What are the responsibilities and job description for the Lead Software Engineer position at The Cypress Group?
We are looking for a deeply hands on staff engineer to help build a production-grade platform from the ground up inside a financial services environment. This is a design, build, and scale from zero opportunity.
You will operate across backend systems and infrastructure, owning everything from async processing and external integrations to cloud architecture, deployment pipelines, and reliability. If you have built greenfield systems that had to actually work in the real world; secure, observable, and resilient than this is your lane.
You will own the core system end-to-end:
- Design and build backend services, async workers, and event-driven workflows powering the product
- Develop and maintain integrations with external enterprise systems and APIs
- Architect workflow and state management systems (think orchestration, retries, failure handling)
- Build the cloud foundation: infrastructure, environments, and deployment architecture
- Own infrastructure-as-code and ensure environments are reproducible and scalable
- Design and implement CI/CD pipelines with a strong focus on safe, reliable releases
- Establish observability across the stack: logging, metrics, tracing, and alerting
- Build for failure: retries, recovery strategies, backups, and disaster readiness
- Partner closely with product and engineering to define system boundaries, contracts, and rollout strategies
Ideal experience:
- Proven experience building 0→1 systems that made it to production in real environments (ideally financial services or similarly regulated domains)
- Strong backend engineering skills in Python, with experience in frameworks like FastAPI (or similar)
- Deep experience with asynchronous systems, job workers, and distributed processing
- Track record integrating external APIs and enterprise platforms in production
- Strong data layer experience (Postgres/SQL, data modeling, performance tuning)
- Hands-on experience with cloud infrastructure (AWS preferred, Azure a plus)
- Strong Terraform (or equivalent IaC) experience
- Experience with containerized deployments (ECS or similar) and cloud networking
- Built and operated CI/CD pipelines with an emphasis on release safety and rollback strategies
- Strong observability mindset (metrics, logs, tracing) and real incident response experience
- Solid understanding of cloud security, secrets management, and access controls
- Systems thinker: you naturally design for reliability, failure modes, and long-term maintainability
Bonus
- Familiarity with AI/model API integrations (e.g., OpenAI or similar)
This role is for someone who wants to own meaningful surface area, make foundational decisions, and build something that doesn’t exist yet while holding a high bar for reliability, security, and real-world operability.