Operating Executive Jobs in Ontario (NOW HIRING)

The opportunity

Ontario Teachers' Pension Plan Board (Ontario Teachers') is a global investor with net assets of ~$279 billion as of December 31, 2025. Ontario Teachers' is a fully funded defined benefit pension plan, and it invests in a broad array of asset classes to deliver retirement security for 346,000 working members and pensioners. Our Private Capital group deploys ~$60 billion across direct private equity investments and private equity funds globally.

The Director will be a senior member of our Services investment team - partnering with our Senior Managing Director and Managing Directors to source, diligence, execute, and manage private investments in the Services sector. This is a development seat with a clear path toward independent deal leadership for a candidate who has already built a strong foundation in private equity investing.

Who you'll work with

Reporting to the Managing Director, the role will be part of a deal team comprising analysts, associates, principals, directors, and managing directors, supported by third-party consultants, operating executives, and legal and accounting advisors dedicated to each transaction.

The Services team invests across sub-sectors including Commercial & Residential Services and Industrial & Infrastructure Services. The Managing Director should have prior expertise in Services investing, with knowledge of emerging regulatory, AI, and digitization themes that are reshaping the sector.

In certain instances, the Director may also work with colleagues in OTPP's global offices on international investment opportunities in Services.

What you'll do

• Serve as a key member of deal teams - conducting industry and company due diligence, building financial models, arranging debt financing, negotiating legal documents, and preparing written recommendations for the Underwriting Committee.

• Lead or co-lead individual deals and workstreams with oversight from the SMD or MD; own specific diligence streams (financial, operational, commercial, legal, tax, insurance) end-to-end.

• Post-close, remain actively involved with portfolio companies - often as board observer or board member - working with management on strategy, value creation, M&A, and refinancing.

• Contribute to deal flow generation through desk research, consultant relationships, operating executive networks, conferences, and relationships with management teams.

• Lead sub-sector deep dives and thematic research as the team evolves its coverage strategy, including emerging AI, regulatory, and digitization themes.

• Manage and develop analysts, associates, and principals on deal teams; provide direct mentorship on diligence, modeling, judgment, and communication.

• Work in a highly collaborative manner, bringing a complex network of stakeholders along (Global and Sector SMDs, MDs, deal teams, Portfolio Solutions team, international office leaders, portfolio companies, etc.). Strike the appropriate balance of being a confident decision-maker and an inclusive leader.

• Build a network of operating executives, CEOs, consultants, bankers, and peer sponsors; progress toward independent deal sourcing by the end of Director tenure.

• Develop value creation expertise in close partnership with the SMD and MDs; contribute to portfolio company initiatives as assigned.

• Exercise judgment within deal teams and surface recommendations to the MD or SMD; lead individual workstreams and, over time, full deals with oversight.

• Provide disciplined thinking, sound judgment, and courage of conviction, with a willingness to take balanced, thesis-driven risk. Intervene directly and effectively when required and escalate issues early.

• Work cross-functionally and collaboratively with other teams to ensure continued alignment with OTPP's mission, vision, and values - including supporting and sharing knowledge with other areas of Investments and responding to ad hoc requests.

What you'll need

• ~10+ years of meaningful work experience, including several years of recent private equity investing. Active M&A in a senior role in corporate development would also be considered. Supplemented by previous experience in management consulting, investment banking, and/or corporations (preferably corporate development or similar roles).

• Experience playing a lead role on deal workstreams, including conducting due diligence, leading multiple diligence streams (financial, operational, legal, tax, insurance), arranging debt financing, and negotiating documentation.

• Direct investment exposure to Services sub-sectors preferred.

• Deep knowledge of Services sector dynamics and the emerging regulatory, AI, and digitization themes reshaping them.

• Some experience serving on "for profit" Boards of Directors or board committees a plus.

• Strong academic background, with a financial designation (MBA, CFA, CBV, or CA strongly preferred).

• Experience playing a leading role in the investment process, including conducting due diligence, arranging debt financing, and negotiating documentation.

• Strong negotiating skills.

• Ability to balance priorities, work independently, lead projects, and thrive in a high-performance team environment.

• Very strong analytical and quantitative skills to perform and guide in-depth, innovative, critical analysis.

• Deep understanding of fundamental investment analysis and private equity value creation.

• Strong interpersonal skills and ability to build constructive relationships with internal and external parties, particularly management teams, boards, and senior advisors.

• Strong communication skills, both oral and written, including IC paper authorship and presentation.

• Willingness and ability to travel across North America and globally.

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What we're offering

• Numerous opportunities for professional growth and development

• Comprehensive employer paid benefits coverage

• Retirement income through a defined benefit pension plan

• The opportunity to invest back into the fund through our Deferred Incentive Program

• A flexible work environment combining in office collaboration and remote working

• Competitive time off

• Our Flexible Travel Program gives you the option to work abroad in another region/country for up to a month each year

• Employee discount programs including Edvantage and Perkopolis

At Ontario Teachers', diversity is one of our core strengths. We take pride in ensuring that the people we hire and the culture we create, reflect and embrace diversity of thought, background and experience. Through our Diversity, Equity and Inclusion strategy and our Employee Resource Groups (ERGs), we celebrate diversity and foster inclusion through events for colleagues to connect for professional development, networking & mentoring. We are building an inclusive and equitable workplace where our talent is respected, accepted and empowered to be themselves. To learn more about our commitment to Diversity, Equity and Inclusion, check out Life at Teachers'.

How to apply

Are you ready to pursue new challenges and take your career to the next level? Apply today! You may be invited to complete a pre-recorded digital interview as part of your application.

Accommodations are available upon request (peopleandculture@otpp.com) for candidates with a disability taking part in the recruitment process and once hired.

Candidates must be legally entitled to work in the country where this role is located.

Ontario Teachers' may use AI-based tools to assist in screening and assessing applicants for this position. These tools may help us identify candidates whose skills and experience align with Ontario Teachers' objectives by analyzing information provided in resumes and applications. Our use of AI does not replace human decision-making.

To learn more about how Teachers' uses AI with your personal information, please visit our Privacy Centre.

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