Director of People

We are a Chicago-based firm that owns and operates businesses across digital marketing, e-commerce, and investing. We’re scaling and need to bring structure and accountability to how we hire, manage, and develop people.

We’re hiring a Director of People to run the people function across the platform.

The responsibilities below are grouped for clarity, but in practice this role moves fluidly across all of them.

•      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.

•      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.

•      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.

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

•      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.