About Alloy River

Alloy River builds agentic applied AI for finance and accounting. Accounting today is fragmented, manual, and reactive. We believe it should be intelligent, structured, and operationally decisive. 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. Instead of accountants moving data between tools and managing checklists, our system produces outcomes, surfaces exceptions, and compounds leverage over time. This is not incremental improvement. It is a ground-up redesign of financial infrastructure for an AI-native world.

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.

Role Overview

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.

What You'll Work On

Strategic partner to the CEO

• Develop a deep understanding of Alloy River's business, priorities, and operating model — well enough to represent the CEO's perspective and act on it.

• Synthesize information from across the company, surface what matters most, and bring clear recommendations.

• Proactively identify risks, gaps, and opportunities before they become problems.

• Excellence in this role means taking work off the CEO’s plate before it even lands there - and doing so with high trust.

Drive cross-functional outcomes

• Own and lead high-priority initiatives from scoping through execution — aligning stakeholders, removing blockers, and ensuring follow-through.

• Interface with lawyers, advisors, and counterparties as part of M&A and corporate development processes.

• Step into ambiguous areas and create structure where none exists.

Improve how we operate

• Bring a high bar for how a company should run, and raise the standard of every operational process you touch.

• Own company-level planning and communication processes — annual planning, OKRs, MBRs, All Hands — and make them sharp, useful, and consistent.

• Design and facilitate leadership meetings that drive clear decisions and accountability.

• Continuously improve operating rhythms and cross-team coordination.

Use AI as a lever

• Bring genuine AI fluency to the role — not as a novelty, but as a core part of how you work.

• Build and evolve workflows that extend the CEO's leverage and improve how the leadership team operates.

• Model best practices and help the broader organization develop fluency with AI tools.

What We're Looking For

• 7–8 years of experience in a Chief of Staff or senior operational role, ideally at a high-growth tech company.

• Exceptional judgment - you know what matters, what can wait, and how to tell the difference.

• S-tier interpersonal skills - you build trust quickly and navigate complexity with grace.

• 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.

• Some days are strategic. Some days are operational. You're good either way.

Bonus experience includes:

• Exposure to M&A and due diligence processes.

• Experience in fintech, accounting, or financial services.

• Management consulting experience.

How We Work

• You’ll work directly with the CEO (exited Sequoia-back founder) in a high trust, high agency, high impact role that touches every part of the company.

• It’s a small, senior team with no hand-holding. You’ll be among peers.

• The feedback loop between your work → results is short and satisfying.

• Your time will be spent building, fixing, and moving things forward, with no red tape.

Why Join Alloy River

• Help create a category-defining product with a real impact on business owners.

• Work in-person with people who are excellent at what they do and fun to be around.

• Join early and shape the future of an industry

• James makes everyone lunch at 12pm.

What We Look For

We hire high agency, AI-forward builders. The title or background matters less than the pattern underneath it.

• High agency. You don't wait to be pointed. You identify the problem, form a view, and act.

• AI-forward. You've changed how you work because of AI - not as a novelty, but because of how it lets you build. Your first instinct is to reach for the agent, not the keyboard.

• Strong opinions. You have a perspective and you share it - in writing, in meetings, in Slack. You think out loud and you’re not afraid to change your mind in public.

• Ownership. You feel responsible for outcomes, not just doing your part. You've built something that didn't exist before you arrived, and you didn't let go until it was right.

• Curiosity. You go deep without being asked. You ask the questions others skip. You tinker.

• Optimistic. You believe that things can improve, problems can be solved, and people are generally trying their best. This is the foundation of how you work and how you treat people.

Compensation & Location

This role pays $150,000–$250,000 CAD, plus equity. The expected range is $150-200k, with top of range reserved for candidates who bring direct M&A experience, a background in management consulting, and prior CoS experience at a fintech company. This role is in-person full-time at our gorgeous office in Liberty Village, Toronto.

Benefits

• Competitive pay

• 100% covered health insurance

• Work laptop provided

• Flexible PTO

AI Usage Policy

We may use AI to help review candidate applications, but the final decision is always made by a human.

Compensation Range: CA$150K - CA$250K