Director of People

Skybox Capital•Chicago, IL

23h•Onsite

About The Position

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.

Requirements

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 Haves

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.

Responsibilities

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.
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.
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.