Director, Implementation

About UpshopUpshop 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 OverviewUpshop 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 ResponsibilitiesTeam Leadership & Talent Development<ul><li style="font-family: arial, helvetica, sans-serif;">Lead, mentor, and develop a team of Implementation Managers, Senior Consultants, and Implementation Consultants.</li><li style="font-family: arial, helvetica, sans-serif;">Foster a culture of accountability, continuous learning, collaboration, and customer obsession.</li><li style="font-family: arial, helvetica, sans-serif;">Establish clear performance expectations, coaching programs, career development plans, and succession strategies.</li><li style="font-family: arial, helvetica, sans-serif;">Drive implementation methodology adoption, process consistency, and operational excellence across the team.</li><li style="font-family: arial, helvetica, sans-serif;">Partner with Professional Services leadership on organizational planning, hiring, onboarding, and workforce development.</li><li style="font-family: arial, helvetica, sans-serif;">Develop implementation Centers of Excellence and reusable delivery assets that scale knowledge across the organization.</li><li style="font-family: arial, helvetica, sans-serif;">Lead the ongoing evolution of Upshop's implementation methodology, delivery frameworks, and best practices.</li><li style="font-family: arial, helvetica, sans-serif;">Identify opportunities to leverage automation, AI, and digital tooling to improve implementation efficiency, consistency, and customer outcomes.</li><li style="font-family: arial, helvetica, sans-serif;">Foster a culture of innovation and adoption of emerging technologies that enhance customer delivery.</li><li style="font-family: arial, helvetica, sans-serif;">Establish measurable delivery standards and KPIs focused on customer adoption, implementation quality, operational efficiency, and team development.</li></ul>Customer Engagement & Delivery Leadership<ul><li style="font-family: arial, helvetica, sans-serif;">Serve as an executive sponsor and escalation point for strategic customer implementations.</li><li style="font-family: arial, helvetica, sans-serif;">Build trusted relationships with customer sponsors, operational leaders, IT stakeholders, and executive teams.</li><li style="font-family: arial, helvetica, sans-serif;">Ensure customer objectives, adoption goals, and success metrics are clearly defined and achieved.</li><li style="font-family: arial, helvetica, sans-serif;">Guide implementation teams through complex deployments, organizational change initiatives, testing, launch activities, and post-launch adoption.</li><li style="font-family: arial, helvetica, sans-serif;">Lead risk identification, mitigation planning, and issue resolution efforts across the implementation portfolio.</li><li style="font-family: arial, helvetica, sans-serif;">Partner closely with Customer Success to ensure smooth transitions from implementation to long-term customer adoption and value realization.</li><li style="font-family: arial, helvetica, sans-serif;">Collaborate with Sales and Solution Consulting to ensure customer expectations, implementation strategies, and success criteria are aligned from project inception.</li></ul>Implementation Excellence<ul><li style="font-family: arial, helvetica, sans-serif;">Own implementation delivery standards, methodologies, playbooks, and best practices across the organization.</li><li style="font-family: arial, helvetica, sans-serif;">Drive consistency across project planning, discovery, solution design, configuration, testing, training, launch, and hypercare activities.</li><li style="font-family: arial, helvetica, sans-serif;">Capture lessons learned and continuously improve implementation frameworks and operational processes.</li><li style="font-family: arial, helvetica, sans-serif;">Ensure implementations are delivered on time, within scope, within budget, and aligned to customer business outcomes.</li><li style="font-family: arial, helvetica, sans-serif;">Establish governance models that improve visibility, accountability, risk management, and delivery quality.</li><li style="font-family: arial, helvetica, sans-serif;">Partner with PMO leadership to improve delivery governance, forecasting, resource planning, and project execution.</li><li style="font-family: arial, helvetica, sans-serif;">Drive continuous improvement initiatives that reduce implementation timelines while maintaining exceptional customer outcomes.</li></ul>Technical Leadership<ul><li style="font-family: arial, helvetica, sans-serif;">Maintain deep knowledge of Upshop's platform architecture, data structures, integrations, and implementation requirements.</li><li style="font-family: arial, helvetica, sans-serif;">Provide guidance on solution architecture, data migration, system configuration, integration strategy, and technical deployment approaches.</li><li style="font-family: arial, helvetica, sans-serif;">Support complex integrations involving ERP, forecasting, inventory, ordering, POS, DSD, EDI, eCommerce, and other retail technology ecosystems.</li><li style="font-family: arial, helvetica, sans-serif;">Partner with Product and Engineering to improve implementation tooling, onboarding workflows, automation capabilities, and customer enablement resources.</li><li style="font-family: arial, helvetica, sans-serif;">Develop organizational expertise around modern cloud technologies, data platforms, integration frameworks, and scalable implementation approaches.</li><li style="font-family: arial, helvetica, sans-serif;">Maintain working knowledge of Microsoft Azure technologies, including Azure SQL Database, Azure Cosmos DB, APIs, data integration patterns, and cloud-based application architectures.</li><li style="font-family: arial, helvetica, sans-serif;">Champion the use of AI-enabled tools to improve project delivery, testing, documentation, training, knowledge management, customer onboarding, and internal operational efficiency.</li><li style="font-family: arial, helvetica, sans-serif;">Leverage data and analytics to identify trends, improve delivery performance, and enhance customer outcomes.</li></ul>Operational Leadership<ul><li style="font-family: arial, helvetica, sans-serif;">Monitor implementation portfolio health through operational, financial, and customer success metrics.</li><li style="font-family: arial, helvetica, sans-serif;">Oversee implementation forecasting, staffing, utilization, and capacity planning.</li><li style="font-family: arial, helvetica, sans-serif;">Support Statement of Work reviews, implementation estimates, change requests, and delivery commitments.</li><li style="font-family: arial, helvetica, sans-serif;">Ensure resource allocation aligns with strategic priorities and customer commitments.</li><li style="font-family: arial, helvetica, sans-serif;">Provide executive reporting on implementation performance, customer health, delivery risks, and organizational trends.</li><li style="font-family: arial, helvetica, sans-serif;">Partner across Product, Support, Customer Success, Sales, and Professional Services to continuously improve the end-to-end customer experience.</li></ul>Required Qualifications<ul><li style="font-family: arial, helvetica, sans-serif;">Bachelor's degree in Business, Information Systems, Computer Science, Supply Chain, Retail Operations, and/or related field/experience.</li><li style="font-family: arial, helvetica, sans-serif;">5+ years of experience leading enterprise software, SaaS, or technology implementations.</li><li style="font-family: arial, helvetica, sans-serif;">3+ years of people leadership experience managing implementation, consulting, delivery, or professional services teams.</li><li style="font-family: arial, helvetica, sans-serif;">Proven experience leading customer-facing delivery organizations supporting enterprise customers.</li><li style="font-family: arial, helvetica, sans-serif;">Demonstrated success building, mentoring, and developing high-performing teams.</li><li style="font-family: arial, helvetica, sans-serif;">Strong knowledge of SaaS implementation methodologies and software deployment practices.</li><li style="font-family: arial, helvetica, sans-serif;">Experience managing multiple concurrent implementations and complex customer engagements.</li><li style="font-family: arial, helvetica, sans-serif;">Exceptional communication, stakeholder management, executive presentation, and relationship-building skills.</li><li style="font-family: arial, helvetica, sans-serif;">Strong analytical, problem-solving, and decision-making capabilities.</li><li style="font-family: arial, helvetica, sans-serif;">Ability to travel up to 25%.</li></ul>Preferred Qualifications<ul><li style="font-family: arial, helvetica, sans-serif;">Grocery retail, food retail, convenience retail, or store operations experience strongly preferred.</li><li style="font-family: arial, helvetica, sans-serif;">Experience with forecasting, ordering, inventory, supply chain, fresh operations, DSD, merchandising, workforce management, or store execution solutions strongly preferred.</li><li style="font-family: arial, helvetica, sans-serif;">Experience with Microsoft Azure technologies, including Azure SQL Database, Azure Cosmos DB, cloud data platforms, and enterprise integration architectures.</li><li style="font-family: arial, helvetica, sans-serif;">Strong understanding of data architecture, system integrations, APIs, EDI, and enterprise application ecosystems.</li><li style="font-family: arial, helvetica, sans-serif;">Experience leveraging AI-enabled tools, automation platforms, or emerging technologies to improve operational efficiency and customer outcomes.</li><li style="font-family: arial, helvetica, sans-serif;">Working knowledge of SQL, databases, Excel, and analytical tools.</li><li style="font-family: arial, helvetica, sans-serif;">Experience with Salesforce, Zendesk, Jira, Wrike, or similar enterprise platforms.</li><li style="font-family: arial, helvetica, sans-serif;">Experience scaling implementation organizations within high-growth SaaS environments.</li></ul>Success ProfileThe successful candidate:<ul><li style="font-family: arial, helvetica, sans-serif;">Is a people-first leader who develops teams, mentors future leaders, and creates a culture of accountability and continuous improvement.</li><li style="font-family: arial, helvetica, sans-serif;">Builds trust with customer executives and serves as a strategic advisor throughout the implementation journey.</li><li style="font-family: arial, helvetica, sans-serif;">Understands grocery and retail operations and can translate customer objectives into scalable implementation strategies.</li><li style="font-family: arial, helvetica, sans-serif;">Balances strategic leadership with hands-on execution when customer success requires it.</li><li style="font-family: arial, helvetica, sans-serif;">Uses metrics and data-driven decision making to improve delivery performance and customer outcomes.</li><li style="font-family: arial, helvetica, sans-serif;">Embraces innovation and continuously seeks opportunities to modernize implementation practices through automation, AI, and scalable delivery frameworks.</li><li style="font-family: arial, helvetica, sans-serif;">Drives cross-functional alignment while maintaining a relentless focus on customer value realization.</li></ul>

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