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Salary: CAD 150,000 - 200,000 / annual
Alloy River builds agentic applied AI for finance and accounting, re-architecting the general ledger from first principles with automation, workflow orchestration, and AI embedded in its core. The company has raised over $30M from top-tier investors including Portage Ventures, Electric Capital, and angels like Tobi Lütke and Balaji Srinivasan.
As VP Portfolio Operations, you will be the operational partner responsible for integrating and scaling Alloy River's acquisition strategy. The company acquires accounting firms that retain their names, teams, and founders while gaining access to capital, AI-powered software, and dedicated operational support. Currently at one firm, the portfolio is expected to grow to 20+ firms within 24 months.
Key responsibilities include:
- Leading integration planning and execution for each acquired firm, coordinating across technology, finance, people, and operations workstreams, then handing ownership back to respective leaders once complete.
- Owning portfolio performance through regular operating cadence with firm leadership, maintaining a unified scoreboard of financial and operational metrics with clear owners and recovery plans for shortfalls.
- Shaping each firm's strategic plan in collaboration with founders, including client growth strategy, service expansion, team evolution, and operational improvements needed to hit targets.
- Evaluating prospective acquisitions by reviewing operating cases and raising concerns about plan viability; bringing cross-portfolio insights to inform acquisition strategy and valuation.
- Understanding each founder and leadership team's strengths and development needs; supporting key hiring and building your own team as the portfolio scales.
- Building scalable playbooks and systems that span firms—such as cross-selling opportunities, vendor consolidation, and standardized processes—converting recurring problems into documented, measurable systems that don't depend on individual people.
This is not a day-to-day operating role; founders and their teams run their firms. You operate with significant autonomy, reporting directly to the CEO, and have real influence over how the operating model evolves. The role requires the ability to challenge founders on strategic direction while maintaining trust, and to hold leaders accountable to plans from an operating or board-level perspective.
You will work in-person with a team that moves fast, holds strong opinions, and maintains high standards. AI is core to how the company works—not just the product, but the operating model itself.
REQUIREMENTS:
- One of the following backgrounds: COO or operations leader at a startup or operating business; or background in private equity, venture capital, or management consulting with hands-on work alongside operating companies.
- Proven record of holding leaders accountable to a plan from an operating seat or board seat.
- Experience overseeing more than one company or business unit simultaneously, with clear evidence of performance improvements under your oversight.
- Experience writing and delivering against value creation plans.
- Track record of building systems and scoreboards that scale and endure.
- Ability to challenge founders on business direction while maintaining trust.
- High agency: you identify problems, form views, and act without waiting to be directed.
- AI-forward mindset: you've changed how you work because of AI, reaching for agents and automation as first instincts.
- Strong opinions, loosely held; comfortable being wrong and sharing perspective in writing, meetings, and async communication.
- Ownership mentality: you feel responsible for outcomes, not just tasks; you've built things from scratch and didn't let go until they were right.
- Curiosity: you go deep without being asked, ask questions others skip, and tinker.
- Optimistic outlook: you believe problems can be solved and people are generally trying their best.
