Senior DevOps Engineer – Azure Cloud & Migration

Description

UpSwell is a fast-growing marketing agency helping businesses across the country grow through innovative direct mail and digital marketing solutions. As a five-time Best and Brightest Company to Work For, we're proud of the talented people, collaborative culture, and entrepreneurial spirit that make UpSwell a great place to build a career.

We're looking for an experienced, hands-on Senior DevOps Engineer to take ownership of our Microsoft Azure cloud environment and lead a critical infrastructure modernization initiative.

• Lead the end-to-end migration of UpSwell's private cloud infrastructure to Microsoft Azure, targeting completion within the first six months.
• Assess existing infrastructure, applications, databases, networks, and dependencies to develop a comprehensive migration strategy.
• Design and implement a secure, scalable Azure architecture aligned with Microsoft best practices.
• Develop and execute phased migration plans, including testing, cutover strategies, contingency planning, and post-migration validation.
• Minimize business disruption while ensuring data integrity, system availability, and operational continuity.
• Coordinate with external migration partners, vendors, and internal stakeholders throughout the project.
• Identify opportunities to consolidate infrastructure, eliminate unnecessary costs, and improve overall system performance.

• Own the day-to-day administration, performance, availability, and reliability of the Microsoft Azure environment.
• Manage Azure infrastructure, including virtual machines, networking, storage, databases, application services, and related cloud resources.
• Establish and maintain monitoring, alerting, backup, disaster recovery, and business continuity processes.
• Proactively identify performance issues, infrastructure risks, and opportunities to improve system reliability.
• Maintain appropriate service-level objectives, recovery procedures, and operational documentation.
• Lead troubleshooting and resolution of infrastructure incidents, including participation in on-call support.

• Implement comprehensive monitoring and visibility across Azure resources, applications, and API integrations.
• Manage and monitor API connectivity, performance, errors, and security using Azure API Management and related tools.
• Utilize Azure Monitor, Log Analytics, Application Insights, and other observability tools to identify issues and improve performance.
• Maintain secure identity and access management practices using Microsoft Entra ID, RBAC, and other Azure security capabilities.
• Implement cloud security best practices, including vulnerability management, access controls, secrets management, and security monitoring.
• Partner with internal teams and external providers to investigate and resolve security concerns.
• Support applicable security, compliance, and audit requirements.

• Design, implement, and maintain CI/CD pipelines using Azure DevOps and/or GitHub Actions.
• Build and manage infrastructure as code using Terraform, Bicep, or similar technologies.
• Automate infrastructure provisioning, deployments, monitoring, and routine operational tasks.
• Support containerization and orchestration technologies, including Docker and Azure Kubernetes Service, as appropriate.
• Identify opportunities to reduce manual processes, improve deployment reliability, and accelerate development workflows.
• Establish scalable technical standards, documentation, and operational best practices.

• Monitor and manage Azure cloud spending, ensuring resources are utilized efficiently.
• Identify opportunities for cost optimization through resource right-sizing, automation, reserved capacity, and other cloud management strategies.
• Develop cloud cost reporting, forecasts, and recommendations for leadership.
• Manage relationships with Microsoft, cloud service providers, migration partners, and external technical vendors.
• Evaluate new technologies and recommend improvements that support business needs and long-term scalability.

• Serve as the primary technical owner of UpSwell's Azure environment.
• Partner closely with the CTO, development teams, IT, security, and business stakeholders to align infrastructure capabilities with organizational priorities.
• Communicate project progress, technical risks, and recommendations clearly to both technical and nontechnical audiences.
• Maintain accurate architecture documentation, system inventories, operational procedures, and recovery plans.
• Take ownership of technical challenges, proactively identify solutions, and follow through to successful resolution.

Requirements

We are looking for a technically strong, resourceful engineer who enjoys solving complex problems and takes pride in building reliable, secure, and efficient cloud environments.

• Bachelor's degree in Computer Science, Information Technology, Engineering, or a related field, or equivalent practical experience.
• 6+ years of experience in cloud infrastructure, DevOps, systems engineering, or site reliability engineering.
• At least 3 years of hands-on experience designing, implementing, and managing Microsoft Azure environments.
• Demonstrated experience leading or playing a significant technical role in an on-premises or private cloud migration to Azure or another major public cloud platform.
• Strong understanding of Azure networking, compute, storage, databases, identity management, and security.
• Hands-on experience with infrastructure as code, preferably Terraform or Bicep.
• Experience building and maintaining CI/CD pipelines using Azure DevOps or GitHub Actions.
• Strong experience with Azure monitoring, logging, troubleshooting, and performance optimization.
• Working knowledge of API management, integrations, and cloud security best practices.
• Proficiency in PowerShell and experience with Python, Bash, or similar scripting languages.
• Experience with cloud cost management and infrastructure optimization.
• Strong analytical, troubleshooting, communication, and organizational skills.
• Ability to independently manage priorities, make sound technical decisions, and deliver projects in a fast-paced environment.
• Ability to participate in an on-call support rotation.

• Microsoft Azure certifications, including Azure Solutions Architect Expert, DevOps Engineer Expert, or Azure Administrator Associate.
• Experience with Azure Migrate, Azure Site Recovery, and database migration technologies.
• Experience with Docker, Kubernetes, and Azure Kubernetes Service.
• Familiarity with Microsoft Defender for Cloud, Microsoft Sentinel, and Azure Policy.
• Experience supporting SOC 2, ISO 27001, or similar security and compliance frameworks.
• Experience managing external migration partners, cloud vendors, or managed service providers.
• Experience supporting cloud infrastructure in a growing, multi-location organization.

• You take ownership. You're comfortable being accountable for the environment you manage and following through from planning to execution.
• You're a problem solver. You enjoy tackling complex technical challenges, identifying root causes, and developing practical solutions.
• You think strategically and execute hands-on. You can design the right solution and roll up your sleeves to implement it.
• You're proactive. You anticipate potential issues, identify opportunities for improvement, and take action before problems escalate.
• You value security and reliability. You understand the importance of building infrastructure that is stable, secure, and scalable.
• You communicate effectively. You can explain technical decisions, risks, and recommendations in a way that makes sense to different audiences.
• You're always learning. You stay current with emerging cloud technologies and continuously look for smarter ways to work.

UpSwell is proud to be an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or any other legally protected status.