• Lead the Engineering Operations Team • Build, mentor, and support a team of infrastructure and operations engineers. • Set clear priorities, goals, and performance expectations for the team. • Foster a culture of ownership, operational excellence, and continuous improvement. • Own Infrastructure Reliability & Operations • Oversee the reliability and performance of infrastructure across AWS and hybrid environments. • Drive improvements in observability, incident response, and operational processes. • Lead root cause analysis and ensure learnings translate into long-term improvements. • Guide Infrastructure & Platform Strategy • Partner with cross-functional groups such as Security Operations, Compliance and diverse Engineering teams to design and operate scalable, resilient infrastructure. • Lead modernization initiatives including cloud adoption, automation, and infrastructure as code. • Provide architectural guidance on systems that support high availability and performance. • Stay Technically Engaged • Review infrastructure designs and technical solutions. • Contribute to troubleshooting complex production issues when needed. • Ensure the team is building and operating infrastructure using modern DevOps practices.

Role Description Reporting to the VP of R&D- eComm in this newly created opportunity, we are looking for someone who will build and evolve a high-performing R&D organization that delivers Descartes/Sellercloud’s Inventory and Order Management Systems (IMS/OMS) with consistent, high-confidence roadmap execution and strong technical health. As Director, you will operate at the portfolio level, strengthening leadership leverage, delivery systems, investment clarity, and long-term scalability. Expected Outcomes - Leadership Scaling: Strengthen and evolve a manager-of-managers R&D organization, coaching R&D Managers and Tech Leads to independently own delivery, trade-offs, and people development. - Predictability & Flow: Deliver measurable improvements in roadmap predictability and flow, establishing consistent operating cadences that surface risks early and provide credible multi-quarter forecasting. - Healthy Technical Investment: Ensure engineering capacity is intentionally allocated across feature growth, architectural runway, and reliability improvements, with transparent trade-offs aligned in partnership with Product Management. - Operational Excellence: Improve key reliability indicators (e.g., incident recurrence, MTTR, change failure rate) by reinforcing shared engineering standards and embedding disciplined post-incident learning that drives systemic improvement. - Organizational Scalability: Define and communicate a forward-looking hiring and capability roadmap (4–6 quarters) aligned to business growth, with team structures designed to minimize bottlenecks and maximize clear ownership. Qualifications - 10+ years in software development with significant experience leading multiple teams through managers in a SaaS environment. - Proven success improving delivery predictability, engineering flow, and operational reliability through scalable systems; not individual heroics. - You design operating mechanisms, investment models, and feedback loops that connect engineering execution to business outcomes. - Experience evolving engineering operating models in growing organizations, building alignment across Product and technical leadership without becoming a bottleneck. - Demonstrated ability to coach and grow managers, build psychologically safe teams, and create durable leadership depth. - You translate complex technical trade-offs into clear business implications and foster transparency across teams. Benefits - Direct influence on how a strategic SaaS platform scales. - High visibility and partnership across Product, Operations, and Executive leadership. - Opportunity to shape the long-term engineering operating model. - Competitive compensation and flexible remote options. - A culture driven by impact that values ownership, clarity, and sustainable performance. - Salary Range: $140,000 - $160,000 CAD annually plus bonus. Company Description Descartes is publicly traded (Nasdaq:DSGX, TSX:DSG) with headquarters in Waterloo, Ontario, Canada, and offices and partners around the world. With record financial performance for more than 16 years, we lead the industry in innovation investment. Every day, logistics service providers, manufacturers, retailers, distributors, and other logistics-intensive businesses of all sizes rely on our scale, stability, and comprehensive solution footprint to move what’s most important to them. At Descartes, we don't just want a "culture fit"—we want someone who adds to our collective strength: - Transparency – Open, honest communication that builds trust. - Excellence & Expertise – High standards and continuous mastery of your craft. - Accountability – Ownership of commitments and outcomes. - Metric-Driven Results – Data-informed decisions focused on measurable impact.

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time. We are seeking a Senior Software Development Engineer with deep, hands‑on experience building and operating backend, platform, and integration services at scale. In this role, you will design and deliver highly available, secure, and compliant microservices that power healthcare data exchange and platform capabilities. The ideal candidate is strong in Java, Spring Boot, RESTful APIs, and event‑driven systems, comfortable operating in cloud‑native environments, and experienced working in regulated domains. You will partner closely with product, architecture, security, and DevOps teams to deliver reliable services that integrate with healthcare ecosystems and third‑party platforms. Responsibilities - Deploy and operate services on Google Cloud Platform (GCP) using cloud‑native patterns (GKE or Cloud Run, IAM, managed data services). - Design, develop, and maintain backend microservices using Java/JEE and Spring Boot, exposing RESTful APIs that are secure, performant, and resilient. - Implement event-driven patterns using Apache Kafka (producers/consumers, schema evolution, partitioning, consumer groups). - Model and exchange data using JSON; ensure robust validation, versioning, and backward compatibility. - Build and maintain CI/CD pipelines including unit/integration testing, static analysis, artifact promotion, and progressive delivery. - Partner with Security and DevOps teams to integrate automated security controls (SAST, DAST, dependency & image scanning, secrets management). - Apply 12‑factor app principles, infrastructure‑as‑code, and configuration management best practices. - Integrate backend services with EHR systems and healthcare data standards such as HL7 v2, FHIR, SMART on FHIR, CCD/C‑CDA, or similar regulated data exchange formats. - Ensure compliance with HIPAA, data governance, and platform security requirements, including encryption in transit and at rest. - Own production readiness: availability, latency, throughput, and cost efficiency for high‑volume backend services. - Diagnose and resolve production issues; perform root cause analysis and drive long‑term reliability improvements (SLIs/SLOs, error budgets). - Implement observability (structured logging, metrics, tracing) to support proactive monitoring and incident response. - Participate in architecture reviews, code reviews, and technical design discussion, mentor junior engineers. Required Qualifications - Bachelor's degree in Computer Science, Information Technology, or related field (or equivalent practical experience). - 5+ years of professional software development experience with Java/JEE and Spring Boot. - Strong experience building RESTful microservices and distributed systems. - Proven hands-on experience with Kafka or similar event-streaming platforms. - Strong understanding of REST API design, JSON data modeling, and OpenAPI/Swagger documentation. - Practical experience with CI/CD pipelines and containerized workloads (Docker; Kubernetes preferred). - Solid grasp of security fundamentals (OAuth2/OIDC, TLS, secrets management). - Experience operating production services in cloud environments, preferably GCP. - Strong debugging, performance profiling, and operational troubleshooting skills. Preferred Qualifications - Experience in healthcare, regulated systems, or large‑scale data integration platforms. - Cloud certification preferred (GCP Professional DevOps Engineer, AWS DevOps Engineer, or equivalent). - Familiarity with Spanner, BigQuery, Cloud SQL, or similar managed data services. - Observability, Monitoring, Alerting Systems familiarity(Grafana, Splunk) - Certified Systems Engineering Professional (CSEP) a plus. Education - Bachelor’s degree preferred; equivalent industry experience and specialized training are acceptable. Anticipated Weekly Hours 40 Time Type Full time Pay Range The typical pay range for this role is: $64,890.00 - $173,040.00 This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong. Great benefits for great people We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families. This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility. Additional details about available benefits are provided during the application process and on Benefits Moments. We anticipate the application window for this opening will close on: 04/13/2026 Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.

ABOUT THIS POSITION Plans, designs, develops and tests software systems or applications for software enhancements and new products including cloud-based or internet-related tools. Use this position if company does not breakout software development positions such as Software Engineer (Applications) or Software Engineer (Systems) and / or is involved in full stack development. Software development engineers using common development methodologies including Waterfall and Agile should be matched to our software development engineering roles. Employees focused on ensuring products (including websites) and hosted networks are designed and developed to be cyber-safe and compliant are typically matched to one of our software development engineering roles. WHAT YOU'LL DO - Design, develop, test, deploy, and maintain robust and scalable software solutions across the full software development lifecycle. - Collaborate with product managers, UX designers, and other engineers to understand requirements, define technical specifications, and deliver features that meet business needs. - Participate in code reviews, ensuring code quality, maintainability, and adherence to engineering best practices. - Troubleshoot, debug, and resolve software defects and production issues in a timely manner. - Contribute to the improvement of development processes, tools, and methodologies. - Document technical designs, architectural decisions, and operational procedures. - Actively learn and apply new technologies and industry trends to enhance our products and services. - Mentor junior engineers and contribute to a collaborative team environment. WHAT YOU'LL NEED - Bachelor's degree in Computer Science, Software Engineering, or a related technical field, or equivalent practical experience. - 2-4 years of professional software development experience. - Proficiency in at least one modern programming language (e.g., C#, Java, Python, JavaScript/TypeScript). - Experience with relational databases (e.g., SQL Server, PostgreSQL) and/or NoSQL databases. - Familiarity with cloud platforms (e.g., AWS, Azure, GCP) and containerization technologies (e.g., Docker, Kubernetes). - Strong understanding of object-oriented programming, data structures, algorithms, and software design principles. - Experience with agile development methodologies (Scrum, Kanban). - Excellent problem-solving skills and attention to detail. - Strong communication and collaboration skills. ABOUT WAYSTAR Through a smart platform and better experience, Waystar helps providers simplify healthcare payments and yield powerful results throughout the complete revenue cycle. Waystar’s healthcare payments platform combines innovative, cloud-based technology, robust data, and unparalleled client support to streamline workflows and improve financials so providers can focus on what matters most: their patients and communities. Waystar is trusted by 1M+ providers, 1K+ hospitals and health systems, and is connected to over 5K commercial and Medicaid/Medicare payers. We are deeply committed to living out our organizational values: honesty; kindness; passion; curiosity; fanatical focus; best work, always; making it happen; and joyful, optimistic & fun. Waystar products have won multiple Best in KLAS® or Category Leader awards since 2010 and earned multiple #1 rankings from Black Book™ surveys since 2012. The Waystar platform supports more than 500,000 providers, 1,000 health systems and hospitals, and 5,000 payers and health plans. For more information, visit waystar.com or follow @Waystar on Twitter. WAYSTAR PERKS - Competitive total rewards (base salary + bonus, if applicable) - Customizable benefits package (3 medical plans with Health Saving Account company match) - We offer generous paid time off for our non-exempt team members, starting with 3 weeks + 13 paid holidays, including 2 personal floating holidays. We also offer flexible time off for our exempt team members + 13 paid holidays - Paid parental leave (including maternity + paternity leave) - Education assistance opportunities and free LinkedIn Learning access - Free mental health and family planning programs, including adoption assistance and fertility support - 401(K) program with company match - Pet insurance - Employee resource groups Waystar is proud to be an equal opportunity workplace. We celebrate, value, and support diversity and inclusion. Qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, national origin, disability status, genetics, marital status, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. This applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.