Engineering Systems Engineer

The Engineering Systems Engineer is the hands-on technical operator at the center of how the Engineering organization's tools, platforms, and standards work every day. This individual contributor owns the administration, configuration, governance, and continuous improvement of the systems that every engineer in the organization depends on — from Azure DevOps pipelines and project structures, to LaunchDarkly feature flag operations, to Flyway database migration standards, to the AI-assisted development tools like Cursor and Claude Code that are reshaping how software is built. The Engineering Systems Engineer is a proactive platform operator who identifies configuration drift before it causes problems, closes adoption gaps before they become patterns, and automates manual administration work before it accumulates into toil. They leverage AI throughout their own workflow — using it to accelerate platform analysis, generate automation scripts, produce enablement documentation, and surface insights from tooling data that would take hours to find manually.

Starting base pay for this role is between $100,000 and $122,000. The actual base pay is dependent upon many factors, such as transferable skills, work experience, business needs, training, location, and market demands. The base pay range is subject to change and may be modified in the future. This role will be eligible for a bonus as well as competitive medical, dental, and vision benefits, wellness reimbursement, life insurance, and a 401(k) with company match. We offer vacation and sick leave benefits (under a flexible time off policy in most states).

Azure DevOps Administration & Governance

• Owns day-to-day administration of Azure DevOps across the Engineering organization — managing organizations, projects, teams, repositories, pipelines, boards, area paths, iteration cadences, and access controls with the consistency, precision, and configuration hygiene that a multi-team Engineering organization depends on.
• Manages Azure DevOps user provisioning, permission models, and access reviews — ensuring access is scoped to least-privilege principles, regularly audited, promptly revoked when no longer needed, and documented to support compliance evidence requirements.
• Monitors Azure DevOps platform health, usage patterns, and adoption metrics — proactively identifying configuration drift, underutilized capabilities, permission anomalies, and opportunities to improve how Engineering teams use the platform before those gaps create friction or risk.
• Serves as the escalation point for Azure DevOps configuration issues — diagnosing platform-level incidents, working with Microsoft support when required, and resolving disruptions with the urgency that a platform used by every engineer in the organization demands.
• Leverages AI tools to accelerate platform analysis and administration work — including AI-assisted pipeline configuration review, AI-generated access audit summaries, and LLM-assisted platform documentation that keeps configuration records current without proportional manual overhead.

LaunchDarkly Administration & Feature Flag Governance

• Owns the administration and governance of LaunchDarkly across the engineering organization — managing projects, environments, user roles, access controls, SDK integrations, API configurations, and webhook connections with operational discipline and consistent configuration standards.
• Administers flag lifecycle governance — applying and enforcing the flag creation policies, naming conventions, targeting rules, retirement processes, and cleanup standards defined by the Engineering Systems Manager, and proactively identifying flags that are stale, misconfigured, or creating technical debt in the flag inventory.
• Partners with the Release Workflow Manager and Engineering teams to ensure feature flags are correctly configured and sequenced within each release cycle — supporting progressive delivery strategies and controlled rollout configurations that match the release plan without requiring last-minute flag adjustments.
• Monitors LaunchDarkly SDK integration health across connected systems — identifying evaluation errors, SDK version drift, and integration anomalies that affect flag reliability across environments, and resolving issues before they impact release operations.
• Builds and maintains LaunchDarkly enablement resources — including flag hygiene guides, SDK integration references, targeting configuration patterns, and best practice documentation — that empower Engineering teams to work with feature flags correctly and independently.

Flyway Administration & Database Migration Standards

• Owns the administration and governance of Flyway across the Engineering organization — managing versioning conventions, environment-specific configurations, and migration execution monitoring with the operational rigor that database changes in production environments require.
• Applies and enforces database migration standards defined by the Engineering Systems Manager — including script naming conventions, version sequencing requirements, migration review checklists, and rollback documentation standards — and identify deviations from those standards before migrations are promoted to production environments.
• Partners with Engineering teams to ensure Flyway migrations are authored, reviewed, and promoted in alignment with release workflow standards — validating migration execution in lower environments and confirming that rollback documentation is complete and tested before production promotion proceeds.
• Monitors migration execution health across all environments — maintaining visibility into migration history execution outcomes, failure patterns, and schema state that supports rapid diagnosis and resolution when migration-related issues occur.
• Identifies and implements automation improvements to the database migration workflow — including CI/CD pipeline steps that automate migration validation, execution monitoring, and failure alerting in ways that reduce manual effort and deployment risk.

Cursor & AI-Assisted Development Tooling

• Owns the provisioning, lifecycle management, and configuration governance of Cursor and other AI assisted development tools across the Engineering organization — ensuring every engineer has consistent, reliable, policy-compliant access to AI development capabilities with zero unnecessary friction.
• Manages licensing, seat allocation, and renewal tracking for Cursor and related AI tooling — maintaining accurate records of seat usage, identifying optimization opportunities, and flagging renewal timelines to the Engineering Systems Manager before they become urgent.
• Establishes and maintains configuration standards for Cursor across the Engineering organization — including workspace settings, AI model configurations, extension integrations, and data handling policy compliance — ensuring the AI tooling environment is consistent across engineering teams and aligned with security requirements.
• Monitors AI tool adoption and usage across Engineering teams — identifying low-adoption patterns, diagnosing root causes (tooling friction, awareness gaps, onboarding deficiencies), and designing targeted enablement interventions that move the needle on adoption and productivity impact.
• Stays current on Cursor updates, new capabilities, configuration best practices, and emerging AI development tooling — proactively testing new features, evaluating their applicability to the Engineering organization, and bringing actionable recommendations to the Engineering Systems Manager before the broader Engineering organization asks.
• Uses AI tooling actively in platform administration work — leveraging Claude Code and Cursor to accelerate automation scripting, platform analysis, configuration review, and documentation production across the Engineering Systems function.

Engineering Standards Administration

• Serves as the operational executor of the Engineering standards program — maintaining, publishing, formatting, and distributing standards documentation for coding conventions, branching strategies, pullrequest practices, code review requirements, and tooling usage as directed by the Engineering Systems Manager.
• Owns the standards repository — ensuring documentation is accurately organized, consistently formatted, discoverable through the Engineering knowledge base, and immediately updated when standards are ratified or revised.
• Monitors Engineering standards adherence across teams — identifying non-compliance patterns in code reviews, pipeline configurations, branch naming, and tooling usage, and bringing specific, data-backed observations to the Engineering Systems Manager and relevant Engineering Managers for follow-through.
• Coordinates the onboarding standards experience for new Engineers — maintaining environment setup guides, tooling provisioning checklists, and standards orientation materials that are current, complete, and effective enough to be executed without handholding.
• Supports standards retrospectives led by the Engineering Systems Manager — collecting adherence data, synthesizing engineering team feedback, and preparing materials that make retrospective sessions productive rather than anecdotal.

Access Management, Security & Compliance

• Maintains access control governance across all administered platforms — including Azure DevOps, LaunchDarkly, Flyway, and Cursor — executing provisioning and de-provisioning requests promptly, enforcing least-privilege access principles, and maintaining accurate access records that support audit evidence requirements.
• Conducts and documents regular access reviews across administered platforms — identifying over- provisioned accounts, stale access grants, and access policy violations, and resolving them in partnership with the Engineering Systems Manager and Security team.
• Supports SOC 2, ISO/IEC 27001, and NIST 800-53 audit readiness by maintaining accurate, current platform configuration records, access inventories, and change histories across all administered systems — treating audit evidence as an ongoing operational discipline rather than a pre-audit scramble.
• Partners with the Security team on access-related incidents, policy enforcement actions, and configuration hardening requirements — responding to security requests with urgency and implementing hardening changes with the precision that security controls require.
• Uses AI tools to accelerate access review, compliance documentation, and configuration audit work — including AI-assisted access inventory analysis, AI generated compliance evidence summaries, and LLM- assisted Tooling configuration documentation that maintains audit readiness without proportional manual effort.

Automation, Improvement & Enablement

• Continuously identifies and eliminates manual administration toil across the Engineering Systems platform portfolio — building automation scripts, pipeline integrations, and workflow improvements that replace repetitive manual steps with reliable, auditable automated processes.
• Builds and maintains internal enablement resources — including training guides, how-to documentation, FAQs, configuration references, and onboarding materials — that empower Engineering teams to use administered platforms correctly and independently, reducing the volume of repetitive support requests.
• Develops and maintains monitoring and alerting for administered platform health — including Azure DevOps pipeline health, LaunchDarkly SDK evaluation errors, Flyway migration failures, and AI tooling provisioning issues — so that platform degradation is detected and resolved proactively rather than reactively.
• Tracks platform health, adoption metrics, support request trends, and standards compliance across administered systems — maintaining the operational data that the Engineering Systems Manager needs to report accurately to the Director of Engineering Systems and to make informed investment decisions.

Senior Engineering Systems Engineer Responsibilities

• Leads the design and implementation of the most complex platform configurations, cross-platform integrations, and large-scale automation initiatives within the Engineering Systems portfolio — owning technical decisions end-to-end and producing implementations that other Engineers can maintain and build on.
• Drives the team's cross-platform automation strategy — identifying the highest-leverage automation opportunities across Azure DevOps, LaunchDarkly, Flyway, and AI tooling, designing the automation architecture, and leading implementation with the Engineering Systems Manager's direction.
• Contributes substantively to the Engineering standards program — drafting new standards, reviewing proposed changes, identifying standards gaps based on observed Engineering team behavior, and producing standards documentation that is clear enough to be adopted without interpretation.
• Serves as the technical mentor less experienced Engineering Systems Engineers — reviewing platform configurations, providing structured feedback on automation quality and documentation standards, and accelerating development into senior-level platform engineers.
• Serves as the technical depth the Engineering Systems Manager relies on for platform architecture decisions — evaluating new tooling, assessing integration approaches, analyzing configuration tradeoffs, and producing recommendations that give the manager the technical grounding needed to direct the team confidently.
• Leads the team's AI tooling strategy within the Engineering Systems function — evaluating new AI platform administration tools, piloting AI-assisted workflows, and establishing the team's best practices for AI- augmented platform operations that other Engineering Systems Engineers adopt as standard practice.

• Ability to legally work in the Dominican Republic
• Strong English reading comprehension and written communication skills are required
• Associates degree or equivilant preferred 
• 2–4 years of experience in an Engineering Systems Administration, Platform Engineering, DevOps, or Technical Operations role within a Software Engineering organization.
• Hands-on experience administering Azure DevOps — including project configuration, pipeline management, access control, board structure, and area path management — at a depth sufficient to independently resolve platform configuration issues.
• Experience managing feature flag platforms — LaunchDarkly strongly preferred — including flag lifecycle governance, environment management, SDK integration health, and flag hygiene practices.
• Familiarity with database migration tooling and versioning practices — Flyway experience strongly preferred —including migration script standards, CI/CD pipeline integration, and migration execution monitoring.
• Demonstrated active use of AI development tools such as Cursor or Claude Code in day-to-day technical work — including AI-assisted scripting, platform analysis, or documentation production.
• Experience managing access controls and user provisioning across engineering platforms with an understanding of least-privilege principles and compliance evidence requirements.
• Strong organizational discipline and attention to detail — able to manage multiple platform domains simultaneously, maintain configuration hygiene across all of them, and track open items without dropping anything.
• Clear written communication skills — able to produce platform documentation, enablement guides, and configuration records that are accurate and usable by engineering teams without requiring significant clarification.

Origami Risk delivers single-platform SaaS solutions that help organizations best navigate the complexities of risk, insurance, compliance, and safety management.

Founded by industry veterans who recognized the need for risk management technology that was more configurable, intuitive, and scalable, Origami continues to add to its innovative product offerings for managing both insurable and uninsurable risk; facilitating compliance; improving safety; and helping insurers, MGAs, TPAs, and brokers provide enhanced services that drive results.

A singular focus on client success underlies Origami’s approach to developing, implementing, and supporting our award-winning software solutions. 

Origami Risk is proud to be an equal opportunity employer. We thrive and benefit from diversity and are committed to creating an inclusive and equitable environment for all employees. We do not discriminate against any individual based upon race, religion, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, color, sex, national origin, age, marital status, military or veteran status, disability, or any other characteristic protected by applicable law.