforms

Back when Dennis Woodside joined Dropbox as its chief operating officer more than four years ago, the company was trying to justify the $10 billion valuation it had hit in its rapid rise as a Web 2.0 darling. Now, Dropbox is a public company with a nearly $14 billion valuation, and it once again showed Wall Street that it’s able to beat expectations with a now more robust enterprise business alongside its consumer roots.

Dropbox’s second quarter results came in ahead of Wall Street’s expectations on both the earnings and revenue front. The company also announced that Dennis Woodside, who has been the chief operating officer for more than four years, will be leaving the company. Woodside joined at a time at Dropbox when it was starting to figure out its enterprise business, which it was able to grow and transform into a strong case for Wall Street that it could finally be a successful publicly-traded company. The IPO was indeed successful, with the company’s shares soaring more than 40% in its debut, so it makes sense that Woodside has essentially accomplished his job by getting it into a business ready for Wall Street.

The stock exploded in extended trading by rising more than 7%, though even prior to the market close and the company reporting its earnings, the stock had risen as much as 10%. Following that spike, things have leveled off a bit, with it up around 2%. Dropbox is one of a number of SaaS companies that have gone public in recent months, including DocuSign, that have seen considerable success. While Dropbox has managed to make its case with a strong enterprise business, the company was born with consumer roots and has tried to carry over that simplicity with the enterprise products it rolls out, like its collaboration tool Dropbox Paper.

Here’s a quick rundown of the numbers:

  • Q2 Revenue: Up 27% year-over-year to $339.2 million, compared to estimates of $331 million in revenue
  • Q2 GAAP Gross Margin: 73.6%, as compared to 65.4% in the same period last year
  • Q2 adjusted earnings: 11 cents per share compared, compared to estimates of 7 cents per share
  • Paid users: 11.9 million paying users, up from 9.9 million in the same quarter last year
  • ARPU: $116.66, compared to $111.19 same quarter last year

So, not only is Dropbox able to show that it can continue to grow that revenue, the actual value of its users is also going up. That’s important, because Dropbox has to show that it can continue to acquire higher-value customers — meaning it’s gradually moving up the Fortune 100 chain and getting larger and more established companies on board that can offer it bigger and bigger contracts. It also gives it the room to make larger strategic moves, like migrating onto its own architecture late last year, which in the long run could turn out to drastically improve the margins on its business.

The company is still looking to make significant moves in the form of new hires, including recently announcing that it has a new VP of product and VP of product marketing, Adam Nash and Naman Khan. Dropbox’s new team under CEO Drew Houston are tasked with continuing the company’s path to cracking into larger enterprises, which can give it a much more predictable and robust business alongside the average consumers that pay to host their files online and access them from pretty much anywhere.

Dropbox had its first quarterly earnings check-in and slid past the expectations that Wall Street had, though its GAAP gross margin slipped a little bit and may have offered a slight negative signal for the company. But since then, Dropbox’s stock hasn’t had any major missteps, giving it more credibility on the public markets — and more resources to attract and retain talent with compensation packages linked to that stock.


By Matthew Lynley