Senior Manager, Finance Systems & Program Delivery

Build something people love

Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $125 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.

We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work.

About The Role

As Wealthsimple scales, the Controllers function, spanning across Accounting, Financial Reporting, Internal Controls, Tax, Procurement, and AP, needs someone who can be the connective tissue between what Finance needs and what our systems and engineering resources can build.

This is a hands-on program owner who gets deep into the operational reality of every Finance team, earns their trust, and translates what they need into a sequenced, evidence-based delivery plan. You're a maker-owner. You see a problem and step in. You don't wait for permission, walk past issues, or settle for how things have always been done. You push work forward and own the outcome.

You'll own the Finance systems roadmap for Controllers, drive programs from diagnosis through go-live, and advocate for the engineering and IT capacity needed to execute. You'll report to the Director, Finance Operations. While your mandate is anchored in Controllers, you will ensure FP&A and Treasury are informed and aligned on prioritization, roadmap direction, and investment decisions — so that Finance-wide systems priorities move in the same direction without duplication or conflict.

In this role you'll have the opportunity to:

The Finance systems roadmap

• Build and maintain a risk-rated, rolling 18-month roadmap across all Controllers programs — sequenced by control risk, efficiency impact, and strategic priority, not just what's loudest in the current quarter.
• Develop a consistent prioritization framework that quantifies the cost of inaction: control exposure, manual effort, audit risk, headcount cost, so that investment decisions are grounded in real data.
• Present roadmap and investment cases to Finance leadership with a clear point of view and trade-offs.

Diagnose and deliver Finance programs

• Facilitate and document discovery sessions with Controller teams to surface operational debt, process gaps, and control weaknesses.
• Diagnose operational debt across Controllers and design scalable workflows with embedded controls and automation.
• Own end-to-end program delivery from scoping through go-live, leading requirements gathering, UAT, operational rollout, training, and change management to ensure benefits are fully realized.

Bridge Finance and Engineering

• Serve as the Finance-side counterpart to Enterprise Systems (IT), consolidating and prioritizing Controller's demand into structured, well-scoped requests that Engineering and IT can act on.
• Advocate for and secure Engineering and IT capacity for Finance-critical programs, building the business case, managing the relationship, and holding delivery accountable.
• Identify automation and AI use cases across Finance workflows and work with our internal AI Builder to scope and deliver solutions.
• Keep FP&A and Treasury counterparts informed on roadmap progress and investment priorities, ensuring alignment across shared systems infrastructure.

Own the Finance tech stack

• Serve as the primary Finance owner for Controllers systems — NetSuite, Workiva, FloQast, Zip, Float, and AuditBoard — ensuring they are well-governed, fit for purpose, and continuously improving.
• Act as the point of escalation for complex Finance systems issues, providing direction and resolution.

What You'll Bring:

• Deep Finance domain knowledge — you understand how AP, procurement, month-end close, reporting, and tax processes work, and how system changes ripple across controls and financials.
• 7+ years in Finance systems, Finance operations, or program delivery — ideally in a fintech or high-growth environment with strong governance, audit readiness, and institutional reporting standards.
• Hands-on experience with enterprise Finance systems; exposure to NetSuite, Workiva, FloQast, or similar platforms is a strong asset. You don't need to be a developer — you need to know enough to ask the right questions and hold IT accountable.
• The ability to build cases that Finance leadership can stress-test, and walk into every room with a recommendation — not just a status update.
• Proven ability to earn trust across Finance teams — people come to you because they see you as the expert who understands their world and can help them solve the right problems.
• Excellent communication skills — you can translate operational detail into executive framing, strategies, ROI/trade-offs.
• CPA, PMP, or equivalent professional designation is an asset, not a requirement.

Why Wealthsimple?

🌸 Top-tier health benefits and life insurance

📈 Long-term group savings with employer match, through Wealthsimple for Business

🌴 20 vacation days, 4 wellness days, and unlimited sick and mental health days per year

✈️ 90 days away: work outside Canada for up to 90 days per year

👥 Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS

🌎 We are a hybrid team with over 1,500 employees across North America. The people are one of the best parts of working here: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.

ICYMI

Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work — whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building.

Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

Accessibility Statement: We're committed to an accessible hiring experience. If you need any accommodations throughout the interview process, please let us know — we'll work with you to make sure you have what you need. We also welcome any feedback on how we can better accommodate candidates with accessibility needs.

AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our team but don't replace human judgment – all final hiring decisions are made by people. If you have questions about how your data is used, reach out to us.

Compensation Range: CA$152K - CA$190K