2023: A year in review

I'm incredibly proud of the team I'm part of at apree health as I think about this past year. We've delivered on some very important milestones for the business and we've done so with our team mostly intact, our processes improving, our team health improving, ourselves improving. I love being at apree because we have the courage to change things up, go after ambitious projects, and pursue revolutionizing healthcare. It's not a company of coasting and maintenance. It's a force of change and requires constant attention and adaptation.

The biggest milestone on the year was successfully finishing our migration to Google Cloud from our two datacenters which was a two year project the teams were able to successfully deliver on a quarter early allowing us to engage more timely with critical driver clients in a way not adding scope to security reviews and audits. This was not easy work, required weekly collaboration and accountability for the full breadth of the project and deep security collaboration as a key property of our GCP infrastructure is a security first mindset. Specials thanks continues to go to some key players (among many, many, more) like Richard Berger the shepherd of our weekly migration syncs and graceful yet direct accountability partner, John Smilanick and Murtuza Bohri who led countless blueprinting sessions and led in architecting various components of the cloud organizational structure, Nicole Perez who early on set us up for success with networking patterns and implementation, Vipul Parikh who must have Hermione's watch in one of his pocket to help with keeping track of all the balls his teams have up in the air at one time and whose teams were core to everything about this migration, Lauren Bui, MBA Chirag Patel Anupam Rastogi Prema R whose teams moved data pipelines in a compressed timeline often working weekends to get the objective met, Cat Schwan who seamlessly planned and built instructions for the actual datacenter to gcp traffic cutover and was able to hand off the tasks to other team members so she could be on PTO during the cutover without any production hiccups caused by the Akamai routing, and Donovan Ellison who architected and built our egress filtering mechanisms in a secure and developer centric way along with helping troubleshoot org policy constraint, CMEK, and other security property blockers along the migration journey.

You all should be incredibly proud of the work you've done and this major milestone. 17 racks of servers filling a 40ft truck is no small change of a migration.

Other key milestones as I see em

Fully committing to the power of Google technology as a business.

This started with our Q1 migration off of Okta for source of identity truth to Google Identity. Consultants thought our timelines were crazy and what we were trying to do was impossible, but we pulled it off and delivered successfully retiring Okta. Reminds me of a conversation I had with my daughter's oncologist years back when we were in the leukemia battle talking about the nature of optimism. I was giving a book summary of "The Rational Optimist" making small talk during our visit about how things really are improving in the world in many ways and she offered a perspective that sticked. For her optimism is the consistent faith that things can get better, they can improve. Faith that gives you the courage to do the science and try and try again with expectation of and belief in outcomes. So much of the battle with delivering on things is the belief that it's possible and going for it.

The next major milestone was moving off of Microsoft O365 and into Google Workspace for all things office suite. This would have been a lot harder without the help of an experienced partner in SADA, An Insight company . This was an important consolidation for us as a business combining directory services from our two separate historical entities (Vera, Castlight) and moving historical files, emails, mailing groups, and all the things. It's a significant retooling and requires consistent education and training to make the various workflows efficient and productive. For me the big takeaway in this one is it's one thing to move a technology and it's another thing to get everyone comfortable and using the new technology. Nevertheless it was a pretty gargantuan effort in itself just to move the tech and the folks on our IT service desk and systems engineering teams helped make this happen. I look forward to continuing to partner in the new year to learn how to better serve our colleagues and get the full value out of this migration.

We significantly improved our security tooling stack implementing technologies like Google Chrome DLP, Enterprise Managed Chrome, Google Workspace DLP, Nightfall.ai to get more granular controls around data loss prevention and rolling out Sysdig Secure for container runtime protection and incident response. Payatu has been a critical partner helping us with increasing our SaaS log ingestion into our SIEM and improving our Application Security Program.

I'm especially grateful for the close collaboration with engineering partners to make our Software Development Lifecycle more consistent and robust. Thank you Jack Dagley for the cat herding and keeping us on track with improvement deliverables, Amit Bhadoria for going heads down on the improvements and help architecting from an engineering leadership perspective, Jim Griswold for kicking new processes on the tires and seeing how they felt from a developer mindset and helping us think through how to make practices secure and scalable, Akshay Mungrey for helping getting teams setup in systems, coverage metrics, and partnership in SAST, DAST improvements. suraj K. for bringing your expertise on threat modeling, internal pentesting, and application reviews into our processes and procedures. You all have been world class to work with.

One last milestone to mention is the successful build out of digital clean rooms led by the Systems Engineering team and Chris Shearin. This took a lot of collaboration across the various use cases of the folks who need to use the clean rooms and flexibility to understand how to do this in an infrastructure as code approach. Thank you to everyone who came around this project in the midst of all the other projects to make it come to life. Thinking of you Lindsey Brockish, PMP , Shon Sherwood , and Donovan Ellison .

It's been amazing to watch the security teams self organize and adapt to the pressures, take care of each other, and grow. I especially enjoy our book club which completed three significant books this year in addition to occasional white papers. It was great to discuss with you Site Reliability Engineering, Container Security, and The Phoenix Project and I can't wait for us to get started these next few weeks on Security Chaos Engineering. Reading these books together help us grow our conceptual understanding together and think about ways to better improve how we do work. It's also great to just to get to spend some time together processing ideas and chatting.

Much gratitude this holiday season for our people and teams. You all make work fun and I'm proud of you. Hope you can enjoy some eggnog, a walk outside with a dog, and some good family time over a board game or puzzle.