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 Upshops Professional Services organization.

The Director of Implementation will also lead the evolution of Upshops 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 Upshops 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 Upshops 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

• Bachelors 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.