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About the Role
This role sits at the center of everything. You will work directly with the CEO across strategy, operations, and execution to make Alloy River run better and move faster. You'll do what the company needs, and have the judgment and experience to know what that is before you're asked.
Responsibilities
- Develop a deep understanding of Alloy River's business, priorities, and operating model.
- Synthesize information from across the company, surface what matters most, and bring clear recommendations.
- Proactively identify risks, gaps, and opportunities before they become problems.
- Own and lead high-priority initiatives from scoping through execution.
- Interface with lawyers, advisors, and counterparties as part of M&A and corporate development processes.
- Bring a high bar for how a company should run, and raise the standard of every operational process.
- Own company-level planning and communication processes — annual planning, OKRs, MBRs, All Hands.
- Design and facilitate leadership meetings that drive clear decisions and accountability.
- Continuously improve operating rhythms and cross-team coordination.
- Bring genuine AI fluency to the role and build and evolve workflows that extend the CEO's leverage.
- Model best practices and help the broader organization develop fluency with AI tools.
Requirements
- 7–8 years of experience in a Chief of Staff or senior operational role, ideally at a high-growth tech company.
- Exceptional judgment.
- S-tier interpersonal skills.
- Experience owning complex, cross-functional initiatives from start to finish.
- Excellent executive communication, both written and verbal.
- Comfortable working directly with senior leaders and sitting with ambiguity.
- High agency: identify the problem, form a view, and act.
- AI-forward: have changed how you work because of AI.
- Strong opinions: have a perspective and share it.
- Ownership: feel responsible for outcomes.
- Curiosity: go deep without being asked.
- Optimistic: believe that things can improve.
Skills
- AI fluency
- Executive communication
- Interpersonal skills
- Strategic thinking
- Operational execution
- Cross-functional leadership
- Problem-solving
- Ambiguity navigation
Location
- Toronto
Work Type
- In-person
- Full-time
Experience Level
- Senior
- 7-8 years
Salary/Compensations
- 150,000–250,000 CAD
- 150-200k CAD
Benefits
- Equity
- Competitive pay
- 100% covered health insurance
- Work laptop provided
- Flexible PTO
About the Company
- Alloy River builds agentic applied AI for finance and accounting.
- Our mission is to transform finance from a slow, labor-intensive, reporting function into a real-time, strategic engine for profit and control.
- We re-architected the general ledger from first principles, and layered automation, workflow orchestration, and applied AI directly into its core.
- We raised over $30m to date from Portage Ventures, Electric Capital, Elad Gil, and angels like Tobi Lütke, Balaji Srinivasan, and many more.
- We’re scaling what we do with the best builders, operators, and craftspeople in the world.
Equal Opportunity
- We may use AI to help review candidate applications, but the final decision is always made by a human.