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.