Director of Implementation, SMB & Mid-Market

This is a senior operational leadership role responsible for scaling implementation delivery across a high-volume SMB and mid-market customer segment.
You will oversee WFM and Payroll implementation operations, supporting hundreds of customer implementations each month while maintaining strong quality and efficiency.
The role combines people leadership, process optimization, technology enablement, and strategic productization in a fast-paced SaaS environment.
You will lead implementation managers, develop distributed teams, and establish the standards, KPIs, and operating rhythms required for consistent execution at scale.
You will also partner closely with Product, Engineering, Sales, and Customer Success to address product gaps, remove delivery constraints, and improve the customer journey.
A key focus will be identifying opportunities for AI, automation, and self-service capabilities to reduce manual work and increase implementation capacity.
This role offers significant influence over how implementation operations evolve as the business grows, with success measured through throughput, quality, cost efficiency, adoption, and revenue realization.

• 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.