Head of Human Resources

About the role

We are seeking a high-caliber, execution-focused Head of Human Resources to support a fast-moving, multi-business entrepreneur overseeing Keystone Advisors and KosmosDX. This hybrid leadership role will serve as both a strategic HR leader and hands-on operator, responsible for building, scaling, and optimizing all people-related functions across both organizations.

Duties and Responsibilities

• Serve as a trusted advisor to executive leadership across both entities
• Align HR strategies with business goals and growth objectives
• Provide HRBP support to leaders across operations, sales, and technology
• Drive organizational design, workforce planning, and talent strategies
• Lead change management initiatives across evolving business needs
• Oversee end-to-end HR operations including:
• Employee lifecycle (hire to exit)
• Policies, procedures, and handbook management
• Performance management processes
• Employee relations and engagement
• Ensure HR systems, workflows, and documentation are accurate and compliant
• Build scalable HR infrastructure to support multi-entity growth
• Lead recruiting strategies across both organizations:
• Insurance agents and agency support roles (Keystone Advisors)
• Technology and operational roles (KosmosDX)
• Partner with leadership to forecast hiring needs
• Implement structured hiring processes and interview frameworks
• Improve candidate experience and time-to-fill metrics
• Oversee compensation structures and workforce budgeting
• Partner with finance/accounting on:
• Payroll coordination and accuracy
• Benefits administration
• Workforce cost tracking
• Support accounts receivable visibility and reporting alignment with operational teams
• Ensure proper documentation and reconciliation of HR-related financial data
• Ensure compliance with:
• Federal & State employment laws
• HIPAA and CMS regulations (where applicable)
• Insurance licensing and certification requirements
• Internal policies across both entities
• Maintain audit-ready HR documentation
• Mitigate risk through proactive policy enforcement and training
• Design and implement performance management frameworks
• Coach managers on employee development and accountability
• Drive employee engagement, retention, and culture initiatives
• Promote a high-performance, results-driven environment
• Oversee HR technology platforms and integrations:
• HRIS systems
• Payroll platforms
• ServiceNow and operational tools
• Optimize workflows, automation, and reporting capabilities
• Ensure cross-functional alignment between HR, operations, and technology
• Balance priorities between:
• Keystone Advisors (60%) – insurance distribution, agency growth, contact center operations
• KosmosDX (40%) – technology, platform solutions, innovation initiatives
• Ensure consistency in HR standards while adapting to each business model
• Streamline shared services across both entities
• Oversee compensation, payroll, and accounting oversight across both entities
• Take an active role in financial operations related to workforce management, including:
• Payroll processing, audits, and reporting
• Commission and incentive tracking
• Workforce cost analysis and budgeting
• Manage and support Accounts Receivable (AR) processes, including:
• Tracking incoming payments and outstanding balances
• Partnering with operations to ensure accurate billing and collections
• Monitoring revenue flow tied to agents, carriers, and services
• Collaborate closely with finance/accounting on:
• Reconciliations and financial reporting
• Budget planning and forecasting
• Expense management and cost controls
• Ensure alignment between HR, payroll, and accounting systems for accuracy and reporting integrity

Qualifications

• Education: Bachelor’s degree in human resources, Business Administration, or related field required. Master’s Degree or HR certification (SHRM-CP, SHRM-SCP, PHR, SPHR) preferred.
• Experience: 7+ years of progressive HR leadership experience. Proven experience as: Head of HR, HR Director, or Senior HR Business Partner. Experience supporting: Multi-entity or multi-business environments, High-growth or entrepreneurial organizations.
• Highly Preferred Experience: Insurance industry (Medicare, ACA, agency distribution), Technology or startup environment, Contact center operations, Hands-on experience with payroll and HR-related financial coordination, Experience working closely with executive leadership / founders.
• Experience/Knowledge/Skills/Abilities/Training: Leadership Competencies, Operational Competencies, Technical Competencies, Professional Competencies.

Why Join Keystone Advisors / KosmosDX

This is a unique opportunity to serve as a strategic HR leader across two high-growth organizations, directly supporting executive leadership and shaping the people strategy that drives business success. You will play a critical role in building scalable systems, strengthening culture, and enabling both organizations to deliver on their mission with excellence. This role is ideal for a hands-on leader who thrives in fast-paced environments, embraces accountability, and is passionate about building strong, high-performing teams.