Head of Human Resources

Keystone Advisors is a full-service marketing company aligned with Top Health Insurance Carriers to provide our partners and clients with a broad and competitive portfolio of Insurance Options. We have over 20 years' experience in Insurance marketing while serving our local communities with Medicare, Individual, Group Health, Life, and Annuity products. The foundation of the company and its employees lies in our core values: Customer service, integrity, compassion, tenacity, & being a team player.

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.

This role requires a unique blend of HR leadership, HR Business Partner (HRBP) capabilities, and operational execution, including oversight of HR operations, talent strategy, compliance, payroll coordination, and light accounting support (including accounts receivable tracking and workforce cost management).

The ideal candidate thrives in an entrepreneurial environment, is highly accountable, detail-oriented, and capable of operating at both strategic and tactical levels while managing multiple priorities across different business models.

Strategic HR Leadership & HR Business Partnering

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

HR Operations & Execution

Oversee end-to-end HR operations including:

o Employee lifecycle (hire to exit)

o Policies, procedures, and handbook management

o Performance management processes

o Employee relations and engagement

Ensure HR systems, workflows, and documentation are accurate and compliant

Build scalable HR infrastructure to support multi-entity growth

Talent Acquisition & Workforce Planning

Lead recruiting strategies across both organizations:

o Insurance agents and agency support roles (Keystone Advisors)

o 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

Compensation, Payroll & Light Accounting Collaboration

Oversee compensation structures and workforce budgeting

Partner with finance/accounting on:

o Payroll coordination and accuracy

o Benefits administration

o Workforce cost tracking

Support accounts receivable visibility and reporting alignment with operational teams

Ensure proper documentation and reconciliation of HR-related financial data

Compliance & Risk Management

Ensure compliance with:

o Federal & State employment laws

o HIPAA and CMS regulations (where applicable)

o Insurance licensing and certification requirements

o Internal policies across both entities

Maintain audit-ready HR documentation

Mitigate risk through proactive policy enforcement and training

Performance Management & Culture Development

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

Technology, Systems & Process Optimization

Oversee HR technology platforms and integrations:

o HRIS systems

o Payroll platforms

o Salesforce and operational tools

Optimize workflows, automation, and reporting capabilities

Ensure cross-functional alignment between HR, operations, and technology

Multi-Entity Coordination

Balance priorities between:

o Keystone Advisors (60%) insurance distribution, agency growth, contact center operations

o KosmosDX (40%) technology, platform solutions, innovation initiatives

Ensure consistency in HR standards while adapting to each business model

Streamline shared services across both entities

Compensation, Payroll, & Accounting Oversight

Oversee compensation strategy, payroll accuracy, and benefits administration across both entities

Take an active role in financial operations related to workforce management, including:

o Payroll processing, audits, and reporting

o Commission and incentive tracking

o Workforce cost analysis and budgeting

Manage and support Accounts Receivable (AR) processes, including:

o Tracking incoming payments and outstanding balances

o Partnering with operations to ensure accurate billing and collections

o Monitoring revenue flow tied to agents, carriers, and services

Collaborate closely with finance/accounting on:

o Reconciliations and financial reporting

o Budget planning and forecasting

o 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:

o Head of HR, HR Director, or Senior HR Business Partner

Experience supporting:

o Multi-entity or multi-business environments

o 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

Strategic thinking with execution focus

High accountability and ownership mindset

Change management and adaptability

Cross-functional leadership

Operational Competencies

HR operations and compliance expertise

Workforce planning and talent strategy

Compensation and benefits administration

Process improvement and scalability

Technical Competencies

HRIS systems and payroll platforms

Microsoft Office Suite

Salesforce CRM (preferred)

Reporting and analytics

Professional Competencies

Strong business acumen

Excellent communication and interpersonal skills

High attention to detail and organization

Problem-solving and decision-making abilities

Ability to manage multiple priorities in a fast-paced environment

Key Performance Indicators (KPIs)

Employee Retention & Engagement

Time-to-Fill & Hiring Effectiveness

HR Compliance & Audit Readiness

Payroll & Operational Accuracy

Workforce Cost Management

Performance Management Adoption

Leadership Satisfaction

Process Efficiency & Automation

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