Jobs at Redwood Software

Leads multiple software development teams building Redwood’s enterprise SaaS automation platform. Responsibilities include technical leadership, distributed-system architecture, engineering process improvement, Agile delivery, cloud-native development, CI/CD and observability, AI-assisted software development, hiring, mentoring, capacity planning, and engineering KPI reporting. The role partners with product, sales, customer success, and executive stakeholders to align engineering priorities and scale resilient, fault-tolerant Java-based services.

Leads global Customer Success operations and customer education strategy, including lifecycle processes, governance, KPIs, customer health, learning programs, technology platforms, Voice of the Customer, and cross-functional executive initiatives. Builds scalable operating models, manages vendors and budgets, and develops multidisciplinary teams to improve onboarding, adoption, customer proficiency, retention, satisfaction, and long-term customer value across enterprise SaaS customers.

Partner with senior finance and G&A leaders to build AI-first talent strategies, apply algorithmic org design, drive data-driven performance management, upskill teams for AI, and use automation/LLMs to streamline HR operations and insights.

The Senior Full Stack Software Developer will design, develop and implement scalable applications, manage system architecture, mentor developers, and drive engineering excellence.

Develop scalable Java applications and microservices using Spring, while applying AI-assisted development and prompt engineering throughout the SDLC. Build and maintain CI/CD pipelines, cloud deployments, containerized services, and observability solutions. Collaborate with product managers, designers, and engineers on architecture, testing, documentation, and complex problem-solving. The role also involves reviewing AI-generated code, working with front-end technologies and databases, and applying agile, TDD, or BDD practices.

Principal Software Engineer leading architecture and implementation of resilient, low-latency distributed systems for the RunMyJobs platform. Responsibilities include technical strategy, full-stack development, AI-assisted software development, CI/CD and observability, code and design reviews, quality improvement, troubleshooting, and mentoring. The role requires expertise in Java, microservices, cloud platforms, containers, frontend technologies, databases, automated testing, and AI developer tools, with broad technical ownership but no direct people management.

Own the strategy, roadmap, backlog, and delivery of internal automation products. Define user stories and acceptance criteria, prioritize features, lead Agile ceremonies, coordinate engineering and QA, assess risks and dependencies, and use stakeholder feedback and performance data to drive product improvements. The role partners with product, engineering, consultants, and field teams to deliver capabilities aligned with business objectives and organizational priorities.

Owns reliability, scalability, observability, and incident response for a mission-critical SaaS platform. Responsibilities include 24x7 on-call support, root cause analysis, automation, AWS infrastructure design, EKS/Kubernetes and Docker operations, Terraform and Helm deployments, CI/CD maintenance, cloud networking, monitoring with Datadog, Grafana, and Prometheus, database operations, and migration toward Kubernetes. The role also develops self-healing systems, documentation, runbooks, and cross-functional customer-focused reliability practices.

Own end-to-end delivery health for a product area: drive roadmap tracking, release readiness, dependency and risk management, build delivery dashboards and Jira workflows, use AI to automate delivery processes, and provide executive reporting and stakeholder communication to ensure predictable, enterprise-grade releases.