Senior Manager, Finance Systems & Program Delivery

Wealthsimple Technologies • ,

4d • Hybrid

About The Position

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.

Requirements

• 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.

Nice To Haves

• CPA, PMP, or equivalent professional designation is an asset, not a requirement.

Responsibilities

• 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.
• 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.
• 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.
• 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.

Benefits

• 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
• Work outside Canada for up to 90 days per year
• Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS

What This Job Offers

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