Regional Sales Manager

Job Description: 

ABOUT CLUB CADDIE

Club Caddie is a fast-growing golf course management software (GMS) company and a member of the Jonas Software family, a division of Constellation Software Inc. (TSX: CSU). Our platform is the operating system for golf, unifying point of sale, tee sheet, member management, food and beverage, and payments into a single connected system for public, semi-private, and multi-course operators.

We are built by operators, for operators, and our brand is anchored in four commitments: Unified Operations, Intelligent Action, Revenue Momentum, and Hospitality Memory. Our mission is to expand Jonas' reputation and market share with public, semi-private, and single-course operators (SCOs), and we're investing in field sales talent that knows these courses inside and out.

THE ROLE

The Sales Manager owns and grows a defined regional territory by winning new single-course operator (SCO) customers. This is a hunting and consultative selling role for a seasoned golf industry professional who knows course operations, understands GMS technology, and can guide owners and general managers from first conversation to signed agreement.

You will report directly to the Vice President of Sales (SCO) and work in close partnership with Marketing, Product, Implementation, and Customer Success to build a healthy territory pipeline, tailor your strategy to regional market dynamics, and deliver a clean handoff to onboarding for every new customer.

The Salary range for this role is between $70,000 - $75,000 USD

WHAT YOU'LL DO

Own and Grow Your Regional Territory

• Build and execute a territory plan that targets high-value SCO opportunities, tailored to the market dynamics of your region.

• Maintain a strong, consistent pipeline from lead generation through close, with steady activity at every stage.

• Use deep industry expertise to tailor Club Caddie's value proposition to each course's operation and goals.

Lead the Full Sales Cycle

• Own the end-to-end process: prospecting, discovery, presentations, demos, negotiation, and contract execution.

• Present Club Caddie's platform with a high level of technical and operational credibility.

• Meet or exceed territory quotas and revenue targets.

Build Industry Relationships

• Develop long-term, trust-based relationships with course owners, general managers, and industry influencers.

• Represent Club Caddie at industry events, trade shows, and regional gatherings to build pipeline and brand presence.

• Act as a trusted advisor and ambassador, positioning Club Caddie as the premier GMS for single-course operators.

Win Against the Competition

• Negotiate and close deals with a clear, defensible value narrative, maximizing revenue per customer.

• Compete effectively against incumbent point-of-sale and tee sheet providers.

Drive Cross-Functional Alignment

• Partner with Marketing on territory-specific campaigns and lead-generation efforts.

• Share market feedback with Sales Leadership, Product, and Marketing to refine go-to-market strategy and competitive positioning.

• Ensure a clean, well-documented handoff from sales to implementation, protecting the customer experience from contract to go-live.

Forecasting & Performance

• Keep activities, pipeline stages, and deal progression accurate and current in HubSpot.

• Deliver regular territory performance reports and forecasts to the VP of Sales (SCO).

• Continuously analyze territory results and refine your approach to improve conversion and revenue growth.

WHAT YOU BRING

• Proven SaaS or enterprise software sales experience, with a strong track record of meeting and exceeding targets; golf industry experience strongly preferred.

• Extensive knowledge of golf course operations, with experience working in or selling to single-course operators.

• Familiarity with GMS platforms, POS systems, and the technology that runs a golf operation.

• Excellent consultative selling skills, with the ability to build trust and credibility with owners, GMs, and front-line operators.

• Strong negotiation and closing skills, including a history of winning deals against established competitors.

• Highly organized and data-driven; disciplined about CRM hygiene, pipeline accuracy, and forecasting (HubSpot experience a plus).

• Self-directed and results-driven, thriving as an individual contributor and able to balance priorities across a large territory.

• A genuine passion for the golf industry and for helping operators run better businesses.

WHY JOIN CLUB CADDIE

• Own a regional territory and be directly responsible for driving its revenue growth.

• Sell a genuinely differentiated, unified platform into an industry you love, with the autonomy to build your own pipeline and strategy.

• Competitive base plus uncapped commission, benefits, and career growth, backed by the scale and stability of Jonas Software and Constellation Software.

• Help shape how Club Caddie wins with single-course operators, not just execute an existing playbook.

Club Caddie is an Equal Opportunity Employer.

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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.