The Path from Technician to Director
My career in technology didn’t start with a CS degree or a coding bootcamp. It started with fixing computers at Geek Squad and a genuine curiosity about how systems work. That hands-on foundation – understanding technology from the ground up – has shaped how I lead engineering teams today.
From there, I moved through technology roles at media companies and global advertising agencies like Ogilvy and BBH, where I learned that technology exists to serve the business, not the other way around. Every system I built, every process I improved, was measured by the impact it had on the people using it.
At Cornell University, I managed client platforms at scale in a complex institutional environment. That experience taught me how to think about reliability, standardization, and supporting diverse user needs – lessons that proved invaluable as I moved into infrastructure and DevOps.
Oscar Health: Where It Clicked
Oscar Health was where my career trajectory shifted. Working at a health-tech startup that was reimagining health insurance through technology, I grew from engineer to senior engineer to lead engineer over three years. I saw firsthand how infrastructure decisions directly impact a product’s ability to serve its users – in this case, people depending on their health insurance to work. The stakes were real, and the technical challenges were substantial.
Peloton: Building from the Ground Up
I joined Peloton as a DevOps Engineer in 2013 when the engineering organization was still finding its footing. I had the rare opportunity to build DevOps practices from scratch – establishing the infrastructure automation, CI/CD pipelines, and operational standards that would need to scale as Peloton grew into a household name with millions of connected users globally.
Over more than a decade at Peloton, I progressed through Lead DevOps Engineer, Manager, Senior Manager, and Director of Engineering. Each step brought new challenges: building teams from 5 to 15+ engineers, hiring and developing talent, aligning technical strategy with business goals, and maintaining engineering excellence while moving at startup speed through hyper-growth. I’ve had the privilege of building the infrastructure foundation that powers a global connected fitness platform, while growing as a leader alongside the company.
How I Lead
I believe the best engineering leaders are the ones who never forget what it’s like to be in the trenches. My leadership philosophy is rooted in:
- Technical credibility – I’ve done the work. I understand what I’m asking my teams to build because I’ve built it myself, from infrastructure automation to CI/CD pipelines to on-call incident response.
- People first – Great technology comes from great teams. I invest heavily in hiring, mentoring, and creating environments where engineers can do their best work. I’ve grown teams from 5 to 15+ engineers through thoughtful hiring and career development.
- Pragmatism over perfection – Ship it, learn from it, improve it. I favor practical solutions that deliver value over architecturally pure systems that never launch. Operational excellence doesn’t mean zero risk – it means calculated risk with proper monitoring and rollback plans.
- Cross-functional partnership – Engineering doesn’t operate in a vacuum. The best outcomes come from tight collaboration with product, design, and business teams. I work closely with C-level executives and stakeholders to align technical investments with business objectives.
- Scale through systems – As organizations grow, leadership shifts from doing to enabling. I build systems, processes, and culture that allow teams to scale without sacrificing quality or speed.
Community & Speaking
I’m an active member of the Mac administration, DevOps, and video technology communities with 2,000+ followers and a network of 500+ professional connections. I contribute to open source projects, share knowledge through technical discussions, and participate in industry conferences.
Conference Participation:
- MacDevOps:YVR – Annual DevOps conference focused on Mac and Apple platform engineering
- MacSysAdmin – European Mac systems administration conference
- MacAdmins Conference at Penn State
- Active participant in MacAdmins Slack community and local DevOps meetups
Community Leadership:
- Host of Video Tech NYC meetup group – bringing together video streaming engineers in NYC
- Active member of video-dev.org Slack community – engaging with video technology professionals globally
- Member of the @autopkg organization
- Maintain 53+ public repositories focused on infrastructure automation and Mac platform engineering
I believe in giving back to the communities that helped me grow, through code contributions, meetup hosting, mentorship, and knowledge sharing.
Languages
Native fluency in both English and Spanish, enabling effective communication with diverse teams and global organizations.
Get in Touch
Whether you’re looking for an engineering leader, want to discuss technology strategy, or just want to connect – I’d love to hear from you.