Original job description
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 owns the due diligence behind every acquisition. You will lead the work that turns a promising target into a confident decision: building the models, interrogating the numbers, and forming an independent view of the merits and risks of acquiring it. Part of the role also involves sourcing: building relationships with founders, owners, and operators before a business comes to market, and helping to keep the pipeline full.
What You'll Work On
Lead the diligence process across financial, operational, and commercial workstreams, surfacing risks early.
Build financial models to evaluate targets and form an independent view of what each target is worth from a valuation perspective, and why.
Build the investment memo for each deal: the recommendation, strategic rationale, financial impact, and the merits and risks that leadership relies on to make the call.
Build relationships with founders, owners, and operators before a business is formally for sale, and maintain a strong pipeline.
Work with external advisors, including legal and financial diligence, to move deals toward close.
Leverage AI to increase the speed and depth of the diligence and analysis work.
What We're Looking For
This role is for someone who has experience working on deals and now wants to own the diligence on the buy side. You are precise with numbers, organized under pressure, and bring the commercial judgment to recognize when the numbers are telling you something that matters.
3-6 years of experience in transaction services, corporate development, private equity, venture capital, investment banking, or management consulting.
Strong financial modelling skills: you can build a model from scratch and know what to look for in one built by someone else.
Experience managing due diligence across multiple workstreams, from initial analysis to deal close.
Clear, confident communicator who can translate complex analysis into something a senior audience can act on.
Highly organized, with the ability to manage tight timelines and multiple priorities simultaneously.
Comfortable working with ambiguity and making progress without perfect information.
Bonus experience includes:
A CPA or CFA designation.
Experience acquiring or advising professional services firms, accounting firms, or SMBs.
Familiarity with AI tools for financial analysis, diligence, or deal management.
How We Work
You will work closely with the Vice President, Corporate Development and have direct exposure to the full deal process, from sourcing through diligence to close.
You will have significant influence over how the diligence function takes shape: its templates, its process, and its standards.
The team is small and moves fast. Rigour and speed are not in tension here. Both are expected.
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. Strong opinions, loosely held. You're not afraid to be wrong.
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 $130,000-$170,000 CAD base, plus a variable component, with an OTE of $150,000-$210,000, plus equity. This role is based in Toronto (in-person).
On Working In-Person
The full team is in the office every day in Toronto, because we believe the best work happens when smart people are in the same room. You get faster decisions, tighter feedback loops, direct access to everyone on the team, and a level of trust that's hard to build over Zoom. If you thrive in that environment, you'll love it here.
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.
