In PersonRegular travel to portfolio firms across Canada and the US.
Business & StrategyBusiness Operations
About the job
Requirements
Experience as a COO or operations leader at a startup or operating business, or in private equity, venture capital, or management consulting with hands-on work alongside operating companies.
A record of holding leaders accountable to a plan from an operating seat or a board seat.
Experience overseeing more than one company or business unit at a time, with clear evidence of what improved under that oversight.
Experience writing a value creation plan and delivering against it.
A track record of building systems and scoreboards that hold up over time.
Ability to challenge a founder on where their business needs to go while maintaining their trust.
Responsibilities
Own the integration plan for every acquired firm, from strategy through execution.
Build integration plans with the owners of technology, finance, people, and operations; hold them accountable for delivery; and hand each workstream back once complete.
Maintain a regular operating cadence with each firm's leadership to understand the business's status, needs, and obstacles.
Track financial, operating, and other key metrics on a single portfolio scoreboard, with a clear owner and recovery plan for every shortfall.
Establish with each firm's leadership which decisions they make independently, which they escalate, and when.
Work with each founder to shape the firm's plan, including client growth, services to add, team evolution, and changes needed to achieve the plan.
Evaluate prospective acquisitions by reviewing the operating case before a deal is signed and raising concerns where the plan does not hold.
Bring insights from across the portfolio to the CEO and Corporate Development team to inform future acquisitions and valuations.
Develop an understanding of each founder, their leadership team, and broader team, including their strengths, support needs, and who is positioned to step up when the founder steps back.
Support hiring key roles when a firm needs them.
Build and lead a team as the portfolio grows.
Identify and implement opportunities spanning firms, such as cross-selling services, shared vendors, and common ways of working.
Convert recurring problems into documented, measurable systems that do not depend on the role holder or the founder.
Build systems at the first firm and deploy them at each subsequent firm.
Operate with significant autonomy while reporting directly to the CEO.
Shape the operating model for acquired firms and scale the team behind it.
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
Alloy River acquires accounting firms and grows them. Each firm keeps its name, its team and its founder, and gains the support of a platform: capital, software that removes manual work, and a partner responsible for making sure the business performs.
As VP Portfolio Operations, you are that partner. You integrate each firm after it closes, then own its results without running it day to day. The work focuses on systems, back-office processes, reporting, targets and go-to-market support. Brands, leadership and offices largely stay as they are.
The portfolio is one firm today and is expected to grow to 20+ over the next 24 months.
This role is central to the success of our acquisitions.
What You'll Work On
Lead each integration
Own the integration plan for every firm we acquire, from strategy to execution.
Build it with the owners of technology, finance, people and operations, hold them to delivery, and hand each workstream back once it is done.
Own the performance of the portfolio
Maintain a regular operating cadence with each firm's leadership, so that you always know where the business stands, where it needs to be, and what is getting in the way.
Track financial, operating and other key metrics on a single portfolio scoreboard, with a clear owner and recovery plan for every shortfall.
Establish with each firm's leadership which decisions they make independently, which they escalate, and when.
Shape each firm's plan
Work with each founder to shape the plan for their firm, including which clients to grow, which services to add, how the team should evolve, and what needs to change to get there.
Help evaluate prospective acquisitions by reviewing the operating case before a deal is signed and raising concerns where the plan does not hold.
Bring insights from across the portfolio back to the CEO and the Corporate Development team to inform which firms we acquire next and how we value them.
Support the teams
Develop a clear understanding of each founder, their leadership team and the broader team: their strengths, where they would benefit from support, and who is positioned to step up when the founder steps back.
Support the hiring of key roles when a firm needs them.
Build and lead your own team as the portfolio grows.
Build the playbooks
Identify and implement opportunities that span firms, such as cross-selling services, shared vendors and common ways of working.
Convert recurring problems into documented, measurable systems that do not depend on you or the founder.
Build these systems once at the first firm and deploy them at each firm that follows.
What This Role Is Not
It is not a day-to-day operating role. Founders and their teams run their firms.
It does not include platform migration. Our deployment team owns that work, and you clear the way for them.
It is not a firefighting role. When a problem recurs, you fix the system behind it.
What We're Looking For
You have overseen operating companies without running them, and delivered results through their leaders. You have worked with founders who have run their businesses for many years and know them better than anyone, earned their trust, and improved performance together. You are more interested in building the operating model for a platform than in running a single business within it.
You bring one of the following backgrounds:
A COO or operations leader at a startup or operating business.
A background in private equity, venture capital or management consulting, with hands-on work alongside operating companies.
A record of holding leaders accountable to a plan, from an operating seat or a board seat.
Experience overseeing more than one company or business unit at a time, with clear evidence of what improved under your oversight.
Experience writing a value creation plan and delivering against it.
A track record of building systems and scoreboards that hold up over time.
The ability to challenge a founder on where their business needs to go while maintaining their trust.
How We Work
You will report directly to the CEO and operate with significant autonomy.
You will have real influence over how the operating model takes shape for the firms we acquire. This is a ground-floor opportunity to build something, then scale the team behind it.
You will work alongside people who move fast, have strong opinions, and hold themselves to a high standard.
AI is a core part of how we work - not just what we build, but how we build it.
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.
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 $175,000–$250,000 CAD base, plus a variable component, with an OTE of $225,000–$325,000 CAD, plus equity. This role is in-person full-time at our gorgeous office in Liberty Village, Toronto, with regular travel to portfolio firms across Canada and the US.
On Working In-Person
The full team is in the office every day, 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
A gorgeous loft office in Liberty Village
Flexible PTO
AI Usage Policy
We may use AI to help review candidate applications, but the final decision is always made by a human.