President

Job Description:

The Company

Club Caddie is a leading provider of golf management solutions for the public, semi-private and multi-course operated industry across the U.S. and Canada. The company delivers integrated platforms that streamline operations, enhance guest/member experiences and provide actionable insights for club management. Known for its innovation, reliability and customer-focused approach, Club Caddie has established itself as a Tier 1 business within Jonas/Constellation Software, supporting clubs with best-in-class technology and services that drive operational efficiency and long-term growth.

Position

We are seeking a proven leader to drive the next phase of growth for Club Caddie. The President will be responsible for all aspects of the business, including strategy, sales, operations, customer experience and innovation. The ideal candidate brings deep software development experience, a track record of scaling customer-focused solutions and a strong orientation toward continuous improvement. This role will champion the adoption of AI-driven development practices to accelerate delivery, unlock client value, and create measurable business outcomes. The President will lead a high-performing team, enhance the customer experience and advance the business to the next level of innovation and market leadership. Reporting directly to the Jonas Club Division Portfolio Leader, the President will serve as a strategic partner within the Club Portfolio senior management team. Ultimately, this leader will ensure Club Caddie continues to deliver exceptional results while maintaining its reputation for excellence.

Job Responsibilities

• Provide full P&L leadership for Club Caddie across the U.S. and Canada, with ultimate accountability for financial performance, growth, and operational excellence
• Develop and oversee annual business plans, operating budgets, and long-range forecasts to consistently meet or exceed financial targets
• Establish and drive a performance culture using KPI frameworks, benchmarking (including CSI standards), and data-driven decision-making
• Ensure optimal organizational design and resource allocation to support scalable growth, operational efficiency, and evolving customer needs
• Act as the executive sponsor for key customer and partner relationships, strengthening market reputation and strategic alliances
• Champion a customer-centric culture, ensuring consistent delivery of exceptional service and long-term client success across all touchpoints
• Champion the adoption and integration of AI-driven Development Life Cycle (AI-DLC) practices to unlock client value, accelerate product innovation and delivery velocity, and drive measurable business outcomes across the organization
• Lead and develop a high-performing leadership team, fostering a culture of accountability, engagement and continuous improvement. Along with leading organizational effectiveness initiatives, including talent development, performance management and succession planning
• Navigate complex business challenges and conflict resolution with sound judgment, speed and a focus on enterprise-wide outcomes

Job Qualifications

• 10+ years of experience in customer-facing operations, ideally within vertical software solutions
• Results-driven and self-motivated, with a strong track record of resolving client issues
• Proven leadership with the ability to develop teams while taking personal accountability for outcomes
• Highly analytical and methodical problem-solver with strong business acumen and forecasting capabilities
• Demonstrated organizational agility and ability to build effective relationships with clients, colleagues and partners
• Experience fostering innovation, including leveraging AI within the Development Life Cycle (AI-DLC)
• Strong communication, negotiation, and influencing skills across diverse stakeholders
• Bachelor’s degree (or equivalent experience)
• Golf/club industry experience considered an asset
• Willingness to travel

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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.