Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale. Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services. Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago.

The Senior HR Generalist will play a critical role within the Human Resources Operations team, serving as a trusted resource for managers and employees while ensuring the effective delivery of HR programs, policies, and services across Lessen LLC. This position is responsible for managing more complex human resource matters, providing expert guidance on policies and compliance, and driving improvements to HR processes and tools. The Senior HR Generalist operates with a high level of independence, supporting business needs across multiple functions and contributing to strategic initiatives that strengthen organizational effectiveness and employee experience.

· Provide HR policy guidance, best practice interpretation, and thoughtful recommendations to managers and employees on a wide range of human resource matters.

· Manage and continuously refine onboarding processes to ensure a smooth and positive new hire experience; oversee I-9 verification and compliance requirements.

· Serve as a subject-matter resource in resolving complex employee leave and accommodation cases, collaborating closely with HR Business Partners, Talent Acquisition, Learning and Development, Benefits, Payroll, and Legal.

· Administer and maintain accurate HR data in Workday, including organizational changes, promotions, compensation adjustments, and compliance-driven reporting.

· Support the development, implementation, and ongoing improvement of HR policies, programs, and processes to enhance consistency and compliance.

· Partner on workforce planning, organizational design, restructures, and succession planning activities in collaboration with HR leadership.

· Analyze HR data and trends to provide insights and recommendations that support decision-making and business objectives.

· Promote a positive and inclusive workplace culture through day-to-day support, coaching, and engagement initiatives.

· Ensure strict confidentiality of employee information and adherence to federal, state, and local labor laws.

· Participate in cross-functional initiatives and contribute to ad-hoc human resource projects that enhance efficiency and employee experience.

· In-depth knowledge of HR principles, labor laws, and best practices, with the ability to apply them in complex situations.

· Strong understanding of legal and regulatory requirements related to employee management, compliance, and risk mitigation.

· Demonstrated ability to independently manage and resolve complex HR issues, including employee relations and policy interpretation.

· Proficiency in Microsoft Office Suite and strong skills in HRIS platforms (Workday preferred) for data accuracy, reporting, and process improvement.

· Strong analytical and problem-solving abilities, with experience using HR metrics and data insights to support decision-making.

· Excellent communication, consultation, and interpersonal skills, with the ability to influence and build credibility with employees and managers.

· Strong organizational skills with the ability to prioritize multiple competing demands in a fast-paced environment.

· Bachelor’s degree in Human Resources, Business Administration, or a related field.

· 5 - 7 years of progressive Human Resource experience, with broad exposure across multiple HR functions (e.g., employee relations, performance management, learning and development, benefits, compliance, and recruiting).

· Proven ability to work independently and handle complex HR issues with minimal supervision.

· Strong knowledge of federal, state, and local employment laws and regulations.

· Experience supporting multi-state or complex business environments (e.g., call centers, high-volume, or fast-paced organizations) preferred.

· Professional HR certification preferred, such as PHR, SHRM-CP, SPHR, or SHRM-SCP

· Demonstrated ability to partner with managers and influence outcomes through strong communication, consultation, and problem-solving skills.

· Analytical skills with experience using HR metrics and systems (Workday preferred).

· Competitive compensation

· Health, Dental, Vision, Life, Disability options

· 401K retirement savings plan

· Paid vacation, federal and floating holidays

· Maternity/Paternity Pay

· Career advancement opportunities

· All the tools you'll need to be successful