Mergers and Acquisitions Manager
About the role
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 non-profit with a mission to support better health for all Canadians. We aren’t just a health and benefits company. We’re the only non-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
Base Salary: CAD $94,406.00 - 142,069.00
The Manager, Mergers & Acquisitions will be responsible for leading and supporting end-to-end execution of acquisition opportunities in support of Greenshield's inorganic growth strategy. This includes supporting origination and screening targets, conducting financial analysis and valuation, coordinating due diligence across cross-functional teams, and supporting deal structuring and close. The Manager will collaborate closely with lines of business across Insurance, Administration, and Health to assess strategic fit, build investment business cases, and advance transactions from initial evaluation through to execution.
This role requires an individual with the analytical depth to build complex financial models independently, the commercial judgment to assess businesses critically, and the drive to manage multiple workstreams simultaneously in a fast-moving environment. They will need to think outside the box, solve complex problems, and be willing to roll up their sleeves across all aspects of a transaction.
The Manager will be a member of Greenshield's Strategy and Acquisitions team and will play a central role in supporting the delivery of Greenshield's strategic plan through inorganic growth. The role reports directly to the M&A Lead and may also directly supervise junior team members, delegating workstreams while remaining accountable for the quality and integrity of deal execution.
DEAL ORIGINATION & PIPELINE MANAGEMENT
Support identification and sourcing of acquisition targets aligned with Greenshield's strategic priorities across health benefits, digital health, pharmacy, insurance and adjacent sectors. Maintain and develop the active deal pipeline, including target tracking, market mapping, and competitive landscaping. Prepare preliminary target assessments and investment theses for leadership review. Review and manage NDAs with targets.
FINANCIAL MODELLING & VALUATION
Build and own complex, dynamic financial models including DCF, LBO, accretion/dilution, merger consequences, and scenario and sensitivity analyses – independently, from scratch. Develop and stress-test valuation ranges using multiple methodologies: comparable companies, precedent transactions, and sum-of-the-parts. Translate model outputs into concise, executive-ready investment recommendations with clear assumptions and identified risks. Partner with lines of business across Insurance, Administration, and Health to identify, develop, and quantify synergies and value creation opportunities, and incorporate these into deal models and investment cases.
DUE DILIGENCE & DEAL EXECUTION
Lead and coordinate due diligence workstreams across financial, commercial, and operational. Coordinate third-party advisors (e.g. legal, financial, tax, consulting) and internal stakeholders across Finance, Legal, and Operations. Synthesize diligence findings into clear status updates and issues logs, support transaction structuring decisions, and ensure key risks and material findings are reflected in transaction documents. Prepare and maintain deal documentation including deal summaries, management presentations, IC memos, and board materials.
INTEGRATION PLANNING
Identify and track integration risks surfaced through due diligence, ensuring they are reflected in integration planning. Contribute to integration frameworks and value capture plans in partnership with business and functional leads, translating deal thesis assumptions into operational priorities. Track post-closing KPIs tied to the investment thesis, monitoring value realization against deal assumptions and surfacing performance variances to leadership.
STRATEGIC & MARKET ANALYSIS
Conduct industry research, sector deep-dives, and competitive analysis to inform Greenshield's inorganic growth strategy. Monitor sector trends, regulatory developments, and the competitive landscape across Canadian and North American health and benefits markets. Provide analytical frameworks to support prioritization of M&A versus organic growth or partnership alternatives.
WHAT WE ARE LOOKING FOR
5+ years of experience in investment banking, private equity, corporate development, or M&A advisory (buy-side or sell-side). Demonstrated ability to independently build complex, multi-scenario financial models. Strong command of valuation methodologies and the ability to contextualize outputs within a strategic investment narrative. Experience managing multiple workstreams simultaneously under tight timelines. Excellent verbal and written communication skills. Experience and comfort presenting analysis and findings to senior stakeholders. Bachelor's degree in Finance, Business, Economics, or a related discipline. MBA considered an asset.
NICE TO HAVE
Professional designations such as CFA or CPA. Professional fluency in French. Prior exposure to health benefits, insurance, digital health, specialty pharmacy, or adjacent regulated industries. Prior experience reviewing or mentoring junior analysts/associates; this role is expected to remain majority hands-on in execution, not primarily managerial.
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!
A FEW 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 requestforaccommodation@greenshield.ca. 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). AI Usage - GreenShield leverages AI to help produce Job Descriptions, and ideate on interview questions. We also leverage AI for interview transcription support.
Not the right fit? Search for Mergers and Acquisitions Manager jobs in Toronto, Ontario, Canada
About Green Shield Canada
GreenShield is an integrated health services organization and the first organization in Canada to operate as a payer-provider – offering insurance, administering benefits, and paying claims as a ‘payer’, while offering medical, mental health and pharmacy services as a ‘provider’. This model allows GreenShield to build care around Canadians, simplify their health care experience, and improve health outcomes.
GreenShield is uniquely structured as a not-for-profit social enterprise. We reinvest earnings and redeploys services to underserved Canadian communities via our social impact brand, GreenShield Cares, with a focus on positively impacting at least one million Canadians by 2025. As the industry’s noble challenger GreenShield continues to innovate, evolving its offerings and services to deepen our purpose of championing Better Health for All.
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Mergers and Acquisitions Manager
About the role
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 non-profit with a mission to support better health for all Canadians. We aren’t just a health and benefits company. We’re the only non-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
Base Salary: CAD $94,406.00 - 142,069.00
The Manager, Mergers & Acquisitions will be responsible for leading and supporting end-to-end execution of acquisition opportunities in support of Greenshield's inorganic growth strategy. This includes supporting origination and screening targets, conducting financial analysis and valuation, coordinating due diligence across cross-functional teams, and supporting deal structuring and close. The Manager will collaborate closely with lines of business across Insurance, Administration, and Health to assess strategic fit, build investment business cases, and advance transactions from initial evaluation through to execution.
This role requires an individual with the analytical depth to build complex financial models independently, the commercial judgment to assess businesses critically, and the drive to manage multiple workstreams simultaneously in a fast-moving environment. They will need to think outside the box, solve complex problems, and be willing to roll up their sleeves across all aspects of a transaction.
The Manager will be a member of Greenshield's Strategy and Acquisitions team and will play a central role in supporting the delivery of Greenshield's strategic plan through inorganic growth. The role reports directly to the M&A Lead and may also directly supervise junior team members, delegating workstreams while remaining accountable for the quality and integrity of deal execution.
DEAL ORIGINATION & PIPELINE MANAGEMENT
Support identification and sourcing of acquisition targets aligned with Greenshield's strategic priorities across health benefits, digital health, pharmacy, insurance and adjacent sectors. Maintain and develop the active deal pipeline, including target tracking, market mapping, and competitive landscaping. Prepare preliminary target assessments and investment theses for leadership review. Review and manage NDAs with targets.
FINANCIAL MODELLING & VALUATION
Build and own complex, dynamic financial models including DCF, LBO, accretion/dilution, merger consequences, and scenario and sensitivity analyses – independently, from scratch. Develop and stress-test valuation ranges using multiple methodologies: comparable companies, precedent transactions, and sum-of-the-parts. Translate model outputs into concise, executive-ready investment recommendations with clear assumptions and identified risks. Partner with lines of business across Insurance, Administration, and Health to identify, develop, and quantify synergies and value creation opportunities, and incorporate these into deal models and investment cases.
DUE DILIGENCE & DEAL EXECUTION
Lead and coordinate due diligence workstreams across financial, commercial, and operational. Coordinate third-party advisors (e.g. legal, financial, tax, consulting) and internal stakeholders across Finance, Legal, and Operations. Synthesize diligence findings into clear status updates and issues logs, support transaction structuring decisions, and ensure key risks and material findings are reflected in transaction documents. Prepare and maintain deal documentation including deal summaries, management presentations, IC memos, and board materials.
INTEGRATION PLANNING
Identify and track integration risks surfaced through due diligence, ensuring they are reflected in integration planning. Contribute to integration frameworks and value capture plans in partnership with business and functional leads, translating deal thesis assumptions into operational priorities. Track post-closing KPIs tied to the investment thesis, monitoring value realization against deal assumptions and surfacing performance variances to leadership.
STRATEGIC & MARKET ANALYSIS
Conduct industry research, sector deep-dives, and competitive analysis to inform Greenshield's inorganic growth strategy. Monitor sector trends, regulatory developments, and the competitive landscape across Canadian and North American health and benefits markets. Provide analytical frameworks to support prioritization of M&A versus organic growth or partnership alternatives.
WHAT WE ARE LOOKING FOR
5+ years of experience in investment banking, private equity, corporate development, or M&A advisory (buy-side or sell-side). Demonstrated ability to independently build complex, multi-scenario financial models. Strong command of valuation methodologies and the ability to contextualize outputs within a strategic investment narrative. Experience managing multiple workstreams simultaneously under tight timelines. Excellent verbal and written communication skills. Experience and comfort presenting analysis and findings to senior stakeholders. Bachelor's degree in Finance, Business, Economics, or a related discipline. MBA considered an asset.
NICE TO HAVE
Professional designations such as CFA or CPA. Professional fluency in French. Prior exposure to health benefits, insurance, digital health, specialty pharmacy, or adjacent regulated industries. Prior experience reviewing or mentoring junior analysts/associates; this role is expected to remain majority hands-on in execution, not primarily managerial.
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!
A FEW 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 requestforaccommodation@greenshield.ca. 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). AI Usage - GreenShield leverages AI to help produce Job Descriptions, and ideate on interview questions. We also leverage AI for interview transcription support.
Not the right fit? Search for Mergers and Acquisitions Manager jobs in Toronto, Ontario, Canada
About Green Shield Canada
GreenShield is an integrated health services organization and the first organization in Canada to operate as a payer-provider – offering insurance, administering benefits, and paying claims as a ‘payer’, while offering medical, mental health and pharmacy services as a ‘provider’. This model allows GreenShield to build care around Canadians, simplify their health care experience, and improve health outcomes.
GreenShield is uniquely structured as a not-for-profit social enterprise. We reinvest earnings and redeploys services to underserved Canadian communities via our social impact brand, GreenShield Cares, with a focus on positively impacting at least one million Canadians by 2025. As the industry’s noble challenger GreenShield continues to innovate, evolving its offerings and services to deepen our purpose of championing Better Health for All.