Director of People

The Role

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

Were hiring a Director of People to run the people function across the platform.

What Youll Own

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

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 shouldnt.

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.

What Were Looking For

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.

Logistics

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.