Our client is a leading digital-only media company in Canada looking for a key leadership hire. They have a strong hyper-local focus in Ontario, with 15 million monthly pageviews and 600K social media followers across content spanning food, real estate, lifestyle, travel, and breaking news.

This is an exciting opportunity for someone who is passionate about the digital space, able to wear multiple hats, and eager to join a growing team. Reporting directly to the CEO, you will oversee sales and business development activities, manage a high-performing sales team, and drive revenue growth for the organization.

About You

This is an exciting opportunity for someone who is passionate about the digital space and eager to join a growing team. In this role, you will help build and lead sales and business development activities, recruit and build a sales team from the ground up, and drive revenue growth.

Responsibilities

- Develop and execute a comprehensive sales strategy to expand customer base, accelerate revenue growth, and enhance regional market presence.

- Develop and execute the strategy to build and scale the sales team from the ground up, including recruiting, onboarding, training, goal-setting, and ongoing performance management, with accountability for establishing a high-performing team that consistently achieves its sales targets.

- Establish and optimize sales processes, pipelines, and CRM systems to drive efficiency and visibility.

- Drive current business acquisition while expanding relationships with existing customers.

- Lead negotiations and close key deals and strategic partnerships when necessary, taking on the role of a player-coach.

- Represent the company at industry events, conferences, and key client meetings.





- Oversee month-end and year-end sales processes, ensuring accurate reporting, pipeline hygiene, and timely close of all revenue-related activities.

- Prepare and present detailed sales, revenue, and expense reports, including accurate forecasts, insights, and recommendations for senior leadership.

- Monitor market trends, competitive activity, and emerging opportunities, and develop strategies to keep the company highly competitive and well-positioned for growth.

- Ensure CRM excellence, maintaining accurate and up-to-date data in HubSpot and reinforcing consistent usage standards across the team.

- Develop dashboards and performance reports using CRM tools and other data sources to track KPIs, analyze team performance, and support data-driven decision-making.

Requirements

- Minimum 5 years of progressive experience in sales leadership, preferably within high-growth or digital-first organizations.

- A measurable track record of selling digital advertising solutions—including display, sponsored content, social media, and video—while consistently meeting or surpassing revenue targets.

- Background in digital publishing, digital media, or advertising sales (highly preferred).

- Proficiency in CRM platforms, ideally HubSpot, along with strong working knowledge of Google Workspace and Microsoft Office.





- Deep understanding of social and digital ecosystems, including, but not limited to, Facebook, Instagram, TikTok, YouTube, and LinkedIn, and how brands leverage these channels for performance and brand marketing.

- Demonstrated ability to lead the full sales cycle—from strategic planning and pipeline development to negotiation and deal closure.

- Exceptional communication, relationship-building, and presentation skills, with the ability to influence both internal and external stakeholders.

- Strong business acumen and leadership capability, including experience coaching and developing growing sales teams.

- Willingness to travel alongside sales executives for client meetings, industry events, and partnership opportunities.

- Based in the Greater Toronto Area, with strong knowledge of the local media, agency, and brand landscape.

- Experience working with media agencies or in media planning is a strong asset.

- Bachelor's degree in Business, Marketing, Sales, or a related field (or equivalent experience).

Why This Role

Our client fosters a collaborative, creative, and impactful culture — one where ideas are celebrated and teamwork drives results. They offer:

- Comprehensive benefits including dental, vision, extended health coverage, and an Employee Assistance Program (EAP)
- Flexible paid time off, including vacation time
- Flexible remote-first work arrangements
- An engaging culture with in-person meetings, social events, and team-building activities
- Opportunities for career growth, professional development, and skills training
- Wellness programs including gym memberships, wellness stipends, and mental health initiatives

📌 Director of Sales (Toronto)
🏢 Junction Collective
📍 Toronto