Canada onlyWho we are:
Mediafly is the leading revenue enablement platform market-facing teams use to plan, predict, coach, and engage at the highest levels. Our unified suite of solutions create immersive buyer experiences; enable sellers to lead with value, allow managers to scale coaching, and empower leaders to forecast with confidence. In today’s unpredictable market, Mediafly is the key to delivering predictable efficient growth.
We are seeking a Staff Software Engineer to take ownership of our cloud infrastructure. This is a senior individual contributor role with broad scope and impact. You will ensure our infrastructure remains secure, resilient, and efficient by leading initiatives in uptime, compliance, developer experience, and cost optimization.
Your work will directly address critical business needs: maintaining uptime, passing penetration tests and audits, managing and evolving our infrastructure, improving developer experience, and optimizing cloud spend.
This role is both technical and strategic: you’ll lead complex cross-cutting initiatives, guide long-term architectural decisions, and roll up your sleeves to implement solutions. As part of the team, you will also participate in the on-call rotation to ensure reliability and responsiveness.
Why Join Us?
This is your opportunity to make a significant impact in a small team supporting a product line with multi-million dollar annual recurring revenue. We're at an exciting inflection point—after years of rapid development on our legacy codebase, we're now focused on strengthening our foundation while continuing to deliver value. You'll help shape the future of our platform by building a foundation rooted in technical excellence.
What You’ll Do
- Ensure infrastructure uptime, resilience, and observability across core platforms
- Lead initiatives to address penetration test findings and remediate risks in a timely manner to protect customer trust and enable sales/renewals
- Partner with security and compliance teams to align infrastructure with SOC 2, ISO, and customer privacy requirements
- Manage and optimize AWS and Azure spend, including savings plans, reserved instances, and account-level discount strategies
- Drive infrastructure upgrades, migrations, and improvements with minimal downtime
- Improve developer experience by strengthening observability, deployment pipelines, and alerting systems
- Provide technical leadership on cloud architecture, DevOps practices, and roadmap decisions affecting the broader engineering organization
- Enable other engineers to own day-to-day DevOps tasks by improving tooling, documentation, and processes
- Coach and mentor engineers to build stronger cloud, DevOps, and infrastructure expertise across the team
- Participate in the on-call rotation to support uptime and operational excellence
We would love to work with you if you have:
- Deep experience with AWS (required) and Azure (preferred) cloud environments
- Strong background in cloud cost management and optimization strategies
- Hands-on expertise with infrastructure-as-code (e.g., Terraform, CloudFormation, Pulumi)
- Track record of maintaining and upgrading infrastructure while minimizing downtime
- Experience improving developer experience through observability, CI/CD pipelines, and alerting practices
- Familiarity with containerized environments (Docker, Kubernetes)
- Strong grasp of IAM, networking, and cloud security best practices
- Demonstrated ability to lead cross-team, strategic initiatives and mentor other engineers
Additional preferred skills:
- Experience with FinOps frameworks or formalized cost optimization practices
- Background in compliance-driven environments (SOC 2, ISO 27001, GDPR)
- Exposure to multi-cloud and hybrid strategies
- Knowledge of data infrastructure cost and performance optimization
What success looks like:
- Penetration test and audit findings are remediated quickly, reducing SOC exceptions and enabling smooth renewals and sales cycles
- AWS spend is stable, predictable, and optimized through proactive discount and rightsizing strategies
- Infrastructure is resilient and secure, with measurable improvements in uptime and incident reduction
- Developer experience improves through better deployment pipelines, observability, and alerting, enabling faster, safer delivery
- Engineering teams maintain velocity by spending less time on cloud operations and more on feature delivery
Location and Work Setup
This is a 100% remote position with a collaborative team that values flexibility and trust. We use modern communication and collaboration tools to stay connected and productive across time zones.
Ready to make an impact on a product that matters? Apply today and help us build the next generation of our platform!
Why Mediafly/Dooly?
Remote based in Canada
Flexible working hours
Generous Paid Time Off
Competitive Salary
Health Benefits
Transparent Career Paths
Generous Paid Parental Leave
Remote Stipend
Mediafly is an equal opportunity employer, which means we do not discriminate on the basis of race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome people of different backgrounds, experiences, abilities and perspectives and encourage all interested individuals to apply.
Thanks to our commitment to employee experience, Mediafly has been recognized as a Best Place to Work from Crain's, Inc. and BuiltIn.
Mediafly's HQ is based in Chicago, IL.
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