Hybrid Director of Advertising Sales

at Octopus HR

• Job title: Director of Advertising Sales
• Job type: Full Time
• Experience level: Lead
• Salary: CA$100,000 per year
• Degree requirement: Bachelor's Degree
• Location requirements: Hybrid, Toronto, Canada

About the role

• Director of Advertising Sales at Blossom, responsible for building long-term partnerships and national revenue in Canada. Engage with senior clients, execute strategies, and mentor teams.

Responsibilities

• Own and grow a multi-million-dollar book of business across leading Canadian ETF issuers and financial brands
• Prospect, pitch, and close new advertising and brand partnerships
• Develop strategic media plans that align closely with client objectives
• Manage long-term client relationships with clear renewal and expansion goals
• Build and maintain a strong network of senior industry contacts across the Canadian wealth ecosystem
• Shape category strategy for how financial brands activate and tell their story on Blossom
• Contribute to sales playbooks, positioning, and go-to-market messaging
• Identify new revenue opportunities, experimental formats, and pilot campaigns
• Partner closely with the CEO, product, and content teams to influence new advertising products
• Mentor and support junior members of the partnerships team through knowledge sharing and informal leadership
• Collaborate with client success, design, content, and product teams to deliver high-quality campaigns
• Oversee timelines, deliverables, and performance across multiple partnerships
• Support problem-solving, communication, and ongoing optimization throughout campaigns
• Support the Head of Brand Partnerships and CEO with proposals, reporting, and strategic planning
• Translate client goals into compelling proposals, presentations, and advertising strategies
• Maintain strong internal organization using tools such as CRM, Notion, Google Workspace, and Figma
• Communicate pipeline health, forecasts, and progress to internal stakeholders

Requirements

• Proven track record of exceeding revenue targets in advertising, media, sponsorship, or enterprise sales
• 7+ years of experience in advertising sales, media partnerships, or related roles with long-term account ownership
• Strong experience leading complex, multi-stakeholder deals from outreach through close and renewal
• Demonstrated ability to manage forecasting, pipeline, and CRM discipline
• Ability to build deep, strategic client relationships across a large portfolio of accounts
• Excellent verbal and written communication skills
• Highly organized, process-driven operating style
• Comfort working with presentation and collaboration tools such as Google Slides, Notion, and Figma
• Interest in investing, finance, or fintech, or the ability to learn the space quickly

Benefits

• Impact: Own and grow a meaningful portion of national revenue at a rapidly scaling fintech
• Ownership: High-visibility role with direct influence on strategy, positioning, and product direction
• Growth: Opportunity for role and compensation growth as the business scales
• Team: Work closely with founders and senior leaders in a collaborative, ambitious environment