Senior software engineer (toledo)

Role Overview

As a Senior Software Engineer on this team, you will own the design and delivery of core backend services, drive integration architecture with third-party platforms, and help establish the engineering patterns. You will work closely with product, design, and customer-facing teams to ensure what gets built solves real problems elegantly.

• Design and build scalable, highly available Java microservices on AWS from scratch
• Define and own the data model for time tracking entities — entries, projects, users, billing cycles
• Architect RESTful and event‑driven APIs consumed by web, mobile, and third‑party clients
• Own the full AWS infrastructure for your services: Lambda, ECS/EKS, RDS/Aurora, SQS, S3, CloudWatch
• Implement CI/CD pipelines using GitHub Actions or AWS CodePipeline, with automated testing gates

• Build bi‑directional sync between the time tracking platform and Airtable bases via the Airtable API
• Integrate with Linear to link time entries to issues, projects, and cycles — keeping both systems in sync
• Develop Slack workflows: slash commands, interactive modals, notifications, and Bolt‑based event subscriptions
• Design an integration framework that can onboard new third‑party connectors without re‑architecting core services
• Handle webhooks, OAuth 2.0 flows, token management, and rate limiting for all external platforms

• Use AI coding assistants (e.G. GitHub Copilot, Claude, Cursor) as a core productivity tool throughout development
• Implement AI‑powered features: intelligent time entry suggestions, anomaly detection, natural language querying of time data
• Leverage LLMs for smart auto‑categorization of time entries based on calendar, Linear activity, or Slack context
• Contribute to prompt engineering, RAG pipelines, or fine‑tuning workflows as the product roadmap evolves
• Evaluate and recommend AI/ML services (AWS Bedrock, SageMaker, OpenAI, Anthropic APIs) appropriate to each use case

• Write clean, well‑tested Java code — unit, integration, and contract tests are non‑negotiable
• Participate in architecture reviews, PR reviews, and cross‑functional planning sessions
• Contribute to runbooks, ADRs (Architecture Decision Records), and internal documentation

• 5+ years of professional software engineering experience
• Backend: Strong Java proficiency
• Spring Boot or Quarkus for microservices;
  experience with reactive frameworks (Vert.X, WebFlux) a plus
• Cloud: Deep AWS expertise
• Hands‑on experience with Lambda, ECS or EKS, RDS/Aurora, SQS/SNS, API Gateway, IAM, CloudFormation or CDK
• APIs: REST API and event‑driven architecture design and implementation
• OAuth 2.0, webhook design, idempotency, and third‑party API integration patterns
• AI Tooling: Demonstrable AI‑first mindset
• Regular use of AI coding tools and willingness to bring LLM‑powered features into production
• Greenfield: Proven ability to contribute meaningfully on a greenfield project — from blank canvas to production

• Airtable API — reading/writing records, managing bases, handling webhooks
• Linear API or GraphQL‑based project management tool integrations
• Slack Bolt SDK — building apps, slash commands, modals, interactive components
• Experience building a reusable integration or connector framework

• Working knowledge of LLM APIs (OpenAI, Anthropic, AWS Bedrock)
• Experience with prompt engineering, RAG, or embeddings in a production context
• Familiarity with AWS SageMaker or similar ML deployment pipelines
• Understanding of responsible AI practices — latency, cost, hallucination mitigation

• Experience in the time tracking, workforce management, or project management SaaS domain
• Frontend exposure — React or TypeScript — to collaborate closely with full‑stack requirements
• Familiarity with multi‑tenancy patterns and SaaS billing / subscription models
• Contributions to open‑source projects or public technical writing
• Experience with observability tooling: Datadog, Open Telemetry, AWS X‑Ray