Job Description:

VP of Revenue

Club Caddie

COMPANY

Club Caddie is one of the fastest-growing SaaS platforms in golf course management, helping operators streamline operations and maximize revenue. As we scale, we need a strategic leader who can drive revenue growth, optimize internal sales and marketing operations, and execute data-driven strategies—all while serving as a trusted advisor to the executive team.

POSITION

This VP will ensure Club Caddie meets and exceeds its EBITA targets while optimizing internal processes and aligning leadership on key objectives.The ideal candidate is an analytical, results-driven leader who thrives at the intersection of revenue generation, operational execution, and data-driven strategic advisory. You should be just as comfortable rolling up your sleeves in HubSpot to track sales data as you are challenging leadership with insights from business cases or preparing data for stakeholder presentations.

JOB RESPONSIBILITIES:

• Oversee sales pipeline management to ensure visibility, accuracy, and predictable revenue.
• Build robust forecasting models to track booked vs. projected revenue.
• Optimize sales development strategies, driving high-quality lead generation.
• Manage HubSpot CRM operations, ensuring data integrity, actionable insights, and sales efficiency.
• Align marketing spend with CAC vs. LTV ratios to maximize ROI across channels.
• Track and prevent revenue leakage, ensuring all contracted revenue is recognized and collected.
• Assist with budget management, staying motivated to drive both growth and profitability.

• Own Club Caddie’s Utopia Grid, tracking revenue opportunities and back-to-base sales.
• Provide real-time visibility into revenue performance for leadership.

• Roll out and track company-wide OKRs, ensuring execution across revenue-driving channels.
• Collaborate with the VP of Sales, Customer Success, Marketing, and Product to align revenue-driving teams.
• Drive cross-functional collaboration, leveraging data to guide decisions and enhance financial predictability.
• Focus on profitable growth opportunities, identifying the best opportunities as they arise.

• Assist in preparing investor reports, board decks, and Quarterly Strategic Review (QSR) materials.
• Ensure clear communication of financial projections, revenue targets, and strategic updates.
• Act as a key contributor to Club Caddie’s long-term growth strategy, keeping investors and stakeholders aligned.
• Proactively flag risks and opportunities, ensuring revenue goals remain on track.
• Provide business cases and data-backed insights to support executive decision-making.

JOB QUALIFICATIONS:

• 7+ years of experience in Revenue Operations, Sales Leadership, Chief of Staff, or Strategy roles
• Preferred: Prior experience in green grass golf operations and knowledge of the North American golf management software market.
• Proven track record in sales pipeline management, revenue forecasting, and strategic growth.
• Strong HubSpot expertise—you know how to track, optimize, and report on revenue performance.
• Excellent communication skills—able to distill complex data into clear, actionable insights.
• High accountability and ownership mindset—you take full responsibility for revenue and strategic execution.
• Experience preparing board and investor materials is a plus.
• Flexibility and commitment – This role requires dedication, including frequent extended hours, weekends, travel, and availability across time zones as needed to meet strategic objectives.

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More About Jonas Software:

Jonas Software is the leading provider of enterprise management software solutions to the Country and Golf Clubs, Foodservice, Construction, Fitness & Sports, Attractions, Salon & Spa, Education, Radiology/Laboratory Information Systems, and Product Licensing industries. Within these vertical markets, Jonas is made up of over 65 distinct brands, which are respected and leaders within their own domain.

Jonas’ vision is to be the branded global leader across the aforementioned vertical markets and to be recognized by customers and respective industry stakeholders as the trusted provider of ‘Software for Life’ and as an ambassador for technology, product innovation, quality, and customer service.

Jonas Software is the valued technology partner of over 60,000 customers worldwide in more than 30 countries. Jonas employs over 2,000 skilled individuals consisting of a cross-section of industry experts and technology professionals. Jonas is headquartered in Canada and also operates offices throughout North America, the United Kingdom, Europe, Australia New Zealand and Africa. Jonas is a 100% owned subsidiary of Constellation Software Inc., headquartered in Toronto and traded on the S&P/TSX 60.