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Director of Operations

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Playbook
Full Time position
Listed on 2026-06-19
Job specializations:
  • IT/Tech
Salary/Wage Range or Industry Benchmark: 110000 - 120000 USD Yearly USD 110000.00 120000.00 YEAR
Job Description & How to Apply Below
Salary Range:$110-120k + Equity Eligibility

Benefits: FREE employee-only medical coverage, a 4% employer 401(k) match, and FREE short-term disability. Other incredible benefits HERE.

Location: Chicago, IL or Houston, TX

Reports to: Chief Experience Officer

Mission

The Director of Operations is responsible for empowering host teams to deliver exceptional, client-centered services that foster connection, well-being, and longevity, ensuring high-quality experiences s role plays a key part in sustaining and scaling Playbook's site operations across our core service lines: fitness center management, hosted meetings and events, tenant and public programming, food & beverage operations, and concierge services. The right person will speak the language of operational rigor, but understands the soul of premium hospitality.

Lasting Impact

As a result of your time in this role, you have helped shape and define the future of work. You have enabled our host teams to do what they do best: spark connection, enhance well-being, and unlock productivity for thousands of people in office spaces across the country. You led Playbook to become a lasting fixture in commercial office buildings.

Outcomes You'll Deliver

1. Operational Architecture & Systems

Translate complex business strategies into clear operating standards (SOPs), financial models, and tech-enabled workflows.
  • SOP & Strategy Translation: Convert strategic initiatives and programming into standardized SOPs, training materials, and resources for Client Delivery teams.
  • Financial & Scalability Modeling: Ensure all new initiatives have a clear financial model and a scalable delivery plan before deployment to support revenue-generating strategies across diverse amenity spaces.
  • Playbook OS Documentation: Own the creation and upkeep of operational resources, user guides, and SOPs for our proprietary technology platform, Playbook OS.
  • Product & Engineering Collaboration: Act as a key operational partner to the Product and Engineering teams, supporting new product updates, feature rollouts, and front-line feedback loops.
  • Tech Stack Ownership: Own the overall operational configuration of the tech stack to ensure smooth day-to-day site workflows.
2. Team Leadership & Collectives

Oversee and guide cross-functional team members and/or committees of subject matter experts in Meetings and Events, Programming, and Wellness.
  • People Management: Lead and coach the Director of Wellness, ensuring their specialized strategy successfully translates to site-level execution.
  • Collective Management: Facilitate the workflow for the Meetings/Events, Programming, and Wellness Collectives. Turn their subject matter expertise into standardized, repeatable programs.
  • Strategic Alignment: Ensures Collectives' outputs are aligned with business goals and support scalability of host teams.
  • Gated Rollouts: Lead pilots and beta tests from site selection to post-mortem. Do not move to a "Full Rollout" until a pilot has proven its ROI and operational feasibility.
3. Learning & Development (L&D)

Own the end-to-end training lifecycle for Host teams, ensuring they are masters of our brand standards, service protocols, and proprietary technology.
  • Operational & Technical Training: Lead trainings for Client Delivery teams on operational functions, including Playbook OS, Site Dashboards, P&Ls, and Budgets.
  • Service Line Training: Facilitate ongoing training for Host teams on core service lines, leveraging subject matter expertise where appropriate.
  • Onboarding & Tool Provisioning: Manage the technical and operational onboarding for new hires, ensuring they are fully trained, set up, and configured on Playbook OS and necessary applications.
  • Knowledge Management: Maintain a centralized, "single source of truth" library for all SOPs, training videos, and resource guides. Ensure no outdated materials are in circulation.
  • Performance Remediation: Partner with Client Operations Managers to identify specific sites or individuals needing additional training based on performance data. Deliver structured feedback reports and support remediation plans if a site fails QA.
  • Proactive Feedback Loops: Actively monitor support tickets, Slack…
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