Who we are

Kilmer Group is a multi-generational platform for business development and investment, built on operational excellence, long-term stewardship, and trusted relationships. Headquartered in Toronto, we invest across three core sectors: Private Capital, Infrastructure & Real Estate, and Sports & Media, partnering with exceptional management teams to build and grow enduring businesses.

Kilmer Group has built a reputation for disciplined investment, active ownership, and creating long-term value. Our approach is grounded in partnership, integrity, and a commitment to building businesses that generate lasting impact for our partners, stakeholders, and the communities we serve.

Who we need

Reporting to the President, Kilmer Capital Partners, we are hiring a Director, Private Capital Investments. In this role, you will lead investments across the full lifecycle, from evaluating opportunities and overseeing due diligence through transaction execution, integration, and ongoing portfolio management. You will combine rigorous financial and investment analysis with practical business judgment to assess opportunities, identify risks and value creation levers, and translate insights into clear recommendations and action. Working closely with portfolio company leaders, Kilmer senior leadership, external advisors, and a team of two Managers, you will help strengthen businesses over the long term while contributing to a collaborative, transparent, and forward-looking culture within the Private Capital Investments team.

This is an existing, full-time opportunity based in the Toronto office, with periodic travel to support portfolio companies and integration activities.

What’s in it for you?

Impact and investment opportunity. You will play a meaningful role in evaluating new opportunities, shaping investment decisions, and working beyond the transaction to help portfolio companies grow and create long-term value.

Breadth and visibility. You will gain exposure to investments across a diverse range of industries rather than specializing in a single sector. Working within a small, experienced team, you will have direct access to senior leadership across Kilmer and work closely with CEOs and executive teams within portfolio companies, giving you the opportunity to see the impact of your thinking and decisions firsthand.

A broader private capital experience. You will have the opportunity to move beyond a high-volume, transaction-focused investment environment and become more deeply involved in the businesses you invest in. From diligence and integration through strategic planning, operational improvement, and ongoing value creation, you will build a broader perspective on what it takes to strengthen and grow businesses over the long term.

Leadership and influence. This role comes with real scope: leading deals, coaching and developing a team, and shaping how Private Capital Investments works together as we grow. You'll bring your own perspective and judgment to the table, build strong relationships across Kilmer and its portfolio companies, and play a meaningful role in shaping the investment function

As our new Director, Private Capital Investments, you will:

Evaluate investment opportunities. You will lead the assessment of potential investments, combining rigorous financial analysis with commercial and operational judgment to understand the business, market dynamics, management team, risks, and long-term value creation potential. You will develop investment theses and translate your findings into clear recommendations for senior leadership and the Investment Committee.

Lead due diligence and transaction execution. You will oversee end-to-end diligence across financial, operational, commercial, tax, legal, and strategic workstreams, coordinating internal stakeholders and external advisors. You will identify risks and opportunities, challenge assumptions, and use your findings to inform transaction structuring, negotiations, and investment decisions.

Drive integration and value creation. You will stay actively involved after an investment closes, partnering with portfolio company leaders to support integration and identify opportunities to strengthen the business. You will bring a long-term ownership perspective to strategic planning, operational improvements, capital allocation, acquisitions, organizational development, and other initiatives that can increase enterprise value.

Monitor and strengthen portfolio performance. You will develop a deep understanding of portfolio company performance, using financial results, operational metrics, KPIs, and market insights to identify trends, risks, and opportunities. You will oversee portfolio reporting and bring forward practical, data-informed recommendations that support better decisions and sustainable growth.

Build trusted partnerships. You will work closely with CEOs, executive teams, Kilmer leadership, boards, lenders, and external advisors, bringing curiosity, sound judgment, and a collaborative approach to complex business challenges. You will act as a strategic partner who can ask the right questions, constructively challenge thinking, and help turn insights into action.

Lead and develop the team. You will coach and develop two Managers, providing guidance across investment analysis, diligence, execution, and portfolio work while creating opportunities for them to expand their capabilities and ownership. You will help foster a collaborative, transparent team environment.

You bring:

The investment experience. You have built your experience in private equity, private capital, transaction advisory, valuations, investment banking, corporate development, or another environment where you have evaluated businesses and supported complex investment decisions. You have led or played a significant role in due diligence and transaction execution, with the ability to move between detailed analysis and the broader investment thesis.

The financial and analytical expertise. You have strong financial modelling, valuation, and investment analysis skills and can confidently assess historical and projected performance, cash flow, working capital, capital structures, and key value drivers. You know how to absorb large amounts of information, identify meaningful trends and risks, challenge assumptions, and turn your analysis into clear recommendations.

The commercial mindset. You look beyond the numbers to understand how a business operates, competes, and creates value. You bring sound business judgment and intellectual curiosity to assessing markets, management teams, operational opportunities, and potential risks, and you can identify practical opportunities to strengthen performance and create long-term enterprise value.

The leadership skills. You have experience guiding and developing others while remaining willing to work alongside your team in the details when needed. You set clear expectations, provide thoughtful coaching, and create an environment where people can ask questions, challenge ideas, and continue building their capabilities.

The relationship-building skills. You can build credibility and trusted relationships with senior leaders, management teams, advisors, and colleagues across different functions. You communicate complex financial and business information clearly, ask thoughtful questions, and can constructively challenge perspectives while remaining collaborative and focused on the best outcome.

The ownership mindset. You bring high standards for accuracy, integrity, discretion, and follow-through. You are comfortable navigating ambiguity and complex decisions, balancing independent thinking with collaboration, and taking accountability for your work from initial analysis through execution and ongoing portfolio stewardship.

The flexibility. You are able to travel periodically to work directly with portfolio companies and support integration and value creation initiatives. A CFA, CBV, MBA, or similar designation would be an asset but is not required.

Why join Kilmer Group?

Today, Kilmer Group continues to build on decades of successful investment and business leadership offering a dynamic and supportive environment with opportunities for growth and development. Beyond our investments, we are committed to strengthening the communities where we live and work through initiatives that support sport, health, research, and community development. Joining Kilmer Group means becoming part of an organization that thinks for the long term, values partnership, and is committed to building a lasting legacy.

Join us

We recognize that no candidate brings every qualification to a role. If your experience is closely aligned with what we are looking for and you are excited by the opportunity to contribute to Kilmer Group, we encourage you to apply. We look forward to learning more about your experience and the perspective you would bring to our team.

What you can expect from our interview process

• A virtual interview with a Talent Advisor to discuss your interest in joining the company and in the role. The conversation will be recorded using BrightHire, an AI-powered video interview tool. More details will be shared when you are invited to interview.
• An in-person interview with the Chief Financial Officer and the Vice President, Talent and Special Projects focused on your experience, collaborative approach, and alignment with the organization and its culture.
• An in-person interview with a panel of senior leaders, including the President of Kilmer Capital Partners. This interview will focus on your investment experience, technical capabilities, approach to diligence and value creation, and alignment with the direction of the Private Capital Investments team. You will also create and present a Case Study to be shared with the team.

Kilmer Group is committed to creating a workplace where people are treated with respect, supported in their development, and empowered to contribute their best work. We recognize that diverse perspectives strengthen our business and help us make better decisions for our organization, our partners, and the communities in which we operate.

We welcome applications from all qualified candidates and are committed to providing an accessible recruitment process. If you require accommodation at any stage of the recruitment process, please let us know and we will work with you to meet your needs.