DevOps Engineer

About Accolade

The multifamily real estate industry is undergoing a massive transformation, and Accolade is at the forefront. We are building the industry's first AI-native Operations Centralization Platform, designed to streamline complex processes, unlock new efficiencies, and create better experiences for residents and operators alike. Our platform uses advanced AI to automate routine tasks, capture critical data, and intelligently manage communications. We're on a mission to help our clients achieve what we call Full Potential Centralization, and we need passionate, experienced builders to help us lead the way.

The Opportunity

This is a pivotal, contract-to-hire role for an experienced DevOps engineer who thrives on building highly automated, secure, and scalable infrastructure from the ground up (0->1). As a Senior DevOps Engineer, you will be the architect and guardian of our engineering foundation. Your mission is to make our developers faster and our platform safer by embracing a rigorous Everything as Code philosophy.

We are looking for a hands-on expert passionate about moving beyond basic cloud provisioning to implement a comprehensive Toolchain-as-Code strategy. You will be instrumental in leveraging Terraform providers to automate the configuration, governance, and integration of our entire technology ecosystem.

What You'll Do

• Drive Toolchain-as-Code Automation:

  Take ownership of automating our entire third-party ecosystem using Terraform providers. You will manage complex configurations and ensure our entire toolchain is declarative and version-controlled. This includes:

• Identity & Access (Auth0/AuthZed):

  Architecting B2B organizations, defining SAML/OIDC enterprise connections (including Home Realm Discovery), and implementing security policies as code.

• Feature Management (LaunchDarkly):

  Defining project structures, implementing fine-grained RBAC (teams and custom roles), configuring environment safeguards (e.g., mandatory approvals), and managing flag architectures declaratively.

• Ecosystem Integration:

  Automating the provisioning and configuration of Databricks, Grafana, Temporal, Ably, and GitHub.

• Architect and Own the AWS Platform:

  Define and manage our entire AWS infrastructure declaratively using both Terraform and the AWS CDK. This includes architecting the Landing Zone, organizational structure, monitoring/logging infrastructure, and workload accounts.

• Build the Developer Paved Road:

  Create and maintain the paved road for our engineering team. You will design, build, and optimize automated CI/CD pipelines using GitHub Actions, manage our container runtime environment (Docker), and ensure developers have a smooth, self-service path to production.

• Champion Reliability and Observability (SRE):

  Implement and manage our monitoring and alerting systems using Grafana and OpenTelemetry. You will work with development teams to establish Service Level Objectives (SLOs) and promote a culture of reliability.

• Lead Technical Compliance (SOC 2):

  Serve as the key technical leader for our SOC 2 readiness. You will translate audit requirements into automated technical controls, harden our AWS environment, apply the principle of least privilege across all systems, and secure data throughout the platform.

What You'll Bring

• 5+ years of professional DevOps or Platform Engineering experience in a cloud-native environment.
• Mandatory, Expert-level proficiency with Terraform. You must have extensive, hands-on experience using providers beyond AWS/Azure/GCP to automate the configuration of third-party tools and services (e.g., Auth0, LaunchDarkly, Datadog, GitHub).
• Deep, practical experience managing production AWS environments (VPC, EC2, S3, IAM) using Infrastructure as Code.
• Proven ability to design, build, and maintain sophisticated CI/CD pipelines, specifically with GitHub Actions.
• Solid expertise with Docker and the deployment of containerized applications.
• Proficiency in scripting with Python and Bash for automation, glue code, and system integration.
• A strong security mindset with practical experience securing cloud infrastructure and familiarity with compliance frameworks like SOC 2.

Our Tech Stack

We believe in using the right tools for the job. You'll get to work with and master:

• Cloud:

  AWS (Core Services, IAM, Security)

• Infrastructure as Code:

  Terraform, AWS CDK

• CI/CD & Automation:

  GitHub Enterprise Cloud, GitHub Actions, Python, Typescript, Bash

• Observability:

  Grafana, OpenTelemetry, Datadog

• Containers:

  Docker

• Key Services:

  Auth0, LaunchDarkly, Databricks, Temporal, Ably, AuthZed, JumpCloud, Atlassian

Bonus Points For

• Deep expertise with the AWS CDK in a production environment.
• Direct experience implementing technical controls and evidence collection for a successful SOC 2 audit.
• Familiarity with advanced identity protocols (SAML, OIDC) and automating Identity Provider configurations via Terraform.

Why You'll Love Working at Accolade

• True Ownership & Impact:

  You won't be maintaining legacy systems. You will have the autonomy to make critical infrastructure decisions and define our foundational Toolchain-as-Code strategy that enables the entire engineering organization.

• Cutting-Edge IaC:

  This is an opportunity to push the boundaries of Everything as Code. You will tackle complex challenges integrating diverse platforms via Terraform, moving beyond standard infrastructure provisioning.

• Accelerated Career Growth:

  We are growing quickly. This contract-to-hire opportunity is designed for ambitious individuals looking to transition into a high-impact, full-time technical leadership role.

• Competitive Compensation:

  We offer an attractive compensation package commensurate with your experience and qualifications.

Our Interview Process

1. Initial Chat (30 min):

   A conversation with our team to discuss your background and interest in the role.

2. Technical Deep Dive (60 min):

   A discussion focusing on your IaC philosophy, Terraform provider expertise, cloud architecture, and systems design approach.

3. Technical Assessment:

   A practical Infrastructure as Code challenge (Terraform/AWS) to see your problem-solving skills in action.

4. Team Interviews (45-60 min each):

   Meet with key engineers and stakeholders to dive deeper into your skills, approach, and cultural fit.