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: 

➡️ Gemini: https://www.csigemini.com/ 

➡️ Constellation Software: https://www.csisoftware.com/ 

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 ) 

• 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 Perseus 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  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.