Director of Advertising Sales

Octopus HR is a fractional HR consultancy that partners with high-growth startups to build exceptional teams. We specialize in talent acquisition, people operations, and HR strategy for innovative companies scaling rapidly. We’re proud to partner with Blossom on this search.

Blossom is seeking an experienced Director of Advertising Sales to lead and scale its Canadian advertising revenue. This role owns a significant portion of national revenue and is responsible for building long-term partnerships with ETF issuers, brokerages, and financial institutions.

You will run full-cycle sales across prospecting, pitching, negotiation, closing, onboarding, and renewal, while helping shape sales strategy, category positioning, and future advertising products. This is a senior, high-ownership role within one of Canada’s fastest-growing consumer fintechs.

• 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

• 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

• Experience working in a high-growth startup environment
• Existing familiarity with the Blossom product or consumer fintech platforms
• Knowledge of the Canadian investing landscape or ETF industry
• Experience selling to financial institutions or regulated industries

• 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

• Location: Toronto (in-person with periods of remote work)
• Type: Full-time
• Compensation: $100K base with $180K–$200K OTE, plus additional upside as the company scales

We value diverse perspectives and encourage candidates to apply even if they don’t meet every requirement listed above.

Applications can be submitted via the provided application link.