Senior Engineering Manager - AI

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.

Read this first: Research shows that while men apply to jobs when they meet an average of 60% of the criteria, women and other marginalized groups tend to only apply when they check every box. If you think you have what it takes, but don't necessarily meet every single point on the job description, please apply. We'd love to have a chat to see what skills/experiences you are able to bring to this team.

The role: We’re looking for a delivery-focused Senior Engineering Manager to lead a cross-platform team on one of our most critical missions: building our next generation of products using AI and Agentic Workflows.. This team owns our new innovation and growth initiatives—shipping fast, solving real customer pain, and driving new customer acquisition and revenue growth. You’ll have the opportunity to lead a high-visibility team, shape how they operate, and elevate both the product and the people behind it. If you're energized by helping teams level up, improve user workflows, and thrive in fast-moving environments, this is a role where you can make a real difference.

What You'll Do:

• Drive delivery for a focused engineering team, working across multiple platforms and product areas. Partner in a high-trust triad with the team’s Product Manager and Designer to align priorities, unblock progress, and ensure consistent product success.
• Lead, coach, and develop a team of software engineers, understanding their skills and fostering their professional growth to achieve daily tasks and long-term career goals.
• Partner with Product and Design to drive customer growth through new Agentic Workflow products.
• Make continuous improvement a habit—refine team processes and retrospective practices to build team confidence, accountability, and sustainable delivery momentum.
• Identify and reduce silos in product knowledge and technical expertise while navigating day-to-day context switching
• Provide people leadership, technical and delivery coaching, and process support—empowering engineers to do their best work.
• Advocate for team needs with clarity—making tradeoffs visible, managing stakeholder expectations, and ensuring we’re resourced to deliver
• Be the key owner of AI and Agentic Workflow development knowledge within Mediafly
• Support a global engineering team with key contacts residing across North America.

You’ll be successful in this role with:

• Previous experience leading the development of AI and Agentic Workflow based products.
• Technical fluency to effectively lead engineers working across multiple stacks including Python, React and Node.JS. You know how to ask the right questions, evaluate tradeoffs, and support technical decision-making even if you're not hands-on every day.
• Enough technical depth to participate in architecture reviews, code discussions, and infrastructure planning—and enough judgment to know when to go deep and when to delegate.
• A strong belief in fast feedback loops: you champion frequent deployments and believe in shipping value regularly.
• A strong delivery and project management mindset; you identify bottlenecks early, prioritize ruthlessly, and bring data to drive decisions and maintain momentum.
• Experience modernizing systems and development workflows—especially around CI/CD pipelines, design systems, and platform architecture.
• The ability to coach engineers across technical and product silos, helping the team align around shared goals and engineering standards.
• A builder's mindset: you’re energized by complex systems, dive deep to solve problems, and scale solutions that improve quality and efficiency.
• Balance of backbone and empathy: you bring accountability and clarity while cultivating trust and psychological safety.
• A track record of hiring and growing high-performing teams.

Nice-to-Have Skills:

• Hands-on experience or working knowledge of AWS and/or Datadog, especially around infrastructure, CI/CD, or cloud-based monitoring.

Salary Range: CAD $185,000 - $215,000

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.

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.