Operator Spotlight
Technical & Product

Meet Atlassian SVP/GM of Product for Work Management Portfolio Erika Trautman McCaddon

Caroline Caswell

“How did they do that? How did they get there?” Companies succeed because of the people who build them - operating leaders who grow businesses to new heights and make decisions every day that can impact entire industries. Each month, our Operator Spotlight gives you the inside track from one of our incredible Operator LPs (Limited Partners) who are changing the game – building and scaling some of the world’s most successful companies. Read on for lessons learned and mistakes made, perspectives from the top, practical advice, and ideas on what’s next. 

This month, we spoke with Erika Trautman McCaddon, SVP/GM of Product for Work Management Portfolio (Trello, Confluence, Jira Work Management, Atlas). Prior to Atlassian, she was Director of Product for Google Drive and Editors, a suite of collaboration tools used by more than 1 billion users. Before helping enterprise teams work better together, Erika was an entrepreneur who founded and successfully sold Rapt Media, a creative platform for interactive enterprise videos.

Tell us a bit about your journey as a Founder & CEO to large enterprises. What were some of the biggest challenges and lessons you learned through that jump? 

Being the CEO of a start-up is the hardest job I’ve ever had. The thing I really didn’t appreciate  until I was in the seat is exactly how much emotional management the job requires. As the founder and CEO, you know exactly where the risk is (or is not)  and how steep the next hill is that you’ll have to climb. And it’s your job to hold that knowledge and let it inform your decision making, all while inspiring your employees, shareholders, and customers to surge forward forward with you. It’s an awful lot of accountability. But it gave me perspective and trained me in resilience in a way that serves me every day.

I think the coolest thing I learned was how amazing it is to build a complete team. If you’re a manager leading just one job function, you wind up specializing in recruiting a certain set of skills and abilities. But when you’re the CEO and you have to build Sales and Engineering, Marketing and Finance, Design and Operations,  you develop a profound appreciation for the very different brain-types that all come together, and I found that really fulfilling.

What’s a key piece of advice you would offer to a founder considering an acquisition? 

Leverage your community - founders who have sold their companies before, tech execs who have been on the other side of the negotiating table. People are here to help and you’ll need it. I found it equally valuable to talk to my CEO friends who sold their companies as it was to talk to people who had bought companies. It’s easy to lose perspective when you’re in the midst of such a high stakes negotiation.

I would also say, landing an acquisition is a hard thing to do. It’s really important that you understand and trust your acquirer and can see how your company can fit into their broader strategy. Getting through the actual sale is just the first step. Make sure you’ve got the people and support in place to go through the multi-year process to make the acquisition successful. It will take effort.

You have a fantastic view into how work products have evolved over the last five years, what’s different about the space now vs when you started at Google?

Well, the pandemic happened, which we all know led to just a massive acceleration of the adoption of digital work products. But that adoption happened very chaotically as workers just grabbed whatever might help them keep doing their jobs from their kitchen tables. While the availability of so many different digital solutions kept us going, it also led to a lot of unintended complications – data siloed across dozens of different apps, security risks, information and team coordination lost in the gaps, and workers just exhausted by a million tiny product paper cuts as they tried to navigate it all. 

The result is that now we’re in a period of reconciliation. Customers want their work products to reduce the friction between tools. They want the work to travel to wherever they are and not have to switch between so many interfaces. They want their data all connected. 

And then, of course, ChatGPT happened. Right now, we’re in the phase of applying LLMs to all the obvious, low-hanging fruit, which I do think will be valuable – predicting and automating repetitive processes, generating first drafts of content, summarizing and deriving action actions, finding the right information for workers at the right moment. 

But I do think once this first wave of innovation settles in, we’ll start to fundamentally rethink how we interact with software. I expect some pretty profound changes over the next several years. Exactly what that looks like, though, is tough to predict.

Your role at Atlassian covers product for Confluence, Trello, Jira Work Management, and Atlas, and you’re responsible for the business outcomes that drive hundreds of millions in revenue - it’s a lot! How do you think about prioritizing?   

It is a lot to juggle but I don’t think it’s rocket science. I start by thinking about what we’re trying to accomplish in the market, for our customers and for our shareholders, over a medium time-horizon - say 2 or 3 years. Then I look at where we are today - what’s the state of the business, the state of the products, the state of the teams, the state of competition? That helps me identify where my problems are, what we need to build and what we need to change. Prioritizing among that set of problems to solve comes down to importance and urgency. I like to create visualizations of what we’re trying to do over time so I can keep track of how, in an ideal world, all the efforts come together. Then if inputs to that plan change, I have a visualization of how that might impact our strategy or execution.

That’s how I derive my broader set of goals and initiatives. And then you just rinse and repeat at a more granular level for the quarterly, monthly, weekly and daily workstreams. 

I definitely go through phases where I get overloaded and just can’t tackle everything. In those moments, I pay attention to which of the balls I’ve got in the air are glass balls (that will break if I drop them). And then I give myself permission to drop any ball that isn’t glass. 

Have you adapted any practices in response to the current macro environment? How are you thinking about your strategy for 2023, and any predictions for what’s to come?  

I think two things have become significantly more urgent in the current macro environment: 

  1. Really deeply understanding what’s happening with our customers and how that is reflected in our business. This has just amped the importance of business and product data significantly. We have shifted to far more frequent data deep-dives across our products.
  2. Speed of execution. We’re tackling this problem from every angle - do we have the right organizational structure? Do we have the right incentives? Do we have the right people in the right roles ? Where can we accelerate decision making? 

After such a long time of growth in the tech industry, a lot of folks haven’t seen a period like this before, so it does take a reset in how we work. 

I know better than to make predictions about the future, except to say that nothing is permanent. This too will pass.

What was one of your first jobs and what’s one big lesson you learned? 

My first real career was in journalism and documentary filmmaking. I was in my early 20s and I was investigating arms dealers, human traffickers, and unethical medical testing conducted on children with cerebral palsy in state hospitals in California. That experience taught me a few really valuable things that have served me really well as I transitioned into tech. 

The first thing that career taught me was really basic but so critically important - if you don’t know the answer to something, find someone who does and ask. Ask enough questions from experts  until you understand. 

The second lesson I learned was about fearlessness. I have been threatened by criminals, I have been in high speed chases, and I have angered people in positions of authority. I didn’t enjoy those experiences but they taught me the difference between fearlessness (good) and recklessness (bad). I try to develop and cultivate fearlessness, which I define as a willingness to face or do hard and scary things calmly, deliberately, and with an objective outlook. When you’re fearless, you can make smart decisions under pressure. You neither paralyze nor panic. 

What’s a piece of advice you would give to yourself 10 years ago, if you had the opportunity? 

Hang out with your daughter. Prioritize exercise and sleep. 

And pay attention to product-market-fit and market sizing. Don’t let your apparent constraints keep you from making big investments to invest in expanding your market opportunity.

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