Senior Director of Engineering

Rare Days

21h • $200,000 - $265,000 • Remote

About The Position

The Senior Director of Engineering at Rare Days will be a strategic leader, guiding the engineering team with a balance of technical vision, operational management, and mentorship. This role is ideal for someone who can drive innovation, operationalize processes, and cultivate an environment where engineers feel empowered to create exceptional digital products. As a key member of the Engineering team, you will work closely with cross-functional peers to align the engineering direction with business objectives, ensuring the company’s growth and success in delivering high-quality products and services to clients. In this position, adaptability, strong communication skills, and a passion for both technology and people are essential. You’ll serve as a mentor to both managers and individual contributors, foster a culture of continuous improvement, and establish a high-performing, collaborative team environment. Additionally, you’ll play a critical role in representing engineering needs and achievements within leadership contexts, in client engagements, and in public forums, helping to reinforce Rare Days’ reputation as a leader in the creator economy. If you're energized by building the systems, culture, and processes that allow world-class engineers to do their best work, and you want to do it in the creator economy space, this role is for you.

Requirements

• 15+ years in software development with 6+ years in engineering leadership roles, including direct management of senior engineers or engineering leads.
• Prior experience in an agency, client services, or consultancy environment is strongly preferred. You understand what it means to deliver for clients with real stakes.
• Demonstrated track record of shipping high-quality digital products end-to-end, from early scoping through market launch.
• Experience managing and growing distributed or remote engineering teams.
• Strong proficiency across the modern web stack: React.js, Next.js, Node.js, and familiarity with PHP and GoLang.
• Solid understanding of cloud infrastructure, particularly AWS, and experience guiding DevOps and CI/CD strategy.
• Experience architecting and overseeing microservice-based and full-stack applications at scale.
• Ability to produce clear, well-reasoned architectural diagrams and technical documentation for both internal and external audiences.
• Exceptional communication skills. You can adapt your register fluidly between engineers, clients, and executives.
• Strong instincts for prioritization and a resourceful, proactive approach to how you spend your own time and your team's time.
• You care deeply about people, not just their output, but their growth, well-being, and sense of purpose at work.
• You thrive in environments where the work is varied, the pace is real, and the standards are high.
• You're comfortable with ambiguity and bring calm, structured thinking to complex or fast-moving situations.

Nice To Haves

• Comfort with mobile application development (iOS/Android or React Native) is a strong asset.
• Genuine enthusiasm for the creator economy and building products that help creators build lasting platforms is a significant plus.

Responsibilities

• Team Leadership & Development Lead, mentor, and develop a team of engineering leads, senior engineers, and managers, helping each person identify their growth trajectory and remove what's in their way.
• Build a culture of continuous learning, psychological safety, and high accountability, a place where developers come to grow.
• Establish consistent feedback loops and performance evaluation practices that are fair, timely, and developmentally focused.
• Partner with the VP of Engineering and Operations on talent planning, including recruiting, onboarding, and long-term team structure.
• Technical Strategy & Execution Own the technical quality bar across all active projects, agency client work and internal products alike, ensuring our work consistently exceeds both our standards and our clients' expectations.
• Drive architectural decisions and technical roadmap planning, with particular attention to scalability, maintainability, and delivery risk.
• Lead the development and documentation of engineering best practices, contributing to a culture of shared standards across distributed teams.
• Create and validate proofs of concept to quickly test new technical directions or de-risk key decisions on active projects.
• Operational Excellence Oversee engineering delivery across a portfolio of concurrent client engagements and product initiatives, proactively identifying and resolving blockers.
• Partner with project leads and PMs to refine scoping, estimation, and delivery processes, ensuring we scope well, commit clearly, and deliver reliably.
• Hold the team accountable to meaningful metrics: cycle time, defect rates, delivery predictability, and client satisfaction indicators.
• Champion DevOps, CI/CD, and deployment best practices to keep our infrastructure healthy and our teams shipping confidently.
• Client & Stakeholder Engagement Serve as a senior technical voice in client relationships, providing architectural guidance and instilling confidence during complex or high-stakes engagements.
• Review and contribute to statements of work (SOWs), technical proposals, and scoping documents, ensuring they reflect realistic and well-reasoned engineering commitments.
• Communicate clearly with both technical and non-technical audiences, translating complexity into clarity for clients, executives, and cross-functional peers.
• Cross-Functional Partnership Work closely with the VP of Engineering to translate company objectives into engineering priorities and org-level initiatives.
• Partner with product and design leadership to ensure engineering perspective is present early in product decisions, from discovery through delivery.
• Represent engineering needs and capacity in leadership planning conversations, advocating for sustainable pace and appropriate investment.

Benefits

• Extended health benefits for Canadian employees
• Flexible working hours and a remote-friendly culture
• Flexible time-off policy for vacation, sick days, and personal time. We actively encourage the team to use it.
• The opportunity to work with world-renowned creators and brands, including Esther Perel, Colin & Samir, Shan Boodram, and Sophia Amoruso

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed