Technical Product Manager, Infrastructure and Dev Ops

Employment Type: Full-Time Location: Chicago, IL – In-Person

Reports to: Head of Product

tastytrade is looking for a Technical Product Manager to own the roadmap for our infrastructure and DevOps capabilities — the systems that keep our trading platforms fast, stable, and secure, and that our engineers rely on to ship code confidently.

You'll drive the strategy for our CI/CD pipelines, cloud infrastructure, and infrastructure-as-code, working closely with the engineers who build and operate them.

This is a hands-on, technical role.

You'll be trusted to dig into architecture and tooling decisions alongside engineers, make prioritization calls, and represent infrastructure priorities clearly to leadership.

• Own the roadmap for infrastructure and DevOps priorities — including CI/CD pipelines infrastructure-as-code and our AWS cloud environment — in partnership with the infrastructure engineering team.
• Work with backend teams (Ruby and Java) to understand where infrastructure or tooling gaps are slowing down delivery or creating risk.
• Prioritize and sequence infrastructure work against the needs of application teams building customer-facing trading platforms, account opening flows, and internal tools.
• Define what "healthy infrastructure" looks like for tastytrade — tracking metrics like deployment frequency, incident frequency/MTTR, and infra cost, and using them to justify roadmap decisions.
• Partner with infrastructure engineers to improve build/test/deploy workflows so engineers can ship changes to production quickly and safely.
• Lead build-vs-buy evaluations for infrastructure tooling and vendors (e.g., containerization, observability, config management), weighing cost, speed, security, and long-term scalability.
• Ensure infrastructure and deployment practices meet the security, compliance, and audit expectations of a regulated brokerage (tastytrade is regulated by FINRA/NFA and is part of IG Group).
• Communicate roadmap, tradeoffs, risks, and progress clearly to engineering leadership and stakeholders.

• 3+ years of product management experience, with meaningful time spent owning infrastructure, DevOps, platform, or developer-productivity products.
• Technical depth: you can discuss CI/CD systems, cloud architecture (AWS), infrastructure-as-code and distributed systems with engineers without everything needing to be explained to you.
• Track record of shipping infrastructure or platform improvements with measurable impact on reliability, cost, or engineering velocity.
• Experience partnering with engineering, security, and compliance teams, ideally in a regulated industry (fintech, brokerage, financial services, or similar).
• Strong prioritization instincts and the ability to navigate tough tradeoff conversations across multiple stakeholder groups.
• Comfortable presenting strategy and tradeoffs to both engineers and leadership.
• Self-directed: you can create clarity and a roadmap out of ambiguity with minimal oversight.
• Bachelor's degree in Computer Science, Engineering, or relevant STEM field, or equivalent practical experience.

Nice to Have

• Prior experience as a software or infrastructure engineer before moving into product management.
• Familiarity with options/futures trading systems, market data, or order execution infrastructure.
• Performance Bonuses

• Medical/Vision/Dental Benefits
• 401k Plan
• 20 Paid Vacation Days (plus an additional paid vacation day the month of your birthday!)

• Commuter Benefits
• Pet Insurance

• Daily catered lunch when in the office
• Full kitchen with snacks and beverages
• In-building gym
• Shuttle to/from Metra