<p>Location: Remote - Canada</p><br/><p>Employment Type: Full-time</p><br/><p>Team: Engineering</p><br/><div><b style="font-size: 16px">Who we are:</b></div><div><span style="font-size: 16px;">At Mediafly, we help the world’s top revenue teams work smarter and achieve measurable impact. Our platform brings together sales enablement, content, and performance insights so sellers have the coaching, tools, and intelligence they need to succeed. By weaving value selling into every workflow, we empower teams to accelerate deal cycles, boost win rates, and prove ROI.</span></div><div><br></div><div><span style="font-size: 16px;">For you, that means joining a company where innovation meets purpose—where your work helps businesses deliver more meaningful buyer experiences and drives results that truly matter. You’ll be part of a collaborative, growth-focused team that values expertise, creativity, and human connection.</span></div><div><br></div><div><span style="font-size: 16px;">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.</span></div><div><br></div><div><span style="font-size: 16px;">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.</span></div><div><br></div><div><span style="font-size: 16px;">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.</span></div><div><br></div><div><b style="font-size: 18px;">Why Join Us?</b></div><div><span style="font-size: 16px;">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.</span></div><h3>What You’ll Do</h3><br/><ul><li>Ensure infrastructure uptime, resilience, and observability across core platforms</li><li>Lead initiatives to address penetration test findings and remediate risks in a timely manner to protect customer trust and enable sales/renewals</li><li>Partner with security and compliance teams to align infrastructure with SOC 2, ISO, and customer privacy requirements</li><li>Manage and optimize AWS and Azure spend, including savings plans, reserved instances, and account-level discount strategies</li><li>Drive infrastructure upgrades, migrations, and improvements with minimal downtime</li><li>Improve developer experience by strengthening observability, deployment pipelines, and alerting systems</li><li>Provide technical leadership on cloud architecture, DevOps practices, and roadmap decisions affecting the broader engineering organization</li><li>Enable other engineers to own day-to-day DevOps tasks by improving tooling, documentation, and processes</li><li>Coach and mentor engineers to build stronger cloud, DevOps, and infrastructure expertise across the team</li><li>Participate in the on-call rotation to support uptime and operational excellence</li></ul><br/><h3>We would love to work with you if you have:</h3><br/><ul><li>Deep experience with AWS (required) and Azure (preferred) cloud environments</li><li>Strong background in cloud cost management and optimization strategies</li><li>Hands-on expertise with infrastructure-as-code (e.g., Terraform, CloudFormation, Pulumi)</li><li>Track record of maintaining and upgrading infrastructure while minimizing downtime</li><li>Experience improving developer experience through observability, CI/CD pipelines, and alerting practices</li><li>Familiarity with containerized environments (Docker, Kubernetes)</li><li>Strong grasp of IAM, networking, and cloud security best practices</li><li>Demonstrated ability to lead cross-team, strategic initiatives and mentor other engineers</li></ul><br/><h3>Additional preferred skills:</h3><br/><ul><li>Experience with FinOps frameworks or formalized cost optimization practices</li><li>Background in compliance-driven environments (SOC 2, ISO 27001, GDPR)</li><li>Exposure to multi-cloud and hybrid strategies</li><li>Knowledge of data infrastructure cost and performance optimization</li></ul><br/><h3>What success looks like:</h3><br/><ul><li>Penetration test and audit findings are remediated quickly, reducing SOC exceptions and enabling smooth renewals and sales cycles</li><li>AWS spend is stable, predictable, and optimized through proactive discount and rightsizing strategies</li><li>Infrastructure is resilient and secure, with measurable improvements in uptime and incident reduction</li><li>Developer experience improves through better deployment pipelines, observability, and alerting, enabling faster, safer delivery</li><li>Engineering teams maintain velocity by spending less time on cloud operations and more on feature delivery</li></ul><br/><div><b style="font-size: 18px;">Location and Work Setup</b></div><div><span style="font-size: 16px;">This is a </span><b style="font-size: 16px;">100% remote position</b><span style="font-size: 16px;"> with a collaborative team that values flexibility and trust. We use modern communication and collaboration tools to stay connected and productive across time zones.</span></div><div><br></div><div><span style="font-size: 16px;">Ready to make an impact on a product that matters? Apply today and help us build the next generation of our platform!</span></div><div><br></div><div><br></div><div><b style="font-size: 18px;">Why Mediafly/Dooly?</b></div><div><span style="font-size: 16px;">Remote based in Canada</span></div><div><span style="font-size: 16px;">Flexible working hours</span></div><div><span style="font-size: 16px;">Generous Paid Time Off</span></div><div><span style="font-size: 16px;">Competitive Salary</span></div><div><span style="font-size: 16px;">Health Benefits</span></div><div><span style="font-size: 16px;">Transparent Career Paths</span></div><div><span style="font-size: 16px;">Generous Paid Parental Leave</span></div><div><span style="font-size: 16px;">Remote Stipend</span></div><div><br></div><div><span style="font-size: 16px">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.</span></div><div><br></div><div><span style="font-size: 16px">Thanks to our commitment to employee experience, Mediafly has been recognized as a Best Place to Work from Crain's, Inc. and BuiltIn.</span></div><div><br></div><div><span style="font-size: 16px">Mediafly's HQ is based in Chicago, IL.</span></div>

Location: Remote - Canada

  

Employment Type: Full-time

  

Team: Engineering

  

 **Who we are:**

At Mediafly, we help the world’s top revenue teams work smarter and achieve
measurable impact. Our platform brings together sales enablement, content, and
performance insights so sellers have the coaching, tools, and intelligence
they need to succeed. By weaving value selling into every workflow, we empower
teams to accelerate deal cycles, boost win rates, and prove ROI.

  

For you, that means joining a company where innovation meets purpose—where
your work helps businesses deliver more meaningful buyer experiences and
drives results that truly matter. You’ll be part of a collaborative, growth-
focused team that values expertise, creativity, and human connection.

  

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.

