Operating Executive Jobs in Ontario (NOW HIRING)

Our client is an innovative, growth-oriented software company focused on providing solutions to the real estate industry. The Company is seeking a Chief Executive Officer to lead the business through its next stage of growth.

This is an exciting opportunity for a high-energy, hands-on, commercially minded leader to take ownership of the Company’s strategy, execution, and financial performance. The ideal candidate has experience growing a software, technology, digital marketing, or sales-driven business, with direct P&L responsibility and a strong ability to manage performance through data, KPIs, and disciplined execution.

• Lead the overall strategy, operations, and financial performance of the Company
• Own the Company’s P&L and be accountable for revenue growth, profitability, cash flow, and enterprise value creation
• Develop and execute a clear growth plan focused on sales productivity, digital marketing performance, customer retention, and product/service expansion
• Set, monitor, and manage key performance indicators across sales, marketing, customer success, retention, product, and finance
• Lead and manage the senior team and broader employee base to ensure alignment, accountability, and execution against the Company’s goals
• Evaluate and improve the Company’s digital marketing engine, including lead generation, conversion rates, customer acquisition cost, channel performance, and return on marketing spend
• Monitor churn, retention, customer engagement, and sales productivity metrics, and implement initiatives to improve customer lifetime value
• Identify and execute operational improvements, including systems, processes, reporting, team structure, and performance management
• Work closely with the Board and shareholders on strategic planning, budgeting, forecasting, and growth initiatives
• Provide leadership, guidance, and accountability to employees while maintaining a strong performance-oriented culture
• Be hands‑on where required, including conducting analysis, reviewing data, solving operational issues, and supporting execution at a detailed level
• Evaluate new product, pricing, market, and partnership opportunities
• Represent the Company with key customers, partners, vendors, and other external stakeholders
• Prepare the Company for a potential future sale or exit, including improving scalability, reporting, retention, and growth predictability
• Oversee the Company’s full P&L, including revenue, gross margin, operating expenses, EBITDA, cash flow, budgeting, forecasting, and resource allocation
• Lead and manage the Company’s product roadmap in partnership with the product/development team, ensuring product priorities are aligned with customer needs, retention, growth opportunities, and overall business strategy
• Oversee customer service, customer success, and retention initiatives, with accountability for improving customer experience, reducing churn, increasing customer lifetime value, and ensuring the Company maintains strong service levels

• Strong digital marketing background, with direct experience managing or overseeing performance marketing, lead generation, paid search, paid social, SEO, conversion optimization, marketing funnels, and customer acquisition economics
• Demonstrated ability to grow revenue through digital marketing‑led customer acquisition, including improving lead volume, lead quality, conversion rates, customer acquisition cost, payback period, and return on marketing spend
• Experience as a CEO, General Manager, business unit leader, Head of Digital Marketing, Head of Growth, VP/Head of Sales, VP/Head of Marketing, or senior operating executive with direct P&L responsibility
• Experience managing sales and marketing teams and holding them accountable to measurable revenue, pipeline, conversion, retention, and profitability targets
• Strong analytical ability, with experience using data, dashboards, and KPIs to make business decisions and improve performance
• Experience in SaaS, software, technology, or tech‑enabled services is preferred
• Experience operating in a high‑churn, B2C, SMB, or subscription‑based environment is a strong asset
• Experience in real estate technology, proptech, or software/services sold into the real estate industry is an asset
• Highly ambitious, energetic, and self‑motivated, with the ability to execute quickly and operate with urgency
• Comfortable operating in a hands‑on environment where the CEO is expected to both lead strategically and get directly involved in execution, including reviewing marketing performance, sales data, churn drivers, customer feedback, and financial performance
• Metrics‑driven and highly accountable for achieving targets and results
• Strong financial acumen, including budgeting, forecasting, profitability management, and resource allocation
• Excellent problem‑solving, communication, leadership, and conflict management skills
• Comfortable working with a Board and shareholders in a high‑accountability environment
• Toronto‑based or able to work primarily from Toronto
• Experience supporting private‑equity‑backed, venture‑backed, or rapidly scaling organizations
• Experience with ERP implementations and finance systems optimization
• Previous people‑leadership experience

The Mason Group is committed to fostering a diverse, inclusive, and accessible recruitment process. We welcome applicants from all qualified candidates. Accommodations are available upon request for candidates participating in all stages of the recruitment process, in accordance with the Accessibility for Ontarians with Disabilities Act (AODA).