Director of People Operations & Total Rewards

Company Description: Pathstone is a dynamic, rapidly growing, partner-owned wealth management firm that serves ultra-high net worth families, single family offices, and foundations and endowments. Our comprehensive range of services and deep expertise goes far beyond investment advice. We provide tax planning and compliance, insurance and risk management, lifestyle management, wealth and estate planning, trust services, and philanthropy services. We have 20+ office locations and more than $100 Billion in Assets Under Advisement and Administration. The number of Pathstone team members has more than doubled in the past five years. 

As a Certified B Corporation, Pathstone seeks to make a difference in the lives of our clients and their families as well as to offer a positive and supportive work environment for our employees. Our team members are encouraged to pursue their passions by serving on committees and initiatives addressing topics of importance to our business. Our talented people are our greatest asset and therefore we offer a competitive, comprehensive, and flexible benefits program that helps meet the needs of our team members and their families. Pathstone’s generous benefits include comprehensive medical, vision, and dental coverage, flexible spending, flexible PTO, life insurance, education support, 401k plan, parental leave, and more. 

Job Description: Pathstone is seeking a strategic, results-driven Director of People Operations & Total Rewards to lead and oversee our HR operations, including compensation, benefits, employee lifecycle, and HR technology systems. This critical leadership role will shape the future of HR, driving innovation and efficiency while optimizing the employee experience for a rapidly growing, remote-first workforce. 

As a core member of the People Leadership Team, the Director will collaborate with business leaders to align HR operations with organizational goals, ensuring a seamless and scalable approach to Total Rewards, HRIS (Ultipro (UKG)), analytics, and employee lifecycle processes like leave management. This role will focus on continuous improvement, process optimization, and leveraging technology to streamline workflows, enhance HR operations, and deliver high-impact results.  This position reports directly to the Chief People Officer of Pathstone. 

Qualifications: 

This is a remote position with the flexibility to work from home. However, we are currently only considering applicants based in the following states:

Arizona

California

Colorado

Virginia

Maryland

Florida

Georgia

Massachusetts

New Jersey

New York

Philadelphia

Rhode Island

Texas

Washington

Wyoming

Required Qualifications: 

• Education: Master’s degree in management, Finance, HR, or related field (or equivalent experience). 

• Experience: 7+ years of progressive experience in HR, experience in a leadership role in a portion of Total Rewards, HR technology, or operations is strongly preferred. 

• Proven success in designing and implementing competitive Total Rewards programs with measurable impact on talent attraction, retention, and cost management. 

• Experience leading large-scale HRIS implementations (Oracle Cloud HCM, Workday, or similar) and optimizing systems to drive efficiency. 

• Extensive experience in managing HR process outsourcing, vendor relationships, and ensuring compliance with HR regulations. 

• Expertise in benefits administration, leave management, and employee lifecycle processes. 

• Strong analytical and data-driven mindset with the ability to generate insights and guide strategic decision-making. 

• Experience in driving process optimization and automation in HR operations. 

Preferred Qualifications: 

• Experience with mergers & acquisitions, particularly in integrating HR systems and programs. 

• HR certifications such as CCP, CBP, SPHR, or similar. 

• Experience in the wealth management, financial services or similar industry preferred. 

• Familiarity with business intelligence software and advanced data analysis techniques. 

Skills & Competencies: 

• Strong leadership and team management skills, with a track record of mentoring, coaching, and developing HR professionals. 

• Excellent communication and influencing skills, with the ability to build relationships and present complex ideas to diverse audiences. 

• Strong strategic thinking and problem-solving abilities, with the capacity to drive change and innovation in a dynamic, fast-paced environment. 

• High emotional intelligence and the ability to engage and inspire cross-functional teams. 

• Expertise in compliance, risk management, and regulatory frameworks impacting HR functions (e.g., ERISA, FLSA, ACA, ADA). 

• Ability to work effectively with both internal teams (Talent Acquisition, Finance, Legal) and external partners to meet organizational goals. 

• Proficiency in Microsoft Excel and HR analytics tools; experience with business intelligence software a plus. Intermediate to advanced Microsoft Excel skills are strongly preferred. 

Job Responsibilities:  

Strategic Leadership & People Operations: 

• Lead the design and execution of a competitive Total Rewards strategy, including base pay, bonuses, equity programs, benefits, and recognition initiatives. 

• Oversee the system administration of employee lifecycle processes such as onboarding, applicant tracking and maintenance and employee data management. 

• Develop and implement policies that ensure compliance with local, state, and federal laws, including ERISA, FLSA, ACA, and ADA. 

• Work closely with leadership to optimize HR systems (e.g., UKG), automate processes, and drive efficiency across People operations. 

Process Optimization & HR Technology: 

• Identify and implement opportunities for process simplification, automation, and optimization within HR operations and systems. 

• Ensure the HRIS platforms (UKG) and associated tools are being fully leveraged to improve operational efficiency and deliver high-quality employee experiences. 

• Develop and execute a technology roadmap for future HR system enhancements, ensuring scalability and integration with business needs. 

• Drive data analytics initiatives, including tracking key metrics, creating reports, and providing insights to guide decision-making. 

Vendor & Compliance Management: 

• Evaluate, select, and manage key HR process outsourcing vendors and contracts, including benefits brokers, retirement account managers, and third-party administrators. 

• Oversee compliance-related activities and ensure adherence to HR regulations and standards in multiple jurisdictions. Ensure compliance reporting is completed on time and as required for compliance.  

Team Leadership & Development: 

• Lead, mentor, and develop a team of HR professionals across various areas including Total Rewards, and HR technology 

• Set clear team goals, ensure accountability, and drive performance to achieve department and organizational objectives. 

• Foster a culture of continuous learning, improvement, and innovation within the People Operations team. 

Collaboration & Stakeholder Management: 

• Partner with business leaders, People teams, and external vendors to identify HR needs and develop solutions that align with the company’s goals. 

• Build and maintain strong relationships with key internal and external stakeholders, ensuring HR initiatives are aligned with organizational priorities. 

• Lead regular communication efforts to ensure alignment and transparency on HR operations and Total Rewards programs. 

Pathstone is committed to creating a diverse environment and is proud to be an equal opportunity employer.