Who 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.
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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
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$140,000 - $200,000 a year
At Mediafly/Dooly, we believe that pay transparency is essential to building
trust, promoting fairness, and driving equity in the workplace. By openly
sharing salary ranges in our job postings, we aim to empower candidates with
clear expectations and ensure that all employees are valued for their
contributions. This commitment reflects our dedication to fostering an inclusive
culture where everyone has access to opportunity and growth. We believe that
transparency not only strengthens our hiring process but also reinforces our
core values of integrity, accountability, and respect.
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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.
We have over 100 employees located globally. 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.
