Senior Manager, Project Management

Restaurant365; Canada; Hybrid; CAD 163,000 - 244,000; Full time

Benefits offered by this job

Competitive compensation package

Remote or hybrid work

Comprehensive medical benefits

401k + matching

Equity Option Grant

Unlimited PTO + Company holidays

Wellness initiatives

Philanthropy events

Job summary

Restaurant365, a leading SaaS provider for the restaurant industry, seeks a Senior Manager of Project Management to lead a high-performing team delivering onboarding experiences for mid-market and enterprise clients. You will drive governance, optimize delivery frameworks, and partner with cross-functional leaders to scale delivery and improve customer outcomes.

You will oversee large SaaS implementations, mentor delivery professionals, manage resources, and track KPIs to ensure on-time delivery

Qualifications

• 8+ years of project management or delivery experience in SaaS, consulting, or professional services environments.
• 3+ years of people leadership experience.
• Extensive experience managing enterprise SaaS implementations with cross-functional coordination.
• Proven ability to establish and enforce delivery governance frameworks and methodologies.
• Advanced organizational and prioritization skills with capacity to manage competing priorities.
• Exceptional communication and executive presence across Product, Sales, Customer Success, Support, and Engineering.
• Strong analytical mindset with delivery KPIs to evaluate performance and forecast capacity.
• Experience with Jira, Smartsheet, Salesforce for program management.

Responsibilities

• Lead, coach, and develop a high-performing team of Project Managers and Implementation Specialists.
• Oversee project performance across a portfolio of SaaS implementation projects for timely delivery and quality.
• Manage resource allocation and team utilization to optimize capacity and delivery efficiency.
• Ensure adherence to standardized delivery methodologies and escalation frameworks.
• Collaborate with Delivery leadership, Solutions Architects, Product, and cross-functional partners to align on project strategies and handoffs.
• Monitor KPIs (TTFV, CSAT, utilization, throughput) to identify risks and drive improvements.
• Serve as escalation point for complex project risks and customer concerns.
• Partner with Sales on designing RFPs and scoping services.
• Ability to travel up to 15%.

Job description

Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides aunique, centralized solution for accounting and back-office operations for restaurants. Restaurant365’s culture is focused on empowering team members to produce top-notch results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be "Best in Class" … and we want that for you too!

The Senior Manager of Project Management leads a high-performing team of Project Managersand Implementation Specialistsresponsible for delivering high-quality, on-time onboarding experiences across mid-market and enterprise clients. This role is accountable for building operational rigor within project delivery, driving consistency across practices, and ensuring alignment with organizational goals. The Senior Manager will partner closely with cross-functional leaders to optimize throughput, scale delivery frameworks, and strengthen customer outcomes.

How you’ll add value:

• Lead, coach, and develop a high-performing team of Project Managersand Implementation Specialists, providing ongoing support through regular one-on-ones,goal-setting, performance feedback, and professional development planning.

• Overseeproject performanceacross a portfolio of SaaS implementation projects, ensuring on-time delivery, scope adherence, and quality standards while maintaining a consistent customer experience.

• Manage resource allocation,project assignmentsand team utilizationstrategically, balancing team capacity, skill sets, and project complexity to drive effective utilization and delivery efficiency.

• Ensure adherence to standardized delivery methodologies, reinforcing project governance, communication protocols, and escalation frameworks to support scalable and predictable outcomes.

• Collaborate with Delivery leadership, Solutions Architects, Product, and other cross-functional partners to align on project strategies, remove blockers, and drive successful handoffs and customer outcomes.

• Monitor and analyze key performance metrics -including Time to First Value (TTFV), CSAT, utilization, and project throughput to identify trends, surface risks, and inform continuous improvement initiatives.

• Serve as the point of escalation for complex project risks and customer concerns, guiding resolution strategies and ensuring stakeholder alignment throughout the project lifecycle.

• Partnering with Sales on designing RFPs, scoping, and selling services.

• Ability to travel up to 15%

• Other duties as assigned.

KEY METRICS FOR SUCCESS

• Team Utilization & Capacity Management

• On-Time Delivery Across Portfolio

• Customer Satisfaction (CSAT)

• Project Portfolio Margin

What you’ll need to be successful in this role:

• 8+ years of project management or delivery experience in SaaS, consulting, or professional services environments, with a proven track record of leading complex, customer-facing initiatives that drive measurable business outcomes (utilization, on-time delivery, CSAT, TTFV, project margin).

• 3+ years of people leadership experience, including direct management of Project Managers or Delivery Leads, with demonstrated ability to coach, mentor, and scale high-performing teams in fast-paced SaaS environments.

• Extensive experience managing enterprise and multi-stakeholder SaaS implementations, including cross-functional coordination, integration management, and alignment with customer business goals.

• Proven ability to establish and enforce delivery governance frameworks and methodologies, ensuring consistency, scalability, and operational excellence across a large portfolio of projects.

• Advanced organizational and prioritization skills, with the capacity to manage team resources across competing priorities while balancing customer needs, business objectives, and long-term scalability.

• Exceptional communication and executive presence, with the ability to influence across functions (Product, Sales, Customer Success, Support, and Engineering) and present delivery strategy and results to senior leadership and client executives.

• Strong analytical mindset with operational rigor, leveraging data and delivery KPIs to evaluate performance, identify risks, forecast capacity, and drive continuous improvement across teams and processes.

• Expertisewithproject management tools, SaaS delivery metrics, and portfolio-level reporting, with experience using platforms such as Jira, Smartsheet, or Salesforce to manage programs and inform leadership decisions.

• Strategic problem-solving and decision-making skills, with the judgment to balance speed, quality, and scalability while navigating ambiguity and ensuring customer success.

• Deep knowledge of delivery best practices and methodologies (Agile, Waterfall, hybrid models), with the ability to adapt frameworks to diverse customer needs and complex implementation scenarios.

• Proven AI Fluency, with experiencebuilding and using repeatable AI workflows tailored to Project Management and Services Delivery, demonstrating measurable gains in efficiency or quality through AI use.

PREFERRED QUALIFICATIONS

• Project management certification (e.g., PMP, PMI-ACP).

• Experience in restaurant technology, hospitality SaaS, or other vertical implementation organizations.

• Exposure to organizational change or cross-functional delivery programs.

• Experience in high-volume implementation environments.

• Experience overseeing change management at scale.

R365 Team Member Benefits & Perks

• Competitive compensation package
• Comp Range: $116,000 - $174,000/annually
• Ability to work remote or hybrid
• Comprehensive medical benefits
• 401k + matching
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives
• Philanthropy events

Why join our amazing team?

• We’re a community that prides itself in creating innovative solutions and producing quality work
• Our product is the secret ingredient that makes a real difference to restaurants nationwide
• The open concept work environment that we’ve created is causal, collaborative, and cultivates communication

DYN365, Inc d/b/a Restaurant365 is an equal opportunity employer.