Site Reliability Engineer

Cloud Operations Engineer III

Function: Engineering

Reports to: Manager, Cloud Operations

Location: Remote - United States

Position Summary

The Cloud Operations Engineer III is a senior member of the cloud operations team, responsible for the reliability, observability, performance, and operational security of our multi-product SaaS platform. This role owns our Datadog observability practice — instrumentation standards, dashboards, SLOs, monitors, and alert routing — and leads the migration off our legacy monitoring stack.

It is an engineering role, not a ticket-queue role: the expectation is that recurring operational work gets replaced with code. The Cloud Operations Engineer III participates in on-call, incident response and is measured on fewer customer-impacting incidents, faster detection and recovery, and less manual work year over year.

The ideal candidate is a proactive problem-solver who thrives in dynamic, evolving environments and works effectively across departments to address complex challenges. They have experience partnering with cross-functional teams to understand and document requirements, then translating those needs into meaningful dashboards that improve service visibility (Observability) and support informed decision-making. They are passionate about automation, process improvement, and eliminating unnecessary manual effort. They confidently propose better approaches when opportunities for improvement arise.

Key Responsibilities

Observability and Datadog Ownership

Own the Datadog platform across all products and environments, including agent lifecycle, instrumentation standards, unified service tagging, and per-cluster configuration.

Instrument services for APM and distributed tracing, log collection, and synthetic monitoring; partner with engineering teams to close instrumentation gaps in both legacy and modern codebases.

Build and maintain the dashboard, monitor, and SLO catalog; define SLIs and error budgets for critical user journeys and use them to drive prioritization with engineering and product.

Design high-signal alerting: reduce noise and duplicate alerts, tune thresholds, and ensure every alert has an owner and a runbook.

Automation and Toil Elimination

Develop and maintain automation in PowerShell, Python, and Bash for provisioning, configuration, diagnostics, remediation, and reporting.

Extend our infrastructure-as-code estate — Bicep modules, Kubernetes manifests, Helm releases, and Azure DevOps pipeline templates — so environments and regions are reproducible and drift-free.

Convert manual runbooks into automated or self-service workflows: cluster upgrades, secret and certificate rotation, tenant provisioning, data retention purges, and access provisioning.

Security, Documentation, and Mentorship

Implement and maintain platform security controls and audit-ready operational evidence: managed identities, secret and key rotation, least-privilege access, and image and dependency scanning.

Author and maintain runbooks, on-call guides, and architecture documentation, and provide technical leadership and mentorship to junior engineers on observability, automation, and incident response.

Skills and Experience Needed

Bachelor's degree in Computer Science, Information Technology, or a related field, or equivalent practical experience.

5-7 years of professional experience in cloud operations, site reliability, platform, or DevOps engineering for production SaaS systems.

Demonstrated hands-on depth with a modern observability platform — Datadog strongly preferred — including APM and distributed tracing, log pipelines and indexing controls, dashboards, monitors, and SLOs.

Strong scripting and automation ability in PowerShell, with the judgment to write tooling that other engineers can safely operate.

Strong knowledge of containers, container orchestration, and the Kubernetes ecosystem, including autoscaling, cluster upgrades, and diagnosing pod-level failures.

Production experience with Azure — Kubernetes Service, Azure SQL, Cosmos DB, Redis, Service Bus, Key Vault, and Entra ID — or equivalent depth in another major cloud.

Experience with infrastructure-as-code and CI/CD pipeline authoring (Bicep or Terraform; Helm or Kustomize; Azure DevOps preferred).

Proven incident response experience in a customer-facing production environment, including on-call participation and leading post-incident reviews.

Experience operating multi-region, multi-tenant systems.

Strong knowledge of platform security and operational best practices: secret and key rotation, least-privilege access, and vulnerability remediation.

Excellent problem-solving and analytical abilities, with strong written communication for runbooks, incident updates, and technical proposals.

Strong communication, and teamwork skills, including the ability to work effectively with legacy systems and their constraints.

Nice to have: experience migrating from a legacy monitoring stack to a consolidated observability platform; relevant Azure, Kubernetes, or Datadog certifications.

Competencies

Accountability

Adaptability

AI Curiosity/Innovation

Applied Learning

Business Acumen

Collaboration

Customer Focus

Dealing w/Ambiguity

Decision Making

Driving for Results

Initiating Action

Planning and Organizing

Technical/Professional Knowledge

About the Company:

Boards set the standard for what organizations can achieve. At OnBoard, our board management software helps boards function at a higher level so every organization can make a bigger difference in the world.

Launched in 2011, today, OnBoard serves as the board intelligence platform for more than 5,000 organizations and their 12,000 boards and committees in 60 countries worldwide. With customers in higher education, nonprofit, healthcare systems, government, and enterprise business, OnBoard is the leading board management provider.

OnBoard has grown from a class project at Purdue University in West Lafayette, Indiana in 2003 into the world’s leading board management software platform today. Backed by JMI Equity and the acquisitions of eScribe and Govenda, OnBoard is positioned to become the industry leader in Board Management and Meeting Solutions for private and public sector entities.

Benefits and Perks:

Fully remote work with company provided equipment (laptop, software, etc.)

Employment with a growing, casual, fun, philanthropic minded company

US Based Employees

Comprehensive, high-quality medical/prescription drug plan options, as well as dental and vision plan offerings.

An employer contribution to your Health Savings Account (HSA) if you participate in a High Deductible Healthcare Plan.

Medical Flexible Spending Accounts available.

Dependent Care Flexible Spending Accounts available.

Basic life insurance in the amount of $50,000 or 1 X’s your salary (whichever is higher) .

Short and long-term disability and Accidental Death and Dismemberment benefits at no cost to you.

401K Retirement Savings Plan with automatic enrollment at the first of the month following 60 days of employment at 5% to help you secure your financial freedom. We offer a generous company match that starts on the first of the month following 60 days of employment. The company match is dollar for dollar on the first 3% of your pay that you contribute and $0.50 on the dollar on the next 2%, for a total match of 4%.

Paid Time Off (PTO)/Holiday

CAN Based Employees

Employer paid Life and Accidental Death Insurance

Contribution to Health Care Spending Account

Dependent Life Insurance

Optional Life Insurance

LTD Insurance

Drug and Paramedical Coverage

Dental Insurance

Vision Insurance

EAP

AUS Based employees

Superannuation rate of 12%

Monthly stipend of $400 AUD to purchase private medical insurance

UK Based Employees (via EPG)

Pension - Aegon

Passageways/OnBoard contributes 8% of the empl