Mergers and Acquisitions Lead

Green Shield Canada (GSC); Toronto; On-site; CAD 120,000 - 150,000; Full time

Job summary

A not-for-profit health organization in Toronto is seeking a Lead, Mergers & Acquisitions to drive strategic initiatives related to growth and acquisitions. The role requires over 10 years of experience in investment banking or corporate development, with proven financial modeling skills and the ability to negotiate complex transactions. You'll collaborate with various stakeholders to enhance growth objectives while leading a high-performing team. Join us in creating better health for all Canadians.

Qualifications

• Minimum 10 years of progressive experience in relevant roles.
• Proven ability to lead complex transactions end-to-end.
• Established network with investment and advisory partners.

Responsibilities

• Lead acquisition pursuits aligned with growth strategy.
• Conduct sector analysis and financial modeling.
• Structure and negotiate transactions effectively.

Skills

Investment banking

Corporate development

Negotiation

Financial modeling

Stakeholder management

Strategic alignment

Valuation

Education

CA or CFA designation

MBA or equivalent graduate degree

Job description

WHO WE ARE

When it comes to health, we’re always looking for ways to push for better. It’s why we were founded in the first place. In 1957, our founder, pharmacist William Wilkinson, witnessed a mother sacrifice her health by forgoing her own medicine to pay for her sick daughter’s prescription. He knew there had to be a better way. So, he introduced North America’s first prepaid drug plan, and GreenShield was born as a not‑for‑profit with a mission to support better health for all Canadians.

We aren’t just a health and benefits company. We’re the only not‑for‑profit social enterprise that brings worlds of coverage and care together, all in one place.
We’re noble challengers, purposefully building a better way and we need the best people to help us create a more holistic approach that takes care of the mind and body.
Our mission is to create better health for all Canadians, and we know that starts with our employees.

THE ROLE IN A NUTSHELL

Reporting to the Executive Vice-President, Head of Finance & Strategy, the Lead, Mergers & Acquisitions will steward GreenShield’s enterprise‑wide strategic initiatives related to mergers, acquisitions, and other corporate transactions. As a key enabler of our growth trajectory toward the 2030 strategy, this role will drive proactive acquisition pursuits—working within defined criteria to identify, evaluate, and execute opportunities that align with GreenShield’s mission and growth objectives. The successful candidate will oversee sector analysis and financial modeling to inform acquisition decisions, structure and negotiate transactions, build and manage external relationships with investment and advisory partners, and ensure post‑transaction performance is optimized and value creation targets are achieved.

Key Responsibilities

• Lead proactive acquisition pursuits by identifying and evaluating opportunities within defined strategic criteria to support GreenShield’s 2030 growth strategy.
• Conduct sector analysis and oversee financial modeling, leveraging outputs and financial metrics to inform acquisition decisions and investment rationale.
• Lead financial valuation and analysis for active pursuits, including modeling, expressions of interest (EOI), letters of intent (LOI), and bidding agreements.
• Collaborate with business leaders to define transaction rationale, financial targets, operational synergies, customer growth opportunities, and revenue/cost efficiencies.
• Build and manage strong external relationships with investment firms, institutional investors, and advisory partners to proactively source and assess strategic opportunities.
• Lead and develop a high‑performing team to support acquisition analysis, modeling, due diligence, and integration efforts.
• Drive and coordinate pursuit efforts across the organization, ensuring alignment with strategic priorities and timely execution.
• Centralize and coordinate M&A activities to eliminate silos, improve knowledge transfer, and leverage best practices across the enterprise.
• Lead all diligence streams, including training teams, preparing diligence materials, managing third‑party advisors, and removing barriers to execution.
• Oversee development of creative deal structures, business cases, synergy analysis, financial budgets, and valuation models.
• Structure and negotiate transactions, including managing seller expectations, business terms, and legal documentation.
• Present acquisition and strategic project reviews to the Executive Team, including analysis, recommendations, risk assessments, and decision options.
• Oversee post‑acquisition integration planning and execution, ensuring strategic alignment and realization of value creation targets.

Leadership Capabilitie

• Demonstrated ability to lead and develop high‑performing, cross‑functional teams in high‑stakes, fast‑paced environments.
• Skilled in collaborative leadership, with the ability to influence through structured reasoning, dialogue, and shared outcomes.
• Proven experience in stakeholder management and strategic alignment across diverse internal and external groups, including investment and advisory partners.
• Strong orientation toward evidence‑informed decision‑making and disciplined execution.
• Ability to operate with precision from strategy design through to delivery, balancing long‑term vision with near‑term execution.

WHO WE'RE LOOKING FOR

• Minimum 10 years of progressive experience in investment banking, corporate development, private equity, or strategic M&A roles, with a strong track record of leading complex transactions and working deals end‑to‑end.
• Professional designations such as CA or CFA required; MBA or equivalent graduate degree preferred.
• Deep financial acumen, with demonstrated expertise in valuation, financial modeling, budgeting, and synergy analysis.
• Proven ability to lead and oversee financial modeling efforts, including the development of business cases, deal structures, and investment rationale.
• Experience structuring and negotiating transactions, including familiarity with competitive deal environments and dynamic capital deployment.
• Established network of external relationships, including investment firms, institutional investors, and advisory partners, with demonstrated success in sourcing and advancing strategic opportunities.
• Demonstrated success in sourcing, negotiating, and executing strategic partnerships, acquisitions, and joint ventures.
• Experience in healthcare, insurance, or social enterprise sectors is considered an asset.

THE CULTURE

We believe a career should be meaningful. Not just a means to earn a living. Our culture is one where everyone's voice is heard and valued. Because that’s what it takes to create better health for all. We dare to challenge the status quo. And we’re driven by people who have challenged theirs. We believe that your workplace should empower you to be the best version of yourself. That’s why we provide a place where you can be inspired, challenged, and rewarded.
Where your growth means our growth.
Where your voice is heard and valued.
Where your work has purpose. And purpose matters.
We believe our people are critical to our overall success. Inclusivity makes us a stronger, smarter and more informed organization. Being intentionally inclusive of diverse backgrounds, perspectives and experiences will enhance our company culture to positively impact how we support our communities. A career at GreenShield isn’t just about personal achievements, it's about making a difference together.
Here’s to Better Health for All!

AFEW MORE DETAILS

Proficiency in English is required for this position. As part of this role, you will be required to communicate with colleagues or customers who use English as their primary language. By requiring English proficiency for this position, we aim to ensure that our employees can excel in their roles, collaborate, and communicate effectively, and contribute to the success of our organization.

GS supports diversity, equity and inclusion in our teams and communities, and we value the unique contributions made by all. Even if your experience doesn’t align perfectly to every requirement, we invite you to apply. We encourage applications from all candidates and will accommodate needs under human rights legislation throughout all stages of the recruitment and selection process. Please let us know of any accommodation through [e-mail]. Information received relating to accommodation will be addressed confidentially.

Providing this information gives GS consent to use your personal information to assess your suitability for specific positions, future opportunities or for your personnel file. Your résumé will be held in strict confidence and will be viewed only by the Organization. Information may be stored outside of Canada and could be used for aggregate statistical purposes (which uses no personal identification).

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