Mergers & Acquisitions Lead; Hybrid

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 Green Shield 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.

Reporting to the Executive Vice-President, Head of Finance & Strategy, the Lead, Mergers & Acquisitions will steward Green Shield’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 Green Shield’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.

• Lead proactive acquisition pursuits by identifying and evaluating opportunities within defined strategic criteria to support Green Shield’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.

• 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…