Our Investment In Esper To Enable The Dev-Ops Of Smart Devices

Today, Madrona Venture Group announced that we’ve led the $7.6M Series A investment in Esper, an investment that Tim Porter and I spearheaded for the firm. Esper is a devops platform for Android IOT devices.

As everything around us becomes smart and connected, developers of devices have many new challenges. We are no longer just designing a single piece of hardware – but developing a full solution spanning many cooperating devices and supporting cloud software. During development, we have a variety of deployment, testing, and versioning requirements. Once deployed, we need to support device maintenance and updates on both hardware and software through a variety of complex deployment variations, while also supporting that rare remote debugging session. We have regular security updates to the firmware, OS, and apps to manage. We need to integrate device signals with CRM systems, billing systems, and more. Like we’ve come to think about a “dev-ops” process for cloud services, we now need to think about a dev-ops process for our smart devices.

For non-phone devices which require a user experience, Android has become the most popular platform due to the free price, broad silicon support, and broad software framework support. Amazon Echos, Peloton Bikes, and many home televisions all run a version of Android. When it comes to managing these devices, there are many options available for corporate IT to manage personal Android phones — but there’s no great solution for devices where a developer needs to manage these endpoints into the dev-ops process of their overall solution.

This is the challenge which the co-founders of Esper lived through as they worked in their prior roles. Yadhu Gopalan, CEO of Esper, most recently led the development and deployment of all the smart devices in the Amazon Go retail stores. Shiv Sundar, COO of Esper, most recently helped lead the Cyanogen Android device ecosystem. Prior to those roles, I worked with Yadhu and Shiv on the development of the Windows embedded operating system. It’s fun to be working with these great engineers once again!

After introducing their solution late last year, Esper quickly started serving many impressive customers across over 50,000 devices. Each customer we talked with discussed how they had tried to use a mobile device management solution designed for personal devices, but it had failed to meet their dev-ops needs. We’re excited to work with the Esper team to scale their solution, delighting developers all over the world as they enable billions of smart devices to do amazing things.

It’s been great to partner with Tim Porter on this investment. His experience with other developer focused investments like Heptio will be invaluable in Esper reaching its full potential.

This blog post was also posted on Terry’s LinkedIn page.

Kicking off Madrona Engineering Community Meetups with a Side of DevOps

If there is one topic that is on every engineering leader’s mind, regardless of the size of the company, it is how to ship more code more often and how to run that code reliably and efficiently. So, it was a no-brainer that we chose to kick off the first of our Madrona Engineering Community (MEC) meetups with an event on DevOps and Agile practices.

MEC meetups foster ongoing knowledge sharing and networking among engineering leaders across the Madrona portfolio. Our members are VPs of Engineering and CTOs across our portfolio companies.

As far as first events go, we started off with a bang! We had a packed house with over fifty of our engineering leaders attending as our panel of experienced speakers dove into the current and future for DevOps. Our panel was:

  • Tom Casey, SVP Engineering at DocuSign
  • John Ludeman, SVP Engineering at Skytap
  • Adam Johnson, Founder/CEO of IOPipe
  • Moderator, Joe Duffy (Founder/CEO of Pulumi

The make up of the panel was by design — to cover companies at different scale. DocuSign, for example, serves hundreds of millions of users and more than 1.5 million documents per day. Skytap is a mid-stage company that has seen its usage quadruple over the last two years, deploying up to 45,000 VMs and serving up to 2 petabytes of storage a day. IOPipe, in contrast, is in the early days of building its product with a distributed team churning out multiple releases every day! The DevOps goals and plans of each of these companies are different, which led to an interesting discussion under the expert probing of our masterful moderator Joe Duffy.

DevOps = ownership + accountability

While Joe did his best to instigate the speakers in taking opposing positions, he had no luck when it came to how they thought of DevOps. To each, DevOps was about aligning engineering teams with creating customer value and achieving business goals. The key, as each speaker emphasized, was to give developers end-to-end ownership (and the accountability that comes with it). Developers must be able to see the value they are delivering to the customers, or not. And, they must be provided with all the tools and processes, and more importantly, the organization and cultural support needed to succeed.

DevOps ≠ shipping more features

In the fog of war, there is often a tendency to add every feature request to the scrum. Shipping, however, is not a good measure of success. Adoption, utilization, learning, and direct revenue are much better measures of value creation. When it comes to DevOps, reemphasizing value creation and not just features shipped is important. DocuSign, for instance, made driving adoption (of their product) a company wide priority because, direct revenue is typically a trailing indicator of feature value. To keep everyone focused, they evaluated every shipped feature in light of adoption. It mostly worked for them.

DevOps is always a work in progress

No matter how small or big the company is, DevOps is never done. John from Skytap, for example, shared how, after operating for a few years, they realized that their organizational structure was getting in the way of shipping code quickly and efficiently. So, they reorganized and refocused the engineering teams to make sure that they stayed agile as the business scaled rapidly. Tom from DocuSign shared a similar experience, done at a greater scale in a more gradual manner. And, they both fully expect to redo their DevOps process and organization multiple times as their businesses continue to grow quickly.

No “no-ops” unless you also believe in unicorns

In this day and age of serverless, the topic of “no-ops” inevitably came up. To much of Joe’s delight, it elicited some strong reaction from the speakers. Long story short, the verdict was that no-ops does not work at scale. Every SaaS company, once it reaches a certain scale, needs specialized ops to ensure it can deliver the best user experience without blowing up its cost budget. DocuSign has “devs who op,” and every company could do with more of them. Similarly, the topic of SRE did not find a lot of love from the panel. The view was that, for most SaaS applications, it is impossible — or, at least not advisable — to insulate the developers from running the application.

Telemetry trumps testing

The other interesting insight that emerged from the discussion was that, no matter how much one invests in testing, telemetry is indispensable and if anything, more important. Skytap, for example, believes investing more in application telemetry than in running exhaustive regression tests. Similarly, DocuSign puts some of its best devs on telemetry. The emphasis on telemetry helps to speed up release cadence and detect unforeseen bugs.

Looking forward …

While most modern companies have adopted DevOps to a certain degree, most also struggle with several issues. First, balancing agile development with predictability (a must to run a business) is always hard. Hence, every engineering leader clamors for effective planning tools. The other issue is how to measure engineering productivity. Lines of code written or number of bugs fixed could be great vanity metrics, but they do not serve the real purpose. Finally, as we get ready for applications running on multiple clouds, we do not yet fully know the new challenges that will bring to DevOps.

Maybe, that’s where we will pick up at the next MEC meetup!