Director, Digital Workplace Adoption

This is a fully remote position, open to applicants in Canada.

📋 Description

• Establish the Digital Workplace & AI (DWA) adoption strategy and roadmap; define annual OKRs that align with business outcomes and customer value.

• Create repeatable DWA service offerings (assessments, pilots, enterprise rollouts, optimization programs) complete with clear artifacts, pricing, and success criteria.

• Lead stakeholder analysis, communications, training, and a champions program to enhance digital workplace and AI adoption across various functions.

• Oversee responsible AI and DWA usage (data access, sensitivity labels, DLP, guardrails) in collaboration with the Security/GRC and Modern Work teams.

• Design role-specific Digital Workplace and AI scenarios along with prompt guidance for executives, managers, individual contributors, and frontline employees.

• Develop telemetry and dashboards (usage, activation, scenario KPIs) and publish reports on value realization.

• Collaborate with Sales & Marketing on pre-sales discovery, proposals/SOWs, and executive briefings; assist with renewals and expansion opportunities.

• Align with Microsoft programs/funding; sustain relationships with Microsoft field and partner teams to boost DWA adoption.

• Manage delivery governance (methods, QA gates, reusable assets); enhance utilization, margin, and customer satisfaction.

• Mentor and supervise a team of DWA adoption practitioners (trainers, change managers, modern work specialists); establish goals, feedback loops, and development plans.

• Coordinate and enhance internal F12 DWA adoption; share exemplars, playbooks, and best practices.

• Identify risks and issues; spearhead corrective actions and ongoing process improvements.

• Standardize intake and approval processes for Copilot features, connectors, and Power Platform and Digital Workplace solutions.

• Conduct post-engagement reviews; document lessons learned and progressively evolve the DWA portfolio.

• Perform additional related duties as necessary.

⛳️ Requirements

• 8–10+ years of experience in Modern Work / Collaboration / Digital Workplace / Change Management roles, including 3–5+ years leading DWA or AI adoption programs within an MSP or SI.

• Proven leadership in practice (people leadership, portfolio management, revenue/margin accountability).

• Practical delivery experience with M365 Copilot, Power Platform, and Digital Workplace adoption: assessments, pilots, rollouts, enablement, and value realization.

• Working knowledge of Microsoft 365, Teams, SharePoint, Viva; Entra ID (Azure AD); Purview/Information Protection; DLP.

• Established change management expertise (Prosci/ADKAR or equivalent) and experience in designing enterprise-scale training programs.

• Ability to implement telemetry and convert insights into business outcomes and executive-level narratives.

• Strong pre-sales and go-to-market experience: discovery, SOW development, proposals, and executive presentations.

• Exceptional attention to detail; strong organization, prioritization, and execution skills in a dynamic MSP environment.

• Eligible to work in Canada; willingness to travel to client locations as required.

🏝️ Benefits

• Three weeks of vacation plus additional Flex Days.

• Leadership development opportunities.

• Growth coaching.

• Reimbursements for educational advancement and certifications.

• Health Spending Account or RRSP matching.

• Extended health care.

• Dental and vision coverage.

• Disability and life insurance.

• Employee assistance program.

• Tuition reimbursement.

• Paid time off.

• On-site parking.

• High-class office amenities.

• Company events.