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Simpay · 1 day ago

Director of People and Culture

United States

Full-time

Remote

Senior Level, Lead/Staff

$120K/yr - $150K/yr

10+ years exp

Simpay is seeking a strategic and hands-on Director of People & Culture to lead the company’s People function during a period of rapid growth. This role will own all People & Culture strategy, operations, and infrastructure while serving as a trusted advisor to executive leadership and department heads.

AppsFinancial ServicesMobile PaymentsPayments

Hiring Manager

Matt Wilkerson

Responsibilities

Serve as the senior HR leader and strategic advisor to the CEO, CFO, executive team, and department leaders

Develop and execute a scalable People & Culture strategy to support growth from 125 to 200+ employees

Build, refine, and standardize HR processes, policies, and workflows that enable consistency and scale

Partner closely with Sales leadership, Finance, and Sales Operations to design, evaluate, and administer sales compensation plans, including commission-only structures

Establish and maintain standardized sales performance frameworks, including KPIs, scorecards, accountability measures, and coaching rhythms

Support sales onboarding and ongoing development programs to drive performance and retention

Ensure sales compensation programs comply with applicable federal, state, and multi-state employment laws, particularly related to commission-only compensation models

Oversee all HR operations, including HRIS (UKG/Kronos), benefits administration, compensation benchmarking, and employee relations

Own performance management processes, annual review cycles, and leadership development initiatives

Ensure ongoing compliance with federal, state, and multi-state employment regulations

Lead employee relations matters with consistency, fairness, and sound judgment

Partner with functional leaders to support team development and overall organizational effectiveness

Foster a collaborative, high-performance culture aligned with Simpay’s values and growth objectives

Lead employee engagement initiatives, internal communication strategies, and culture-building programs

Own onboarding and offboarding experiences in partnership with Recruiting and business leaders

Collaborate with Talent Acquisition to align hiring plans, onboarding processes, and workforce readiness

Partner with Finance on compensation structures, headcount planning, and forecasting

Work with Sales, IT and Operations to ensure smooth and compliant employee lifecycle processes

Qualification

HR operationsSales compensationEmployment law complianceUKG/KronosHR infrastructureExecutive presenceInfluence skillsPayments industry experienceFintech experienceSaaS experienceHR certificationsCommunication skills

Required

10+ years of progressive HR experience, with at least 4–6 years serving as the most senior HR leader or second-in-command in a scaling organization

Demonstrated experience supporting sales organizations, including sales compensation, commission-only plans, quota and territory frameworks, and sales performance management

Strong expertise in HR operations and employment law compliance across multiple states

Hands-on experience with UKG/Kronos

Proven ability to build and scale HR infrastructure in a fast-paced, growth-oriented environment

Exceptional communication skills, executive presence, and ability to influence at all levels of the organization

Bachelor's degree required