Director, Implementation

Company Overview

Upshop is a leading provider of Total Store Operations solutions for grocery and convenience store markets. Their AI-driven SaaS platform integrates fresh, center, eCommerce, and DSD department operations, enabling a smarter, more connected store experience. Currently, over 150 retail chains rely on Upshop's software across more than 30,000 stores in 9 countries spanning 3 continents. This results in notable improvements in sales, shrink reduction, food safety, and sustainability for customers.

Position Summary

Upshop is searching for a strategic Director of Implementation to head its Implementation team and ensure the successful deployment of its Total Store Operations platform for customers. This position involves leading, mentoring, and developing a talented team of Implementation Managers and Consultants while guaranteeing excellent customer outcomes throughout their onboarding journey. Candidates with a background in enterprise SaaS deployments and knowledge of retail operations, particularly grocery, convenience, or food retail sectors, will thrive in this role.

Key Duties

• Provide leadership and career development to a team consisting of Implementation Managers, Senior Consultants, and Implementation Consultants.
• Champion a culture focused on accountability, continuous improvement, collaboration, and strong customer orientation.
• Define and enforce performance benchmarks, facilitate coaching programs, and manage succession planning.
• Establish and promote consistent implementation methodologies and operational best practices throughout the team.
• Collaborate with leadership in Professional Services on workforce planning, recruitment, and onboarding.
• Create and maintain Centers of Excellence and share reusable delivery assets to expand organizational knowledge.
• Lead ongoing refinement of implementation frameworks, driving automation and AI adoption for efficient service delivery.
• Oversee customer engagement by acting as an executive sponsor and trusted advisor on major implementation initiatives, ensuring alignment with client goals.
• Guide teams through complex deployments, including testing, launch, change management, and post-launch support.
• Manage risk and resolve issues within the implementation portfolio while ensuring smooth handoffs to Customer Success for long-term value realization.
• Control delivery standards and documentation, enforce governance models that increase transparency and accountability, and utilize project management office resources to optimize execution.
• Maintain expertise in Upshop’s platform architecture, integrations (ERP, POS, DSD, EDI, eCommerce), and technical deployment strategies, including cloud technologies and data platforms such as Microsoft Azure.
• Advocate for AI-enabled tools to enhance project delivery, testing, knowledge management, and overall operational efficiency.
• Monitor key operational and financial metrics to sustain a healthy implementation portfolio, align staffing, capacity, and resources with strategic priorities.
• Provide executive dashboards and reports on performance, risks, and trends while partnering across departments to improve the holistic customer experience.

Qualifications

• Bachelor’s degree in Business, Information Systems, Computer Science, Supply Chain, Retail Operations, or a related discipline.
• Minimum of 5 years managing enterprise software or SaaS implementations.
• At least 3 years in leadership roles overseeing implementation, consulting, or professional services teams.
• Proven success handling multiple simultaneous large-scale customer projects.
• Strong expertise in SaaS deployment best practices and stakeholder engagement, including executive presentations.
• Willingness to travel up to 25% of the time.

Preferred Experience

• Background in grocery, food retail, convenience stores, or store operations.
• Familiarity with inventory management, forecasting, supply chain, merchandising, workforce management, or direct store delivery (DSD) solutions.
• Experience working with Microsoft Azure, including Azure SQL Database, Cosmos DB, APIs, and enterprise integration frameworks.
• Technical knowledge in data architecture, APIs, EDI systems, and modern cloud platforms.
• Experience implementing AI-driven tools and automation to boost efficiency and outcomes.
• Proficiency with SQL, Excel, Salesforce, Zendesk, Jira, Wrike, or similar platforms.
• Track record of successfully scaling implementation teams in high-growth SaaS companies.

Candidate Profile

• A people-first leader who nurtures teams and encourages ownership and continuous advancement.
• An advisor trusted by customer executives to navigate complex implementation landscapes.
• Deep understanding of retail operations enabling translation of client needs into scalable deployment strategies.
• A balanced leader who combines strategic oversight with hands-on involvement when necessary.
• Data-driven decision-maker focused on improving performance and customer outcomes.
• Innovative, embracing new technologies including automation and AI to optimize delivery frameworks.
• A proactive collaborator who ensures cross-team alignment and persistent focus on customer value.