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

· 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

· 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

· 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

· 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:

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

· 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

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