Director, Implementation

About Upshop

Upshop is the market leader in Total Store Operations solutions for the Grocery and C-Store markets. We offer an AI-powered, SaaS platform connecting Fresh, Center, eCommerce, and DSD department operations to deliver a simplified, smarter, more connected store experience. Customers running Upshop realize significant improvements in sales, shrink, food safety and sustainability across the entire store. 150+ retail chain accounts trust our software in over 30k+ stores, 9 countries, and 3 continents. 

Role Overview

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.

Key Responsibilities

Team Leadership & Talent Development

• 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.

Customer Engagement & Delivery Leadership

• 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.

Implementation Excellence

• 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.

Technical Leadership

• 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.

Operational Leadership

• 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.

Required Qualifications

• 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%.

Preferred Qualifications

• 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.

Success Profile

The successful candidate:

• Is a people-first leader who develops teams, mentors future leaders, and creates a culture of accountability and continuous improvement.
• Builds trust with customer executives and serves as a strategic advisor throughout the implementation journey.
• Understands grocery and retail operations and can translate customer objectives into scalable implementation strategies.
• Balances strategic leadership with hands-on execution when customer success requires it.
• Uses metrics and data-driven decision making to improve delivery performance and customer outcomes.
• Embraces innovation and continuously seeks opportunities to modernize implementation practices through automation, AI, and scalable delivery frameworks.
• Drives cross-functional alignment while maintaining a relentless focus on customer value realization.