Implementation Supervisor

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

Serving over 5,000 small businesses today, we aspire to be the most relied-upon partner a business owner never has to think about. From Hourly Time Tracking and Time Clock software to Scheduling and automated Payroll and HR, we've built an easy-to-use platform with features that save our customers time and money.

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 these truths matter:

• reliability,
• compassion,
• knowledge

[A good sense of humor helps, too!]

SALARY BAND: $90,000 - $110,000 Annual

• 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.

Minimum Qualifications

• 5+ years of payroll implementation experience
• 2+ years of direct people management or team lead experience in 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
• Balanced Execution
• Crisis management
• Open, approachable, and positive attitude
• Bias towards action

COMPANY CONFORMANCE STATEMENT

In performance of their respective responsibilities, all employees of Fingercheck are expected to:

• Complete quality work within deadlines.
• Interact professionally with other employees, customers, and suppliers.
• Work effectively as a team contributor on all assignments.
• Communicate and coordinate work efforts with other employees, customers and suppliers.
• Perform other duties as assigned.
• Attend work regularly based on the assigned schedule.

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. You can say goodbye to the stress and time-consuming tasks of payroll and HR management, including taxes and compliance – we've got you covered!

Our advanced AI and automation technology saves you time and money, so you can put energy into growing your business. And the best part? Our team is dedicated to providing top-notch support. We take the time to understand your needs and offer personalized solutions to make your internal processes quick, easy, and accurate.

For more information, please visit fingercheck.com or follow us on LinkedIn, Facebook, Twitter & Instagram.

Disclaimer

Fingercheck is an equal opportunity employer that values diversity, inclusion, and belonging. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law.