Director of People

ABOUT WORKBOX

Workbox is a national workspace operator that goes beyond coworking–our ecosystem accelerates ambition, cultivates connections, and helps businesses thrive. In addition to office space and coworking solutions, we offer connection to a network of investors, professional specialists, and high growth businesses across our entire portfolio. Our workspace products include private offices, reserved desks and floating memberships, as well as meeting rooms and event spaces. We currently operate 13 locations, encompassing over 400,000 square feet, in seven cities across the U.S. and our differentiation has led to us being one of the fastest growing workspace operators in the country.

ABOUT THE OPPORTUNITY

As we continue to grow, we are seeking a full-time Director of People to be based in our Chicago headquarters. This role is a high-impact, high-visibility position, providing comprehensive support in all aspects of the employee lifecycle. The Director of People will report directly to the EVP, General Counsel and partner closely with leadership across community operations, sales, marketing, IT, and finance.

This role will own and execute the full employee lifecycle, with a significant focus on talent acquisition: end-to-end recruiting, employer branding, candidate experience, onboarding, and retention. A successful Director of People will be an HR generalist, able to build relationships across the company, and a strategic thinker, helping us to shape HR policy, culture, performance management, and people operations that align with our organizational goals. This role involves handling sensitive employee information and requires a high level of professionalism and confidentiality.

KEY RESPONSIBILITIES

Recruiting and Talent Acquisition

• Partnering with hiring managers to define position descriptions, hiring plans, and recruitment strategies.
• Managing full-cycle recruiting: sourcing, screening, interviewing, offer negotiation, and background/reference checks.
• Building employer brand, candidate pipeline, and proactive talent sourcing.
• Administering Employee Referral Bonus Program.
• Using applicant tracking software system and tracking recruiting metrics.
• Driving effective candidate experience and conversion.
• Partnering with talent acquisition vendors, if needed.

Onboarding, Training and Development

• Administering onboarding (new hire paperwork, orientation, benefits enrollment) and offboarding, in coordination with PEO.
• Facilitating overall corporate and departmental training for new employees.
• Partnering with leadership to identify, implement, support, and evaluate the effectiveness of training and development programs throughout the organization.
• Providing guidance to managers and employees on career development and succession planning.

Culture, Engagement & Growth

• Partnering with leadership to support culture initiatives, recognition programs, and employee engagement surveys.
• Serving as a point of contact for employees and addressing complaints and concerns.
• Mediating conflicts between employees.
• Promoting a positive workplace culture.
• Helping to evolve HR programs that promote our mission of member success and a dynamic workplace culture.

Performance Management

• Assisting in the development and implementation of performance evaluation processes and tools.
• Training and coaching managers in conducting performance appraisals and reviews.
• Partnering with leadership to establish clear, measurable and achievable goals that align with our strategic objectives.
• Implementing a culture of continuous feedback that includes positive reinforcement and constructive criticism.
• Developing a clear process for managing underperformance.

HR Operations & Compliance

• Evaluating our current PEO partnership and service levels, developing recommendations for continuation or transition to alternative solutions, and overseeing vendor performance and management.
• Ensuring compliance with labor laws and regulations.
• Conducting market research to ensure competitive compensation packages.
• In coordination with PEO, managing benefits enrollment and communication.
• Conducting internal investigations.
• Maintain HRIS data integrity, produce regular reporting (headcount, turnover, recruiting KPIs).
• Assisting in developing, updating, communicating, and enforcing company policies and procedures.
• Maintaining accurate and up-to-date employee records.
• Handling documentation and reporting for regulatory requirements.

Requirements

• Bachelor’s degree in human resources, business or related field.
• 5-7 years of HR generalist experience in a fast-paced environment (startup or high-growth company preferred).
• Familiarity with coworking or multi-site operations a plus.
• Knowledge of federal/multi-state/local employment laws and regulations.
• Detail-oriented and proven ability to manage multiple responsibilities, prioritize tasks effectively, and meet deadlines.
• Relationship builder with exceptional interpersonal and communication skills for fostering collaboration and resolving conflicts.
• Leadership and coaching skills.
• Resourceful thinker who takes initiative to identify issues and implement creative, practical solutions.
• Hands on, team player who thrives in service-oriented environments and exudes a “no job too small” mindset.
• Comfortable working in a changing/ambiguous environment.
• Data-driven mindset: comfortable leveraging recruiting metrics and HR analytics to drive decisions.

Benefits

• Anticipated salary range: $75,000-$90,000 annually, based on experience and qualifications
• Comprehensive health benefits, including medical, dental and vision coverage
• Company-paid life insurance
• 401(k) plan
• Generous PTO
• FSA, HSA and commuter benefits
• Opportunity to build the HR function and shape culture at a scaling company