Jobs at tastylive

Own and improve the Linux production infrastructure, including performance tuning, incident response, configuration management, container orchestration, networking, proxies, virtualization, secrets, observability, and automation. Develop Bash and Python tooling, manage infrastructure through Git and code review, support Redis and RabbitMQ, write postmortems and runbooks, and guide reliable system design in a regulated, revenue-sensitive fintech environment.

Define and implement the company’s SRE practice, including customer-focused SLOs, error budgets, burn-rate alerting, reliability patterns, and observability standards. Embed circuit breakers, retries, bulkheads, and load shedding into Ruby, Java, and Elixir services. Extend Prometheus, Honeycomb, and OpenTelemetry monitoring, support scaling on HashiCorp Nomad, mentor engineers, and establish blameless incident review practices.

Supports paid media planning, channel strategy, campaign logistics, ad trafficking, paid search copywriting, campaign tracking, reporting, and agency coordination. Manages DV360, CM360, and Floodlight setup and delivery while keeping launches on schedule. Uses AI tools to improve efficiency and processes. The role is Chicago-based with in-person work three days per week.

Coordinates the operational health of marketing initiatives by tracking timelines, deliverables, budgets, purchase orders, invoices, workflows, resourcing, and vendor relationships. Maintains project visibility, identifies bottlenecks, prepares status reports, supports cross-functional teams, and uses AI tools to streamline recurring work. The role requires strong organization, communication, project management, financial tracking, and multi-project prioritization skills.

Own the performance, availability, backup and recovery, observability, upgrades, migrations, and disaster recovery of high-throughput PostgreSQL environments across on-premises infrastructure and Amazon RDS. Review application code and database migrations, automate operations, lead incident response, conduct failover and restore testing, support capacity planning, and maintain technical documentation. Participate in on-call rotations and collaborate closely with development teams.

Own the company’s organic growth strategy across SEO, generative AI search optimization, and app store optimization. Define KPIs, build performance dashboards, lead and develop the organic team, and connect search insights to traffic, rankings, pipeline, and acquisition outcomes. Partner with Product, Content, Brand, Engineering, Compliance, and experimentation teams to improve website structure and content while maintaining regulatory alignment. Manage the organic growth technology stack and report performance and strategy to marketing leadership.

Design, build, and own backend systems supporting order handling, ledgers, settlement, and production operations. Partner with product and cross-functional teams to plan and deliver features, provide technical leadership and mentorship, conduct high-quality code reviews, establish engineering standards, troubleshoot complex production issues, evaluate new technologies, and participate in on-call support.

Provide 24/7 weekend and overnight trading support and risk monitoring for futures, options, and 24-hour products. Resolve trade disputes, monitor account risk, perform customer callouts, troubleshoot platform issues, escalate incidents, document handoffs, and collaborate with Risk, Compliance, Banking, and Engineering. Make independent decisions under pressure and support customers via phone, email, and chat.

Provides high-volume customer support for a retail brokerage through phone, chat, and email. Assists self-directed investors with complex options order execution, account management, trading platform functionality, futures and options on futures, and portfolio margin accounts. Analyzes customer positions, explains strategy advantages and disadvantages, identifies customer needs, and delivers timely trading solutions. The role is fully in-person in Chicago, Monday through Friday, and requires FINRA Series 3, 7, and 63 certifications.

Own product design execution across web, desktop, and mobile trading platforms. Build design-system foundations including tokens, components, guidelines, navigation standards, and documentation. Partner with product and engineering teams on scope and implementation quality, maintain high visual and interaction standards, and mentor designers. The role requires experience designing complex, data-dense interfaces, demonstrating measurable outcomes, and working in regulated financial environments.

Lead design for complex trading features across web, desktop, and mobile. Own end-to-end product design, participate in discovery and user research, propose and analyze A/B tests, collaborate closely with PMs and engineers, mentor designers, and connect design work to business metrics like conversion, retention, and engagement.

Lead and scale tastytrade's fraud investigations function: build program and taxonomy, hire and manage analysts, own detection and monitoring across the customer lifecycle, evaluate tooling/vendors, coordinate with product/tech/compliance, define KPIs and budget, and report to senior leadership.