Engineering Manager, Core Systems

Title: Engineering Manager, Core Systems Location: Canada

Lead the team building the foundational systems that keep Seesaw reliable, scalable, and easy for product teams to build on. 

About the Role 

Seesaw is looking for an Engineering Manager to lead our Core Systems team - the team  responsible for many of the foundational capabilities that power Seesaw and enable our product  teams to build and scale effectively.

This role sits at the intersection of engineering leadership, systems architecture, reliability, and  product delivery. You'll lead a team of experienced engineers working on systems that need to  operate reliably at significant scale while continuing to evolve as Seesaw grows into new markets,  customer segments, and product capabilities.

We're looking for a manager who is comfortable operating in technically complex areas, can help  engineers make good architectural decisions, and knows how to turn long-term platform  investments into incremental, measurable progress.

You won't need to be the person writing every design document or solving every technical  problem - but you should be technically strong enough to ask the right questions, challenge  assumptions, understand tradeoffs, and help the team navigate difficult engineering decisions.

What You'll Do 

Lead and grow a strong engineering team 

• Manage, coach, and develop a team of software engineers working on critical shared systems.
• Build a high-performing team with clear expectations around ownership, technical quality,  collaboration, and delivery.
• Help engineers grow their technical and leadership capabilities through regular feedback, coaching, and thoughtful assignment of responsibilities.
• Partner with engineering leadership on hiring, organizational planning, and building the  capabilities the team will need over time.

Own critical systems and technical outcomes 

• Provide leadership for foundational systems that support Seesaw's products and engineering  organization.
• Work with senior and staff engineers to establish clear architectural direction and make thoughtful  technical tradeoffs.
• Ensure systems are designed for reliability, scalability, security, maintainability, and operational  simplicity.
• Balance improvements to existing systems with investments in longer-term architecture and  platform capabilities.
• Drive down unnecessary complexity, operational burden, and recurring technical debt.

Deliver meaningful platform improvements 

• Translate broad technical and business goals into clear, executable engineering plans.
• Break large architectural initiatives into incremental milestones that create value along the way.
• Establish clear ownership, priorities, success measures, and decision points for the team.
• Identify execution risks early and work across teams to resolve dependencies and blockers.
• Create enough structure and predictability for stakeholders without introducing unnecessary  process.

Make other engineering teams more effective 

• Treat internal engineering teams as important customers of Core Systems.
• Build APIs, services, tools, and platform capabilities that make it easier for product teams to move  quickly and safely.
• Partner closely with product engineering teams to understand recurring pain points and identify  opportunities for shared solutions.
• Establish clear boundaries and ownership between shared platform capabilities and product specific functionality.

Operate critical systems well 

• Build a strong operational culture around the systems the team owns.
• Use observability, incidents, capacity planning, and production data to continuously improve  reliability.
• Lead thoughtful incident reviews and ensure the team addresses systemic issues rather than simply  fixing symptoms.
• Help the team make pragmatic decisions about reliability and resilience based on customer and  business impact.

What We're Looking For 

• Experience managing software engineering teams responsible for complex production systems.
• A strong software engineering background and the technical depth to participate meaningfully in  architecture and system-design discussions.
• Experience designing, operating, or leading teams responsible for distributed systems, backend  services, shared platforms, or similarly foundational technology.
• A track record of delivering significant technical initiatives involving multiple systems or  engineering teams.
• Strong judgment about when to invest in architecture and when a simpler solution is the right  answer.
• Experience building systems where reliability, scalability, security, and operational quality matter.
• Ability to communicate complex technical topics clearly to both engineers and non-technical  stakeholders.
• Strong people-management skills, including coaching experienced engineers and creating clear  accountability without micromanagement.
• Comfort operating in environments where the path is not always obvious and technical decisions  involve meaningful tradeoffs.

Nice to Have 

• Experience operating large-scale cloud systems, particularly in AWS.
• Experience with distributed data systems, service-oriented architectures, or high-scale backend  platforms.
• Experience evolving mature systems while maintaining high availability for customers.
• Experience with multi-region, multi-tenant, or data-residency architectures.
• Experience building internal platforms or shared capabilities used by multiple product engineering  teams.
• Experience working in SaaS, education technology, or another environment with significant  security and privacy requirements.

How We Think About Success 

In your first year, success in this role will look like:

• The team has clear ownership, priorities, and technical direction.
• Engineers on the team are growing and operating with increasing autonomy.
• Core systems are becoming more reliable, understandable, and easier to evolve.
• Major architectural investments are progressing through pragmatic, incremental delivery rather  than large open-ended rewrites.
• Product engineering teams can move faster because foundational capabilities are easier to use and  better supported.
• Engineering leadership has clear visibility into the health, risks, and long-term direction of the  systems the team owns.