Company Description

At Wyn Ryan, we are building a high-growth holding company (Holdco) focused on acquiring and operating established lower middle-market businesses, typically with revenues between $1M and $10M, in fragmented industries. We use disciplined acquisition strategies and operational improvements to consolidate markets and create scalable platforms that deliver long-term value to customers, employees, and stakeholders. Our mission is aggressive industry consolidation not incremental improvement. We seek exceptional partners who share our obsession with execution and building enduring value.

Role Description

Wyn Ryan is seeking a Chief Financial Officer (CFO) to join our core executive leadership team (alongside the CEO, Chairperson and Business Development lead) as we scale through acquisitions. This is a part-time hybrid role (initially ~20–25 hours/month, scaling to full-time as the Holdco grows through multiple deals), based in the Greater Toronto Area with flexibility for remote/hybrid arrangements.

As an executive director on the board, you will:

Lead all financial aspects of the Holdco, including financial planning, cash-flow management, performance monitoring, and preparing accurate financial statements and reports.
Play a hands-on role in acquisition due diligence, deal structuring, financial modeling, and integration of acquired companies.
Develop and execute financial strategies to support rapid growth through industry roll-ups, capital raising, and operational efficiency.
Ensure regulatory compliance (particularly Canadian standards) while providing wise counsel to the leadership team on high-stakes decisions.
Collaborate closely with the founder/CEO to turn the vision of building a public-company-ready platform into reality.

This is not a traditional desk-based finance role. It demands a "natural born workaholic" who wears their clothes out from the inside, someone who thrives on action, turns dreams into executed results, and is fully aligned with our high-performance, no-excuses culture.

Compensation & Equity

We offer free founders’ equity (in the Holdco, with vesting based on performance and contribution) instead of (or alongside) high upfront cash compensation. We do not want your money, we want your expertise, loyalty, and relentless execution. As the Holdco scales (targeting 10–15+ acquisitions), the role transitions to full-time with competitive salary + equity upside.

Qualifications & Characteristics We Seek

We prioritize proven competence, attitude, ethics, and results over pure academic credentials. Ideal candidates will demonstrate most of the following:

Deep financial and deal-making expertise: A “damn fine numbers person” with strong skills in financial oversight, deal structuring, acquisition due diligence, financial modeling, cash-flow management, and financing strategies. Experience in lower middle-market companies, acquisitions, or roll-ups is highly valued.
Execution-oriented workaholic with high energy.
High ethics, loyalty, and wisdom.
Strong analytical and people skills.
Alignment and commitment to equity-based upside.

Education & Designations: Bachelor’s degree in Finance, Accounting, or related field required. Professional designations (CPA, CFA, or equivalent) are preferred but secondary to proven track record.

What We Do NOT Want: Theorists, nine-to-five mindsets, or candidates seeking high immediate salary without skin in the game.

WYN RYAN Jobs

Chief Financial Officer