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Meet BetterCloud's New VP of Site Reliability Engineering, Stephen Dick

Richard Moy

June 10, 2021

7 minute read


Stephen Dick recently joined BetterCloud as its VP of Site Reliability Engineering (SRE). Prior to joining BetterCloud, Stephen championed and implemented DevOps practices at some of the most recognizable tech companies on the planet, including MuleSoft and Salesforce.

We recently sat down with Stephen for an informal chat about his career path, the history and future of DevOps, and his vision for Site Reliability Engineering at BetterCloud.

Editor’s note: This transcript has been edited lightly for clarity.

A few weeks ago, [CTO Jamie Tischart] and I talked about this fork in the road that engineers typically get to where they either move into management or commit to writing code for the rest of their careers. What got you interested in taking the executive leadership path?

I think about how a person feels about their work, how they’re seen and valued, how they’re appreciated and celebrated and how their contribution gets recognized. How a person feels about these areas can have ripple effects on other aspects of their lives. It can affect their relationships with their families, friends, and partners. It can affect their support networks. It can affect their mental state. People who feel like they’re contributing in valuable ways can often take that positive energy into other interactions. It can be a multiplier effect. It can have a generational impact.

I think about that impact constantly. I grew up in an amazing environment back in Ireland, but the environment was such that being heard and understood and individual recognition were of secondary importance.

As I progressed in my career, I started to realize that one of my deeply held personal values was leading as an introvert. I noticed over time how listening to someone just to listen and make them feel heard can help people understand and normalize their own experiences.

Over time, my personal mission began to develop and I became really passionate about helping the world feel heard. I see certain aspects of my role as a way to enable that, and to have a huge amount of fun doing it as well.

That’s awesome. So you’ve been at BetterCloud for a few months, listening and collecting feedback from our customers, partners, and internal stakeholders. What are the biggest challenges that you’re thinking about from an SRE perspective? What are you laser-focused on right now?

The ability to build customer trust is critical. Oftentimes, in the SRE space, we will focus on uptime, availability and performance of our products and see those areas as our critical contributions. At BetterCloud, one of our values is “Strive to Delight.” We ensure our products are always available as a baseline and we delight our customers when we deliver on our commitments and by communicating openly and transparently no matter what.

It can be a moving set of goalposts because our product is always evolving and so we’re also evolving our SRE function continuously. SRE ensures that we provide an outstanding level of service, but we’re evolving to get ahead of the curve. As new products are released, we will be embedding our team earlier into the value chain so we can prevent problems before they occur.

You mentioned offline that the SRE team is set to double in size. How are you imagining structuring your team, and how might it look a little different than SRE at other companies?

Yes, we’re doubling the team size. Exciting times! There are two parts to ensuring customer trust.

Firstly, we get proactive to ensure our product is available and performant. To achieve that, we’re starting what I call “SRE: Active Embedded.” We’re a centralized team right now and we’ll be moving to distribute some team members into other engineering teams so they can impact software delivery earlier in the value stream, where it’s cheaper and easier to detect future challenges and prevent them. We call it “Active Embedded” because our engineers are not passive recipients. We’re here to coach, train, and mentor the organization in how to think about software at scale.

Secondly, we must communicate openly and transparently no matter what and move quickly to resolve technical issues when they disrupt the service we provide. This is commonly known as “Incident Management” and at BetterCloud, we see it as “Incident Prevention” where, through a learning culture, we never run into the same technical challenge twice.

I’m assuming that you’re not looking for candidates who are willing to deal with floppy disks anymore, so what are some of the qualities you’re looking for?

I look for intrinsic curiosity, flat out. It’s a personality trait that can manifest in a variety of ways and you can spot it when a candidate likes to go and figure stuff out because of a deep sense of personal joy that they find in doing that. These are the candidates that have side hustles, unusual hobbies, home automation projects. They’re candidates that are involved in the open source community, or they have a test work bench at home.

It’s an important trait, because when you build a team around it, you end up with a highly innovative team. A team that will challenge the status quo. That will move the needle. That will make work easier, more joyful.

It’s no secret that competition for top SRE talent is intense. If I were a candidate who had a handful of job offers on the table, what would you tell me to convince me to join BetterCloud?

The opportunity within the SRE team is not only to come in and help us pioneer our Active Embedded model, but to come in and leave your mark. This is an ideal place for candidates who have thought, “I just wish my previous team would have done that differently.”

More broadly, BetterCloud is riding a wave of digital transformation and it’s a super exciting time to join. The old IT paradigm—where provisioning and control of IT infrastructure, software, and costs were centralized—has faded with the proliferation of the SaaS model and the explosion of cloud-based applications being adopted in a more decentralized way by end users. While this trend can really accelerate business and allow companies to achieve results more quickly, it exposes them to a lot more risk. Costs can quickly increase, new attack vectors can open up, and confidential data can become more exposed. So, there is a real need for businesses to have a way to discover, manage, and secure their SaaS applications. The opportunity at BetterCloud to deliver on this value prop is very clear.

Let’s talk about the SRE landscape as a whole. Are there any ways that you see the work of an SRE evolving? Are there any ways that you think the role should evolve?

I like to go back to the DevOps roots of SRE. DevOps is about bringing teams together to achieve shared outcomes and it converges many different practices and frameworks, which allows the principles to be used in a wide variety of contexts. We’ve adopted poka-yoke and Kanban that both come from Toyota Manufacturing. We draw from learning organizations theory and safety culture. We use many elements of Lean theory and leverage Agile practices. We tackle operations problems from an engineering perspective.

I see business leaders taking these concepts, repackaging and reapplying them in novel ways.

For example, BetterCloud’s CIO Tommy Donnelly has taken some of the DevOps principles and applied them to an IT department.

I’ll wrap up with two questions about BetterCloud. When you think about people management, are there tactics or approaches that might evolve to serve the existing team?

Part of being remote optimized is blending your activities into your interactions, rather than blurring out the background. For example, my team will see me walking on my treadmill at home while talking during a meeting.

Zoom meetings can be effective but can be overused. Staring at another person’s face just isn’t particularly natural. I’ve learned to lean heavily on an asynchronous culture and try to build that early on.

We can make it fun also! I use this static camera for more formal discussions, but I’ve got a smart camera mounted up here.

Oh, interesting.

Yeah, that camera will follow you around the room and give you a much more natural feel to a conversation as you move around to the whiteboard I have set up here, a screen I have on my desk, or even when I just get up for some coffee. That transforms the nature of the conversation from a very limited view of a person to where you’ve got a lot more context, which has been helpful.

I’m following more niche technology trends that may be coming of age. VR for example is really interesting. My son and his cousin in Ireland were doing a virtual boxing match recently. While that’s novel, I think about a day when technology could enable a truly beneficial and additive experience to how we work across borders.

Have you found those technologies to be even more important for the folks you work with at BetterCloud, where this work from home environment is still new to some people? How have things like your smart camera helped people adjust?

You know, I’ve experienced that some people will always just see the obstacle that gets in the way. But if we’re curious and if we’re open and if we find joy in the work we do, we often find the obstacle is the way forward. The way to make progress, to change, to open new possibilities, to accelerate results. When we look at asynchronous frameworks, and our teams see the smart camera moving, when they see the virtualized whiteboards and experience the human freedom to walk and stay healthy while being in a meeting, we see people experiencing life in a new way. That positivity can have a ripple effect into other aspects of their lives. It can have a positive generational impact.

One more question about BetterCloud before we wrap up our conversation. Where do you see the company this time next year? And how do you hope that SRE enables BetterCloud to get to that point?

We started by talking about how a person feels and how their work environment can have a ripple effect on other things. SRE itself will have a ripple effect within the larger organization as well. One of the things that’s becoming clear is if you think about trend lines, BetterCloud is definitely going up and to the right.

We’re on a growth trajectory. SRE plays a big part in that because as bigger customers adopt BetterCloud, they need to be able to trust us. SRE is our fundamental bridge between indispensable customers and indispensable software. We’ll be having that ripple effect, not just because we provide that bridge, but also because we’re the only team in the company whose entire founding purpose was around bringing teams together to achieve shared outcomes. That’s been a big part of our agenda in the initial couple of months. We’re getting aligned on shared objectives and bringing our teams closer together so we share the same goals.

That’s great. I like to end these conversations by asking about a hobby or something else that you’re looking forward to when the pandemic is over.

I think about adapting to life as it is. Every challenge has an interesting opportunity and an obstacle can be what gets in the way, or it can be the way forward. The pandemic was brutal. It’s been devastating for a lot of people, for a lot of families. Yet, despite the social distance, I’ve found joy in using technology to close the distance for the most important relationships in my life. We’re always moving towards joy or moving towards fear. I choose joy.

Want to learn more about the interesting and complex challenges that our engineering folks are tackling? Check out our Careers page to learn more about open roles on the team.


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