Lead DevOps Engineer

Retail Success is seeking a Lead DevOps Engineer to join our team in Overland Park, KS. This position is responsible for leading and supporting critical infrastructure initiatives, including observability, CI/CD development, and large-scale migration of on-premises systems to AWS. The ideal candidate is a hands-on professional who can partner across engineering teams, establish best practices, and ensure reliable, scalable, and cost-effective infrastructure.

Retail Success is a business-to-business FinTech company based in Overland Park, Kansas. From marketing and loyalty to eCommerce and payments, our software solutions give retailers the power to connect and sell to the world. Our robust solutions include Retail Success custom software solutions, Wayroo, and Freedom Software.

Why is this a great opportunity for you?

• Big things are happening at Retail Success – we recently expanded our development team to power up our platform and expand our market reach.
• If you enjoy rolling up your sleeves and tackling complex infrastructure challenges, this is a great role for you.
• In addition to our fun and collaborative work culture, we offer comprehensive health, dental, vision, disability, life insurance, 401(k), and Paid Time Off.

What Success Looks Like:

• Reliable, scalable infrastructure with clear observability and alerting
• Smooth, low-disruption migration of on-prem systems to AWS
• Well-defined standards and processes adopted across engineering teams
• Cost-efficient infrastructure aligned with business goals

Work Location:

• This role follows a hybrid schedule (3 days in the office, 2 days remote) based in our Overland Park, KS office. Candidates must live in the Kansas City metro area or be willing to relocate.

Required Qualifications:

• Bachelor’s degree in related field
• Minimum 5-7 years related work experience
• Experience supporting or leading on-premises to AWS migrations
• Familiarity with AWS migration tools such as MGN and DMS or comparable technologies
• Experience working with CI/CD pipelines and modern infrastructure tooling
• Understanding of infrastructure-as-code principles and cloud architecture best practices

This is a W-2 position. Applicants must have work authorization that does not now or in the future require sponsorship for employment authorization (such as an H-1B, O-1, or other employment-based visa) to continue working in the United States.

Preferred Qualifications

• Experience with observability tools and practices (monitoring, logging, alerting frameworks)
• Familiarity with data infrastructure platforms and orchestration tools
• Ability to collaborate cross-functionally with engineering and leadership teams
• Experience mentoring or supporting junior team members

Responsibilities:

• Establish and own observability practices, including metrics, logging, alerting, and on-call runbooks
• Partner with engineering teams to define infrastructure-as-code standards and contribute to architectural decisions
• Mentor and guide junior engineers on platform and infrastructure best practices
• Design, build, and maintain CI/CD pipelines using tools such as GitHub Actions, AWS CodePipeline, or similar
• Build and operate the data infrastructure layer, including pipeline tooling, storage systems, and orchestration platforms
• Lead end-to-end migration of on-premises workloads to AWS, including scoping, planning, sequencing, and execution with minimal production disruption
• Define and manage migration runbooks, cutover plans, and rollback procedures for datacenter services
• Inventory existing on-premises infrastructure and map dependencies to inform migration sequencing and risk assessment
• Execute or support lift-and-shift migrations using AWS migration tools such as Application Migration Service (MGN), Database Migration Service (DMS), or equivalent
• Proactively manage cost optimization across cloud and physical infrastructure
• Participate in mid- and long-term capital planning initiatives

Retail Success, LLC is committed to the principles of Equal Employment Opportunity. We believe our continued success depends on the full and effective utilization of qualified persons without regard to race, color, creed, religion, national origin, sex, age, disability, veteran or any other classifications protected by applicable laws.

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Employee assistance program
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Vision insurance

Application Question(s):

• Will you now or in the future require sponsorship for employment authorization (such as an H-1B, O-1, or other employment-based visa) to continue working in the United States?
• Are you willing to undergo a background check in accordance with applicable laws and regulations?
• In which U.S. City and State do you currently reside?
• Are you able to commute to our Overland Park, Kansas office?
• If you are not based in the Kansas City metro area, would you be willing to relocate without relocation assistance?
• What is your desired salary range?
• Do you have a minimum of 5-7 years related work experience?
• Do you have experience supporting or leading on-premises to AWS migrations?
• Do you have familiarity with AWS migration tools such as MGN and DMS or comparable technologies?
• Do you have experience working with CI/CD pipelines and modern infrastructure tooling?
• Do you have an understanding of infrastructure-as-code principles and cloud architecture best practices?

Education:

• Bachelor's (Required)

Work Location: Hybrid remote in Overland Park, KS 66210