My Path To Management

From an early point in my career I have always wanted to lead. Not out of ego, but I have always loved helping others.

In high school I was part of a small company (woo Spearfish Industries, thanks Steve and Dave ;)) that helped local businesses with the internet, websites, graphic design, and videography. This was my entry into computer science and I absolutely loved it I went from the lead graphic designer to the network admin and started to really enjoy setting up routers and explaining the settings to grandmas and business owners alike.

Cue to university where I made a small mistake, much to my friends future-sight, of majoring in business rather than engineering. I knew I had made a bad choice in my second semester but barely making ends meet with 2 part time jobs and no connections a degree is better than nothing I thought. So I continued on with ease and taking all the math my schedule would allow. Then graduated with a BS in Human Resources Management in 3 years.

Afterwards, I was extremely lucky to get a job a huge place (the US government) as a technical recruiter for their cooperative education program. After a year a two (and starting my masters in engineering) I was able to transfer to a technical office that took a chance on me (infinite thanks to Jackie and Dave) and I found a new love, network protocols.

Protocols are the formats and standards of information transfer and understanding them and their specifications (RFCs) is a wonder. I got to see brand new things, reverse engineer modifications, and write software (think Wireshark but not in Lua) to accurately and efficiently parse them.

I was good at this. Really good. In just a year, I was a respected team lead and selected for a lot of really amazing opportunities that I cannot go into too much details on.

I then was able to accept a special assignment teaching protocols and software development in England. It was a blast and I really enjoyed getting the opportunity to live and travel so much (not bad for someone who got their passport at 23!). I took full advantage of this opportunity and soon came to realize I wanted more and the leadership aspect came back.

After leading some really cool projects with the ELK stack, refining proper software engineering guidelines, and implementing Rust in production software I was not moving and advancing fast enough (cue red tape). I then decided it was time to leave the government and take some risks for my career development.

My next opportunity was short but no less amazing. I got the amazing ability to work with Machine Learning as a strict software developer at Carnegie Mellon University’s Software Engineering Institute (CMU, SEI). Thank you to Matt, Dave, Ritwik, Erik, Jay, and Carol. My favorite thing I got to do there was xView2 it was an amazing humanitarian project (thanks Nirav and Bryce ;)) that helps first responders understand and accesses damage to areas by satellite imagery and Machine Learning on the edge.

After that project was done I did understand ML, but I knew it wasn’t my passion and I needed to follow what I truly wanted to do. I really enjoy both Rust (I think that’s obvious if you made it this far) and using technology for good. One lucky day I saw a job opportunity in This Week in Rust for a little company called 1Password.

After some research into this company I was sold. Managing passwords for everyone including grandparents and fellow developers with strong technical challenges and an amazing reputation for being kind and helping others, what’s not to love?!

That gamble, at the time anyone in the US was considered an independent contractor, definitely paid off. I was a Senior Rust Engineer (I am so proud of myself as I look back on this). I never thought I make it this far (thanks to Roo, Dave, Roustem, Beyer, and Mathieu). The work here has been amazing, I have helped with so much (localization, build and release, permission checking and hardening, performance and optimization, countless bug fixes, and so much more) and yet the most I got enjoyment from was again, helping others. Every time I helped someone succeed with building our project the happier I got.

Then I got to a crux, I am a great developer but my skills are most satisfied and amplified when I put them to use helping my peers. Also my manager had about 60 reports at the time! So I proposed that we start hiring engineering managers in our organization at this 250 person company. The response was “Yes! I don’t know how to get you there but help me hire the first one”.

It wasn’t a long process (Hello and thanks Chris ;)), then I got the ask “Would you like to be one as well?” and accepted my first management role! It was the best decision I’ve made yet. I was offered to take on the iOS team for 1Password and help maintain 1Password 7 for iOS and macOS as well as ship 1Password 8 for iOS.

This was both extremely exciting and a huge challenge. OPI8 was not quite ready and we had a “development pause” while the Desktop applications shipped their versions. During this time I was also learning the fundamentals of being a manager such as; holding 1:1s, resolving disputes, planning and organizing features, hiring, coordinating developers for sub teams, and also contributing Rust code that was helpful for my team.

To get out of the pause I had planned (a post on this coming in the future) a large scale re-ignition effort and push to eliminate the current tech debt and set us up nice for the final push to release. This period lasted 2 months and we were able to finish exact on time with all issue on our Milestone closed! Really a huge effort and monumental win for the team, something I am very proud of to this day.

After that, we were ready to begin the push for both a TestFlight and eventually a final release to the world. We started many initiatives and helpful models that enabled us to keep development focused and hit our goals for release. We worked very close (closer than every before at our company) with design and product to ensure all features were development ready when the designs were completed and product made the final decisions to include at our initial launch.

Then the time came! OPI8 was released to the world with, honestly a resounding success! Our customers really love 1Password 8 for iOS and I am very proud of the team (Kevin, Rudy, Chad, Craig, Craig, Drew, Brian, Chris, Chris, Alessandro, Julieta, Jeanine, you all rock!). It’s one of the best moments I’ve had in my career by far, over 1 million people using an application I helped lead to success!

We’re almost to the present day I swear.

My experience in my current role began soon after the OPI8 release; a reorganization! The entire engineering organization at 1Password went through a reorganization that lead to me getting to not only really build a new team that is very different the my OPI team, but also help (thanks to Katherine, Emily, Avi, Chris, and Chris!) shape an entire organization since we reported directly to the CTO who filled the positions of Director and VP of Engineering.

It was here where I was able to learn and try new things that gave me a lot of experience with a vastly different group of engineers. I now manage Rust, Swift, Kotlin, and Typescript engineers on a Frameworks team that focuses on designing scaleable, efficient, testable, and safe APIs for other developers to use.

The team is now functioning well and I am successfully leading them to update our APIs and create easy-to-use frameworks for development that allow us and other teams to not worry about discovery or how to model the problem because we have strong guidelines on that already.

Thank you if you’ve made it this far as you’re up-to-date with my career now! I’ll keep adding to this as things change but I am hoping this at least gives you a glimpse into what makes Ricky himself at work.

  • RH