Director of Implementation, SMB & Mid-Market

Accountabilities:: Lead and develop WFM and Payroll Implementation Managers by setting clear expectations, establishing accountability, coaching leaders, and driving consistent operational results. Own delivery across commercial WFM and payroll implementations, establishing performance metrics, SLAs, quality standards, and operating processes that support high-volume execution. Identify implementation bottlenecks and continuously optimize workflows, capacity, and processes to improve throughput, quality, and cost efficiency. Provide strategic input into productization initiatives, partnering with Product and Sales to develop a roadmap toward greater self-service and reduced dependence on professional services. Define performance standards and operational expectations for offshore implementation teams, continuously improving training, workflows, processes, and delivery quality. Build and evolve scalable implementation processes, playbooks, and operating models across WFM and Payroll. Establish operational reporting and dashboards covering implementation volume, quality, cost per implementation, productivity, and other key performance indicators. Partner with Product, Engineering, Sales, and Customer Success to identify implementation challenges, product gaps, scaling constraints, and opportunities for improvement. Lead the adoption of AI and automation across onboarding, configuration, integrations, and error checking, evaluating opportunities and driving solutions that reduce manual effort and increase capacity. Manage third-party and distributed delivery teams by setting clear expectations, monitoring performance, and continuously improving the offshore operating model. Balance growth velocity with implementation quality, ensuring that operational expansion does not compromise customer outcomes or delivery standards. Track success through measures including bookings-to-revenue conversion, revenue realization, time-to-first-value, customer adoption at handoff, implementation throughput, cost per implementation, error and rework rates, customer satisfaction, and AI automation adoption. Requirements: 8+ years of experience in operations, implementation, customer success leadership, or a related function within high-volume, scaled environments. Proven experience managing managers and developing leaders who build and scale high-performing teams. Demonstrated success leading high-volume onboarding or implementation operations involving hundreds of customers per month. Strong operational leadership capabilities, with experience establishing standards, driving accountability, and using data to improve team performance. Strong process and systems thinking, including the ability to identify bottlenecks, design scalable workflows, and continuously improve operating models. Technical depth in integrations, data flows, system configuration, and technology-enabled implementation processes, with the ability to balance quality, speed, and cost. Experience managing distributed, offshore, or third-party teams and optimizing delivery models across geographically dispersed environments. Demonstrated ability to identify, evaluate, and scale operational improvements, automation, and technology-enabled efficiencies. Experience partnering with Product and Engineering teams to influence roadmaps, resolve product challenges, and address scaling constraints. Strong cross-functional communication and stakeholder management skills, with the ability to align teams around priorities and drive decisions. Comfort with data analysis, operational metrics, and building or using dashboards to inform decision-making. Background in hospitality, retail, payroll, or adjacent industries is strongly preferred. Ability to work for extended periods in a computer-based environment and perform light physical tasks related to onsite training. Willingness to travel approximately 15–20%, primarily for internal onsite activities. Benefits: Fully remote: Remote employment available in eligible U.S. states including AZ, CA, CO, CT, DC, FL, GA, ID, IL, IN, LA, MA, MD, ME, MI, MN, MS, NC, NE, NJ, NM, NV, NY, OH, OK, OR, PA, SC, TN, TX, UT, VA, and WA. Unlimited PTO to support flexibility and work-life balance. Medical, dental, and vision insurance coverage. 401(k) match to support long-term financial planning. Parental leave for eligible employees. Company-provided laptop and equipment to support remote work. Leadership scope: Opportunity to shape implementation operations across a rapidly scaling SMB and mid-market customer segment. Technology and automation exposure: Opportunity to lead AI, automation, self-service, and process modernization initiatives. Cross-functional influence: Direct partnership with Product, Engineering, Sales, and Customer Success on strategic operational challenges. Distributed leadership: Experience leading managers and offshore teams across a broad implementation organization.