Sr. Software Engineer II (DevOps)

Overview Insurance touches people during some of the most challenging moments in their lives. Hi Marley is on a mission to transform how the P&C industry communicates, making those moments faster, easier, and more empathetic for carriers and the customers they serve. We build AI-powered software that keeps everyone in the claims conversation informed and connected. If you believe insurance can combine operational excellence and automation with a human touch, we’d love to meet you. Position We are looking for a Sr. Software Engineer II (DevOps) to help us build and scale the infrastructure that powers both our core platform and our rapidly growing agentic AI services. You will be at the intersection of cloud infrastructure, AI operations, and platform engineering—building the foundation that enables Hi Marley to operate reliably at enterprise scale while deploying autonomous AI agents in regulated insurance workflows. You’ll also be expected to raise the bar for the teams around you—setting infrastructure standards, driving technical decisions in ambiguous situations, and helping less experienced engineers grow their operational instincts. Teamwork and shared enthusiasm are a core part of our culture, which is why this role involves joining us in the Boston office for 2–3 days each week. What You’ll Do Design and operate cloud infrastructure on AWS that supports both our core SaaS platform and our agentic AI services, ensuring reliability, scalability, and cost efficiency. Build and maintain AI/ML infrastructure and monitoring for LLM-powered agentic services. Establish and enforce infrastructure-as-code standards using Terraform, defining the patterns other engineers follow for environment parity, drift detection, and automated compliance validation. Implement observability beyond availability—data integrity monitoring, SLO frameworks with error budgets, and automated regression detection for both platform and AI services. Build deployment automation including pre-deployment verification, migration script validation, and codified rollback procedures to eliminate human-memory dependencies. Support big data infrastructure: data pipelines, warehousing (Redshift), and analytics tooling that enables reporting, BI, and AI training workflows. Implement security and compliance controls for AI workloads operating in regulated carrier environments— including audit logging, access governance, and configuration management. Drive environment parity across all infrastructure with automated drift detection and remediation. Improve disaster recovery capabilities: documented and rehearsed DR procedures, defined RTO/RPO by service tier, and tested recovery runbooks. Lead architecture reviews for new services, integrations, and AI agent deployments—partnering with engineering, product, and security to ensure infrastructure decisions are sound before they ship. Innovate on developer experience: reduce friction in testing environments, CI/CD pipelines, and local development workflows. Act as a technical anchor for infrastructure decisions across teams—providing clarity when requirements are ambiguous and helping the organization converge on consistent, scalable approaches. What We’re Looking For 6+ years of DevOps/SRE/Platform Engineering experience. 2+ years of experience building or operating AI/ML infrastructure (model serving, inference, LLM orchestration, or agentic systems). Bachelor’s degree in Computer Science, Engineering, or equivalent experience. Built and operated infrastructure for traditional and AI/ML workloads at a SaaS company. Natural ability to lead technical conversations and be sought out by cross-team members when infrastructure decisions get complicated. Deep experience with AWS cloud services (ECS, Lambda, SageMaker, Bedrock, S3, DynamoDB, Redshift, or equivalent). Strong infrastructure-as-code skills with Terraform and understanding of state, modules, and multi-environment configurations. Experience with data infrastructure: pipelines, warehousing, ETL/ELT, and enabling analytics at scale. Thoughtful approach to observability beyond dashboards—focus on data integrity, SLOs, error budgets, and catching silent failures. Experience with compliance-sensitve environments and understanding of audit trails, access governance, and change management. Comfortable operating in a fast-moving environment where AI capabilities evolve rapidly and infrastructure decisions have regulatory implications. Strong communication skills with both engineering and non-technical stakeholders. Track record of leading cross-team technical initiatives and mentoring engineers on infrastructure and operational best practices. Strong proficiency in at least one programming language (Python, Go, TypeScript, or similar). Experience with: Container orchestration (ECS, EKS) Monitoring and observability platforms (Datadog, CloudWatch) Data infrastructure (Redshift or similar data warehousing; Airflow, dbt, Dagster or similar pipeline tools) is a strong plus. Experience in regulated industries (insurance, financial services, healthcare) is a strong plus. Genuine curiosity about AI and emerging technologies, paired with the judgment to apply them thoughtfully and responsibly. Compensation, Benefits & Perks At Hi Marley, we are committed to fair and transparent pay practices. The annual base salary for this role is expected to fall within the range of $119,000–$221,000, depending on experience, skills, qualifications, and location. Offers are determined based on these factors as well as internal peer equity. It’s most common for new hires to start near the midpoint of the range, allowing room for growth as employees develop in their role. Equity grants for all employees. A 4% matching 401(k) program. Medical, dental, vision, disability, and life insurance coverage for employees working 30+ hours per week. Monthly wellness stipend. Paid parental leave. A flexible vacation policy—flexible, hybrid work environment that values balance and trust. Who We Are Max Courage – We encourage our team, customers, and their customers to dream big, try new ideas, and maximize impact by measuring risk. Be Humble – We lead with appreciation and promote a culture of humility, compassion, and openness to learn from anyone, anywhere. Ubuntu ("I am because we are") – We believe true success is much bigger than any single individual or company. By aligning our individual aims behind a shared purpose, we can achieve our fullest potential together. Life at Hi Marley A fun, lively startup culture that embraces creativity and innovation. Core values-based leadership that guides our decision-making and daily interactions. A culture of engagement, diversity, inclusion, and belonging—all voices matter. Flexible, hybrid work environment that values balance and trust. Ample opportunities to learn, take on new challenges, and make an impact in a fast-growing organization. Meaningful work that directly supports our mission to help people and organizations communicate with empathy and clarity. Equal Employment Opportunity Statement Hi Marley is proud to be an equal employment opportunity employer. We celebrate diversity and do not discriminate based on gender, sexual orientation, gender identity, religion, race, veteran status, disability status, or any other characteristic protected by applicable law. We are committed to building an inclusive work environment representing a variety of backgrounds, perspectives, and skills, where all employees are encouraged to be their authentic selves. E-Verify Hi Marley participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. For more information, please review the documents under "E-Verify Poster" at #J-18808-Ljbffr Dormont Manufacturing Co