Director of People

Building the foundation

• Select, implement, and own the core people tech stack (HRIS, PEO, performance, payroll integrations) across multiple entities.
• Write, update, and maintain employee handbooks, policies, and people documentation for each operating business, respecting where they legitimately differ and standardizing where they shouldn’t.
• Establish compensation philosophy, bands, and review cadences; partner with Finance on headcount planning and total rewards.

Hiring and onboarding

• Partner with hiring managers and external recruiting partners to run a disciplined, high-signal hiring process across roles ranging from frontline to executive.
• Own offers, onboarding, and the first-90-days experience so new hires ramp quickly and feel oriented from day one.
• Improve interview practices, structured interviews, calibrated scorecards, values-based assessment, and coach managers on how to use them.

Manager enablement and performance

• Design and run performance review and development cycles that are useful, not ceremonial.
• Coach managers on feedback, difficult conversations, and team development.
• Serve as a trusted, confidential sounding board for employees and leaders on sensitive matters.

Culture and engagement

• Lead culture and engagement initiatives, including team events, engagement surveys, and recognition programs that reinforce connection across entities.

Compliance, benefits, and operations

• Own benefits strategy and administration across entities; manage broker and PEO relationships where applicable.
• Ensure compliance with federal, Illinois, and multi-state employment law, including leave, pay transparency, and classification.
• Oversee employee lifecycle operations end-to-end, offers, transitions, separations, with the accuracy and discretion this work demands.

Strategy and analytics

• Define the people metrics that matter for this business and report on them honestly to the principals.
• Advise on organizational design, leveling, and workforce planning as the operating businesses scale.
• Translate what you see and hear across the organization into clear recommendations for leadership.
• Drive cross-departmental alignment on internal operations and communication flow to keep the platform cohesive as it scales.

We care more about judgment and track record than a specific pedigree. That said, the following are genuinely required:

• 10+ years in HR, People Operations, or a closely related function, with at least 3 years in leadership or management capacity.
• Direct experience building a people function, not just running one that already exists. You have selected HRIS systems, written handbooks, and designed review cycles from a blank page.
• Working fluency with U.S. employment law, benefits administration, and multi-entity or multi-state compliance.
• Demonstrated ability to operate across populations with different cultures, compensation structures, and operating rhythms — e.g., professional services alongside operating companies, or corporate alongside frontline.
• The judgment and discretion required to be the confidant of principals and employees alike.

Nice to have:

• Experience inside a family office, holding company, or PE platform — or supporting a portfolio of businesses with distinct identities.
• Experience scaling an organization through 100, 250, or 500 employees.
• SHRM-SCP, SPHR, or equivalent certification.

Location: Chicago. This is an in-office role, based at our downtown office.

Structure: Reports directly to the principals of the family office. Partners closely with the leaders of each operating business.

Compensation: Competitive base salary, performance bonus, comprehensive benefits, and a retirement plan with employer contribution. Specific range shared in first conversation.