Senior DevOps Engineer – Azure Cloud & Migration

Description

About UpSwell

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 a team of smart, driven, and curious people who move quickly, solve problems, challenge ideas, and take pride in delivering exceptional work. We believe in giving people the opportunity to make an impact, take ownership, and grow as the business grows.

As we continue to expand, we're looking for exceptional people who bring fresh perspectives, strong technical expertise, and a genuine desire to make things better.

About the Opportunity

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.

This is a high-impact opportunity for someone who enjoys building, improving, and managing cloud environments—not simply maintaining them. You'll play a central role in migrating our existing private cloud infrastructure to Microsoft Azure, establishing a secure and scalable cloud foundation, and ensuring our systems are reliable, efficient, and positioned to support continued business growth.

Reporting directly to the CTO, you'll have significant technical ownership and the opportunity to influence our cloud architecture, infrastructure strategy, automation, security, and operational practices.

The ideal candidate combines deep Azure expertise with strong problem-solving skills, sound technical judgment, and the ability to independently drive complex initiatives from planning through execution.

We're looking for someone who can see the bigger picture, anticipate challenges, take initiative, and build solutions that support the business today while preparing us for what's next.

Key Responsibilities

Cloud Migration & Infrastructure Modernization

• •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.

Azure Cloud Management & Reliability

• •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.

Monitoring, Integrations & Security

• •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.

DevOps, Automation & Continuous Improvement

• •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.

Cloud Cost Management & Vendor Coordination

• •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.

Cross-Functional Collaboration & Technical Ownership

• •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.

Required Qualifications

• •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 participa