Director of Operations

Playbook•Chicago, IL

17d•Onsite

About The Position

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 at scale. This 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. 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.

Requirements

5–7+ years of progressive operational leadership experience in premium hospitality, amenity management, wellness services, or related fields.
At least 2–3 years managing multi-site portfolios or regional operations.
Demonstrated success executing large-scale rollouts, change management strategies, and end-to-end learning and development (L&D) programs across a distributed footprint
High tech-literacy and systems fluency. While advanced proficiency in G Suite (sheets, decks, dashboards) is required, you must also be highly comfortable learning, documenting, and teaching proprietary software, collaborating with product teams, and leveraging tools like Slack and ticketing systems to optimize workflow
Strong financial acumen. Demonstrated proficiency in creating proformas, financial models, and analyzing P&L statements
A strategic thinker who elevates company performance. You have strategically moved the needle for past organizations by seeing the big picture, understanding the interconnectedness of decisions and activities, and using that insight to drive revenue and exceed your goals.
A hyper-organized ball juggler. You stay extremely organized and are constantly reprioritizing your own work because it’s what makes you most effective. Everyone refers to you as a stellar multi-tasker.
Analytical and solution-oriented mindset. You are an inherently inquisitive problem-solver who consistently identifies root causes, develops actionable strategies independently, and drives them to resolution. You have a proven ability to tackle complex challenges, optimize existing workflows, and implement efficient, long-term fixes.
Clear and concise communicator. Demonstrates exceptional interpersonal, written, and verbal communication skills, effectively conveying operational goals and strategies to diverse teams, levels of the organization, and external stakeholders.
Ability to coach and influence. Strong ability to coach and inspire others toward achieving desired outcomes. Uses a supportive and guidance-driven approach to foster growth, drive change, and achieve measurable results across teams.
Silo-breaking collaborator. You proactively engage with external teams and departments to understand their unique constraints, foster mutual accountability, and co-develop integrated solutions. You focus on building alignment to ensure that cross-departmental workflows are smooth, efficient, and scalable.

Responsibilities

Translate complex business strategies into clear operating standards (SOPs), financial models, and tech-enabled workflows.
Convert strategic initiatives and programming into standardized SOPs, training materials, and resources for Client Delivery teams.
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.
Own the creation and upkeep of operational resources, user guides, and SOPs for our proprietary technology platform, Playbook OS.
Act as a key operational partner to the Product and Engineering teams, supporting new product updates, feature rollouts, and front-line feedback loops.
Own the overall operational configuration of the tech stack to ensure smooth day-to-day site workflows.
Oversee and guide cross-functional team members and/or committees of subject matter experts in Meetings and Events, Programming, and Wellness.
Lead and coach the Director of Wellness, ensuring their specialized strategy successfully translates to site-level execution.
Facilitate the workflow for the Meetings/Events, Programming, and Wellness Collectives. Turn their subject matter expertise into standardized, repeatable programs.
Ensures Collectives’ outputs are aligned with business goals and support scalability of host teams.
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.
Own the end-to-end training lifecycle for Host teams, ensuring they are masters of our brand standards, service protocols, and proprietary technology.
Lead trainings for Client Delivery teams on operational functions, including Playbook OS, Site Dashboards, P&Ls, and Budgets.
Facilitate ongoing training for Host teams on core service lines, leveraging subject matter expertise where appropriate.
Manage the technical and operational onboarding for new hires, ensuring they are fully trained, set up, and configured on Playbook OS and necessary applications.
Maintain a centralized, "single source of truth" library for all SOPs, training videos, and resource guides. Ensure no outdated materials are in circulation.
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.
Actively monitor support tickets, Slack channels, and member surveys. Look for technical or operational patterns that indicate a need for a process change or a targeted training update.
Establish metrics for new initiatives to determine if they are meeting intended revenue or engagement targets, going beyond simple adoption rates.
Drive the successful rollout of new initiatives, ensuring high adoption rates through effective project management and structured communication.
Own the strategic Roadmap Calendar, managing what gets rolled out and when to prevent initiative fatigue or overload on Host teams.
Manage the roadmap communication pipeline between the Advisory team and the Client Delivery team.
Own the monthly host team meeting as the main vehicle for communicating new initiatives and the upcoming calendar. Solicit input from other stakeholders and ensure the meeting content is balanced.
Manage weekly communication updates to host teams.
Own and moderate host team support channels within Slack to maintain clear lines of daily communication.
Align with People Team to incorporate Mission and Culture related messaging and L&D sessions into relevant host communications.