Director, Digital Project Management

Date: Jan 16, 2026

Location: Toronto, ON, CA Chicago, IL, US

Company: Softchoice

Why you’ll love Softchoice:
We are a software-focused IT solutions and services provider that equips organizations to be agile and innovative, and for their people to be engaged, connected, and creative at work. That means moving them to the cloud, helping them build the workplace of tomorrow, and enabling them to make smarter decisions about their technology. By doing these things we help them create success for their customers and their people. 

We stand proudly for our people and support their success through career development and advancement. We are recognized and respected for our culture of inclusion and belonging, continuously striving to do what’s good for our people and communities. 
 

The impact you’ll have:

A dynamic, strategic and resourceful digital first thinker. A leader and facilitator responsible for all activities related to managing the delivery of multi-faced AI development initiatives. An effective communicator, you will be responsible for managing, enabling and empowering a cross functional team with the goal to deliver outstanding, profitable work for the clients within that team, while striving for a positive team environment and engaged staff.

The Digital Project Director will build relationships with AI, Innovation, IT, Marketing clientele and work alongside sales personnel to support the WWT Digital team in the development of new strategies that help our customers and prospects identify and then ultimately realize AI transformation through the entire portfolio of AI services that WWT has to offer. The Digital Project Director will drive the architecture of the Digital Project Management discipline including team best practice development and implementation.

The Digital Project Director reports to the Senior Director, Workplace Transformation.

 

What you’ll do:

  • You will be accountable for the entire project lifecycle on digital projects, working alongside the commercial & strategy teams and managing multidisciplinary teams from Strategy, Research, & AI.
  • Key participant in the business development process; leading business development efforts from a delivery perspective and coordination of team sales enablement and new business pitch efforts.
  • The role is client facing, managing all communication channels (meetings, workshops, email & documentation) and forums within the project.
  • Assigned to large and complex projects, you'll be expected to raise risks early and find solutions to fit the client's needs whilst sticking with project expectations.
  • Manage the technical, business and personnel aspects of consulting and development engagements.
  • Manage the invoicing, backlog and resource management activities for the assigned engagements in coordination with the Digital Operations and Managing Directors
  • Oversee multiple AI or delivery teams at once, provide leadership, guidance and standardized process, reporting and client communication.
  • Ensure deliverables are of the highest quality to promote client satisfaction.
  • Ensure key project management deliverables are produced such as project charters, project plans, resource plans, risk mitigation plans, change management plans, etc.
  • Serve as a key member of the solution delivery team by facilitating requirements/design sessions and producing deliverables.
  • Monitor project team engagement and performance and provide feedback; ensure involvement of the appropriate teams and individuals during each project phase.
  • Develop strong client relationships.
  • Assist in develop overall estimates of the effort / resource requirements / schedule.
  • Lead the risk assessment efforts during the proposal process and recommend appropriate risk mitigation strategies.
  • Drive development of the AI Project Management discipline including identification and implementation of AI project management best practices.
  • Lead team development including AI Project Manager mentorship and performance evaluation; manage workloads and project assignments.
  • Provide oversight and guidance on digital team tools and organizational processes.

 

What you’ll bring to the table:

Education

  • Bachelor’s Degree

Work Experience

  • At least 15 years of Project Management experience with at least 2 of those in the AI Tech space.

Specialized Knowledge, Skills, and Abilities

  • Demonstrated experience managing, reviewing and analyzing project scopes, budgets & resources to include change and resource requests.
  • Proven experience working with and managing multidisciplinary teams both internally and externally as required from strategy, research, AI
  • Exhibits superior communication skills, both oral and written; is clear, concise, sincere and persuasive. Is also a good listener and shows an interest in what others have to say.
  • Advanced problem-solving skills; ability to identify and remove roadblocks.
  • Demonstrated experience managing cross-functional teams and driving team engagement. Ability to enable direct and healthy communications across all team members.
  • Confident in both client engagement and operational / delivery management.
  • Strong scope management and ability to set programs up for success.
  • Excellent documentation skills.
  • Excellent time management skills.
  • Takes ownership and responsibility for work, is proactive.
  • Demonstrates initiative and creativity in all work efforts. Pursues objectives beyond what is required or expected. Able to mobilize and empower others.
  • Ability to plan and manage at both strategic and tactical levels to consistently meet/exceed planned objectives.
  • Extensive experience in digital climates both creative and technical and the ability to measure success of such efforts.
  • Demonstrated ability to work alongside a small internal staff and external partners where necessary.
  • Effective facilitation and public speaking skills and presence.
  • Agile/ Scrum experience working within an agency or design/tech consultancy.
  • Demonstrated ability to mentor Digital Project Team members, manage and develop an internal team.
  • Ability to architect and implement team-wide digital project and resource management best practices tools and processes.

Working Conditions

  • Possesses a high level of Integrity. Acts ethically and is above reproach. Builds trust through their honesty, reliability and authenticity. Possesses a strong concern for the needs of his/her colleagues. Takes tough principled stands even if they are unpopular. Meets commitments and keeps promises.
  • Demonstrates Self-control. Manages his/her impulsive feelings and distressing emotions and operates without any personal agenda. Stays composed, positive and unflappable even in trying moments. Thinks clearly and stays composed and focused under pressure.
  • Must be Flexible. Smoothly handles multiple demands, shifting priorities and rapid change. Is able to work collaboratively to get things done. Proactively seeks the advice and suggestions of peers, subordinates and superiors. Adapts strategies and tactics to fit fluid circumstances. Is flexible in how he/she sees events.
  • Is Optimistic. Demonstrates a positive mental attitude. Persists in seeking goals despite obstacles and setbacks. Operates from a hope of success rather than a fear of failure. Sees setbacks as due to manageable circumstances rather than a personal flaw.
  • Continuously Develops Others. Committed to the continuous process of education and development of self and colleagues. Acknowledges people's strengths and accomplishments. Offers useful feedback and helps to identify others' needs for future growth and improvement. Mentors and gives timely coaching that fosters an individual's skills.
  • Is able to Intuitively Understand the way people think and work. Understands the forces that shape views and actions of clients, customers or competitors. Accurately reads an organizational and external reality.
  • Models Leadership qualities. Articulates and arouses enthusiasm for a shared vision and mission. Leads by example.
  • Is a catalyst for Change. Recognizes the need for change and removes barriers. Challenges the status quo to acknowledge the need for change. Champions the change and enlists others in its pursuit.
  • Fosters Excellence in Communication. Is effective in give-and-take, registering emotional cues in attuning their message. Deals with difficult issues straightforwardly. Listens well; seeks mutual understanding and welcomes the sharing of information fully. Fosters open communication and stays receptive to bad news as well as good.

 

Direct reports

Manages Associate Digital Projects Director, Senior Digital Project Manager, Digital Project Manger

 

Pay Range:

The typical pay range for this role in

Ontario is $146,400 - $183,000.

Chicago is $154,400 - $193,000.

 

Note: the pay range represents the full pay range for this position. Each individual offer will take into consideration a range of factors, including prior experience and geographic location.

 

In addition to the base salary, this role is eligible for additional elements of compensation including (cell allowances, annual bonus, or commissions etc.), as well as a comprehensive benefits plan.

 


Not sure if you qualify? Think about applying anyway:
We understand that not everyone brings 100% of the skills and experience for the role.

At Softchoice, we offer opportunities to a diverse group including those with a variety of workplace experiences and backgrounds.  Whether you are new to corporate tech, returning to work after a gap in employment, or looking to transition and take the next step in your career, we are excited to learn more about you and encourage you to apply.  

 

Why You’ll Love Working Here:

  • The People: You’ll thrive in our collaborative environment, surrounded by incredible colleagues who foster support and innovation, driving our collective success
  • High-Performing Culture: At Softchoice, we are dedicated to achieving our goals and committed to success for our customers and each other
  • Flexibility: Plan your workdays in a way that suits you best
  • Award-Winning Workplace: Proudly recognized as a Great Place to Work for 20 consecutive years
  • Inclusive Culture: We are committed to an inclusive culture where every team member can be their authentic self
  • Competitive Benefits: Benefit from competitive perks that start on day one


Inclusion & Equal opportunity employment:
We are an equal opportunity employer committed to diversity, inclusion & belonging. People seeking employment at Softchoice are considered without regard to any protected category including but not limited to, race, color, religion, national origin, age, sex, marital status, ancestry, disability, veteran status, gender identity, or sexual orientation.

Require accommodation? We are ready to help:
We are proud to provide interview & employment accommodation during the recruitment and hiring process. If you require any accommodation to apply or interview for a position, please reach out directly to asktalentacquisition@softchoice.com. We are committed to working with you to best meet your needs.

Our commitment to your experience:
We are committed to the safety of all applicants and team members. With that in mind, we have implemented digital interviewing for everyone. We understand that you may need to interview with distractions around you (such as children or furry friends) and we will be doing the same.

Before you start with us, we will conduct a criminal record check, verify your education, and check your references.

When you join Softchoice, we will onboard you remotely. Don't worry. It's quick, simple and you'll be connected with your new team in no time.

 

Job Requisition ID: 7201
EoE/Vet/Disability