Head of Human Resources

Keystone Advisors•Houston, TX

10d•$98,000 - $128,000•Hybrid

About The Position

Keystone Advisors is 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.

Requirements

Bachelor’s degree in human resources, Business Administration, or related field required
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
Hands-on experience with payroll and HR-related financial coordination
Experience working closely with executive leadership / founders
Strategic thinking with execution focus
High accountability and ownership mindset
Change management and adaptability
Cross-functional leadership
HR operations and compliance expertise
Workforce planning and talent strategy
Compensation and benefits administration
Process improvement and scalability
HRIS systems and payroll platforms
Microsoft Office Suite
Reporting and analytics
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

Nice To Haves

Master’s Degree or HR certification (SHRM-CP, SHRM-SCP, PHR, SPHR) preferred
Insurance industry (Medicare, ACA, agency distribution)
Technology or startup environment
Contact center operations
Salesforce CRM (preferred)

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, Salesforce 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 strategy, payroll accuracy, and benefits administration 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