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The hidden benefits of adding a CTO to your board

The pandemic forced companies around the world to adjust to a “new normal,” which caused many leaders to pivot their business strategies and adopt new technologies to continue operations. In a time of chaos and change, there is no senior leader that can navigate this sort of change better than a CTO.

Not only do CTOs understand the ever-changing tech landscape, they also provide invaluable insights to help organizations go beyond traditional IT conversations and leverage technology to successfully scale businesses.

Boards are facing pressure to be strategic and thoughtful on how to evolve in the rapidly iterating world of technology, and a CTO is uniquely positioned to address specific challenges.

There are now more reasons than ever to consider adding a CTO to your board. As a CTO myself, I know how important and impactful it can be to have technical-minded leaders on a company’s board of directors. At a time when companies are accelerating their digital transformation, it’s critical to have diverse technical perspectives and people from varying backgrounds, as transformations are a mix of people, process and technology.

Drawing on my experience on Lightbend’s board of directors, here are five hidden benefits of making space at the table for a CTO.

A unique mind (and skill) set

Currently, most boards of directors are composed of former CEOs, CFOs and investors. While such executives bring vast experience, they have very specific expertise, and that frequently does not include technical proficiency. In order for a company to be successful, your board needs to have people with different backgrounds and expertise.

Inviting different perspectives forces companies out of the groupthink mentality and find new, creative solutions to their problems. Diverse perspectives aren’t just about the title –– racial ethnicity and gender diversity are clearly a play here as well.

Deep understanding of tech

For a product-led company, having a CTO who has been close to product development and innovation can bring deep insights and understanding to the boardroom. Boards are facing pressure to be strategic and thoughtful on how to evolve in the rapidly iterating world of technology, and a CTO is uniquely positioned to address specific challenges.

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Puppet announces $40 million debt round from BlackRock

Puppet, the Portland, Oregon-based infrastructure automation company, announced a $40 million debt round today from BlackRock Investments.

CEO Yvonne Wassenaar says the company sees this debt round as part of a longer-term relationship with BlackRock . “What’s interesting, and I think part of the reason why we decided to go with BlackRock, is that typically when you look at how they invest this is the first step of a much longer-term relationship that we will have with them over time that has different elements that we can tap into as the company scales,” Wassenaar told TechCrunch.

In terms of the arrangement, rather than BlackRock taking a stake in the company, Puppet will pay back the money. “We’ve borrowed a sum of money that we will pay back over time. BlackRock does have a board observer seat, and that’s really because they’re very interested in working with us on how we grow and accelerate the business,” Wassenaar said.

Puppet has been in the process of rebuilding its executive team, with Wassenaar coming on board about 18 months ago. Last year she brought in industry veterans Erik Frieberg and Paul Heywood as CMO and CRO, respectively. This year she brought in former Cloud Foundry Foundation director Abby Kearns to be CTO.

All of these moves are with an eye to a future IPO, says Wassenaar. “We’re looking at how do we progress ultimately, ideally on a path to an IPO, and what is it going to take for Puppet to go through that journey,” she said.

She points out that in some ways, the pandemic has forced companies to look more closely at automation solutions like the ones that Puppet provides. “What’s really interesting is […] that the pandemic in many ways has put wind in our sails in terms of the need for corporations to automate and think about how they leverage and extend from a technology perspective going forward,” she said.

As Puppet continues to grow, she says that diversity is a core organizational value, and that while the company has made progress from a gender perspective (as illustrated by the presence of her and Kearns in the C Suite), they still are working at being more racially diverse.

“Where I believe we have a lot more work and there’s a lot more focus right now is further complementing that [gender diversity] from a racial perspective. And it’s an area that I have personally taken on, and I’m committed to making changes in the company as we go forward to support more racial diversity as well,” she said.

Previously the company had raised almost $150 million, with the most recent round being a $42 million Series F in 2018, according to Crunchbase data. The company previously took $22 million in debt financing in 2016, prior to Wassenaar coming on board.

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Puppet names former Cloud Foundry Foundation executive director Abby Kearns as CTO

Puppet, the Portland-based infrastructure automation company, today announced that it has named former Cloud Foundry Foundation executive director Abby Kearns as its new CTO.

Current Puppet CTO Deepak Giridharagopal will remain in his role and focus on R&D and leading new projects, while Kearns will focus on expanding the company’s product portfolio and communicating with enterprise audiences.

Kearns stepped down from her role at the Cloud Foundry Foundation earlier this month after holding that position since 2016. At the time, she wasn’t quite ready to reveal her next move, though, and her taking the CTO job at Puppet comes as a bit of a surprise. Despite a lot of usage and hype in its early days, Puppet isn’t often seen as an up-and-coming company anymore, after all. But Kearns argues that a lot of this is due to perception.

“Puppet had great technology and really drove the early DevOps movement, but they kind of fell off the face of the map,” she said. “Nobody thought of them as anything other than config management, and so I was like, well, you know, problem number one: fix that perception problem if that’s no longer the reality or otherwise, everyone thinks you’re dead.”

Since Kearns had already started talking to Puppet CEO Yvonne Wassenaar, who took the job in January 2019, she joined the product advisory board about a year ago and the discussion about Kearns joining the company became serious a few months later.

“We started talking earlier this year,” said Kearns. “She said: ‘You know, wouldn’t it be great if you could come help us? I’m building out a brand new executive team. We’re really trying to reshape the company.’ And I got really excited about the team that she built. She’s got a really fantastic new leadership team, all of them are there for less than a year. they have a new CRO, new CMO. She’s really assembled a fantastic team of people that are super smart, but also really thoughtful people.”

Kearns argues that Puppet’s product has really changed, but that the company didn’t really talk about it enough, despite the fact that 80% of the Global 5,000 are customers.

Given the COVID-19 pandemic, Kearns has obviously not been able to meet the Puppet team yet, but she told me that she’s starting to dig deeper into the company’s product portfolio and put together a strategy. “There’s just such an immensely talented team here. And I realize every startup tells you that, but really, there’s actually a lot of talented people here that are really nice. And I guess maybe it’s the Portland in them, but everyone’s nice,” she said.

“Abby is keenly aware of Puppet’s mission, having served on our Product Advisory Board for the last year, and is a technologist at heart,” said Wassenaar. “She brings a great balance to this position for us – she has deep experience in the enterprise and understands how to solve problems at massive scale.”

In addition to Kearns, former Cloud Foundry Foundation VP of marketing Devin Davis also joined Puppet as the company’s VP of corporate marketing and communications.

Update: we updated the post to clarify that Deepak Giridharagopal will remain in his role.

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Canonical’s Mark Shuttleworth on dueling open-source foundations

At the Open Infrastructure Summit, which was previously known as the OpenStack Summit, Canonical founder Mark Shuttleworth used his keynote to talk about the state of open-source foundations — and what often feels like the increasing competition between them. “I know for a fact that nobody asked to replace dueling vendors with dueling foundations,” he said. “Nobody asked for that.”

He then put a point on this, saying, “what’s the difference between a vendor that only promotes the ideas that are in its own interest and a foundation that does the same thing. Or worse, a foundation that will only represent projects that it’s paid to represent.”

Somewhat uncharacteristically, Shuttleworth didn’t say which foundations he was talking about, but since there are really only two foundations that fit the bill here, it’s pretty clear that he was talking about the OpenStack Foundation and the Linux Foundation — and maybe more precisely the Cloud Native Computing Foundation, the home of the incredibly popular Kubernetes project.

It turns out, that’s only part of his misgivings about the current state of open-source foundations, though. I sat down with Shuttleworth after his keynote to discuss his comments, as well as Canonical’s announcements around open infrastructure.

One thing that’s worth noting at the outset is that the OpenStack Foundation is using this event to highlight that fact that it has now brought in more new open infrastructure projects outside of the core OpenStack software, with two of them graduating from their pilot phase. Shuttleworth, who has made big bets on OpenStack in the past and is seeing a lot of interest from customers, is not a fan. Canonical, it’s worth noting, is also a major sponsor of the OpenStack Foundation. He, however, believes, the foundation should focus on the core OpenStack project.

“We’re busy deploying 27 OpenStack clouds — that’s more than double the run rate last year,” he said. “OpenStack is important. It’s very complicated and hard. And a lot of our focus has been on making it simpler and cleaner, despite the efforts of those around us in this community. But I believe in it. I think that if you need large-scale, multi-tenant virtualization infrastructure, it’s the best game in town. But it has problems. It needs focus. I’m super committed to that. And I worry about people losing their focus because something newer and shinier has shown up.”

To clarify that, I asked him if he essentially believes that the OpenStack Foundation is making a mistake by trying to be all things infrastructure. “Yes, absolutely,” he said. “At the end of the day, I think there are some projects that this community is famous for. They need focus, they need attention, right? It’s very hard to argue that they will get focus and attention when you’re launching a ton of other things that nobody’s ever heard of, right? Why are you launching those things? Who is behind those decisions? Is it a money question as well? Those are all fair questions to ask.”

He doesn’t believe all of the blame should fall on the Foundation leadership, though. “I think these guys are trying really hard. I think the common characterization that it was hapless isn’t helpful and isn’t accurate. We’re trying to figure stuff out.” Shuttleworth indeed doesn’t believe the leadership is hapless, something he stressed, but he clearly isn’t all that happy with the current path the OpenStack Foundation is on either.

The Foundation, of course, doesn’t agree. As OpenStack Foundation COO Mark Collier told me, the organization remains as committed to OpenStack as ever. “The Foundation, the board, the community, the staff — we’ve never been more committed to OpenStack,” he said. “If you look at the state of OpenStack, it’s one of the top-three most active open-source projects in the world right now […] There’s no wavering in our commitment to OpenStack.” He also noted that the other projects that are now part of the foundation are the kind of software that is helpful to OpenStack users. “These are efforts which are good for OpenStack,” he said. In addition, he stressed that the process of opening up the Foundation has been going on for more than two years, with the vast majority of the community (roughly 97 percent) voting in favor.

OpenStack board member Allison Randal echoed this. “Over the past few years, and a long series of strategic conversations, we realized that OpenStack doesn’t exist in a vacuum. OpenStack’s success depends on the success of a whole network of other open-source projects, including Linux distributions and dependencies like Python and hypervisors, but also on the success of other open infrastructure projects which our users are deploying together. The OpenStack community has learned a few things about successful open collaboration over the years, and we hope that sharing those lessons and offering a little support can help other open infrastructure projects succeed too. The rising tide of open source lifts all boats.”

As far as open-source foundations in general, he surely also doesn’t believe that it’s a good thing to have numerous foundations compete over projects. He argues that we’re still trying to figure out the role of open-source foundations and that we’re currently in a slightly awkward position because we’re still trying to determine how to best organize these foundations. “Open source in society is really interesting. And how we organize that in society is really interesting,” he said. “How we lead that, how we organize that is really interesting and there will be steps forward and steps backward. Foundations tweeting angrily at each other is not very presidential.”

He also challenged the notion that if you just put a project into a foundation, “everything gets better.” That’s too simplistic, he argues, because so much depends on the leadership of the foundation and how they define being open. “When you see foundations as nonprofit entities effectively arguing over who controls the more important toys, I don’t think that’s serving users.”

When I asked him whether he thinks some foundations are doing a better job than others, he essentially declined to comment. But he did say that he thinks the Linux Foundation is doing a good job with Linux, in large parts because it employs Linus Torvalds . “I think the technical leadership of a complex project that serves the needs of many organizations is best served that way and something that the OpenStack Foundation could learn from the Linux Foundation. I’d be much happier with my membership fees actually paying for thoughtful, independent leadership of the complexity of OpenStack rather than the sort of bizarre bun fights and stuffed ballots that we see today. For all the kumbaya, it flatly doesn’t work.” He believes that projects should have independent leaders who can make long-term plans. “Linus’ finger is a damn useful tool and it’s hard when everybody tries to get reelected. It’s easy to get outraged at Linus, but he’s doing a fucking good job, right?”

OpenStack, he believes, often lacks that kind of decisiveness because it tries to please everybody and attract more sponsors. “That’s perhaps the root cause,” he said, and it leads to too much “behind-the-scenes puppet mastering.”

In addition to our talk about foundations, Shuttleworth also noted that he believes the company is still on the path to an IPO. He’s obviously not committing to a time frame, but after a year of resetting in 2018, he argues that Canonical’s business is looking up. “We want to be north of $200 million in revenue and a decent growth rate and the right set of stories around the data center, around public cloud and IoT.” First, though, Canonical will do a growth equity round.

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Puppet raises $42M led by Cisco as its DevOps automation platform passes 40,000 businesses

DevOps — the branch of enterprise IT that involves both products and best-practices for developers to build, test and run apps and other software — is on track to be worth nearly $13 billion by 2025. Now, a startup that is building DevOps tools is announcing a significant funding round to capitalize on that opportunity. Portland, Oregon-based Puppet (formerly Puppet Labs) has raised $42 million in funding in a venture round with a number of strategic and key financial investors.

The funding was led by Cisco, with Kleiner Perkins, True Ventures, Singapore’s EDBI and VMware also participating.

The company isn’t readily disclosing its valuation — although we are trying to find out — but according to PitchBook, its last disclosed valuation was in 2014, when it raised $40 million and was valued at $652 million post-money.

But Puppet has grown more than two-fold in the last four years: back then, it had 18,000 customers, including the likes of Google, Twitter, Salesforce and AT&T. Now, it says it has more than 40,000 companies as customers, “including more than 75 percent of the Fortune 100” using both its open source and commercial products — and it’s expanded internationally and has made a couple of acquisitions (including the startup Reflect earlier this month).

All this would imply that Puppet, which now has raised $150 million to date, is likely valued at significantly more than $700 million, and may well be approaching the $1 billion-mark.

“Our rapid growth and international expansion is a testament to the rising demand for DevOps transformation, software automation and the pressing need for enterprises to navigate the new world of software delivery. That’s why we’ve been so focused on expanding our product portfolio—to empower customers to discover, deliver and operate software across their cloud and containerized environments,” said Sanjay Mirchandani, CEO, Puppet, in a statement. “I’m thrilled by the momentum we’re experiencing. It helps us better support our customers’ journey to pervasive automation.”

The growth of cloud services, and the ubiquity of digitization, have led to a wide slate of functions in a business falling under the category of developer-led operations.

This has, in turn, driven a bigger demand for better processes to run these operations and the infrastructure that they touch. Puppet is not the only company in this area: in addition to large players like Cisco and CA Technologies and EMC, there are startups like Docker, Chef and more.

Puppet’s solutions cover applications, cloud services, containerized services and networking devices, and that mix is part of what is attractive about the company, as many businesses today are not all-in on modern architectures, but are grappling with hybrids of old and new, cloud and on-premises, and so on. (Indeed, the “Puppet” name is a reference to how it works: developers can control the actions of the their applications over the network as puppeteers control puppets, without being seen).

“ServiceChannel has an aggressive technology roadmap. One that not only takes advantage of cloud native capabilities and containerized applications, but also requires modernization of existing, critical systems. Automation is necessary to help us deliver on that roadmap within the constraints of business—safely and at scale,” said Mark Trumpbour, VP of DevOps at ServiceChannel, in a statement.

Investors Cisco and VMware are themselves already key players in the area of DevOps (and Cisco and VMWare, both previous investors, already work with Puppet), while another backer, EDBI, holds investments in a number of companies that are potential customers for the startup.

“Businesses put increasingly massive pressure on enterprise IT—so, it’s important that those IT organizations partner with technology providers with compelling innovation, world-class support and a global community of experts. Puppet has a track record of empowering its customers with all of these critical elements,” said Rob Salvagno, VP of Corporate Development and Cisco Investments, in a statement. “We look forward to working even more with Puppet as the global demand for automation technology and innovation continues to accelerate.”

“In today’s digital age, companies face increasing complex IT challenges dealing with their dynamic and diverse IT infrastructure. Puppet’s automation and management platform transforms how companies manage and improve the efficiency of their IT assets and can help companies in Singapore realize productivity gains while ensuring compliance,” said Swee-Yeok CHU, CEO and president EDBI, in an additional statement. “Leveraging our network, we look forward to helping Puppet scale up its local talent pool to address the region’s opportunities through its APAC Regional HQ in Singapore and to augment Singapore’s digital transformation strategy.”

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Puppet Labs Secures $22M Credit From Silicon Valley Bank

puppet-labs-string Portland, Ore.-based DevOps company Puppet Labs today announced that it has secured a $22 million credit facility from Silicon Valley Bank.
In addition, the company today appointed former Genentech CFO Lou Lavigne to its board, where he will be the chairman of its audit committee — a critical role Puppet had to fill as it prepares for a future IPO. Read More

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