Tech Lead

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 OpenTelemetry 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 annual discretionary bonus. The discretionary bonus will be dependent upon the individual's skills, experience, qualifications, and firm performance.

Salary Range $175,000 - $250,000 USD

Most teams at CTC, with the exception of Trading, follow a hybrid workplace model, subject to change based on business need.

We strongly believe in the well-being of our employees and their families so we offer outstanding benefits to support you both professionally and personally. These benefits include generous time off, insurance coverage, paid parental leave, free breakfast and lunch (plus healthy snacks, of course), wellness reimbursement, and a variety of other benefits focused on providing the best employee experience.

(Disclaimer: interns and contractors are not eligible for benefits at CTC)

At CTC, we aim to cultivate a workplace that celebrates diversity and each person feels included, engaged and empowered. Where each of us feels we belong. We are committed to having a diverse workforce and are proud to be an equal opportunity employer. CTC does not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform crucial job functions, and to receive other benefits and privileges of employment.

If you have a disability and believe you need a reasonable accommodation in order to search for a job opening or to apply for a position, please contact us at View email address on click.appcast.io. Note that emails sent to this email account for non-disability related issues, such as following up on an application, will not receive a response.

Information submitted by job applicants may be subject to review and analysis by automated systems, including Artificial Intelligence (AI), as part of the recruitment process. Such systems are utilized to enhance the efficiency and effectiveness of our hiring procedures. Applicants are advised that any information provided may be evaluated by AI tools to ensure an equitable and thorough assessment.