Episode 44: Devops, Security, & Cloud Automation Puppet with Yvonne Wassenaar, Chief Executive Officer

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Intro


Mike: Hello, and welcome to Open Source Underdogs. I’m your host, Mike Schwartz, and this is episode 44 with Yvonne Wassenaar, CEO of Puppet. Yvonne is the third CEO of Puppet. Luke Kanies was the founder, we interviewed him in the episode 22.


Sanjay Mirchandani succeeded him, and Yvonne took over from Sanjay in January of 2019, about a year before we recorded this episode. A CEO who takes over a company like Puppet needs a different skill set than your typical founder. Whereas the founder needs deep domain knowledge, usually a hands-on approach to business development, CEOs for companies, in later stages of growth, need this intangible corporate leadership ability. It’s hard to say what it is, but you know what it is when you see it. Yvonne has it, and she also has the values and an understanding of the culture that complements where Puppet is in its corporate life cycle. I don’t want to spoil any of the content, so I hope you enjoy this interview. Here we go.

Why Take On The CEO Role At Puppet?

Mike: Yvonne, thank you so much for joining us today.

Yvonne: Absolutely. It’s great to be here, Mike.

Mike: When you joined Puppet early last year, as CEO, why did you want to take on this enormous responsibility, steering the ship with hundreds of employees and thousands of customers?

Yvonne: You frame Puppet so well in terms of, it is a large employee base. We do have a lot of customers, and I’d extend it even further into we’ve got a massive community around the globe. And I did think really long and hard around was I the right person to take on the responsibility to bring Puppet and the impact of Puppet, the company, in the community to the next level.

And the reason I said yes to that that question, to myself and to the board, is, as I thought about the opportunity, Puppet to me represented a perfect place for my step, next step in my journey, for the following reasons.

One, the values that are represented by Puppet, and the Puppet community aligned really well with my own, in the sense that we are really focused around – you know, being open-source core kind of the democratization of technology diversity and inclusion, having impact at the practitioner level, and really making a difference in the world around us.

And to me, I feel life’s very short, and having strong value alignment is really important. And what Puppet represented resonated very much with me.

The second thing is really around the technology and the problem that we solve. I deeply believe that Puppet and the technology that we build and work, standing upon with the community and with our own team, makes a difference in the world around us, makes a difference not only in eliminating soul-crushing work, which is what Luke started with, but makes a difference in terms of enabling companies to achieve the agility that they want, in a secure and scalable way.

And as an ex CIO, the risk of cyber security I think sometimes is underestimated, and it’s really beholding upon all of us to think about not only how do we leverage technology to make the world a great place, but how do we do it in a safe way.

So, to me, if I think about the values, and I think about the actual product and offerings that we’re bringing to market through the community and with our commercial offerings, that resonated really well. So, the third component was, “Can I personally make a difference?”
 
Given my experience across companies like New Relic, VMware, and my time in Accenture, I felt I had a good breath of experience that I could, not necessarily bring the answer, but ask the right questions and bring the right team on board to really deliver our true potential as a company.

So, those three things combined, all aligned up, and having been here a year, it was definitely the right decision. It’s been a great ride, I think we’re doing amazing stuff, and I can’t wait for what’s yet to come.

Why Expand Product Surface Area from Configuration Management?

Mike: In the past, I might have described Puppet as being a Configuration Management Platform, but today, Puppet’s moving into areas like continuous compliance, incident remediation, and continuous delivery – why expand the product surface area? And I’m also wondering, how do you evaluate the risks that come along with that expansion?

Yvonne: Puppet as a Configuration Management Platform, I’d even say tool, has been the market perception of who we are. And that very much is grounded on where we started.

To me, the fascinating part of your question really comes down to the fact that the big shift that Puppet made in this last year was going from talking about what I would call “feature functionality”, which what Puppet does, is, really, we automate infrastructure in really, really powerful ways, to talking about the use cases and the business problems that we solve.


So, what’s interesting is, from a technology standpoint, what Puppet has built out over the years is going from a declarative approach to infrastructure automation, which is where we started, which is, we’re turning environment to a known, good state, to extending that into both declarative and task-based automation, which we leverage our open-source project, Bolt, to support and drive. And Bolt integrates with Puppet enterprise. So, it’s both declarative and task-based, both agent and agentless. Now, we are extending even further into workflow, event-based automation.

The tool has gotten more robust in terms of the types of things that people can do with it, but the real shift, I think, from an impact standpoint, is, we’ve started to really be able to harvest from our customers, what do they use that tool in capability for. So, you know, certainly some people are using Puppet truly to manage the configurations in their environments, and that’s the main driver. They’re looking for that efficiency and scalability of what they’re doing.

We also found, however, that some people are deeply dependent on Puppet for compliance. And that understanding that that’s the business use for the tool, or one of the business uses for it, allows us to better serve up and meet those needs.

And interestingly, from an incident remediation standpoint, again, there’s a lot Puppet does from a declarative model standpoint that was always kind of remediating your environments in some way, shape or form, if you think about it. But it’s a very simple extension into integration with security scanners like Tenable, Qualys and Rapid7, to really start to go, having a scan, and then, manual process, and sorting through PDFs and Excel files, to get to business impact to saying, “Hey, I can ingest that information, make it contextually aware in the environment, and allow people to act on it in a much automated way.” Which not only reduces the work effort, but very importantly, to my earlier comment on cybersecurity, reduces the time to remediation of a known vulnerability, which improves your security profile.

So, the big shift, I think Puppet for a while has been making the tool or the platform more robust, but the shift that I think you’ve seen in the marketplace perspective is more around how we characterize what our technology can do in the context of business problems and business outcomes.

Priorities After Joining as CEO

Mike: In your first few months as CEO, what were your priorities, and did you feel like you needed to pivot the business after coming in after the founder? And I’m wondering, was there really a pivot needed? Or did you see that it was more of a requirement to incrementally improve what Puppet was doing?

Yvonne: Yes, it’s always challenging when you take a company over as CEO, in part because there’s a huge piece of the culture and the connection with the people that comes with that top job that you have to be sensitive to.

When I look at the journey of Puppet – Luke actually ran the company for the first many, many years very successfully, and the creation of this new market, and the proliferation of the technology at that practitioner level, there was actually another gentleman, Sanjay Mirchandani, who took over from Luke and ran Puppet for three years. And what Sanjay focused on was really selling higher up into the enterprise, and kind of, to your previous question, looking at going beyond configuration management, what was important in the marketplace.

As I took Puppet over a year ago, the key things that I noticed, one was that we were very much on the right trajectory, and it was more some fine tuning and focus that we had to drive to the business. And my real time and attention in the first year, first and foremost, was on appreciating that a CEO change, no matter how great I may or I may not be, is an experience that you need to work through with your employees and with your community.

So, my first focus was on the team and the community and really aligning around purpose. And kind of your first question, why was I even there, did I care about the same things they did, were my values aligned, how are we going to come together as a team and really drive the next level of the journey – I think that’s important advice for anybody taking on a senior level role.

Start with the people, and then, really, from a business perspective, looking at how could we get the biggest impact with these things that we have, how can we simplify and focus what we are doing to those that would make the biggest difference.

So, we did trim the product portfolio a little bit, we doubled down on areas where we felt we had differentiated capability, we started to focus a lot more on the engagement with the community, we had drifted a little bit away from that which happens sometime.

So, really looking at, we did our first ever in person contributor summit, looking at how could we really nurture both, the community who has gotten us to really where we are, as well as being in meaningful service to our enterprise customers, who, at the end of the day, are a critical part of the business model as well, and scaling what is now a relatively large company that has a strong open-source base, and also has a sustainable, monetary business model to care as well for.

Puppet Value Proposition

Mike: What would you say the value proposition is for Puppet today?

Yvonne: I believe that Puppet has gone from being a kind of a practitioner tool that eliminates soul-crushing work, which is a really, really important thing that we have extended a prawn, that value proposition, to being a platform that enables business agility in a safe and secure way. And the way that I see us, really bringing this to market is, if you think about the modern enterprise and open-source projects, they are here to service to everybody. We really focus our commercial efforts on what I would call the Global 1000. And in that segment, those companies are going to be in a hybrid, or multi-cloud world for many years, if not decades, to come.

And Puppet is uniquely positioned to, in some regards, be their automation everywhere platform, be it in the data center or into the cloud, and increasingly across the Internet of Things. And we’re able to do that because we have a portfolio of automation capabilities, so different types of automation are actually required for different types of use cases in needs.

And so, whereas before, the world was a little black and white, you know, it’s either declarative or it’s imperative, and there were religious battles, it’s like now we realize that many different types of automation are needed when you operate at that scale. And we offer all of them in a coherent way. And we’re starting to build out the intelligence from that practitioner level up through the executive level, and helping people do things, all the way from, get the work done, to create the reports and the insights that the auditors need to get you through that compliance check.

So, for me, the real value proposition for Puppet in the commercial space is being that automation everywhere platform that gives you the action that makes things like your ServiceNow and Splunk implementations complete, because they might be able to tell you what to do or where the problems are.

But it’s really when they integrate with Puppet, that you get that completion of that loop, that everybody needs to truly get the business impact.

Market Segmentation

Mike: So, Global 1000 is still a very horizontal market with all sorts of different vertical segments. I’m wondering, from tactical sales and marketing perspective, when you’re trying to convey business value to these different segments, do you have to change the marketing a little bit? Or is there any vertical marketing or segmentation going on, and how you look at the customers, and how to sell to them?

Yvonne: Yeah, absolutely. I love the question that you asked because there are so many horizontal technologies in the world, and I work with many companies, back in the day, BEA, and VMware, all very horizontal in terms of a capability. What’s interesting, however, is the importance that you highlight, which is differentiating how a product is built versus how a product is bought and consumed.

And that’s when you do benefit I think from taking a more vertical or use case approach to a technology. And, for us, for example, we do a lot in highly-regulated industries, and financial services is a great callout.

So, even though the Puppet product offerings are the same, whether in service to retail, or financial services, or tech, or government, how we speak about the technology can start to vary in terms of those segments.

And at the enterprise level, referential buying is a real thing. You know, if I’m a large bank, I’m greatly comforted if I know five other large banks also use that same technology. And you can start to help them understand the financial services banking problems that you can solve, and as I mentioned, compliance or certain compliance requirements in those industries.

So, you can start to make it much easier for your customers to get value out of your technology and to trust your technology, when you can speak in their language, and when you can connect them with their peers, who are in a similar way using your technology to solve problems.

So, what we have done – to answer your question from a segmentation standpoint – one is, recognized where are our open-source solutions most relevant and valued, and continuing to feed and nurture those. And then, being really thoughtful on where our commercial offerings are most valuable, and drive the greatest impact.

And on the commercial side then, further sub-segmenting into vertical industry, and then, as we talked about use case, are you looking to solve problems around incident remediation and reduce time to vulnerability remediation, are you more interested in compliance reporting.

At the end of the day, I like to kind of joke, Puppet is a Swiss army knife, they can do a lot of things. That’s a blessing and a curse. And when you work with large enterprise, then, more specific you can be on the problem you solve – I kind of use the analogy of an IKEA furniture – at the enterprise level, they really don’t want the big box of IKEA furniture showing up in a bunch of little pieces, without an instruction manual they have to solve it themselves.

Some people like that and get a lot of joy. It’s usually not my customers, they want to have a simple easy way to get to business outcome. So, we’ve really done a lot to make that clear and easier for them.

How To Balance Open Source Investment

Mike: I thought it was interesting how you mentioned that you were, let’s say, investing a little bit in the open-source community, for example, an event for contributors. I’m wondering if you could talk about how do you prioritize investments in the commercial product versus the open-source product?

Yvonne: I think about open source a lot. For me, personally, I think we are where we are in terms of the rapid technological advancement because of open source, and how that’s really proliferated around the globe in so many ways. And I do believe that it is a great way to democratize access and contribution to technological development, particularly with underrepresented groups in countries and locations, where they may not have otherwise been able to participate at that highest level.

So, I’m a big believer in the whole concept, and I’m really proud to work at a company that appreciates and celebrates that, and invests in it. What I think is really important in the seat that I sit in is appreciating the fact that open source has in our case almost moral and principle value, but it’s also a critical component of our strategy. It is not the business model itself, but it’s a key part of our strategy.

And I think of open-source in a couple different components. We have open source tools, Puppet open-source Bolts, those are tools that our community members can contribute to and benefit from. We have open-source content, which, in our case lives on the forge, which makes the tools even richer. And we have some people who only contribute to content, and some who only contribute to the tool, and some who contribute to both. And then we have the users of that open-source content.

And to me, it’s important when I think about the open-source community, I think about all those constituencies because they’re all critical players even though they’re playing in different roles. And I’m very proud to say we have over 75% of our commits still coming from the community. We have a very active community.

For me, what’s important is that we are continuing to nurture the creativity, the innovation, the access, in what I would call that “ground level of capability”, and that we’re allowing people, who have interest in ownership and institutions that we’ve built, to be able to contribute and get the benefits over time.

So, we do a lot of things, from – we did a contributor summit in Budapest last year, we are doing Puppet camps again, so we’ve reinvested in that, more currently, in the process, we’re making them virtual just because of the environmental challenges, this coronavirus. But we are looking for ways that we can help people who are part of the Puppet community be able to have a platform to speak about, what they’re doing with the technology, the impact it’s having, and help others.

We have obviously community managers, we’ve got slack channels, we’ve got some interesting ways that we’re looking at engaging with the community from the support perspective. So, there are many different aspects to it.

And to me, one of the beautiful things is I think open source has evolved a lot in the last decade. And I like to think of Puppet as one of the folks who are leading through that evolution, and how you continue to give back, and you know, garner benefit in a very, very productive way. So, super-excited about what we’ve done. I’m sure we’re looking to evolve, but I do think it’s part of what makes Puppet special.

Evolution of Sales Motion

Mike: So, originally, I’m sure open source was one of the primary let’s say distribution channels for finding customers who are going to engage with you commercially. But I’m sure that the sales, you know, processes, and motion has gotten very mature as a company has grown. How does it work today? Would you say that the open source still really is a driver for business? And, if it’s changed, like, how have you adapted to that change?


Yvonne: The go-to-market side of Puppet has evolved a lot. And open source has, as you suggested, played a critical role, and I believe it still does, but it’s shifted.

In the beginning, a lot of people who bought the Puppet commercial products came from the community, and they were the practitioners who were bringing that technology into that environment.

Many of the open-source users never felt the need to actually go and buy commercial products, they scaled up, and they built their own UIs and their own ways of advancing the open-source project in their company.

And so, we did go through a phase, where, in the early days, there was a lot of inbound. And what I would say is, now, the two things that have shifted, one is, as our ability to drive impact across an enterprise has increased, as the maturity of our solutions have increased, we’re actually selling to higher-level individuals in a company.

So, what I’d like to say is, we’re not just selling to the hands-on keyboard people, we’re selling to people who may never actually touch Puppet, the technology themselves. And yet, the fact that there are Puppet practitioners in their company is super important. So, I think one open source serves us today because it keeps a rich set of talents in the marketplace that can work on, and scale and execute the technologies that we’re bringing to the enterprise customers.


The other thing that we found is, many of our enterprise customers have in some way, shape, or form, or division, used, or are using, open source. And they have just set a point where it’s no longer differentiating for them to do all the work around, upgrading the open-source and everything else, to do it that way. And they rather move to the commercial version, take advantage of the incremental feature functionality, have a simpler upgrade process, have 24/7 support.

So, for us, I would say, in some regard, open source is still the land, people are using it, and then they’re starting to realize open source isn’t free. You’re just making different choices, do you want to have the engineering talent work on, keeping your open-source implementation healthy and current, and to build around it.

That’s the right choice for some. For others they are saying, “Hey, open source was a great way to get something started. Now it’s starting to run a critical component of my business. Maybe I’m better off, from an opportunity cost perspective, to engage with Puppet, to have Puppet provide me those services of incremental feature functionality, and reporting and support. And I can spend my valuable engineering talents time on other things that might differentiate me as a retailer, or manufacturer, or a bank.”

Is Puppet Open Core?

Mike: Would you say that Puppet is open core?

Yvonne: What I would say is, Puppet has – and I think this has been the big shift in terms of how we think as a company – certainly Puppet open source is a very mature, very impactful projects that many people can build on top of, frankly, around globe, which is wonderful to see.

What I would say is, as we think about the broader Puppet, what we are looking at is, how do we create open-source capabilities that people can stitch together in different ways to self-problems. And we don’t just look anymore at, we have to be the sponsor of those open-source projects, we absolutely contribute upstream to other projects, we leverage other open-source solutions in some of what we do. For example, Terraform and Puppet work great together, there’s actually some great webinars on how you leverage Bolt and Terraform to drive provisioning, and configuration and actioning on that.

So, we’ve really taken a much more open-minded approach, and thought about open source, almost from a component or an ingredient standpoint, that can be stitched together into whatever solution that you need. And some of those solutions we stitched together in a commercial way for our large complex enterprise customers. And others were providing the componentry that companies can stitch together in the way that they need if they want to do something all open source, or put their own secret sauce magic to it.

Pricing

Mike: Pricing is I think really hard for every company, surprisingly difficult. And it seems like the impact and the value of Puppet is so enormous to organizations – how do you find the rate gate to figure out or to find the right strategy for pricing? And you’ve only been there for a year, but have you seen that change? Do you think that the pricing model that you’ve figured out is going to be stable?

Yvonne: Pricing is an incredibly challenging topic I think to your point for pretty much everybody, and to me, what I learned early on, back in my consulting days, is one of the best ways to think about what the right pricing model is, for your company is, to start with the value chain of what you’re bringing to your customers.

If I take an early-day example of like an eBay, you know, market place, you are bringing value creating community. You’re making value by letting people sell through that community, you’re making value by letting people buy through that community. You are making value by providing different ways to attract attention.


You can kind of map out all the different value points, and then, you can make decisions on where do you want to price to be able to get a return on the value you’re creating. So, eBay for example, could have chosen to say, “Hey, you’ve got to pay to get in, and then everything else is free.” Or, you can get in for free, “There’s value in there, but let me give you that for free, and you’re going to pay these other steps.”

So, I think every company needs to go through that process and figure out where the value is, their driving for their audience that’s worth having an exchange. The interesting thing is, it can easily become way too complex. So, simplicity is an important rule of pricing in my experience, and then longevity.

Particularly if you’re in the enterprise space, you don’t want to be changing pricing all the time, and it runs through your systems. So, I feel Puppet, in terms of where we’ve come from, that we have a pricing model that has worked well for us and for our customer base, on where we’re at. Are there opportunities to fine tune it and evolve over time? I’m confident there are. I’ve never seen a company that hasn’t at some point in time started to shift and think differently about their pricing.

But, to me, whatever you do with pricing, it has to center around what is the value that you’re bringing your customers, and can you come up with something that’s simple and easier for them to understand that will scale out for a meaningful period of time. Because a hard thing to do is change your pricing all the time. That’s an easy way to upset your customers, and make a lot of enemies in procurement. And nobody wants to do that.

How to Encourage More Women in Open Source Business?

Mike: Yvonne, you might have noticed that the male to female ratio in Open Source Underdogs is currently 41:2. And we’re trying to improve that ratio this year, but it does reflect the reality of the tech market, which is that men are overrepresented, especially at the C-level. What can we do as an industry, or even more tactically, what can I do, as a founder of a software company, to improve that ratio?


Yvonne: I love that you’re asking the question, what can you do to improve the ratio, because I believe at the end of the day, it has to start with individual ownership in action. And we can talk about really lofty things we could do, but at the end of the day, we need to create the future reality that we want. And we all have a role in it, whether we’re male and female, different types of necessities and so forth, if we want a diverse world, we have to create the opportunities for that, or diverse roles in leadership I should say.

And what I believe you could do, first and foremost, I appreciate this opportunity, just showcasing Puppet and myself, and having different types of role models in your podcast. I’ve had numerous women come up to me and tell me that they aspire to be a CEO, and in part, they aspire to be a CEO because they see me doing it. That’s incredibly humbling, but it’s also a great reminder that, for many people, if you can’t see it, you can’t believe it.


So, I think, first and foremost, showcasing different types of role models, that it’s not just one type that a successful leader looks like, but there’s many. The second thing is sponsoring and encouraging people to step up to that next level.

What I have found working with underrepresented folks is that – myself included – we can often tend to be much risk-averse. So, encouraging people to retire to build that confidence that they can go to that next level. Sometimes to give them that nice gentle push, maybe not so gentle sometimes, as I had in my career. Sometimes, you just need that.

So, I think creating the models, I think giving the pushes. And then giving the opportunities, take a risk on somebody. You’ll be amazed at what they’ll do with the right sponsorship and support. So, I think there’s a lot we can do across the board, but those are three tactical things that, at an individual level we can engage in, things that I try to do all the time.

Advice for Founders

Mike: Last question, any advice for entrepreneurs who are looking to use open source as part of their business?

Yvonne: Absolutely. I live in Silicon Valley, and I run into a lot of people who get really confused on open source, and – when I say “get confused on open source”, they confuse perhaps a desire and a belief around the power of open source as a way to democratize technology and bring important solutions into the hands of everybody, with the fact that somehow you’re going to have to figure out how you’re going to make money.


And so, to me, it’s really important to understand you can get both, I think Puppet does both, but you have to be really thoughtful what is the role that open source is going to play in your business model, because it is not a business model into itself. That’s kind of a rule number one.


The second thing that I would say is, community, community, community. I don’t think that you’re going to get a lot of benefit out of just open-source thing, the technology you build if you’re the only one building it. Certainly people might use it, they’re not going to pay you for it, they might benefit from it, they might like that it’s open source, but I think part of what’s made Puppet powerful from an open-source perspective is the community engagement, and the fact that we’re collaboratively building these different open-source projects, and that we are collaboratively building content – that is what I think truly makes open-source most powerful.

So, I really think if you’re going to do an open-source solution or have that be part of your solution model, how are you going to invest in, and engage, and nurture, and grow, and sponsor, and give a voice to your community, so that you keep them engaged, so that it truly is really executing open source at what I think is the most powerful level and form.

Closing

Mike: Yvonne, thank you so much for your time and sharing your great insights today.

Yvonne: Great. Mike, thank you, it’s been wonderful. And, again, I really appreciate the opportunity.

Mike: Special thanks to the Puppet team for helping to coordinate this episode. Audio editing by Ines Cetenji. Transcription by Marina Andjelkovic. Music from Broke for Free, Chris Zabriskie and Lee Rosevere.The podcast Twitter handle is @fosspodcast.
Please, tweet at us if you have any comments on this episode. Next time, we talk to Tracy Regan from DeployHub, a great technologists and founder CEO.

Stay safe everyone. Until next, time thanks for listening.

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