Implementation Supervisor

About the role

As the Implementation Supervisor, you will operate as a player-coach with a clear 50/50 focus: spending half your time actively managing complex client accounts and critical escalations, and the other half coaching your team and optimizing operational strategy. This role will report to the Senior Implementation Manager. Whether remote or working from our Brooklyn-based office, you'll find a team-oriented environment where reliability, optimism, compassion, and knowledge matter (a good sense of humor helps, too!).

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 and 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.
• 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.

Requirements

• Bachelor's degree required
• 5+ years of payroll implementation experience
• 2+ years of direct people management or team lead experience in a SaaS environment
• 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

Skills

• Balanced execution
• Metrics-driven leadership
• Crisis management
• Strong project management skills
• Open, approachable, and positive attitude
• Bias towards action

Pay

Salary band: $90,000 – $110,000 annually.

About Fingercheck

At Fingercheck, we're about making life easier for small business owners. We know payroll and HR can be a total headache, so we created a platform that simplifies everything. Our advanced AI and automation technology saves you time and money, so you can put energy into growing your business. The team is dedicated to providing top-notch support, taking the time to understand your needs and offering personalized solutions to make your internal processes quick, easy, and accurate.