Director of Sales

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.

If you are a sales leader with strong enterprise experience, a passion for transformation, and the ability to influence senior stakeholders—this role offers the opportunity to build, modernize, and truly make your mark.

Advantages
- Lead a high-impact transformation:
Drive the shift from legacy selling models to modern, tech-enabled, subscription-style offerings.
- Warm enterprise portfolio:
Manage and grow relationships with established, high-profile clients - no cold building from scratch.
- High visibility role:
Report directly to senior leadership with influence over strategy, pricing, and go-to-market direction.
- Modernization mandate:
Work with emerging AI tools and automation capabilities that significantly enhance content production and delivery.
- Collaborative leadership culture:
Join a team that is open to ideas, flexible in approach, and committed to continuous innovation.
- Strong total rewards:
Competitive base compensation, annual performance bonus, four weeks of vacation, comprehensive benefits, and hybrid flexibility.

Responsibilities
Sales & Growth Leadership
- 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.

Transformation & Change Leadership
- 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.

Team Management & Development
- 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.

Client & Market Strategy
- 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.

Qualifications
- 7+ years of progressive B2B sales experience, including senior leadership in enterprise environments.
- Background in SaaS, Mar Tech, 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…