Chief Executive Officer

About the Company

Our client is a pioneering software company dedicated to offering innovative solutions for the real estate sector. They aim to enter a new phase of expansion and are seeking a Chief Executive Officer to spearhead this growth.

Role Overview

This exciting leadership position requires a dynamic, hands-on, commercially savvy executive to oversee the company’s strategic direction, daily operations, and financial health. The ideal candidate will have proven experience driving growth within software, technology, digital marketing, or sales-focused businesses, with direct profit and loss accountability, and a strong aptitude for leveraging data, KPIs, and disciplined operational execution.

Key Responsibilities

• Drive the company’s overall strategy, operational management, and financial outcomes.
• Own full P&L responsibility including revenue growth, profitability, cash flow, and enhancing enterprise value.
• Create and implement a growth strategy emphasizing sales efficiency, digital marketing effectiveness, customer retention, and expanding product and service offerings.
• Establish and monitor critical KPIs across sales, marketing, customer success, retention, product development, and finance.
• Lead the senior leadership team and broader workforce to maintain alignment and accountability towards corporate objectives.
• Enhance the digital marketing framework, focusing on lead generation, conversion rates, customer acquisition cost, channel effectiveness, and marketing ROI.
• Track and improve metrics related to customer churn, retention, engagement, and sales productivity to maximize lifetime value.
• Identify and implement operational improvements across systems, processes, reporting, team configuration, and performance management.
• Collaborate with the Board and shareholders in strategic planning, budgeting, forecasting, and expansion initiatives.
• Provide strong leadership, direction, and accountability throughout the employee base while cultivating a performance-driven culture.
• Be actively involved as needed in detailed analysis, data review, operations problem-solving, and execution support.
• Assess new opportunities including products, pricing models, markets, and partnerships.
• Represent the company externally with key customers, partners, and vendors.
• Prepare the organization for potential future exit events by enhancing scalability, reporting, retention, and predictability of growth.
• Manage the complete P&L, including revenue, gross margin, operating expenses, EBITDA, cash flow, budgeting, and resource allocation.
• Work closely with the product and development teams to align product roadmaps with customer needs, retention goals, and business growth strategies.
• Oversee customer service, success, and retention efforts aiming to elevate customer experience, reduce churn, and increase customer lifetime value while maintaining high service standards.

Candidate Profile and Requirements

• Extensive background in digital marketing, including managing or overseeing performance marketing, lead generation, paid search, social media campaigns, SEO, conversion optimization, marketing funnels, and understanding customer acquisition economics.
• Proven success growing revenue through digital marketing led customer acquisition by enhancing lead quality, conversion rates, customer acquisition costs, payback periods, and marketing returns.
• Experience as a CEO, General Manager, business unit leader, or senior executive with direct profit and loss responsibility.
• Track record of managing sales and marketing teams with accountability for revenue, pipeline, conversion, retention, and profitability goals.
• Strong analytical skills with the capability to make informed business decisions using data, dashboards, and KPIs.
• Preferably experienced within SaaS, software, technology, or tech-enabled service environments.
• Advantageous experience in B2C, SMB, subscription-based, or high-churn markets.
• Familiarity with real estate technology, property technology, or software/services oriented toward the real estate industry is a plus.
• Highly motivated, energetic, ambitious, and able to act decisively with urgency.
• Comfortable balancing strategic leadership with hands-on involvement in evaluating marketing performance, sales data, customer feedback, churn, and financial results.
• Strong focus on metrics and accountability for meeting targets and delivering results.
• Robust financial expertise encompassing budgeting, forecasting, profitability management, and allocation of resources.
• Excellent problem-solving aptitude, communication, leadership, and conflict resolution capabilities.
• Experience working closely with Boards and shareholders in environments demanding high accountability.
• Based in Toronto or able to work primarily onsite in Toronto.
• Prior experience with private equity-backed, venture-backed, or fast-growing organizations is beneficial.
• Knowledge of ERP implementations and financial systems optimization.
• Demonstrated experience in leading and managing people effectively.

Additional Information

The Mason Group promotes a diverse, inclusive, and accessible hiring process and welcomes applicants from all qualified backgrounds. Accommodations can be provided throughout the recruitment stages under the Accessibility for Ontarians with Disabilities Act (AODA).

The position is currently open for immediate hiring.