Job Description

Were seeking an empathetic, self-sufficient, technically skilled Director of People and Culture to own all aspects of Middle Seats people and culture for our fully remote and unionized team. Operating as a department of one, your role will be responsible for designing and managing HR systems, ensuring compliance, leading recruitment, and driving initiatives that keep our team engaged and supported.

Reporting directly to the COO, this role is ideal for someone who has independent HR experience at a small-ish company, who thrives without heavy corporate infrastructure, and is excited to incorporate a strong equity lens to the business.

This role is not part of the bargaining unit.

Key Responsibilities

HR Operations & Compliance

• Manage all HR operations for a fully remote, majority-bargaining-unit team.
• Administer benefits and people systems, partnering with our PEO to ensure payroll, benefits, and compliance run smoothly.
• Maintain policies, the employee handbook, and compliance with federal and local regulations (FMLA, ADA, OSHA) and the collective bargaining agreement.
• Handle sensitive employee matters, investigations, and conflict resolution with discretion and professionalism.
• Maintain and build scalable HR processes for onboarding, offboarding, policy rollouts, and internal communications.
• Act as company point of contact for all employee communications

HR Systems & Operations

• Optimize the companys HRIS, benefits, and engagement tools to make processes efficient and employee-friendly.
• Serve as the technical owner of all HR systems (PEO, payroll, benefits platforms, and HR processes).
• Manage company Google Workspace and compliance with IT security policy.
• Track and analyze workforce data for capacity planning, retention strategies, and diversity reporting.

Workplace Culture & Employee Success

• Embed diversity, equity, and inclusion principles into hiring, policies, and team culture.
• Foster connection and engagement in a fully remote environment through thoughtful communication, recognition, and team-building initiatives.
• Regularly assess team feedback and propose improvements to support a healthy, sustainable workplace.
• Serve as the lead point of contact on all new hire onboarding and orientation programs, setting up structures for people-focused areas including new hire onboarding, client onboarding, hiring, people-related process roll outs.
• Create professional development opportunities, leadership pathways and mentorship to help develop and retain staff, including managers
• Work with managers to refine, standardize, and manage performance review process and establish effective supervisory relationships and leadership skills
• Counsel the management team of different departments by providing advice on managing employees and cultivating better culture
• Strengthen working relationships between staff and help set successful culture of communication, including guiding Middle Seat culture as fully remote staffers
• Coordinate staff appreciation efforts including end-of-year gifts and organize staff bonding activities such as virtual happy hours, virtual game nights, etc.
• Plan team building activities and events, including annual in person and virtual retreats

Recruitment & Talent Development

• Lead recruitment efforts from job posting to offer letter, including front-facing salary negotiations.
• Build diverse talent pipelines through strategic sourcing and partnerships.
• Partner with managers to implement performance reviews, leadership pathways, and professional development plans.
• Lead team member orientation, including working with managers to ensure training is completed for all new hires
• Liaise with union representatives of plans to hire new staff or plans to engage with new independent contractors when appropriate

About You

Youre a hands-on HR leader who thrives in small, fast-moving organizations. You bring both the technical HR skills and the people-first mindset to build a workplace that works for everyone. Additionally you will possess:

• 7-10 years of HR experience working with 50100 employee companies (bonus points if you are experienced with unionized teams and collective bargaining agreements. )
• Systems-builder mentality; you are someone who can implement and manage PEOs, HRIS, and benefits platforms yourself.
• Remote workforce expertise with experience applying HR policies and engagement strategies to distributed teams.
• An equity-driven mindset, with a track record of embedding DEI into policies, recruiting, and culture initiatives.
• Discreet and self-directed, equally comfortable writing policies, troubleshooting systems, and coaching managers through complex employee matters.

Why Middle Seat?

Were values-driven, impact-obsessed, and committed to building a team that reflects the world we want to create. We lead with transparency, equity, and the belief that progressive work deserves operational excellence.

• Profit-sharing + 401k match (6%yes, really)
• Fully covered health, dental, and vision100% employer paid
• 20 days PTO + your birthday + work anniversary off
• Unlimited sick leave + 12 weeks paid parental leave
• $350 mental health reimbursement + $100 student loan stipend + $50 cell phone stipend

Compensation commensurate with experience and location: $90,000 $105,000 annually

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