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.

Key Responsibilities

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 explicit 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

Requirements

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

Additional Information
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).

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📌 Chief Executive Officer (Ontario)
🏢 The Mason Group
📍 Ontario