Program director Jobs in Oakville, ON

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, 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.

Summary
We’re hiring a Director of Sales to help lead a major digital transformation within a large enterprise content solutions organization. You’ll guide a senior team of account managers, drive revenue strategy, expand enterprise relationships, and champion the shift toward AI-enabled, subscription-based offerings. This hybrid Mississauga-based role is perfect for a tech-savvy, strategic sales leader with deep enterprise experience and a passion for modernization and change.

Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada. As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees. In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada's workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.

Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle. We ask that all job applications please identify any accommodation requirements by sending an email to accessibility@randstad.ca to ensure their ability to fully participate in the interview process.