Staff Software Engineer - AI & Fullstack

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’re looking for a Staff Software Engineer with expertise in AI-driven applications and fullstack development. In this role, you will design, build, and optimize AI-powered systems while also working on traditional fullstack development. You’ll collaborate with product, design, and infrastructure teams to deliver high-impact features and guide technical strategy.

This is an individual contributor (IC) leadership role, where you'll influence architecture, set technical direction, and get hands on with complex engineering challenges.

At Mediafly/Dooly, you’ll play a key role in shaping AI-driven workflows that power a multi-million ARR product, directly impacting thousands of users. We thrive on collaboration, innovation, and continuous growth—your ideas won’t just be heard, they’ll help drive our future.

Responsibilities of a Staff Software Engineer:

• Design, develop, and integrate AI agents into existing products.
• Train and optimize LLMs for performance, scalability, and efficiency in production environments. Conduct evaluations and perform cost-performance tradeoffs to enhance response quality and system reliability.
• Work fullstack to build scalable, observable, and maintainable web application features.
• Architect and implement APIs, databases, and cloud services to support both AI and traditional product features.
• Lead and collaborate on all portions of the SDLC including technical discovery to break down large, complex, and ambiguous problems into clear, actionable initiatives and tasks to drive successful outcomes.
• Raise the bar for code quality and engineering standards, ensuring that all solutions are robust, testable, observable, maintainable, secure, and scalable.
• Mentor engineers and provide technical guidance on best practices.

We would love to work with you if you have (required):

• Experience: 8-12+ years in software engineering, with 3-5+ years in a senior or technical leadership role.
• Technical Expertise: Deep knowledge across the stack, particularly with: Python, Node.js, React.js. You have expertise in building AI-driven systems, particularly AI Agents, AI search, and Retrieval-Augmented Generation. You have hands-on experience with vector databases, MLOps, and working alongside other engineers to bring AI products to production.
• Architectural Skills: Proven ability to design scalable, distributed, and robust systems.
• Collaboration & Communication: You excel at working across teams, and are able to translate complex technical concepts for non-technical stakeholders. You value open discussions, give and receive feedback well, and thrive in a collaborative environment.
• Curiosity & Problem-Solving: You love diving deep into complex systems, understanding how they work, and finding creative ways to improve them. Whether it's optimizing existing architecture or rethinking processes, you bring a thoughtful approach to problem-solving. You’ve likely worked on challenging tech before and enjoy the satisfaction of making things more efficient, scalable, and future-proof.
• Product Mindset: You care about more than just the code—you’re curious about the why behind what you’re building. You think about the business impact, user experience, and long-term value of your work, ensuring that technical decisions align with broader company and customer goals.
• Versatility & Leadership: You’re comfortable switching between big-picture strategy and hands-on execution. Whether you're engaging in high-level architectural discussions, exploring new opportunities, or rolling up your sleeves to debug and build, you adapt seamlessly to what the situation calls for.

Nice to haves:

• Experience with DevOps with preference for AWS

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?

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.