HR Generalist (Remote, Part-Time, Contract)

About the Role

We’re looking for an experienced HR Generalist to join Huckleberry on a part-time contract basis (10 - 20 hours per week, 1099). This is a dual-hat role that blends traditional HR with people operations, ideal for someone who is equally comfortable navigating legal compliance as they are designing the systems and processes that shape how teams work, grow, and thrive.

You’ll help keep our people practices grounded, fair, and forward-thinking. From owning our performance feedback cycle end-to-end to handling sensitive employee relations with discretion and care, you will build the infrastructure that enables Huckleberry’s team to do their best work.

This is a high-impact role for someone who loves operational detail, thinks in systems rather than one-offs, and brings a calm, level-headed approach when navigating complexity.

People Operations & Employee Experience

• Run the rollout and ongoing management of performance feedback cycles, including building the process, managing all communications, tracking completion, and facilitating follow-ups.

• Foster a culture of growth, collaboration, and innovation, aligned with Huckleberry’s values.

• Partner with team managers to set up systems that make team development consistent and effective, ensuring managers are equipped to lead performance conversations.

• Support employee engagement by identifying patterns, surfacing root causes, and proactively recommending improvements to how the team works together.

HR Compliance & Employee Relations

• Serve as a trusted, confidential resource for employee relations issues by listening with empathy, establishing the facts, investigating professionally, and guiding all parties toward constructive, amicable resolutions.

• Ensure all HR practices and policies are legally compliant with federal and state laws, including multi-state employee and contractor compliance.

• Manage performance management processes as a compliance and development tool, ensuring documentation and practices meet legal standards.

• Navigate HR issues with composure and sound judgment, serving as a stabilizing guide through challenging situations.

• Maintain and improve HR processes and records that are accurate, organized, and compliant. Attention to detail is key.

• 5+ years of HR experience spanning both traditional HR and people operations functions.

• Demonstrated expertise in employee relations: tactful, a strong listener, respectful of confidentiality, and skilled at de-escalating situations while identifying root causes.

• Solid understanding of HR legal compliance across multiple U.S. states, including employee and contractor classification.

• Systems thinker: you build processes and frameworks rather than making reactive, one-off decisions. You use first-principles thinking to get to the root of performance issues and design for lasting impact.

• Proven ability to own a project end-to-end from system design through communication, rollout, and follow-up.

• Crisis management capability: you stay level-headed under pressure and know how to guide an organization through HR challenges in a compliant, professional manner.

• Exceptional attention to detail and strong organizational skills.

• Comfortable operating independently in a part-time, remote, contract capacity.

• Working knowledge of employer benefits administration—including annual open enrollment periods, sign-up processes, and employee communication—without necessarily owning vendor negotiations.

• Experience supporting a high-growth startup or consumer app company.

• Familiarity with HRIS or people ops tools.

• Background in building or scaling HR functions from the ground up.

• SHRM certification (SHRM-CP, SHRM-SCP) or equivalent HR certification preferred.