Most companies don’t announce their first venture investment after almost 20 years in the business, nor do they announce that round is the equivalent of a good startup’s entire private fundraising history. But Articulate, a SaaS training and development platform, is not your typical company and today it announced a whopping $1.5 billion investment on a $3.75 billion valuation.

You can call it Series A if you must label it, but whatever it is, it’s a hefty investment by any measure. General Atlantic led the round with participation from Blackstone Growth and Iconiq Growth. GA claims it’s one of the largest A rounds ever, and I’m willing to bet it’s right.

CEO Adam Schwartz founded the company with his life savings in 2002 and hasn’t taken a dime of outside investment since. “Our software enables organizations to develop, deliver, and analyze online training that is engaging and effective for enterprises and SMBs,” Schwartz explained.

He says that the company started back in 2002 as a plug-in for PowerPoint. Today it is a software service with the goal of helping enable everyone to deliver training, even if they aren’t a training professional. Articulate actually has two main products, one is a set of tools for companies building training that connects to an enterprise learning management system or LMS. The other is aimed at SMBs or departments in an enterprise.

Its approach seems to be working with the company reporting it has 106,000 customers across 161 countries including every single one of the Fortune 100. Schwartz was loath to share any additional metrics, but did say they hope to use this money to grow 10x over the next several years.

Company president Lucy Suros, who has been with the organization for a decade, says even with this success, they see plenty of opportunity for growth and they felt taking this capital now would really enable them to accelerate.

“We are the most dominant player by far in course authoring apps, but when you look at that whole ecosystem and you think about where companies are in transforming from instructor-led training to online training, they’re still really in the early innings so there’s a lot of opportunity,” she said.

Anton Levy, co-president and managing director at General Atlantic, who is leading the investment for the firm, says that this is a “big, bold, incredible business” and that’s why they’re making an investment of this size and scope. “The reason we’re stepping up in such a large way, and what’s such a large check for us, is because of the business they’ve built, the team they’ve built, and frankly the market opportunity that they’re playing in and their ambition,” he said.

Today the company has 300 employees and they have been working as a remote company long before COVID. With the new capital, that number could triple over the next several years. Suros says that when she started at the company, there were 50 employees, mostly male engineers and she went to work to make it a more diverse work environment.

“We’ve put emphasis and a lot of just structural things in place to ensure that we are bringing more [diverse] people to the table, and then supporting folks once they’re here,” she said. With the new capital, the company announced a lot of new benefits and she said those were developed with the idea of helping break down barriers for under-represented groups in their ranks including covering gender transition-related costs.

She says that one of the benefits of becoming more visible as a company is being able to talk about and their human-centered organization framework, the set of principles the company put in place to define its values. “[We think about] how that can impact the employees and drive human flourishing for its own sake, and that also happens to lead to better business outcomes. But we’re really also interested in it from [the standpoint that] we want to be good and do good in the world and promote human flourishing at work,” she said.

The company seems to have been doing just fine up until now, but with this kind of capital, it aims to take the business to another level, while trying to be good corporate citizens as they do that.

JFrog, the company best known for a platform that helps developers continuously manage software delivery and updates, is making a deal to help it expand its presence and expertise in an area that has become increasingly connected to DevOps: security. The company is acquiring Vdoo, which has built an AI-based platform that can be used to detect and fix vulnerabilities in the software systems that work with and sit on IoT and connected devices. The deal — in a mix of cash and stock — is valued at approximately $300 million, JFrog confirmed to me.

Sunnyvale-based, Israeli-founded JFrog is publicly traded on Nasdaq, where it went public last September, and currently it has a market cap of $4.65 billion. Vdoo, meanwhile, had raised about $70 million from investors that include NTT, Dell, GGV and Verizon (disclaimer: Verizon owns TechCrunch), and when we covered its most recent funding round, we estimated that the valuation was somewhere between $100 million and $200 million, making this a decent return.

Shlomi Ben Haim, JFrog’s co-founder and CEO, said that his company’s turn to focusing deeper on security, and making this acquisition in particular to fill out that strategy, are a natural progression in its aim to build out an end-to-end platform for the DevOps team.

“When we started JFrog, the main challenge was to educate the market on what we saw as most important priorities when it comes to building, testing and deploying software,” he said. Then sometime around 2015-2016 he said they started to realize there was a “crack” in the system, “a crack called security.” InfoSec engineers and developers sometimes work at cross purposes, as “developers became too fast” the work they were doing has inadvertently led to a lot of security vulnerabilities.

JFrog has been building a number of tools since then to address that and to bring the collective priorities together, such as its X-ray product. And indeed, Vdoo is not JFrog’s first foray into security, but it represents a significant step deeper into the hardware and systems that are being run on software. “It’s a very important leap forward,” Ben Haim said.

For its part, Vdoo was born out of a realization as well as a challenging mission: IoT and other connected devices — a universe of some 50 billion pieces of hardware as of last year — represents a massive security headache, and not just because of the volume of devices: Each object uses and interacts with software in the cloud and so each instance represents a potential vulnerability, with zero-day vulnerabilities, CVEs, configuration and hardening issues, and standard non-compliance among some of the most common.

While connected-device security up to now has typically focused on monitoring activity on the hardware, how data is moving in and out of it, Vdoo’s approach has been to build a platform that monitors the behavior of the devices themselves on top of that, using AI to compare that behavior to identify when something is not working as it should. Interestingly, this mirrors the kind of binary analysis that JFrog provides in its DevOps platform, making the two complementary to each other.

But what’s notable is that this will give JFrog a bigger play at the edge, since part of Vdoo’s platform works on devices themselves, “micro agents” as the company has described them to me previously, to detect and repair vulnerabilities on endpoints.

While JFrog has built a lot of its own business from the ground up, it has made a number of acquisitions to bolt on technology (one example: Shippable, which it used to bring continuous integration and delivery into its DevOps platform). In this case, Netanel Davidi, the co-founder and CEO of Vdoo (who previously co-founded and sold another security startup, Cyvera, to Palo Alto Networks) said that this was a good fit because the two companies are fundamentally taking the same approaches in their work (another synergy and justification for DevOps and InfoSec being more closely knitted together too I might add).

“In terms of the fit between the companies, it’s about our approach to binaries,” Davidi said in an interview, noting that the two being on the same page with this approach was fundamental to the deal. “That’s only the way to cover the entire pipeline from the very beginning, when they go you develop something, all the way to the device or to the server or to the application or to the mobile phone. That’s the only way to truly understand the context and contextual risk.”

He also made a note not just of the tech but of the talent that is coming on with the acquisition: 100 people joining JFrog’s 800.

“If JFrog chose to build something like this themselves, they could have done it,” he said. “But the uniqueness here is that we have built the best security team, the best security researchers, the best vulnerability researchers, the best reverse engineers, which focus not only on embedded systems, and IoT, which is considered to be the hardest thing to learn and to analyze, but also in software artifacts. We are bringing this knowledge along with us.”

JFrog said that Vdoo will continue to operate as a standalone SaaS product for the time being. Updates that are made will be in aid of supporting the JFrog platform and the two aim to have a fully integrated, “holistic” product by 2022.

Along with the deal, JFrog reiterated financial guidance for the next quarter that will end June 30, 2021. It expects revenues of $47.6 million to $48.6 million, with non-GAAP operating income of $0.5 million to $1.5 million and non-GAAP EPS of $0.00 to $0.01, assuming approximately 104 million weighted average diluted shares outstanding. For Full Year 2021, revenues are expected to be $198 million to $204 million, with non-GAAP operating income between $5 million and $7 million and an approximately 3% increase in weighted average diluted shares. JFrog anticipates consolidated operating expenses to increase by approximately $9-10 million for the remainder of 2021, subject to the acquisition closing.

In 2020 lots of workloads shifted to the cloud due to the pandemic, but that doesn’t mean that figuring out how to migrate those workloads got any easier. Device42, a startup that helps companies understand their infrastructure, has a new product that is designed to analyze your infrastructure and make recommendations about the most cost-effective way to migrate to the cloud.

Raj Jalan, CEO and co-founder, says that the tool uses machine learning to help discover the best configuration, and supports four cloud vendors including AWS, Microsoft, Google and Oracle plus VMware running on AWS.

“The [new tool] that’s coming out is a multi-cloud migration and recommendation [engine]. Basically, with machine learning what we have done is in addition to our discovery tool […] is we can constantly update based on your existing utilization of your resources, what it is going to cost you to run these resources across each of these multiple clouds,” Jalan explained.

This capability builds on the company’s core competency, which is providing a map of resources wherever they exist along with the dependencies that exist across the infrastructure, something that’s extremely hard for organizations to understand. “Our focus is on hybrid IT discovery and dependency mapping, [whether the] infrastructure is on prem, in colocation facilities or in the cloud,” he said.

That helps Device42 customers see how all of the different pieces of infrastructure including applications work together. “You can’t find a tool that does everything together, and also gives you a very deep discovery where you can go from the physical layer all the way to the logical layer, and see things like, ‘this is where my storage sits on this web server…’,” Jalan said.

It’s important to note that this isn’t about managing resources or making any changes to allocation. It’s about understanding your entire infrastructure wherever it lives and how the different parts fit together, while the newest piece finds the most cost-effective way to migrate to the cloud it from its current location.

The company has been around since 2012, has around 100 employees. It has raised around $38 million including a $34 million Series A in 2019. It hasn’t required a ton of outside investment as Jalan reports they are cash flow positive with “decent growth.”

As enterprises and carriers gear up for operating and scaling IoT services and monitoring the activity of their devices, machines and more globally, a startup that is building technology to make this easier and cheaper to implement is announcing some funding.

FloLive, which has built a cloud-based solution to stitch together private, local cellular networks to create private global IoT 5G networks for its customers, has raised $15.5 million, funding that it will be using to continue expanding its service, both through investing and building out its tech stack, upgrading its network to 5G where it’s being used, and building a global SIM2Cloud offering in partnership with an as-yet unnamed global cloud provider.

Intel Capital, the investment arm of the chip giant, is leading the investment, with Qualcomm Ventures, Dell Technologies Capital, 83North and Saban Ventures also participating. Intel, Qualcomm and Dell are all strategic backers here: the three work with carriers and enterprises to power and manage services and devices, and this will give them potentially a better way of integrating a much more flexible, global technology and network to provision those services more seamlessly across different geographies.

This is an extension to a $21.5 million round that London-based FloLive raised last year, bringing the total for the Series B to $37 million. From what we understand, the startup is also now working on its Series C.

As we move towards more ubiquitous 5G networks and services that use them, the challenge in the market that FloLive is addressing is a critical one to get right.

In a nutshell, enterprises and carriers that are building networks for managing IoT and other connected devices face a scaling issue. Typically, IoT networks to cover services like these are built on national or even more localized footprints, making it a challenge — if not completely impossible — to control or monitor devices in a global network in a centralized way.

“If you look on high level at tier one networks, you see two main things,” Nir Shalom, FloLive’s CEO, said in an interview. “These networks are built for local footprints, and they are mainly built for consumers. What we do is different in that we think about the global, not local, footprint; and our data networks are for IoT, not only people.”

Of course there are some carriers that might look at building their own networks to rival this, but they will often lack the scaled use cases to do so, and may in any case work with providers like FloLive to build these anyway. The bigger picture is that there are 900 larger mobile network operators globally, Shalom said, and the majority of that group is far from being able to do this themselves.

FloLive’s approach to fixing this is not to build completely new infrastructure, but to stitch together networks from different localities and to run them as a single network. It does this by way of its software-defined connectivity built and implemented in the cloud, which stitches together not just 5G networks but whatever cellular technology happens to be in use (eg 4G, 3G or even 2G) in a particular locale.

FloLive’s tech lives in the core network, where it builds a private radio access network that it can integrate with carriers and their capacity in different markets, while then managing the network for customers as a single service.

This is somewhat similar to what you might get with a enterprise virtual private network except that this is focused specifically on the kinds of use cases that might use connected objects — FloLive cites manufacturing, logistics, healthcare and utilities as four areas — rather than laptops for employees.

The resulting network, however, also becomes a viable alternative for companies that might otherwise use a VPN for connectivity, too, as well as carriers themselves needing to extend their network for a customer. In addition to its IoT focused core network, it also provides business support systems for IoT, device management, and solutions targeted for specific verticals. FloLive supports devices that use SIM or eSIM or “softSIM” technology to connect to networks. That’s one part that likely interested those strategic investors as it allows for significantly easier integration.

“We are truly excited about floLIVE’s unique cloud-native approach to IoT connectivity,” said David Johnson, MD at Intel Capital, in a statement. “Cloud-native architectures bring efficiency, scalability and flexibility which are important for IoT services. In addition, floLIVE’s cloud-based core can provide consistency of features across many independent private and public networks. We look forward to the expansion of floLIVE’s products and services enabled by this investment.”

Updated to note the round is $15.5 million, not $15 million.