Observability Lead

Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options market making. Our collaborative culture fuels innovation in quantitative research, systematic trading strategies, and cutting-edge trading technology. For over three decades CTC has provided critical liquidity across derivatives exchanges worldwide - making them fairer, more transparent, and more efficient.

We strive to be the most innovative firm in the industry today, tomorrow, and long into the future while upholding ethical excellence. We believe that CTC makes a positive impact on the markets, the lives of our employees, and all the communities to which we belong. Started in 1995 by a team of forward-thinking Traders, we are proud to call ourselves an industry leader that keeps making markets and each other better.

We are seeking an Observability Lead to own the strategy, execution, and technical direction of CTC's observability platform. In this role, you will lead a small, high-impact team responsible for the tools and systems that give our engineers, quants, and traders visibility into the health and performance of critical infrastructure and applications. This is an opportunity for a senior technologist who is passionate about building reliable, developer-friendly observability solutions and who thrives in an environment where the work directly impacts business outcomes.

WHAT YOU'LL DO

* Define and drive the observability roadmap, aligning platform capabilities with the needs of engineering teams, quantitative researchers, and trading operations.

* Lead the design, implementation, and continuous improvement of monitoring, alerting, logging, tracing, and metrics infrastructure at scale.

* Own the end-to-end developer experience of observability tooling - reducing friction, improving self-service adoption, and ensuring engineers can quickly diagnose and resolve production issues.

* Manage and grow a small team of engineers, providing technical mentorship, setting clear expectations, and fostering a culture of ownership and accountability.

* Partner with infrastructure, platform, and application teams to ensure observability is deeply integrated into the development lifecycle, CI/CD pipelines, and incident response workflows.

* Establish and enforce best practices for instrumentation, SLOs, alert quality, and operational readiness across the engineering organization.

* Evaluate emerging tools, frameworks, and approaches in the observability space, driving adoption where they deliver measurable value.

WHAT WE'RE LOOKING FOR

* 8+ years of technical engineering experience, with at least 3 years focused on observability, monitoring, or site reliability engineering.

* Demonstrated expertise designing, building, and operating observability platforms at scale - including metrics, logging, tracing, and alerting systems; deep experience with Datadog and Open Telemetry strongly preferred.

* Proven experience leading or managing a small engineering team, with a track record of developing talent and delivering results through others.

* Strong understanding of distributed systems, micro-services architectures, and the observability challenges inherent in complex, high-throughput environments.

* Hands-on experience with Kubernetes and bare-metal infrastructure; understanding of the unique observability challenges across both containerized and traditional deployment models.

* Advanced programming proficiency in at least one of Python, Go, or Java; familiarity with C++ or low-latency systems is a strong plus.

* A product-oriented mindset - you think about observability as a service to internal customers and obsess over the developer experience of the tools you build.

* Exceptional communication skills with the ability to partner across engineering, operations, and business stakeholders.

* Financial sector experience (trading, prop trading, hedge funds) and familiarity with the demands of low-latency, high-reliability systems are strongly preferred.

* Advanced degree (MS, PhD) in Computer Science, Engineering, or related field is a plus.

Compensation

The salary range for this role is listed below. This role is also eligible for an…