People Generalist

Who we are:
At Mediafly, we help the world’s top revenue teams work smarter and achieve measurable impact. Our platform brings together sales enablement, content, and performance insights so sellers have the coaching, tools, and intelligence they need to succeed. By weaving value selling into every workflow, we empower teams to accelerate deal cycles, boost win rates, and prove ROI.

For you, that means joining a company where innovation meets purpose—where your work helps businesses deliver more meaningful buyer experiences and drives results that truly matter. You’ll be part of a collaborative, growth-focused team that values expertise, creativity, and human connection.

Mediafly is seeking a well-rounded People Generalist who builds strong relationships with employees and supports positive, consistent experiences across the full employee lifecycle, with specific experience navigating multistate employment and compliance laws in a fully remote environment. This role partners with employees and leaders to support core HR programs, including onboarding and employee lifecycle administration, HRIS and benefits management, reporting and tracking, compliance, and employee engagement and retention initiatives. The People Generalist serves as a primary point of contact for employee questions and works closely with senior HR leadership to ensure best practices and continuity across the organization.

Responsibilities of a People Generalist: :
• Work under limited supervision to provide guidance to employees and managers on HR-related needs of varying complexity.
• Ensure HR policies, benefits, payroll and employee practices remain compliant with multistate and local employment laws across our fully remote workforce, monitoring and implementing state-specific changes while supporting a consistent experience across jurisdictions.
• Provide guidance and support to employees and leaders on multistate-specific requirements and the administration of leaves of absence including FMLA, PFML, Pregnancy Disability, STD/LTD, SDI, and other job-protected or wage-replacement programs, by monitoring regulatory changes and ensuring compliant, scalable HR processes.
• Serve as the primary internal point of contact for employee and manager Rippling inquiries, with daily hands-on administration of HRIS functions across payroll, benefits, and employee data, ensuring accuracy and smooth system operations.
• Facilitate the onboarding process for new hires, including orientations, benefits, training, and organizational culture.
• Provide day-to-day employee support by understanding people needs and assisting with the execution of people programs, including leading occasional training sessions.
• Support benefits administration by ensuring accurate benefit elections, processing qualified life events (QLEs), coordinating with benefits brokers, and administering COBRA through Clarity.
• Support recruiting and hiring efforts by coordinating interview logistics, assisting with offer preparation (including offer letters and total rewards reviews), and ensuring a smooth transition from offer acceptance to onboarding.
• As needed, step in to support full-cycle recruiting activities.
• Ensure administrative record keeping and employment practices are compliant with all applicable laws and regulations.
• Maintain compliance with federal, state, and local employment laws and regulations by supporting audits, record keeping, and policy reviews in line with best practices.
• Support managers with performance management processes, including documentation, coaching guidance, and disciplinary actions, in partnership with senior HR leadership.
• Assist with employee relations matters and investigations by supporting issue resolution, documentation, and follow-up, escalating as appropriate.
• Stay up-to-date on HR best practices and industry trends to continuously improve HR processes.
• Partner cross functionally with the Operations and Finance teams on ad-hoc tasks as required.

We would love to work with you if you have the following::
• 3-5 years of experience in Human Resources or People Operations, supporting multiple HR functions such as employee relations, performance management, compensation, benefits administration, recruiting, and HR operations.
• Solid understanding of U.S. employment laws, compliance requirements, and HR best practices in a multi-state and remote environment.
• Bachelor’s degree preferred in Human Resources, Business Administration, Organizational Development, or a related field; PHR or SHRM-CP a plus.
• Working knowledge of leave of absence administration, including FMLA, parental and medical leave, ADA accommodations, and other job-protected leave programs.
• Experience working with HRIS and Applicant Tracking Systems (e.g., Rippling, Lattice, Lever, or similar platforms).
• Strong emotional intelligence and interpersonal skills, with the ability to communicate effectively with employees and leaders in a remote setting.
• Strong organizational, problem-solving, and collaboration skills, with the ability to manage multiple priorities.
• Willingness to balance people program support with hands-on, tactical HR work.
• High attention to detail with a focus on accurate data entry, record keeping, and follow-through.
• Ability to work independently in a fully remote environment, while partnering closely with cross-functional teams.

Why Mediafly?

Remote-First Culture
Flexible working hours
Generous & Flexible PTO
Competitive Salary
401K Retirement Plan with match
Transparent Career Paths
Medical, Dental, Vision
Generous Paid Parental Leave
Company-wide Stipends
Work in a creative environment with high energy

Mediafly is an equal opportunity employer, which means we do not discriminate on the basis of race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome people of different backgrounds, experiences, abilities and perspectives and encourage all interested individuals to apply.

Thanks to our commitment to employee experience, Mediafly has been recognized as a Best Place to Work from Crain's, Inc. and BuiltIn.

Mediafly's HQ is based in Chicago, IL.