6-Month Contract | Potential Full-Time Opportunity | Remote (US)

Engagement: Six-month contract, approximately 40 hours per week, with potential extension or conversion to permanent employment

Location: Remote, United States, with substantial Eastern Time business-hour overlap

Start: As soon as possible

We're looking for a highly experienced, hands-on DevSecOps / AWS Platform Engineer to help strengthen and modernize our cloud infrastructure, application security, and development operations.

This engagement encompasses two major initiatives: improving our cloud and application security infrastructure and migrating business-critical legacy systems into AWS.

You'll work closely with our engineering and technology leadership teams, with significant autonomy to recommend solutions, make technical decisions, and implement improvements.

This is not a purely advisory or architectural role. We want an engineer who enjoys designing solutions, writing code, automating infrastructure, and delivering working systems.

While initially structured as a six-month contract, we're building a long-term internal technology capability, and the right candidate may have an opportunity to transition into a permanent position.

RequirementsCloud & Application Security

• Evaluate and strengthen application and AWS security, including identity, authorization, data protection, and infrastructure controls.
• Implement automated security monitoring, vulnerability management, and incident response capabilities.
• Embed security practices into our development workflows without unnecessarily slowing delivery.

AWS Infrastructure & Migration

• Lead the technical migration of legacy production workloads into -managed AWS environments.
• Design secure, reliable, cost-effective AWS infrastructure supporting modern applications and traditional business systems.
• Implement infrastructure as code, backup and recovery, monitoring, and operational automation.
• Coordinate migration testing, validation, cutover, and stabilization with internal stakeholders.

DevOps & Platform Engineering

• Improve CI/CD pipelines, deployment automation, and environment management.
• Integrate security scanning and automated safeguards into development workflows.
• Establish practical infrastructure standards and reusable deployment patterns.
• Support cloud infrastructure needs for applications incorporating generative AI and agentic workflows.
• Document architecture, operating procedures, and technical decisions so our internal team can maintain and evolve the environment.

QualificationsRequired:

• 4+ years of hands-on experience in DevOps, cloud infrastructure, platform engineering, SRE, or related disciplines.
• Strong AWS expertise, including networking, compute, databases, IAM, security, monitoring, and infrastructure architecture.
• Demonstrated experience migrating production workloads from legacy or third-party environments into AWS, preferably including Windows-based applications.
• Practical experience implementing application and cloud security controls.
• Proficiency with infrastructure as code, such as Terraform or AWS CDK.
• Experience with GitHub Actions or comparable CI/CD systems, automated security scanning, and deployment automation.
• Strong understanding of backup, disaster recovery, production monitoring, and incident response.
• Ability to work independently, communicate clearly, and collaborate with a small, fast-moving engineering team.

Especially Valuable, Preferred:

• Experience with multi-tenant SaaS platforms.
• Amazon Bedrock, AgentCore, or other AI infrastructure.
• Secure development practices involving AI coding tools.
• Financial application or legacy enterprise system migrations.
• PCI DSS or SOC 2 readiness experience.
• Experience balancing security, reliability, infrastructure costs, and rapid product delivery.

What Makes This Opportunity Different

We're a product-driven company making a substantial investment in technology. Our engineering team is small, entrepreneurial, and actively embracing AI-assisted development.

You'll have the opportunity to:

• Own meaningful technical initiatives from design through production.
• Work directly with decision-makers with minimal bureaucracy.
• Influence the architecture and operational foundations of a growing technology platform.
• Build automated systems and guardrails that make engineers more productive.
• Potentially grow into a permanent role as our technology organization expands.

We value practical problem-solvers who favor thoughtful, maintainable solutions over unnecessary complexity.

What Success Looks Like

At the end of the initial engagement, we expect to have materially improved our security posture, modernized important AWS infrastructure, advanced or completed our priority migrations, and established more consistent and efficient deployment and operating practices.

Just as importantly, the systems and processes you build should be well-documented, maintainable, and ready for our internal team to operate.

How to Apply

Please submit your resume and a brief description of one or two relevant projects you've personally led, particularly involving AWS migration, cloud security, or DevOps automation.

We're especially interested in candidates who can demonstrate hands-on ownership of complex production environments and sound engineering judgment.

About

Travel Group is a growing travel technology and services company serving thousands of independent travel advisors, travel entrepreneurs, and corporate travel clients.

We're investing heavily in our next generation of technology, including an integrated advisor operating platform, consumer travel applications, and AIVIA, our AI-powered workspace.

Our technology strategy centers on AWS, modern software development, automation, and AI. We're building a platform designed to transform how travel professionals operate their businesses.