Manager, Brokerage Tax Operations

Toronto or Remote (Canada)

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Wealthsimple is the simple way to grow your money like the world's most sophisticated investors. No-maintenance portfolios, expert investment advisers and low fees.

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Wealthsimple is on a mission to help everyone achieve financial freedom, no matter who they are or how much they have. Using smart technology, Wealthsimple takes financial services that are often confusing, opaque and expensive and makes them simple, transparent, and low-cost. We're the company behind some of Canada's leading digital financial products, and are growing faster than ever.
Our team is reimagining what it means to manage your money. Smart, high-performing team members will challenge you to learn and grow every day. We value great work and great ideas — not ego. We're looking for talented people who love a fast-paced environment, and want to ship often and make an impact with groundbreaking ideas.
We’re a remote-first team and output is more important than face time, so where you choose to work is up to you — as long as you have internet access, you can work from anywhere in Canada. Be a part of our Canadian success story and help shape the financial future of millions — join us! Read our Culture Manual and learn more about how we work.
Wealthsimple Core Services (WS Core) is the business unit that provides the back-end technology, operations and platformthat powers Wealthsimple’s products. It originated as a brokerage and continues to expand to deliver a wider breadth offinancial services to our clients.

In this role, you will:

  • Enable accurate & reliable tax reporting to all stakeholders:
  • Project manage and execute a cross-functional roadmap to scale Wealthsimple’s brokerage tax operations as we grow
  • Partner with Engineering and Product on prioritization of initiatives, balancing ‘quick wins' and longer term goals/objectives
  • Lead seamless, cross-functional execution throughout each tax season:
  • Deliver all tax reporting on or before stated deadlines with 99.99% accuracy
  • Create a scalable process for investigating and solving all client-related tax questions
  • Oversee communications and submissions to government agencies
  • Build and lead a lean, high performing Brokerage Tax team:
  • Establish your team as the content experts, informing & validating all tax-related engineering & operational decisions
  • Lead the coaching, development, hiring and staffing of our tax operations team
  • Play and integral advisory role in the coaching and hiring for our tax product & engineering teams
  • Partner and share best practices across our Core Operations and Finance teams

We’re looking for people who:

  • Have a CPA accounting designation and significant client tax reporting experience in the financial services industry
  • Are experienced in performing technical tax research and providing tax interpretations to management
  • Have a deep understanding of registered plans and Canadian tax slip reporting requirements
  • Have strong knowledge of Qualified Intermediary requirements including client documentation and withholding tax
  • Have a clear vision for how a high performing tax function operates, and can build a plan to get there
  • Have experience managing a team and possess an inclusive, direct and growth-mindset leadership approach
  • Are naturally curious and a problem-solver; if something seems off, they want to figure out what’s going on. They enjoy navigating uncertainty, bringing clarity to ambiguity and don’t wait for a playbook to be written
  • Are deeply analytical. They are comfortable navigating large sets of data and pull insights from it; Strong experience in Excel is a must, familiarity with database querying (e.g., SQL) and Oracle is an asset
  • Are organized with a strong attention to detail and the ability to meet tight deadlines
  • Are relentless when investigating issues as well as identifying and eliminating root causes
  • Are passionate about technology, specifically fintech
  • Have awesome people skills and a positive attitude; you will be working in a highly collaborative environment
Job perks/benefits: Startup environment
Job region(s): North America
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