Implementation Supervisor

IMPLEMENTATION SUPERVISOR 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, optimism, compassion, andknowledge[A good sense of humor helps, too!] SALARY BAND: $90,000 - $110,000 Annual Essential ResponsibilitiesOwn 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 metricsBuild 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 QualificationsBachelor’s degree required5+ years of payroll implementation experience2+ years of direct people management or team lead experience in SaaS environmentAbility to thrive in a fast paced environment that requires multi taskingDemonstrated 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 integrationsBalanced ExecutionMetrics driven leadershipCrisis managementStrong project management skillsOpen, approachable, and positive attitudeBias towards action COMPANY CONFORMANCE STATEMENTIn 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 FingercheckAt 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. DisclaimerFingercheck 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.