Company Description Trusted Financial is a premier strategic finance and advisory firm that supports founders, CEOs, and business owners of middle-market companies through complex financial inflection points. The firm provides tailored solutions in M&A;, recapitalization, and financing, designed to protect value, accelerate growth, and optimize exits. Guided by a mission to turn financial complexity into chance, Trusted Financial operates with uncompromising fiduciary integrity and a focus on creative, value-enhancing structures.

The firm emphasizes partnership over transactions and builds long-term relationships based on confidence and transparency.

Trusted

Financial serves clients across major North American markets, including Toronto, Ottawa, Vancouver, Winnipeg, Calgary, New York, San Diego, and Los Angeles.

Role Description The Managing Director is a full-time, on-site leadership role based in the Greater Toronto Metropolitan Area. This position is responsible for originating and executing strategic finance and advisory mandates, including M&A;, recapitalizations, and complex financings for middle-market clients. Day-to-day responsibilities include building and managing client relationships, leading deal teams, overseeing financial modeling and analysis, and developing bespoke transaction structures that align with client objectives.

The Managing

Director will guide clients through key decision points, negotiate terms with counterparties and capital providers,



and ensure that all engagements reflect the firm’s standards for fiduciary integrity and transparency. The role also includes mentoring junior professionals, contributing to business development strategies, and representing Trusted Financial in the local and broader financial community.

Qualifications

- Strong background in corporate finance and capital markets, including experience with M&A;, recapitalization, and financing transactions.
- Demonstrated skills in financial analysis, valuation, and modeling, with the ability to interpret complex data and develop actionable insights.
- Proven client advisory capabilities, including relationship management, strategic thinking, and clear, persuasive communication with senior leaders.
- Deal leadership experience, including project management, team coordination, negotiation, and execution under tight timelines.
- Knowledge of middle-market business dynamics, industry trends, and transaction structures relevant to founder- and owner-led companies.
- Track record of ethical decision-making, fiduciary responsibility, and maintaining high levels of confidentiality and professionalism.
- Ability to mentor and develop team members, foster collaboration, and contribute to a supportive, high-performance culture.
- Bachelor’s degree in finance, accounting, economics, business, or a related field; an MBA, CFA, or other relevant designation is strongly preferred.
- Comfort working on-site in the Greater Toronto Metropolitan Area, with flexibility to travel as required for client and deal-related responsibilities.

📌 Managing Director (Winnipeg)
🏢 Trusted Financial
📍 Winnipeg