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A fast-growing, market-leading organization in the content solutions and retail marketing space is undergoing a major digital transformation—and is now searching for a strategic Director of Sales to lead the next chapter of their growth. This team works with large enterprise brands on high-volume, multi-channel content programs, and is in the process of evolving from a traditional service model to a technology-enabled, AI-supported platform approach. As part of this shift, they are launching new tools that streamline content creation, accelerate workflows, and modernize the customer experience. In this role, you will be responsible for shaping the commercial vision, driving revenue growth, and leading a tenured sales/account team through meaningful change. You will play a key role in helping the business transition toward subscription-based offerings, digital automation, and value-driven enterprise partnerships.
Job Responsibility:
Own the sales strategy and revenue performance across a large enterprise client portfolio
Develop and execute growth plans to expand existing business and tap into new verticals
Create and manage key performance metrics to guide forecasting, pipeline health, and client success
Strengthen value-based selling by elevating conversations around ROI, operational efficiency, and digital adoption
Lead the transition from legacy pricing models to subscription and recurring revenue structures
Champion the adoption of AI-driven tools that accelerate content creation, personalization, and workflow automation
Support both internal teams and clients as they adopt new technology, processes, and commercial models
Collaborate with product and technology teams to align market needs with platform enhancements
Lead, mentor, and coach a team of senior account managers across Ontario and Quebec
Enable the team to evolve from traditional account servicing to consultative, strategic, solution-oriented selling
Drive a culture of accountability, collaboration, and innovation
Strengthen executive-level relationships with large enterprise clients in the retail and consumer sector
Identify opportunities to introduce new digital workflows, platform capabilities, and modern service offerings
Use analytics and insights to refine pricing, segmentation, and overall go-to-market planning
Requirements:
7+ years of progressive B2B sales experience, including senior leadership in enterprise environments
Background in SaaS, MarTech, AdTech, digital media, or technology-enabled services is preferred
Proven experience leading teams through digital transformation, change management, or adoption of new platforms/tools
Strong track record selling into large/complex organizations with multiple stakeholders
Demonstrated success with subscription-based or recurring revenue models is preferred
Exceptional communication, executive presence, and strategic thinking capabilities
Ability to work in a hybrid environment (2–3 days/week in the Mississauga office) and travel as needed
Nice to have:
Background in SaaS, MarTech, AdTech, digital media, or technology-enabled services
Demonstrated success with subscription-based or recurring revenue models