Group Leader I CEO

Jonas Software - Canada; Remote; CAD 120,000 - 160,000; Full time

Job summary

A leading software firm is seeking a Group Leader to oversee a portfolio of 5–7 business units. This role involves driving growth and operational excellence across the group, coaching leaders, and guiding AI/ML applications for product and internal efficiency. Ideal candidates will have over 10 years of leadership experience in the software industry, strong financial acumen, and the ability to foster a high-performing culture. The position is remote, offering competitive salary and flexibility.

Benefits

Competitive base salary

Performance-based bonus

Flexible work options

Qualifications

• 10+ years of leadership experience in the software industry, ideally in vertical SaaS.
• Proven record of scaling multiple businesses—both organically and through M&A integration.
• Strong leadership and people development capability.

Responsibilities

• Oversee a portfolio of 5–7 business units within the CORA Group.
• Drive growth, operational excellence, and product innovation.
• Act as Integration Manager for newly acquired entities.

Skills

Leadership

Stakeholder management

Financial acumen

Experience in vertical SaaS

Communication

Education

Bachelor's degree

MBA or relevant graduate education

Job description

Group Leader

CORA Group - Jonas Software • Remote Canada

About CORA Group

CORA Group is an operating group of Jonas Software under Constellation Software Inc. (TSX:CSU). We acquire, strengthen and grow vertical market software companies across a range of industry‑specific segments. Our “buy‑and‑hold forever” model delivers long‑term value, operational discipline, and entrepreneurial freedom.

Role Summary

As Group Leader, you will oversee a portfolio of 5–7 business units within the CORA Group. Your mandate is to drive growth, operational excellence, and product innovation across your group. You will coach Presidents (Business Unit Leaders), introduce best practices, and support diligence and integration for new acquisitions. You will also guide leaders in identifying practical AI/ML applications that strengthen product value or internal efficiency, ensuring AI use remains realistic and business‑driven.

Key Responsibilities

• Strategic leadership: define long‑term growth plans, operational KPIs, and innovation opportunities. Support AI adoption roadmaps where they clearly accelerate efficiency or customer value.
• Mentor business unit leaders and their teams: enable best practices, promote cross‑unit knowledge sharing, and foster a high‑performing culture. Provide light‑touch coaching on AI/automation opportunities and readiness.
• Ensure operational excellence: monitor and drive recurring revenue growth, profitability, churn/net retention, customer satisfaction, implementation velocity, and cost‑to‑serve.
• Lead acquisition integration: act as Integration Manager for newly acquired entities; oversee commercial, operational and back‑office assimilation into the CORA model. Highlight integration opportunities where AI/automation can streamline processes.
• Lead and support product innovation: help BU leaders evaluate enhancements to product strategy and customer experience. Where relevant, assess the feasibility of adding ML, predictive analytics, or generative AI features tied to customer value.
• Analyze vertical markets: deep‑dive into market dynamics, competitive landscape, win/loss reasons, pricing optimization and positioning.
• Cascade key metrics across business units: align targets with corporate goals and regularly review progress via weekly, monthly and quarterly reporting.
• Promote data‑driven decision making: lead financial reporting and forecasting, identify efficiencies, and challenge underperforming units. Encourage the use of analytics or automation tools that strengthen forecasting or reporting accuracy.
• Act as change agent: embed CORA/Jonas culture, promote innovation, and ensure that decentralization does not compromise discipline.

Required Qualifications & Experience

• 10+ years of leadership experience in the software industry, ideally in vertical SaaS.
• Proven record of scaling multiple businesses—both organically and through M&A integration.
• Strong leadership and people development capability.
• Comfortable in a fast‑changing, decentralized environment with a bias for execution.
• Financial acumen with experience managing to P&L.
• Experience guiding teams in identifying or evaluating AI/automation opportunities is a strong asset (not a requirement).
• Outstanding communication and stakeholder management skills.
• Bachelor’s degree required; MBA or relevant graduate education preferred.

Desired Characteristics

• Curious and adaptive; proactive in learning emerging tools and frameworks.
• Entrepreneurial, execution‑focused, and practical.
• Culturally aligned with CORA/Jonas.
• Appreciates the role of AI as an enabler, not a replacement for operational leadership.

Compensation & Benefits

Competitive base salary + performance‑based bonus. Long‑term incentive opportunities reflecting Constellation’s philosophy. Flexible work options, comprehensive benefits, and strong career path opportunities.

Why Join Us?

Play a pivotal role in shaping growth across a portfolio of vertical software companies. Operate at the intersection of strategy, execution, and innovation. Access deep operational knowledge from across the Constellation Software network.

Contribute meaningfully to CORA’s evolving AI strategy while maintaining focus on disciplined operations and strong leadership development.

More About Jonas Software

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.