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About the Role

This is a senior, strategy-facing role focused on M&A, reporting directly to the CEO. You will own the front end of the M&A process, from market strategy and target identification through to signed term sheets, with a mandate to close multiple acquisitions in 2026.

Responsibilities

• Expand acquisition strategy within the professional services sector.
• Build and maintain a pipeline of acquisition targets through direct outreach, relationship development, industry events, and intermediary networks.
• Track deal activity, competitive dynamics, and emerging opportunities.
• Develop long-term relationships with founders, business owners, operators, and advisors.
• Represent Alloy River with credibility and judgment to earn trust from counterparties.
• Lead early-stage conversations and manage the transition from relationship to active deal.
• Form an independent point of view on deal structure, valuation, and terms.
• Support active deals through diligence and toward close with the Manager, M&A and external advisors.
• Own the LOI process and support transaction negotiations through to execution.
• Help shape Alloy River's M&A process, philosophy, and approach.
• Ensure smooth post-close transitions and successful integration of acquired businesses.

Requirements

• Must have originated and closed deals, not just supported them.
• 8-10 years of experience in M&A, corporate development, private equity, or investment banking.
• Demonstrated track record of sourcing and closing deals.
• Strong commercial instincts and ability to form an independent view on target attractiveness and valuation.
• Experience working with founders and owner-operators.
• Confident, credible communicator capable of representing Alloy River at a senior level.
• Comfortable operating with a high degree of autonomy in a fast-moving environment.
• Experience acquiring professional services or accounting firms (bonus).
• Existing relationships with intermediaries and advisors in the SMB professional services space (bonus).
• Experience building or scaling a corporate development function from the ground up (bonus).

Skills

• Market strategy
• Origination
• Relationship development
• Deal structuring
• Deal execution
• Valuation
• Negotiation
• Communication
• Autonomy
• High agency
• AI-forward thinking
• Strong opinions
• Ownership
• Curiosity
• Optimism

Location

• Toronto (in-person)
• Remote in Chicago
• Remote in New York

Work Type

• In-person
• Remote

Experience Level

• Senior
• 8-10 years

Salary/Compensations

• $200,000–$250,000 CAD base
• OTE of $250,000–$350,000 CAD
• Plus equity

Benefits

• Competitive pay
• 100% covered health insurance
• Work laptop provided
• Flexible PTO

About the Company

• Alloy River builds agentic applied AI for finance and accounting.
• Transforms finance from a slow, labor-intensive, reporting function into a real-time, strategic engine for profit and control.
• Re-architected the general ledger with automation, workflow orchestration, and applied AI.
• Raised over $30m to date from Portage Ventures, Electric Capital, Elad Gil, and other notable investors.
• Scaling with the best builders, operators, and craftspeople.

Equal Opportunity

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