Operations Management in Digital World

The Prime View had the pleasure to interview Chad Kalmes, Vice President of Technology and Risk at PagerDuty.

Chad Kalmes is a technology veteran with immense experience and success under his belt of implementing digital roadmaps, security and risk management programs, developing products, and building business-changing analytics at Twilio, Protiviti, and now PagerDuty.

Chad, can you tell us a bit about the steps in your career and how your career has led you to this point?

I started my career in professional services and then transitioned into technology over time. My primary focus was initially on security and risk, which was over twenty years ago before the security industry matured to what it is today. 

What I liked about starting in professional services and then transitioning into technology was that I got to see how a lot of companies operated and a variety of different approaches to solving the same challenge.

Direct exposure to how Fortune 100 and Fortune 50 companies operated was a great experience – you quickly learn that there’s no singular way to do things.

That became foundational in how I approach my own work when I became the owner of those technology stacks. 

That approach also helped me bring a balanced perspective, understanding how larger companies, very traditional infrastructure companies operated. This, again, was when most companies were still living physically in on-prem data centers and then seeing how that transition was happening over the course of my career working more with technology startups living in cloud-native environments, SaaS environments, and then focusing on hypergrowth. 

Chad Kalmes

Vice President, Technology and Risk at PagerDuty

Getting to see both ends of that spectrum and how people accomplish the same thing differently was an eye-opening introduction to technology. Understanding the core of the issue and what your user’s needs are, is the first and foremost step in the journey to building a solution.

As you have a long and successful career in a variety of technology companies in leadership positions. I assume you had to hire a lot of people for different roles. What’s your secret to building high-performance teams?

I do think that diversity is critical in hiring. I have always valued it. This approach goes back to my consulting days, where I brought in different perspectives, backgrounds, and other experiences. When ten different people in a room look at a problem, and they come from different backgrounds, you’re likely to come up with ten ways to solve that problem versus just one.

Also, I don’t want people in my teams to agree with me a hundred percent of the time. I know what I know. Now, I want to know what they know. And I think that diversity and the different perspectives gives a lot of autonomy – I’ve never built my organizations around micromanaging.

My role as a leader is setting a clear vision and direction and maybe calling out some key milestones or stops along the way.

But I shouldn’t prescribe how my people get from point A to point B. I think that’s the power of leveraging the experiences of those people. If teams align on where you’re going and know what they need to accomplish, letting those people take their own experience and run the things becomes super valuable. 

Another critical aspect of being successful with technology is listening to your customers, whether internal or actual customers of your company’s product. So, I always look for good listeners because part of the job is understanding the customers’ point of view, challenges, and motivations. Sometimes it might mean pointing them in a different direction. Nevertheless, you’ve got to begin with listening. 

The last point I would make is that you should honestly hire people that are better than you. Don’t be afraid to highlight those folks as the real power of your organization versus yourself. I want my teams to continue without a blip, even if I get hit by a bus tomorrow. You can’t do that by building a team of B-players who are not strong enough to take over.

You cannot hire a lot of great players and then keep them in the shadows. To be a successful leader means you have to bring in the best people and let them shine.

What type of individuals do you look to bring to your organization to foster innovation culture?

I’m a big fan of finding “T-shaped” resources – people who have excellent skills and experience in one particular area, and yet can flex to cover areas outside their general expertise.

Early on, when I was doing a lot of hiring in technology, I focused primarily on core technical skills, like specific X, Y, and Z technologies. However, I’ve noticed that better performers in my organizations tended to enjoy having things thrown at them outside their core expertise. They would get excited by new challenges rather than retreat to the comfort zone. That “T-shaped” individual or even that mindset is important because there’s no right way to do things. The more those people get excited by thinking about different ways to solve a problem or tackle a particular challenge, even if it’s something they’ve never done before, the higher the chances of finding the solution. 

For several years you were in a leadership position at Twilio Inc. Twilio demonstrated outstanding growth over the past 5 years. In your opinion, what are the most notable Twilio’s success factors?

Even though it’s been a few years, I look at what was core to the company, which attracted me to Twilio in the first place and made them successful when I was with them, which was a strong central vision for the product. I would assume that hasn’t changed much.

Twilio® was always focused on solving actual, day-to-day challenges for customers. Communication was core to the vision that Jeff Lawson (Ed. CEO of Twilio) set out. He knew the pain he was trying to solve, and there was a laser focus on helping customers reinvent communication, critical to every company, and democratizing it.

The vision at Twilio was about opening up communications, which had largely been a black box in most organizations – and making it transparent for developers. 

That was super powerful. Many things may have changed at the company since I’ve been there, but I’d be willing to bet that the laser focus on solving real-world problems for customers and democratizing how companies communicate is still core to what they’re doing at Twilio. That’s going to continue to drive their success.

The Digital Operations Management space is a very high-growth and competitive industry, how does PagerDuty maintain its competitive edge to remain a leader in Operations Management?

Digital Operations is still a nascent space, with many opportunities for growth. We are continuously connecting with our customers to understand what their pain points are to make sure that our product engineering teams are continually adding features, functionality, and improvements to the platform in a way that addresses those needs while maintaining flexibility and agility.

To succeed in this space, and continue to adapt in an industry that’s still very much growing and evolving, you need to retain that agility and flexibility because the way that a problem is solved today may be different from how you want to solve it tomorrow. You don’t want to architect your platform or your solution so precisely that it can only meet that one need.

We look at PagerDuty as a digital nervous system for customers as they expand their digital operations, the tools, and the technologies in their company. 

We want to make sure that we can continue evolving and expanding our platform as that footprint changes. Through that lens, it’s not just about our platform at PagerDuty, but it’s also how we integrate with and play a part in that broader ecosystem of tools and solutions. Most companies today probably have tens, if not hundreds, of software and SaaS solutions in place. One of our goals is to continue to simplify that complexity and that sprawl to allow our customers to stay laser-focused on finding the signals in their environments that need action immediately and connecting the right people, the right teams, to those problems to get them solved in real-time. We can’t do that successfully if we’re not looking at that entire ecosystem and understanding how all of those pieces are part of that journey for our customers. 

In terms of how important data and analytics are to PagerDuty’s success – what kind of Big Data tools do you use internally, or what capabilities do you plan to invest in, to be able to continue serving customers’ growing demand?

Data is essential to our platform and the services we deliver to our customers.

That is also important to how we run our company from an operational standpoint. To that end, we have dozens of different technologies involved in delivering services. There’s no one size fits all. 

Though, if I had to look broadly across our environment, I’d say two cornerstone technologies stand out as areas of investment. We’ve recently partnered with Snowflake® to relaunch how we handle many of those needs internally. Our old environment was custom-built and had many custom tools and technologies that were great for us as a younger company, but as we started looking to the future and considered how each of those components would need to scale for us to be successful, it was clear that we needed to find some way to simplify that architecture. Snowflake became that tool that would allow us to unify many services going forward. It gives us a platform and a path to the future. It will enable us to go even deeper and add more functionality and customization to our environment.

We democratize data going from company-wide, broader metrics and analytics down to department-by-department, even team-by-team to get the timely insights into the hands of our users.

We could have found a way to do that with our older tools, but leveraging a platform like Snowflake was a powerful and simpler way for us to scale, and it will be really foundational for our future analytics offerings.

The other broad category that applies both to our customer-facing product and internally is AI/ML. Internally, we continue to adopt more and more machine learning solutions, to push the analytics curve farther into the future. We are moving from historical analytics and understanding real-time data in the present, to building predictive models and formulas and using that data to inform how we approach the business further in the future. We’re still experimenting with a lot of AI/ML technologies. We’re looking at Sagemaker from AWS, Einstein from Salesforce, Watson from IBM. They all have various strengths and approaches, but we are just starting to tap the power of what they can bring, both to our platform and our company. We’re excited about these tools that are becoming increasingly accessible and available to anyone.

Could you share with our audience more details about what other tools and technologies you are using at PagerDuty to build robust and scalable systems?

We start our solutions with some essential building block tools or approaches, whether that’s a platform like Salesforce or the tools and technologies that AWS brings to our environment. We spend a lot of time finding those core tools and thinking about how they will integrate across workstreams and processes, and create an excellent customer experience – whether internal or external. We tend to take a little bit more of an engineering-centric approach to some of that development – starting with core building blocks, but creating a lot of custom glue and integration to make the experience more seamless. We may start with a platform like Salesforce or a tool like Slack, but we need to take a step back and look at it from the users’ perspective – what are users trying to accomplish in those platforms, and how do we go beyond what just the off-the-shelf tool offers to make the experience better? 

Integration tools like Mulesoft, which Salesforce acquired a couple of years ago, become critical in our environment. Mulesoft allows us to be more flexible in the solutions we ultimately deliver and reduce some of the longer-term engineering burdens by helping us to ‘glue’ a lot of those different platforms together more seamlessly. 

Most of the teams are working remotely because of the Covid-19 pandemic. Being an engineer and a technical leader, maybe you could share that secret ingredient in keeping your teams productive and focused on their tasks?

We are looking for people excited by the challenge and like doing things differently, people who are motivated and diverse and approach things from a new angle. That helps with resilience in crisis times, and it helps with mental resilience in your teams because they’re used to dealing with change; they’re used to flexibility and adaptability. 

From a technology standpoint, we’ve always built our environments to be location agnostic. 

As a company, we invoked our crisis leadership team within the first week of the initial quarantine lockdown in the United States, and one of the main focuses of that group started with the mental health and well-being of our employees. While some of us focused on the business and the economic impacts, we wanted to make sure that there was also a big focus on supporting our people, knowing that supporting and maintaining physical and mental health while everyone was isolated would be challenging.

I believe it ultimately comes back down to communication – you’ve got to talk to people on your teams and understand how they’re doing. Not just from a work perspective, but from a personal perspective. People have to know that it’s OK to carve out time to cover their personal life. That might mean different working arrangements or flexibility of deadlines and timelines. Though, I’ve never really cared that much where, how, or when people get their jobs done as long as they get them done.

As a leader, you need to be explicit in calling that out and letting people know that it’s OK to make space for themselves. 

“People first” is one of our core company’s values at PagernDuty, and that’s not new because of Covid. That’s just who we are as a company. We know that one of our core strengths is the people that work for us; that’s part of our DNA.

Chad, thanks so much for taking the time to speak with The Prime View and for bringing about meaningful change to the Operations Management industry by leveraging innovative technologies and forward-thinking approaches to management.

Stay tuned for the next interviews!