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 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.

We're looking for an experienced, hands-on Senior Dev Ops 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.

• 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…