Senior Director of Engagement Managers

Title: Director of Engagement Managers Location: Canada (Remote)

How will you help us make an impact? 👩‍💻👨‍💻

Reporting to the Head of Professional Services, the Director of Engagement Managers (Principal Engagement Manager) is Clariti's most senior client-facing delivery leader: a recognized thought leader, trusted executive advisor, and force multiplier for the broader Professional Services organization. Operating at the Expert level across all competency pillars, you won't simply manage implementations - you'll define how they are delivered, shape the frameworks the organization scales with, and mentor the next generation of Clariti delivery talent. While this is not a management role, you will leverage your experience to influence and develop the team.
At this level, you see beyond the project to the system. You unlock new business opportunities, forecast trends before they surface, and balance customer, partner, and business priorities with the nuance that comes only from deep institutional knowledge and battle-tested judgment. You hold the attention of executive audiences, navigate the most complex stakeholder dynamics, and build the organizational structures and cultures through which great delivery consistently happens.
If you have a proven track record of leading high-visibility, high-risk programs across government and civic technology - and you're driven to shape how a high-growth SaaS company delivers transformation at scale - this role is built for you.

As a Director, Engagement Managers at Clariti, you’ll be accountable of:

Strategic Delivery Leadership

• Own the end-to-end delivery of Clariti's most complex, highest-visibility engagements, managing project governance, schedules, budgets, milestones, and success criteria across concurrent implementations with multiple client organizations.
• Articulate clear delivery vision and strategic priorities to align large, cross-functional teams, including Implementation Consultants, Delivery Architects, Technical Account Managers, and Product and Engineering, ensuring every team has clear authority and targets that ladder up to shared outcomes.
• Support continuously improving Clariti's repeatable delivery frameworks, structured retrospectives, and customer feedback loops, pioneering innovative solutions where no standard playbook yet exists and driving sustainable process improvement across the PS organization.
• Anticipate risks and crises before they materialize; proactively devise and execute contingency plans, managing project scope changes and emerging threats with high autonomy and minimal escalation.

Executive Advisory & Stakeholder Management

• Serve as a trusted strategic advisor to the most senior client stakeholders, mayors, CIOs, department directors, and agency heads, building deep relationships before dependencies arise and breaking down barriers between client functions and Clariti teams.
• Lead recurring executive steering committees and check-ins, connecting project progress to city outcomes in a way that holds the attention of, and inspires, senior audiences, adjusting presentations in real time based on audience reaction and handling challenging Q&As with confidence.
• Anticipate stakeholders' agendas and potential objections; proactively prepare and deploy effective engagement strategies that gain alignment across competing motivations and diffuse tension before it escalates.
• Understand and manage the full spectrum of stakeholder interests, across regions, functions, and organizational levels, determining the appropriate style and depth of engagement for every interaction.

Delivery Excellence & Quality

• Champion a delivery culture grounded in structured, data-backed metrics and storytelling, connecting performance to tangible government outcomes such as reduced permitting times, faster intake cycles, and measurable throughput improvements that give stakeholders the evidence to trust and advocate for Clariti.
• Design systems and organizational structures for delivery teams that translate into consistently high-quality output, including resource models, delegation frameworks, and performance review cadences that keep teams engaged and accountable.
• Apply advanced process improvement principles to deploy sustainable delivery initiatives; build a data-driven culture of continuous improvement and defect reduction across PS engagements.
• Implement rigorous quality control processes; ask targeted questions that surface potential challenges without getting lost in the weeds, and validate impact through structured, transparent performance reviews.
• Plan and prioritize resources across multiple concurrent engagements to ensure sufficient resourcing for targeted timelines, balancing utilization, team health, and delivery quality without burnout.

Organizational Learning & Knowledge Leadership

• Build city personas, engagement playbooks, and scalable frameworks that translate project-level insights into organizational learning, distributing knowledge across PS and feeding structured product feedback into Clariti's roadmap.
• Surface customer insights that influence Clariti's product and go-to-market strategy, acting as the voice of the customer in cross-functional conversations with Product, Engineering, Sales, and executive leadership.
• Teach and develop the next generation of Clariti delivery talent, mentoring Principal ICs, Lead ICs, and Engagement Managers through coaching, modeled behavior, and structured development opportunities.
• Leverage network and external influence to recruit and hire strong delivery talent; use institutional knowledge to identify and champion high-potential team members.
• Consistently seek out new sources of knowledge and best practices; develop and distribute written knowledge pieces, playbooks, guides, frameworks, that enrich Clariti's delivery capability at scale.

Reporting & Cross-Functional Contribution

• Provide regular reports and updates to the PS Director of Implementation and COO on the performance, risks, and strategic progress of all assigned engagements, structured for executive consumption and actionable by leadership.
• Engage senior leadership through planning cycles, progress reports, and presentations for highly visible, broad-scale programs requiring extensive cross-functional coordination.
• Contribute to Clariti's strategic planning by identifying new business opportunities with measurable impact to company objectives, informed by deep understanding of customer and partner nuances.

What do you bring to the team? 🧠

Experience & Track Record

• 12+ years of experience leading and delivering enterprise-level or government transformation engagements in a SaaS, professional services, or civic technology environment.
• Demonstrated track record of managing the most complex, highest-risk, multi-stakeholder programs end-to-end, including situations requiring recovery from dissatisfied clients or failed prior implementations.
• Acknowledged thought leader within at least one prior organization on delivery methodology, client engagement, or public sector implementation.
• Experience designing and owning delivery frameworks and feedback loops at an organizational level, not just executing within them.

Expert-Level Competencies

• Business Acumen:  Sees and unlocks new business opportunities with measurable impact; leverages understanding of customer and partner nuances to balance competing priorities; forecasts trends and builds strategic relationships across functions.
• Financial Acumen: Own and actively manage engagement-level financial performance, including project budget forecasting, cost tracking, margin analysis, and variance reporting across a portfolio of concurrent engagements. Apply expert-level financial acumen to model delivery scenarios, assess trade-offs between scope, cost, and timeline, and make or recommend resource allocation decisions that protect both client outcomes and Clariti's financial health.
• Communication:  Holds the attention of large executive audiences; adapts presentations in real time; handles challenging Q&As and ad hoc speaking requests without preparation; structures all communication types for any audience.
• Continuous Improvement:  Identifies problems before they surface; persuades cross-org stakeholders to undertake innovative process improvement; pioneers solutions where no standard exists; builds data-driven improvement cultures.
• Customer Centricity:  Intimately understands customer journey; builds and inspires a culture of high-quality service across the organization; drives NPS improvement through cross-functional collaboration and influence.
• Executional Excellence:  Designs organizational systems and structures for teams that translate into high-quality output; motivates and inspires through challenging periods; plans across multiple initiatives without burnout.
• Functional Expertise:  Recognized thought leader and go-to advisor for delivery and implementation; teaches next-generation experts; uses network to recruit and develop strong talent.
• Planning & Organizing:  Articulates clear strategic vision; manages high-visibility, high-risk, broad-scale programs; proactively manages scope changes, crises, and contingencies.
• Problem Solving:  Drives organizational alignment for solutions affecting Clariti's overall position; develops new frameworks for complex problems; operates efficiently at top-level stakeholder scale.
• Stakeholder Management:  Breaks down barriers across functions and organizations; invests in relationships before dependencies arise; effectively manages complex conflict and ensures productive cross-team relationships.
• Teamwork:  Cultivates collaborative environments across levels, functions, and geographies; champions and develops high-potential team members; balances team protection with broader company objectives.

Technical & Methodological

• Deep expertise in project management and agile methodologies with demonstrable evidence of applying them to large-scale transformation.
• Strong data literacy, ability to establish baselines, define the right success metrics, connect project health to measurable outcomes, and communicate data-backed stories to executive audiences.
• Proficiency in leading organizational change and managing ambiguity; exceeds customer expectations in dynamic, high-growth environments.
• Familiarity with public sector or civic technology projects strongly preferred.
• Ability to travel within the United States and Canada approximately 30-40%.

Bonus Points 🎉

• Experience with Salesforce-based platforms or GovTech/civic technology ecosystems
• Familiarity with permitting, licensing, or government service delivery workflows
• Experience managing System Integrator (SI) partner relationships on joint delivery programs
• Background in organizational change management (Prosci, ADKAR, or equivalent)
• Demonstrated interest or hands-on experience applying AI tools to improve implementation workflows, documentation, or delivery efficiency
• Experience in teams or practices transitioning toward AI-assisted delivery models

What’s in it for you?🫵

We invest in and empower our team members with competitive compensation packages, well deserved time off and benefits to keep you and your family healthy! *

💰 The base salary range for this role is expected to be between $195-235K CAD based on the candidate’s skills, experience, and qualifications while considering internal pay equity and our broader pay philosophy. 💰

If you have questions about compensation as we move through the process, we’re happy to discuss further.

*Benefits depend on employment type (full-time, part-time, contract, etc).