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Chief of Staff Director

Job in Regina, Saskatchewan, S4M, Canada
Listing for: Affirm
Full Time position
Listed on 2026-02-21
Job specializations:
  • Finance & Banking
    Financial Manager, CFO, Corporate Finance, Financial Consultant
  • Management
    Financial Manager, CFO
Salary/Wage Range or Industry Benchmark: 191000 - 271000 CAD Yearly CAD 191000.00 271000.00 YEAR
Job Description & How to Apply Below
Affirm is reinventing credit to make it more honest and friendly, giving consumers the flexibility to buy now and pay later without any hidden fees or compounding interest.

The Chief of Staff is charged with directly supporting the Chief Financial Officer as well as the Finance organization y will serve as a thought partner to the CFO and Finance leadership on all matters—from how to operationalize and prioritize the Finance agenda, to financial and company strategy development and execution.

In this role, they will help turn strategy into execution through disciplined goal setting, development and optimization of business and financial reporting mechanisms, leading communications across the Finance leadership team, and supporting broader strategic communications across the company.

The Chief of Staff acts as the connective tissue across Finance and key cross‑functional partners, helping the CFO anticipate challenges, surface insights, and “look around corners.” Success in this role requires strong judgment, executive presence, and the ability to quickly understand organizational dynamics and build the tools, forums, and operating mechanisms that strengthen and accelerate execution.

This role requires a strategic problem‑solver who is an effective influencer with strong business and financial acumen. The individual must develop a deep understanding of Affirm’s business and financial model and rapidly demonstrate impact and value.

The ideal candidate brings a blend of strategy, finance, operations, and technology experience and thrives in a high‑growth, fast‑paced environment. This is a high‑visibility role where executive presence, discretion, and clear communication are essential.

What You’ll Do

Directly support the CFO day‑to‑day by planning, prioritizing, and executing on critical financial and business needs

Support and partner with Finance leadership and key cross‑functional stakeholders to develop and evolve processes that enable an effective Finance operating model, including long‑term goal setting and leadership coordination

Serve as a trusted adviser to the CFO and relevant partners during strategy formulation, development, and execution

Support program management across complex, Finance‑led and cross‑functional initiatives by monitoring progress, generating insights, challenging assumptions, and flagging risks in executive forums

Turn strategic ideas into actionable plans, ensuring alignment across the executive team and key stakeholders

Develop strong, collaborative relationships across Finance and the broader company to ensure alignment and effective execution

Facilitate collaboration through regular executive leadership meetings and quarterly offsites, influencing key decisions and strategic alignments

What We Look For

Experience in management consulting, finance, strategy, operations, or strategy & operations roles at a technology or financial services company (or similar)

BA/BS in a relevant field (Finance, Economics, Business, or Operations preferred)

Strong time and project management skills with a proven ability to build cross‑functional relationships and drive work forward without formal authority

Experience applying structured problem‑solving and operating frameworks to improve efficiency and execution

Practical experience in strategic planning, growth strategy execution, and sophisticated financial analysis

Demonstrated ability to ask the right questions and apply sound business judgment when working with a wide range of stakeholders

Clear, mature communicator able to convey complex ideas succinctly to both business and technical audiences, including executives

Proven ability to build trust, influence senior leaders, and operate effectively in ambiguous, fast‑moving environments

Base Pay Grade: S

Equity Grade: 6

CAN base pay range per year: $191,000 - $271,000

Affirm focuses on providing a simple and transparent pay structure which is based on a variety of factors, including location, experience and job‑related skills.

Base pay is part of a total compensation package that may include monthly stipends for health, wellness and tech spending, and benefits (including 100% subsidized medical…
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