Vice President, Finance

Ingressivecapital; Toronto; On-site; CAD 180,000 - 240,000; Full time

Benefits offered by this job

Competitive salary

Brand collaborations

Collaborative culture

Benefits package

Industry access

Job summary

Kensington Grey Agency Inc. seeks an experienced VP, Finance & Strategic Operations to drive financial planning, cross-border strategy, and executive-level governance across North America. This role blends hands-on accounting with strategic leadership to support a scaling, sales-driven organization.

The ideal candidate will lead a lean finance team, develop robust reporting, and partner with the CEO/COO to shape company strategy and investment decisions in a fast-growing agency environment.

Qualifications

• 12-15+ years of progressive finance leadership experience.
• Experience across US and Canadian markets with cross-border tax/transfer pricing.
• CPA designation or equivalent professional accounting qualification.

Responsibilities

• Own accounting end-to-end across US/Canada entities.
• Lead cross-border financial strategy and governance.
• Develop KPIs and performance dashboards for leadership visibility.
• Advise CEO and senior leadership on growth, profitability and risk.

Skills

Cross-border financial strategy

Financial planning & analysis

Leadership at SLT

CPA designation or equivalent

Education

CPA designation or equivalent

Tools

Finance systems/tools

Job description

About Kensington Grey

Kensington Grey Agency Inc. is an award-winning management firm dedicated to elevating underrepresented voices in the creator economy. We represent the most culturally relevant creators with the most powerful stories to tell, opening doors and shaping long-term careers for talent whose perspectives are often overlooked. Kensington Grey partners closely with talent to provide strategic guidance, visibility, and access to high-impact opportunities. The company is committed to inclusive representation, equitable growth, and building pathways for creators to thrive on a global stage.

Position Overview

We are seeking an experienced VP, Finance & Strategic Operations to serve as a senior strategic and financial leader within a fast-growing, entrepreneurial organization operating across North America.

This is not a traditional, accounting-led finance role. This role services as a senior member of the organization sitting on our SLT. The role covers many facets including financial planning & analysis, accounting operations, and cross-border financial strategy, while building the systems, processes, and team structure needed to support a scaling, sales-driven organization. The ideal candidate is equally comfortable operating in the details — AP/AR, reporting, commission structures — and operating at the executive table, shaping company strategy and presenting business insight to senior leadership.

Duties & Responsibilities

Accounting and Organizational Stewardship

• Own the accounting function end-to-end, including accounts payable, accounts receivable, and adherence to accounting best practices.
• Ensure accurate, timely financial record-keeping and close processes across US and Canadian entities.
• Bring CPA-level rigor to the agency's books, policies, and financial practices.
• Lead cross-border financial strategy, including US/Canadian tax considerations and transfer pricing between entities.
• Own and continually strengthen the company's commission and bonus program, ensuring it is effective, well-governed, and aligned to a sales/commission-based business model.
• Build operational structure from the ground up including lead evaluation and implementation of finance systems/tools (e.g., accounting, expense, and payroll platforms) to support scalable, automated reporting.
• Operate as a hands‑on leader within a start‑up environment, building a lean, scalable team structure that can grow with the business.
• Recruit, lead, and develop a finance team setting the tone for a high-performing, collaborative function.

Commercial Economics and Business Governance

• Bring commercial fluency to rate structures, talent deal economics, and fee/margin conversations, supporting pricing and scope decisions.
• Develop frameworks for understanding profitability by client, business unit, service offering, market and revenue stream.
• Provide strategic recommendations regarding revenue growth, margin expansion, cost structure, resource allocation and capital deployment.
• Build and strengthen financial planning, forecasting, reporting, and business insight across the organization.

Strategic Leadership

• Serve as a senior financial advisor to the CEO, COO, CoSS, and fellow Senior Leadership Team members, providing clear recommendations on growth, profitability, investment and risk.
• Develop KPIs and performance dashboards that give leadership timely visibility into the health of the business.
• Hold a leadership seat at the table, bringing an enterprise-wide perspective to leadership conversations, developing and influencing overall company strategy.
• Partner cross-functionally with business development, talent, and operations teams to translate financial insight into decisions.
• Identify, assess and execute potential acquisitions, investments, strategic partnerships and joint ventures.

Experience / Background

• 12-15+ years of progressive finance leadership experience, including significant experience in senior finance leadership roles.
• Experience working across both US and Canadian markets, with a strong understanding of cross-border strategies including taxation and transfer pricing.
• Proven experience building operational and team structure, including developing new processes and systems from scratch.
• Experience leading and developing a team of at least two people.
• Hands‑on leadership experience in a start‑up environment, comfortable with small and scalable team structures.
• Advanced analytics skills, with the ability to build complex financial models to drive informed decision-making.
• CPA designation or equivalent professional accounting qualification.
• Experience developing executive‑level reporting materials for senior leadership teams and business stakeholders.
• Experience in a sales/commission-based environment, including ownership of an effective commission or bonus program.
• Experience managing organizations with multiple legal entities and intercompany relationships is considered a bonus.
• Previous experience within a marketing, advertising, media, communications, talent, influencer, creator or related agency business is ideal, but not required.

At Kensington Grey, we believe in fostering a dynamic and rewarding work environment where talent thrives.

Benefits

• Competitive Compensation – We recognize your expertise with a salary and commission structure that reflects your impact.
• Exciting Brand Collaborations – Work with top‑tier talent, global brands, and high‑profile campaigns that shape the entertainment and digital landscape.
• Innovative & Collaborative Culture – Join a passionate team that values creativity, fresh ideas, and a hands‑on approach to success.
• Comprehensive Benefits Package – Enjoy health insurance, retirement plans, and additional perks that make a difference.
• Networking & Industry Access – Gain exclusive access to industry events, brand partnerships, and top‑tier connections that fuel your professional growth.

Be part of a company that values your contributions and empowers you to make an impact.

Thank you!