Director of Operations

Playbook•Chicago, IL

19d•$110,000 - $120,000•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 Playbookâ€™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

Nice To Haves

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 itâ€™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.
Oversee and guide cross-functional team members and/or committees of subject matter experts in Meetings and Events, Programming, and Wellness.
Own the end-to-end training lifecycle for Host teams, ensuring they are masters of our brand standards, service protocols, and proprietary technology.
Drive the successful rollout of new initiatives, ensuring high adoption rates through effective project management and structured communication.