Chief of Staff

Gemini Group is looking for a Chief of Staff. In this role you will work closely with all department leads Including Sales, Marketing, Product, Finance, and Development to identify business opportunities, execute strategic product roadmaps and drive organic growth initiatives for the business. This role is designed to help you develop an understanding of our best practice framework for investing in and operating Vertical Market Software businesses.

Gemini Group is a division of Perseus Group under Constellation Software Inc. (TSX: CSU), a global leader in acquiring and growing vertical market software businesses. Our portfolio is made up of niche software companies across industries like automotive, healthcare, specialty retail, and more — giving them the tools, expertise, and capital to scale while preserving their independence.

We’re long-term investors in people and businesses. Our decentralized model means our teams stay close to their markets, supported by a network of shared knowledge and a culture built on trust, autonomy, and continuous learning.

Learn more about us here:

Preference will be given to candidates based in the Kitchener-Waterloo or Greater Toronto Area who are able to work in a hybrid model and attend our Waterloo or Toronto, Ontario office as needed. Other candidates may be considered based on experience.

This role also includes ad-hoc travel related to M&A activities.

About the Role In this role, you will help support the management and growth of businesses within the portfolio, as well as integrations of new acquisitions. Duties and responsibilities include:

Lead initiatives and special projects: provide value-added insight into the performance of each business. Identify opportunities for improvement or best practice sharing with other Perseus businesses

Financial Analysis: complete financial modelling and prepare analysis for presentations. Draw insights based on analysis performed, provide insight into possible improvements. Work with cross-functional finance resources to participate in quarterly business reviews, improve financial and operational performance metrics

Support M&A activities: including evaluating contracts, financial and operational analysis. You will gain exposure to the entire software acquisition cycle, ranging from evaluation of acquisition opportunities, financial modelling, and due diligence

Operational Support: work with Portfolio Manager and cross-functional teams to review monthly and quarterly business performances and improvements. Assist in developing effective action plans to implement, track, and assess the performance of approved initiatives

Education and Experience

4-8 years of work experience, with a minimum of two in management consulting (including strategy, integration, financial advisory), private equity, principal investment shop, or investment bank analyst program

Academic performance with an Undergraduate Degree in Business (MBA or CPA is considered an asset but not required)

Ability to establish credibility with senior business leaders

Proven research, analytical, and financial modelling skills

Comfortable with ambiguity and limited oversight; able to proactively identify opportunities to leverage skill set

Able to work independently and seek out guidance and learning/development opportunities from colleagues

Highly competent in excel with financial modelling experience

Desire to carve a long-term career path at Gemini Group, Constellation Software

What’s important to us at Gemini

Make long term investments: In people, technology, and customers. What goes around comes around and when possible, we try to pay it forward.

Growth through learning: Learning is the key to success. We encourage employees to share their expertise and best practices with their peers. That way, we all grow together.

Autonomy: Our staff operate independently in a decentralized structure. Whenever possible, we provide the independence required to drive growth and success.

Trust comes first: We believe in full transparency and ongoing communication; if there is a problem, we try to work collaboratively on solutions.

Salary Transparency & Total Rewards Trust Comes First - We aim to be transparent about our pay practices. We post what we reasonably expect to pay for this position at the time of posting, based on factors such as role scope, market data, internal equity, and experience. Beyond base salary, we offer a comprehensive total rewards package that may include health and wellness benefits, paid time off, learning and development opportunities, and other employee programs designed to support your well‑being and growth.

Human-Centered, AI-Supported We may use AI tools to support and streamline parts of our recruitment process, such as scheduling, application review, and note-taking. AI helps us work more efficiently and consistently, but it never replaces human judgment. All hiring decisions are made by people not machines. Interviews are conducted by real team members who want to get to know you and your experience. AI is used to reduce bias, improve fairness and streamline processes, while keeping human connection and individual stories at the heart of our process.

We follow a robust job requisition process at Gemini to ensure that posted jobs are open and available.

Salary Range (Ontario & BC Only) The estimated base salary range for this role is CAD$126,000.00 - CAD$154,000.00 per year. We include salary ranges in job postings only where required by applicable pay transparency laws, based on the jurisdictions in which the role may be performed. The posted range is a good faith estimate and reflects factors that are subject to change. Final offer amounts may vary based on job-related factors, including work location, candidate experience and expertise, and other relevant considerations.

We recognize the value and importance of diversity and inclusion in our communities and in the workplace. We celebrate diversity and one of our goals as an employer is to create an inclusive work environment for all employees. We are an equal opportunity employer and do not discriminate against any employee or applicant because of race, religion, sex, sexual orientation including gender identity or expression, pregnancy, national origin, age, marital status, veteran status, disability status, or any other category or characteristic protected by law.

Applicants with disabilities who would like to require a reasonable accommodation related to any part of the application process may contact us at Perseus_HR@constellationhbs.com.

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