Senior Manager, DevOps

TrueML is a mission-driven financial software company that aims to create better customer experiences for distressed borrowers. Consumers today want personal, digital-first experiences that align with their lifestyles, especially when it comes to managing finances. TrueML’s approach uses machine learning to engage each customer digitally and adjust strategies in real time in response to their interactions. 

The TrueML team includes inspired data scientists, financial services industry experts and customer experience fanatics building technology to serve people in a way that recognizes their unique needs and preferences as human beings and endeavoring toward ensuring nobody gets locked out of the financial system.

What You'll Do (Technical Leadership & Strategy):

• Define and execute the long-term strategic vision for Infrastructure as Code (IaC), CI/CD evolution, and cloud-native architecture to support TrueML’s scaling needs.

• Lead the design and implementation of self-service internal platforms to reduce developer cognitive load, enabling feature teams to deploy and manage services with minimal friction at increased velocity.

• Act as the primary stakeholder for cloud spend (AWS); drive cost-optimization initiatives and lead contract negotiations for the DevOps toolstack and third-party vendors.

• Ensure the infrastructure architecture supports strict High Availability (HA) requirements and robust Disaster Recovery (DR) protocols, maintaining system integrity across multiple regions.

• Oversee the implementation and evolution of comprehensive monitoring, logging, and distributed tracing systems, leveraging AIOps to move from reactive to predictive system maintenance.

• Champion security by design by integrating automated vulnerability scanning, secret management, and compliance checks directly into the automated build pipelines.

• Serve as the ultimate escalation point for major production outages, facilitating blameless post-mortem reviews that focus on systemic improvements rather than individual error.

• Maintain deep technical currency in container orchestration (Kubernetes), serverless patterns, and modern automation frameworks to provide meaningful mentorship and architectural guidance to senior engineering staff.

What You'll Do (Hands-On Engineering & Technical Execution):

• Maintain the ability to write and review high-quality code in languages like Python, Go, or Bash to automate complex operational tasks and system integrations.

• Hands-on development of Terraform  Infrastructure as Code for resource provisioning.

• Directly architect and troubleshoot complex CI/CD workflows (GitHub Actions, ArgoCD, Atlantis), ensuring build-and-deploy cycles are optimized for speed and reliability.

• Proactively manage and tune container orchestration environments, including hands-on configuration of Ingress controllers, declarative GitOps workflows, and cluster autoscaling.

• Lead from the front during critical incidents by conducting deep-dive technical analysis across the EKS stack, troubleshooting Node-level kernel panics, VPC CNI networking bottlenecks, and RDS performance constraints to minimize MTTR

• Conduct hands-on audits of cloud configurations and IAM policies, implementing "least privilege" access controls and automated remediation scripts.

• Directly manage the integration and API configurations between various tools in the DevOps stack (e.g., connecting Jira, VictorOps, Slack, and Observe for seamless incident flow).

What You'll Do (People Leadership & Engineering Collaboration):

• Recruit, hire, and develop a world-class team of DevOps Engineers; provide career pathing and technical mentorship to foster a culture of continuous learning.

• Partner closely with Engineering Managers to align infrastructure deliverables with product roadmap, ensuring DevOps is an accelerator rather than a bottleneck.

• Collaborate with the Quality Engineering and Security leadership to define and enforce "Definition of Done" standards that include automated testing and security gates.

• Set clear, measurable goals (KPIs and OKRs) for the team, conducting regular performance reviews and providing feedback to drive individual and collective excellence.

• Lead internal Brunch & Learns to educate the broader engineering organization on modern cloud-native patterns and self-service capabilities.

Who You Are (Qualifications):

• Bachelor's degree in Computer Science, Engineering, or a related technical field, or equivalent practical experience.

• 10+ years of experience in DevOps, Site Reliability Engineering (SRE), or Software Engineering; 5+ years of experience managing engineers

• Expert-level mastery with AWS and experience managing multi-region, high-availability deployments

• Advanced experience with Kubernetes (K8s) and Docker, including cluster management, networking, and scaling in a production environment.

• Proficiency in Terraform to drive consistency and automation across all infrastructure layers. Experience with Atlantis is a plus. 

• Deep experience designing and maintaining complex pipelines (GitHub Actions, GitLab CI, or Jenkins) and mastery of scripting languages like Python, Go, or Bash.

• Hands-on experience with modern monitoring, observability, and tracing stacks (Datadog, Observe) and a firm grasp of SRE principles (SLIs/SLOs/Error Budgets).

• Experience acting as an Incident Commander for high-severity outages and fostering a "blameless" post-mortem culture.

• Demonstrated ability to influence executive leadership and collaborate cross-functionally with Product, Engineering, and Security teams.

• Experience integrating AI-assisted productivity tools (Cline, GitHub Copilot) into the engineering workflow to accelerate delivery.

Ways to "Stand Out":

• Experience leading organizational platform migration, including the development of rollback strategies, stakeholder communication plans, and post-migration validation

• Prior experience working with high-velocity, product-driven early-to-mid stage technology companies where reliability, extensibility, and availability were mission-critical to success

• AWS or Kubernetes Certifications a plus -- but not in lieu of hands-on experience with the same within production environments

• Notable contributions to Open Source projects or communities

What We Offer (Perks & Benefits)

• Flexible vacation

• Medical/dental/vision insurance

• Traditional/Roth retirement savings options

• Company-paid disability and life insurance

• Flexible Spending Account & Limited FSA

• Family-friendly parental leave, volunteer and voting time off

• On-demand wellness platform access for you and 5 friends and family

• PerkSpot discount program for 900+ merchants nationwide

This role supports a global, cross-functional business and operates primarily in a Remote-First environment. However, flexibility outside of standard business hours and occasional local or international travel may be necessary for global operations support, company meetings, training, offsites, and collaborative projects.

This position primarily involves computer-based work, requiring extended periods at a computer, participation in virtual meetings, and use of standard office technology. We will consider reasonable accommodations to enable individuals to perform the essential functions of the role.

Maintaining a reliable internet connection and a professional work environment is expected. The ability to protect confidential company, employee, customer, and business information while working outside of a company office is also required.

We collect personal information for employment purposes. We do not sell personal information. Most of the information we have is provided to us by you and/or collected as part of the employment process. For more details on how we use, share, and delete personal information see our Privacy Policy.

We are  an equal opportunity employer. We promote, value, and thrive with a diverse and inclusive team. Different perspectives contribute to better solutions and this makes us stronger every day. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or other protected characteristics.