Director, Implementation

Upshop•Mississauga, ON

1d•Remote

About The Position

Upshop is seeking a Director of Implementation to lead our Implementation organization and drive successful customer deployments across our Total Store Operations platform. This leader is responsible for developing and mentoring a high-performing team of Implementation Managers and Consultants while ensuring customers achieve successful business outcomes throughout their implementation journey. The ideal candidate combines enterprise SaaS implementation leadership with a strong understanding of retail operations, preferably within grocery, convenience, or food retail environments. This individual will serve as a trusted advisor to customers, a mentor to implementation leaders, and a key contributor in scaling Upshop's Professional Services organization. The Director of Implementation will also lead the evolution of Upshop's implementation practices, championing automation, AI-enabled delivery capabilities, and operational excellence initiatives that improve efficiency, accelerate customer outcomes, and create a more scalable and consistent delivery model.

Requirements

Bachelor's degree in Business, Information Systems, Computer Science, Supply Chain, Retail Operations, and/or related field/experience.
5+ years of experience leading enterprise software, SaaS, or technology implementations.
3+ years of people leadership experience managing implementation, consulting, delivery, or professional services teams.
Proven experience leading customer-facing delivery organizations supporting enterprise customers.
Demonstrated success building, mentoring, and developing high-performing teams.
Strong knowledge of SaaS implementation methodologies and software deployment practices.
Experience managing multiple concurrent implementations and complex customer engagements.
Exceptional communication, stakeholder management, executive presentation, and relationship-building skills.
Strong analytical, problem-solving, and decision-making capabilities.
Ability to travel up to 25%.

Nice To Haves

Grocery retail, food retail, convenience retail, or store operations experience strongly preferred.
Experience with forecasting, ordering, inventory, supply chain, fresh operations, DSD, merchandising, workforce management, or store execution solutions strongly preferred.
Experience with Microsoft Azure technologies, including Azure SQL Database, Azure Cosmos DB, cloud data platforms, and enterprise integration architectures.
Strong understanding of data architecture, system integrations, APIs, EDI, and enterprise application ecosystems.
Experience leveraging AI-enabled tools, automation platforms, or emerging technologies to improve operational efficiency and customer outcomes.
Working knowledge of SQL, databases, Excel, and analytical tools.
Experience with Salesforce, Zendesk, Jira, Wrike, or similar enterprise platforms.
Experience scaling implementation organizations within high-growth SaaS environments.

Responsibilities

Lead, mentor, and develop a team of Implementation Managers, Senior Consultants, and Implementation Consultants.
Foster a culture of accountability, continuous learning, collaboration, and customer obsession.
Establish clear performance expectations, coaching programs, career development plans, and succession strategies.
Drive implementation methodology adoption, process consistency, and operational excellence across the team.
Partner with Professional Services leadership on organizational planning, hiring, onboarding, and workforce development.
Develop implementation Centers of Excellence and reusable delivery assets that scale knowledge across the organization.
Lead the ongoing evolution of Upshop's implementation methodology, delivery frameworks, and best practices.
Identify opportunities to leverage automation, AI, and digital tooling to improve implementation efficiency, consistency, and customer outcomes.
Foster a culture of innovation and adoption of emerging technologies that enhance customer delivery.
Establish measurable delivery standards and KPIs focused on customer adoption, implementation quality, operational efficiency, and team development.
Serve as an executive sponsor and escalation point for strategic customer implementations.
Build trusted relationships with customer sponsors, operational leaders, IT stakeholders, and executive teams.
Ensure customer objectives, adoption goals, and success metrics are clearly defined and achieved.
Guide implementation teams through complex deployments, organizational change initiatives, testing, launch activities, and post-launch adoption.
Lead risk identification, mitigation planning, and issue resolution efforts across the implementation portfolio.
Partner closely with Customer Success to ensure smooth transitions from implementation to long-term customer adoption and value realization.
Collaborate with Sales and Solution Consulting to ensure customer expectations, implementation strategies, and success criteria are aligned from project inception.
Own implementation delivery standards, methodologies, playbooks, and best practices across the organization.
Drive consistency across project planning, discovery, solution design, configuration, testing, training, launch, and hypercare activities.
Capture lessons learned and continuously improve implementation frameworks and operational processes.
Ensure implementations are delivered on time, within scope, within budget, and aligned to customer business outcomes.
Establish governance models that improve visibility, accountability, risk management, and delivery quality.
Partner with PMO leadership to improve delivery governance, forecasting, resource planning, and project execution.
Drive continuous improvement initiatives that reduce implementation timelines while maintaining exceptional customer outcomes.
Maintain deep knowledge of Upshop's platform architecture, data structures, integrations, and implementation requirements.
Provide guidance on solution architecture, data migration, system configuration, integration strategy, and technical deployment approaches.
Support complex integrations involving ERP, forecasting, inventory, ordering, POS, DSD, EDI, eCommerce, and other retail technology ecosystems.
Partner with Product and Engineering to improve implementation tooling, onboarding workflows, automation capabilities, and customer enablement resources.
Develop organizational expertise around modern cloud technologies, data platforms, integration frameworks, and scalable implementation approaches.
Maintain working knowledge of Microsoft Azure technologies, including Azure SQL Database, Azure Cosmos DB, APIs, data integration patterns, and cloud-based application architectures.
Champion the use of AI-enabled tools to improve project delivery, testing, documentation, training, knowledge management, customer onboarding, and internal operational efficiency.
Leverage data and analytics to identify trends, improve delivery performance, and enhance customer outcomes.
Monitor implementation portfolio health through operational, financial, and customer success metrics.
Oversee implementation forecasting, staffing, utilization, and capacity planning.
Support Statement of Work reviews, implementation estimates, change requests, and delivery commitments.
Ensure resource allocation aligns with strategic priorities and customer commitments.
Provide executive reporting on implementation performance, customer health, delivery risks, and organizational trends.
Partner across Product, Support, Customer Success, Sales, and Professional Services to continuously improve the end-to-end customer experience.