Remote Payroll Implementation Lead — Player-Coach

Fingercheck; United States; Hybrid; USD 90,000 - 110,000; Full time

Job summary

Fingercheck is seeking an Implementation Supervisor to lead a player-coach team, balancing hands-on client implementations with coaching and operational strategy. The role reports to the Senior Implementation Manager and can be performed remotely or from our Brooklyn office, with a team-oriented culture centered on reliability, compassion and knowledge.

You will own end-to-end implementations, configure payroll software, manage escalations, mentor staff, and build dashboards to track progress.

Qualifications

• 5+ years of payroll implementation experience.
• 2+ years of direct people management or team lead experience in SaaS.
• Ability to thrive in a fast-paced environment that requires multi tasking.
• Demonstrated ability to act as a player-coach. Simultaneously manage direct reports while directly onboarding implementations.
• Payroll Certification (FPC or CPP).
• Deep technical expertise in payroll administration, multi-state tax compliance and time & attendance software integrations.
• Balanced Execution
• Crisis management
• Open, approachable, and positive attitude
• Bias towards action

Responsibilities

• Own end-to-end implementations to include high-value, complex, or multi-entity accounts, serving as their primary point of contact through their set-up & initial payroll runs.
• Hands-on configuration of advanced payroll software features, complex time/attendance rules, multi-state tax structures, PTO policies and custom general ledger (GL) mapping.
• Serve as the immediate operational escalation point for high-risk accounts, technical bottlenecks, and client disputes, stepping in directly to troubleshoot issues and stabilize client relationships.
• Manage, coach, and develop a team of direct reports, conducting regular 1:1s, performance evaluations, and career pathing.
• Balance team bandwidth and capacity, strategically assigning incoming accounts based on account tier, configuration complexity, and implementation specialist workload.
• Shadow specialist calls, audit account setups, and provide real-time feedback to elevate technical execution and white-glove communication across the team.
• Own performance metrics
• Build and maintain operational dashboards to monitor project velocity, track specialist performance, and report weekly progress to executive leadership.
• Build, update, and execute standardized training curriculums and onboarding playbooks for new hires and existing team members.
• Partner with Product, Engineering, and Sales to support onboarding handoffs, clear system bugs, and continuously streamline workflows.

Skills

Payroll implementation

Team leadership

SaaS experience

Escalation management

Time management

Education

Payroll Certification (FPC or CPP)

Job description

Fingercheck is seeking an Implementation Supervisor to lead a player-coach team, balancing hands-on client implementations with coaching and operational strategy. The role reports to the Senior Implementation Manager and can be performed remotely or from our Brooklyn office, with a team-oriented culture centered on reliability, compassion and knowledge.

You will own end-to-end implementations, configure payroll software, manage escalations, mentor staff, and build dashboards to track progress.