VP, Sales

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 600 000 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.

What You’ll Do

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

Lead, mentor, and manage the sales team – including recruiting, onboarding, training, goal‑setting, and ongoing performance management – ensuring the team consistently reaches their quotas.

Identify skill and knowledge gaps within the team and implement targeted coaching, training programs, and development initiatives to strengthen capabilities.

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

Drive new business acquisition while deepening relationships with existing customers.

Lead negotiations and close large enterprise deals and strategic partnerships, acting as a player‑coach when needed.

Develop and manage sales compensation plans, quotas, and incentive structures.

Represent our client 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 forecasts, insights, and recommendations – for senior leadership.

Monitor market trends, competitive activity, and emerging opportunities, developing strategies to keep the organization well‑positioned for growth.

Champion CRM excellence, maintaining accurate data in HubSpot and reinforcing consistent usage standards across the team.

Build dashboards and performance reports using CRM tools and other data sources to track KPIs and support data‑driven decision‑making.

What You Bring

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

A proven track record 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 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 through 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 experience coaching and developing high‑performing sales teams.

Willingness to travel 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

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