Sr Manager Software Development, Delivery & AI Platform

Wealthsimple

20d • Remote

About The Position

Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing, opaque and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with over 3+ million users who trust us with more than $100 billion in assets.

Our teams ship often and make an impact with groundbreaking ideas. We're looking for talented people who keep it simple and value collaboration and humility as we continue to create inclusive and high-performing teams where people can be inspired to do their best work.

Platform Engineering at Wealthsimple builds the foundational systems, tools, and infrastructure that enable our engineering organization to deliver secure, reliable software at scale. We treat our platforms as products, with our internal engineering teams as our customers. Our mission is to accelerate development velocity, improve system reliability, and create an exceptional developer experience across the organization.

As a Senior Manager, Software Development in Platform Engineering, you'll lead two critical areas: the Delivery Platform team, which owns the complete deployment lifecycle from code commit through production, and a new Platform AI Foundations team that will enable Wealthsimple's AI capabilities. You'll be responsible for scaling these teams, defining technical strategy, and shaping how hundreds of engineers build and ship software.

In this role you'll have the opportunity to:
Lead and scale multiple high-performing teams. Manage 8-12+ engineers across two platform teams, including Engineering Managers and Staff+ engineers who provide technical and team leadership. You'll be responsible for developing leaders, building organizational capability, and creating an environment where engineers at all levels can do their best work. You'll drive hiring strategy and build a culture of technical excellence, collaboration, and continuous improvement across both teams.
Build the Platform AI Foundations team from the ground up. Define the mission, strategy, and roadmap for a new team that will enable AI capabilities across Wealthsimple. You'll recruit the initial team members and leaders, establish the team's technical direction, and partner with stakeholders across engineering, product, security, and compliance to shape how Wealthsimple builds with AI responsibly and at scale.
Scale the Delivery Platform team and capabilities. Lead the evolution of our deployment infrastructure to support a rapidly growing engineering organization. You'll drive improvements in deployment velocity, reliability, and consistency while ensuring the team can sustainably operate critical CI/CD systems, progressive delivery capabilities, and deployment observability that hundreds of engineers depend on daily.
Define and execute platform engineering strategy. Partner with senior engineering leadership to set the technical vision and roadmap for platform capabilities at Wealthsimple. You'll make strategic decisions about technology investments, prioritization across teams, and how platform engineering supports the company's broader technical strategy and 2026 reliability mission.
Drive operational excellence and delivery at scale. Establish metrics, processes, and practices that ensure your teams deliver reliably and predictably. You'll balance competing priorities across stakeholders, manage complex dependencies, and ensure both teams operate with clarity on goals, impact, and success criteria.
Influence engineering culture and standards. Shape engineering practices, technical standards, and ways of working beyond your immediate teams. You'll partner with peer Senior Managers, Directors, and VPs to drive platform adoption, improve engineering efficiency, and build best practices that scale across the entire engineering organization.
Build strategic partnerships across the organization. Work closely with product, security, compliance, data science, and other engineering teams to understand needs, align roadmaps, and deliver platform capabilities that enable their success. Your work will require strong cross-functional relationships and the ability to influence outcomes across organizational boundaries.

Requirements

• 10+ years of experience in software engineering, with deep expertise in platform engineering, DevOps, CI/CD, infrastructure, or site reliability engineering. You have strong technical credibility and understand what it takes to build systems that support engineering organizations at scale.
• 5+ years of engineering management experience, including managing other Engineering Managers or senior technical leaders. You have a proven track record of building and scaling teams, developing engineering talent at all levels, and delivering complex technical initiatives across multiple teams. You know how to hire and grow strong engineering leaders.
• Exceptional people leadership skills. You're passionate about developing engineering careers, building inclusive teams, and creating environments where people thrive. You excel at providing clear feedback, managing performance, navigating organizational dynamics, and building trust with teams and leadership alike.
• Strategic thinking and execution. You can define technical vision and strategy while ensuring teams execute effectively. You balance short-term delivery with long-term platform investments, make thoughtful trade-offs under uncertainty, and adapt plans as context evolves.
• Deep platform engineering expertise. You have hands-on experience with modern deployment technologies (Kubernetes, GitOps, progressive delivery), CI/CD infrastructure at scale, observability platforms, and building internal tools that serve hundreds of engineers. You can engage deeply in technical discussions and guide teams through complex architectural decisions.
• AI curiosity and platform mindset. While deep AI/ML expertise isn't required, you're genuinely curious about AI technologies and excited to learn how to enable AI capabilities responsibly at scale. You understand how to treat internal platforms as products with clear metrics, user feedback loops, and measurable impact.
• Proven ability to build teams from scratch. You've successfully hired, structured, and launched new teams or capabilities. You know how to define a team's mission, recruit strong talent, establish processes, and deliver value quickly while building for the long term.
• Operational excellence and data-driven decision making. You establish effective processes, measure what matters, and use data to drive improvements. You're skilled at managing multiple priorities, coordinating across stakeholders, and ensuring teams deliver reliably and sustainably.
• Influence and communication. You build strong relationships with senior leadership, peer managers, and cross-functional partners. You can communicate technical concepts clearly to diverse audiences, influence decisions without direct authority, and drive alignment across complex organizations.

Responsibilities

• Lead and scale multiple high-performing teams.
• Build the Platform AI Foundations team from the ground up.
• Scale the Delivery Platform team and capabilities.
• Define and execute platform engineering strategy.
• Drive operational excellence and delivery at scale.
• Influence engineering culture and standards.
• Build strategic partnerships across the organization.

Benefits

• Competitive salary
• Retirement savings matching plan using Wealthsimple for Business
• Generous PTO offerings
• A wide variety of peer and company-led Employee Resource Groups (ie. Rainbow, Women of Wealthsimple, Black @ WS)

What This Job Offers

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