Senior DevOps Engineer

Hi Marley; Boston (MA); On-site; USD 140,000 - 190,000; Full time

Benefits offered by this job

Open vacation policy

Matching 401k program

Medical, dental, vision, disability, &

Life insurance

Job summary

Hi Marley is seeking a Sr. DevOps Engineer II to build and scale infrastructure powering core platform and AI services. You will drive cloud design on AWS, implement IaC with Terraform, and ensure reliability, security, and cost efficiency across multi-environment deployments.

You’ll lead cross-team initiatives, mentor engineers, and shape infrastructure standards in a fast-paced, regulated insurance workflows setting. Strong AI/ML infra experience and data warehousing expertise are valued.

Qualifications

• Bachelor's degree or equivalent experience in a technical field.
• 6+ years of DevOps/SRE/Platform Engineering experience.
• 2+ years building or operating AI/ML infrastructure (model serving, inference, LLM orchestration).
• Experience with AWS cloud services and regulated environments.

Responsibilities

• Design and operate cloud infrastructure on AWS for core SaaS and AI services.
• Build and maintain AI/ML infrastructure and monitoring for agentic services.
• Establish IaC standards using Terraform and enforce environment parity.
• Implement observability with SLOs, error budgets, and regression detection.
• Automate deployments with drift detection, rollback procedures, and CI/CD support.
• Support data pipelines, warehousing (Redshift), and analytics tooling.
• Implement security/compliance controls for AI workloads in regulated environments.
• Lead architecture reviews and mentor engineers on infra and ops best practices.

Skills

Terraform

AWS cloud services

Observability

AI/ML infra

Programming (Python/Go/TypeScript)

Container orchestration (ECS/EKS)

Compliance in regulated environments

Data pipelines & warehousing

Security & config management

Education

Bachelor's degree in Computer Science, Engineering, or equivalent

Tools

Terraform

AWS

Datadog

CloudWatch

Airflow

dbt

Dagster

SageMaker

Redshift

Job description

• We are looking for a Sr. DevOps Engineer II 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 tooperatereliably at enterprise scale while deploying autonomous AI agents in regulated insurance workflows
• You’llalso 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
• Design andoperatecloud infrastructure on AWS that supports both our core SaaS platform and our agentic AI services, ensuring reliability, scalability, and cost efficiency
• Build andmaintainAI/ML infrastructureand 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 toeliminatehuman-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 workloadsoperatingin regulated carrier environments including audit logging, access governance, and configuration management
• Drive environment parity across all infrastructurewith automated drift detection and remediation
• Improvedisaster 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

Benefits

• A fun, lively startup culture
• Core values-based leadership
• A culture of employee engagement, diversity and inclusion
• Open vacation policy - we all work hard and take time for ourselves when we need it
• Ample opportunities to learn and take on new responsibilities in a fast-paced, growth-mode startup
• Full benefits package including parental leave, a matching 401k program, and medical, dental, vision, disability, and life insurance
• Generous stock options - we all get to own a piece of what we're building

You have strong infrastructure-as-code skills with Terraform and understand how to manage state, modules, and multi-environment configurationsTrack recordof leading cross-team technical initiatives and mentoring engineers on infrastructure and operational best practicesYou naturally step up to lead technical conversations, and people across teams seek you out when infrastructure decisions get complicatedYou have experience with compliance-sensitive environments and understand why audit trails, access governance, and change management matterYou are comfortable operating in a fast-moving environment where AI capabilities are evolvingrapidlyand infrastructure decisions have regulatory implicationsYou communicate well with both engineering and non-technical stakeholdersBachelor's degree in Computer Science, Engineering, or equivalent experienceYou understand data infrastructure: pipelines, warehousing, ETL/ELT, and how to support analytics at scaleYou have built and operated infrastructure fortraditional andAIorML workloads at a SaaS companyYou have deep experience with AWS cloud services (ECS, Lambda, SageMaker, Bedrock, S3, DynamoDB, Redshift, or equivalent)6-+ years of DevOps/SRE/Platform Engineering experienceYou think about observability as more than dashboards you care about data integrity, SLOs, error budgets, and catching silent failures2+ years of experience building or operating AI/ML infrastructure (model serving, inference, LLM orchestration, or agentic systems)Strongproficiencyin at least one programming language (Python, Go, TypeScript, or similar)Experience in regulated industries (insurance, financial services, healthcare) is a strong plusContainer orchestration (ECS, EKS)Monitoring and observability platforms (Datadog, CloudWatch)Data infrastructure (Redshift, or similar data warehousing; Airflow,dbt,Dagsteror similar pipeline tools) is a strong plusA genuine curiosity about AI and emerging technologies, paired with the judgment to apply them thoughtfully and responsibly