Observability Engineer

Who We Are

Accommodations Plus International (API) is a technology and services company focused on driving innovation across the travel and transportation industry. We partner with organizations in the airline, cruise, and rail sectors to deliver solutions that improve layover operations, enhance customer experience, and support long-term growth.

Our mission is to make layovers simpler and more efficient for crew members-and we bring that to life through deep industry expertise and a practical, results-driven approach.

Today, API’s platform powers over 18 million crew room nights each year for 100+ airlines and travel operators worldwide. Our Global Reach ensures that airline crews are rested, transported, and connected so global aviation runs on time.

At API, we’re building a culture rooted in succeeding and thriving together. It’s a place where people are encouraged to take ownership, develop their skills, and contribute to work that matters.

If you’re looking to grow your career in a company that values steady progress, real impact, and long-term development, we’d like to meet you!

Job Overview

This senior role owns the design, integration, and administration of the AWS cloud-based applications and infrastructure observability toolchain, Datadog, JIRA Service Management (JSM), and xMatters, driving automation and AI-assisted workflows to reduce manual effort and improve operational reliability.

As the technical owner, you will lead the evolution of the observability toolchain across Incident, Change, and Problem Management, ensuring availability SLAs are met for, cybersecurity requirements (including patching) are addressed, and continuous improvement is delivered through scripting, API integration, and Generative AI tooling. The role is focused on leveraging automation to improve teamwork, operational clarity, and effectiveness.

Key Responsibilities

• Workflow Design & Implementation: Design and implement complex workflows, automation rules (triggers, conditions, actions), and integrations between Datadog, JSM, and xMatters to optimize Incident, Change, and Problem Management delivery.
• Scripting & Development: Develop automation workflows using Python, PowerShell, Unix Scripts, and REST APIs, both for in-house tooling and third-party vendor integrations.
• System Administration: Serve as the administrative owner of Datadog, JSM, xMatters, and any in-house observability tools, ensuring availability, functionality, and compliance with cybersecurity requirements.
• Collaboration: Partner with product owners, development, QA, support, and business teams to identify operational needs and deliver effective observability toolchain solutions.
• Support & Maintenance: Act as the primary technical owner of the observability toolchain, accountable for uptime, incident resolution, patching, and continuous improvement.

Key Skills & Qualifications:

• Proven experience with Atlassian products (Jira, Confluence, Bitbucket).
• Strong understanding of RESTful APIs, JSON, and data transformation.
• Scripting (Python/PowerShell) and integration tool experience.
• Problem-solving, analytical, and communication skills.
• Familiarity with IT Service Management (ITSM) best practices, Tech Ops/Technical Support, ITIL, DevOps, CI/CD, and enterprise IT environments.
• Experience with AI/ML concepts is a plus for advanced roles.

Required Qualifications

• 5+ years of experience with Information Technology Service Management (ITSM) and Information Technology Infrastructure Library (ITIL) toolchain integration.
• 5+ years of experience supporting Change, Incident, and Problem Management function.
• 5+ years of experience in a Platform, CI/CD, SRE, or Observability role.
• Proven hands-on experience with Atlassian (JSM/JIRA), Datadog, and xMatters.
• Strong proficiency with Java, RESTful APIs, JSON, and data analytics.
• Experience in Java, Python, PowerShell, and/or Unix shell.
• Familiarity with ITIL best practices, DevOps, and enterprise IT environments.
• Experience with microservices architecture, secure authentication, and performance optimization.
• Strong problem-solving skills and ability to navigate ambiguity to define clear solutions.
• Excellent verbal and written communication skills.
• Strong understanding of Generative AI, AI agents (Agentic AI), and AI-assisted software development practices.
• Experience identifying and implementing opportunities where AI can improve engineering productivity, operational efficiency, and customer outcomes.
• Demonstrated proficiency with Generative AI and AI-powered development tools, including prompt engineering, AI-assisted coding, workflow automation, and AI-enabled problem solving.
• Experience leveraging AI agents and automation frameworks to streamline engineering processes and improve productivity.

Preferred Qualifications

• Experience in technical support or service delivery role.
• Experience with AI/ML concepts or Gen AI tooling applied to operational automation.
• Familiarity with cloud environments (AWS), CI/CD pipelines, and observability tools (OpenTelemetry).
• Experience with PINGFederate, SAML, or enterprise identity and access management.
• Knowledge of Java, Node.js, or full-stack frameworks in the context of toolchain customization.
• Degree in Computer Science, Software Engineering, or a related field - or equivalent practical experience.
• Proven experience using AI tools to design, develop, debug, review, and optimize code, scripts, and automation solutions.
• Demonstrated proficiency in leveraging Generative AI and AI-assisted development tools (e.g., GitHub Copilot, Microsoft Copilot, ChatGPT) to accelerate software development, troubleshooting, automation, testing, and documentation while maintaining high standards for code quality, security, and reliability.

Education

• BSc/BA in Computer Science or Software Engineering or related field.

Position Type and Expected Hours of Work

• This is a full-time position. Standard days and hours of work are Monday through Friday, during normal core business hours. Occasional evening and weekend work may be required as job duties demand.

Supervisory Responsibility

• None

What’s In it for You

RRSP with employer matching

• Paid Time Off
• Extended health insurance, LTD, life insurance, and Employee Assistance Program
• High-growth oriented environment with results-driven team

Compensation

• Good faith annual salary range for this position is $90,000 to $110,000 CAD. Compensation will be commensurate with experience. This position is also eligible for an annual discretionary bonus.

Other Duties

Duties, responsibilities and activities may change at any time according to business needs.

The performance of additional responsibilities if you are designated as a Data Protection Champion (DPC), Senior Information Risk Owner (SIRO) or Information Assurance Accounting Officer (IAAO).

Work Environment

This position operates in a professional office environment. This role routinely uses standard office equipment such as computers, phones, photocopiers, filing cabinets and fax machines.

Physical Demands

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. While performing the duties of this job, the employee is regularly required to talk or hear. The employee frequently is required to stand, walk; use hands to finger, handle or feel; and reach with hands and arms.

AAP/EEO Statement

Accommodations Plus International is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, alienage or national origin, ancestry, citizenship status, age, disability or handicap, sex, marital status, veteran status, sexual orientation, genetic information, arrest record, or any other characteristic protected by applicable federal, state or local laws. Our management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities and general treatment during employment.

Privacy Statement

API may use the contact information you provide to communicate about this role, including via text message. See our [Privacy Policy] for details. By clicking "Apply" you agree to Rippling's Terms of Service /User Privacy Notice .

ensure smooth technical operations that directly support and enhance the experience of users globally