[Remote] DevOps Lead at StraighterLine

Remote

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$150,000 – $220,000Compensation

Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

Education, SoftwareIndustries

Requirements

Proven experience designing and operating cloud infrastructure (preferably in AWS)
Deep understanding of IaC, CI/CD systems, and automated deployment strategies
Experience with monitoring and observability tools such as CloudWatch, Grafana, or Datadog
A security-first mindset in infrastructure design and operations
Strong scripting and automation skills using JavaScript, TypeScript, Bash, or similar languages
Strategic thinker with the ability to translate business needs into scalable solutions
Comfortable leading cross-functional initiatives and aligning diverse technical teams
Strong communicator—able to document systems, guide decisions, and collaborate across departments
Committed to mentoring and team development; leads by example

Responsibilities

Maintain 99.9% uptime across all critical systems
Implement infrastructure-as-code (IaC) using tools like Terraform, AWS CDK, or Ansible across all environments
Define and drive CI/CD best practices using Bitbucket Pipelines, AWS CodePipeline, or similar tools
Own and evolve the organization’s enterprise-wide infrastructure, ensuring it’s scalable, visible, and aligned with business goals
Assess and articulate the current and future state of enterprise architecture, setting a clear direction for platform growth
Mentor and upskill software engineers, fostering a culture of DevOps learning and growth

Skills

Key technologies and capabilities for this role

TerraformAWS CDKAnsibleCI/CDBitbucket PipelinesAWS CodePipelineCloudWatchGrafanaDatadogJavaScriptTypeScriptBashInfrastructure-as-CodeAutomationCloud InfrastructureEnterprise ArchitectureScriptingMonitoringObservability

Questions & Answers

Common questions about this position

What technical skills are required for the DevOps Lead role?

The role requires proven experience designing and operating cloud infrastructure (preferably in AWS), deep understanding of IaC, CI/CD systems, and automated deployment strategies, experience with monitoring tools like CloudWatch, Grafana, or Datadog, a security-first mindset, and strong scripting skills using JavaScript, TypeScript, Bash, or similar.

What leadership qualities are needed for this position?

Candidates need to be strategic thinkers who translate business needs into scalable solutions, comfortable leading cross-functional initiatives, strong communicators who document systems and collaborate across departments, and committed to mentoring and team development.

What are the company's core values?

The company's values are Purposeful (connecting work to real-world impact), Collaborative (thriving in team environments), Bold (taking initiative), Determined (following through when tough), and Spirited (bringing energy and curiosity).

Is this a remote position or does it require office work?

This information is not specified in the job description.

What is the salary or compensation for the DevOps Lead role?

This information is not specified in the job description.

StraighterLine

Online platform for affordable college courses

About StraighterLine

StraighterLine offers an online education platform that provides low-cost, self-paced courses for college credit. The platform is designed for students and adults who want to earn college credits at their own pace. It partners with over 180 higher education institutions, allowing students to transfer credits easily and continue their education. The subscription-based model enables students to pay a monthly fee for access to a variety of courses, with additional fees for specific courses. With more than 70 courses available in fields like business, healthcare, and IT, StraighterLine has supported over 350,000 students. The company also offers career pathway bundles to help students achieve their career goals more quickly.

Baltimore, MarylandHeadquarters

2008Year Founded

$11.3MTotal Funding

SERIES_BCompany Stage

EducationIndustries

51-200Employees

Benefits

Health Insurance

Dental Insurance

Vision Insurance

401(k) Company Match

Parental Leave

Paid Holidays

Risks

Competition from similar online platforms may erode StraighterLine's market share.

Technological advancements require continuous investment, straining financial resources.

Changes in accreditation standards could affect course transferability to partner institutions.

Differentiation

StraighterLine offers affordable, self-paced courses for college credit at $99 monthly.

The company partners with over 180 institutions for seamless credit transfers.

StraighterLine's acquisition of ProSolutions Training expands its early childhood education offerings.

Upsides

Increased demand for online learning boosts StraighterLine's potential user base.

Partnership with Acadeum enhances course-sharing opportunities with other institutions.

New courses in early childhood education address workforce shortages in the sector.

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