Chicago Office Manager Jobs (NOW HIRING)

Position Summary

The Office Manager is a highly visible, multifaceted role that combines proactive executive support, event planning, and workplace experience to help leaders and employees operate at their best.
This role provides support to a number of designated leaders while helping support the workplace experience for approximately 130 employees across multiple MGUs sharing the Chicago office. Responsibilities include managing complex calendars, meetings, travel, communications, and expenses, as well as planning and executing a regular cadence of leadership meetings, employee events, and business gatherings.
What differentiates this position from a traditional administrative role is its Workplace Experience lens. This individual looks beyond individual requests to connect leaders, employees, events, visitors, and office operations, creating a cohesive and professional experience across the businesses we support. Success requires someone who can anticipate needs, exercise sound judgment, and comfortably shift between planned priorities and real-time needs throughout the day.

What will your job entail?

Core Responsibilities

Executive & Leadership Support

• Provide proactive Executive Assistant support to designated leaders, managing complex calendars and meetings, anticipating needs, resolving scheduling conflicts, and helping leaders effectively manage their time and priorities.
• Coordinate business travel, itineraries, accommodations, and related expense reporting.
• Draft, prepare, and organize correspondence, presentations, reports, meeting materials, and other business documents.
• Serve as a trusted point of contact for internal and external stakeholders and support special projects and evolving business priorities.
• Handle confidential and sensitive information with sound judgment and discretion.

Event Planning & Execution

• Plan and execute leadership gatherings, employee events, business meetings, celebrations, and other experiences from concept through completion.
• Partner with leaders, MGUs, and the broader Workplace Experience team to create experiences aligned with the audience, purpose, and business need.
• Manage event logistics, vendors, communications, materials, technology, budgets, and onsite execution.
• Bring creative ideas forward and continuously look for ways to make meetings and events more intentional, engaging, and effective.

Workplace Experience & Engagement

• Create a cohesive, welcoming, and professional workplace experience within a shared office supporting multiple MGUs.
• Build relationships across the businesses to understand employee and leadership needs while helping create connection across the shared workplace.
• Provide a polished onsite experience for employees, executives, candidates, clients, brokers, and other visitors.
• Partner with the broader Workplace Experience team to bring firmwide culture initiatives, recognition, community efforts, and employee programs to life locally.
• Use employee feedback and workplace observations to identify opportunities to strengthen connection and the overall employee experience.
• Serve as a visible ambassador for the organization's culture, values, and Workplace Experience standards.

Office Operations

• Oversee day-to-day office operations to ensure the shared workplace remains organized, professional, safe, functional, and prepared for business needs.
• Manage shared workplace resources including meeting spaces, supplies, food and beverage programs, amenities, common areas, mail and deliveries, seating, new-hire readiness, and visitor access.
• Serve as the primary liaison with building management and service providers for repairs, maintenance, access, security, cleaning, HVAC, and other facilities needs, tracking issues through resolution.
• Manage office vendors, purchasing, invoices, expenses, contracts, and operational documentation within established budgets and processes.
• Proactively identify office needs, recurring issues, and potential disruptions and address or escalate them before they create larger business impact.
• Develop repeatable processes and resources that improve consistency and efficiency, and recommend better approaches when existing processes are unnecessarily manual, costly, or ineffective.

How This Role Is Expected to Operate

Anticipation & Ownership

• Looks ahead, connects the dots, and takes responsibility for outcomes through completion.

Sound Judgment & Prioritization

• Navigates competing demands, makes thoughtful trade-offs, and knows when to act independently, reset expectations, or escalate.

Service & Partnership

• Builds trusted relationships while balancing responsiveness with appropriate boundaries, accountability, and business needs.

Creativity & Experience Mindset

• Considers not only whether something gets done, but how people experience it, bringing thoughtful ideas forward to improve meetings, events, and the workplace.

Adaptability & Professionalism

• Moves comfortably between executive support, events, workplace needs, and changing priorities while maintaining discretion, composure, and attention to detail.

Qualifications & Experience

• 3+ years of relevant experience in executive support, event planning, workplace experience, hospitality, business operations, or a related field preferred.
• Demonstrated experience supporting executives or senior leaders, including calendar, meeting, travel, and expense management.
• Experience planning and executing meetings, events, or employee experiences from concept through completion.
• Strong organization, attention to detail, communication, and follow-through with the ability to independently manage multiple priorities and stakeholders.
• Strong problem-solving skills with the confidence to anticipate needs, evaluate options, and recommend solutions.
• Experience with vendors, budgets, purchasing, facilities, or workplace operations preferred.
• Ability to handle confidential and sensitive information with professionalism and discretion.
• Bachelor's degree preferred. Equivalent combination of education and relevant professional experience will also be considered.

This is an onsite role with occasional early morning or evening availability required to support events, leadership meetings, and other business needs.

The Person Who Will Thrive in This Role

• The right person enjoys being at the intersection of people, details, and experiences.
• They can manage an executive's changing schedule, plan an important event, welcome a client, anticipate a workplace need, and coordinate across multiple businesses while still recognizing what matters most.
• They do not simply complete tasks or respond to requests. They anticipate what comes next, bring ideas and solutions forward, and take pride in creating experiences that feel thoughtful, seamless, and intentional.

Ryan Specialty is an Equal Opportunity Employer. We are committed to building and sustaining a diverse workforce throughout the organization.Our vision is an inclusive and equitable workplace where all employees are valued for and evaluated on their performance and contributions. Differences in race, creed, color, religious beliefs, physical or mental capabilities, gender identity or expression,sexual orientation, and many other characteristics bring together varied perspectives and add value to the service we provide our clients, trading partners,and communities.This policy extends to all aspects of our employment practices, including but not limited to, recruiting, hiring, discipline, firing, promoting, transferring, compensation, benefits, training, leaves of absence, and other terms, conditions, and benefits of employment.

How We Support Our Teammates

Ryan Specialty seeks to offer our employees a comprehensive and best-in-class benefits package that helps them - and their family members - achieve their physical, financial, and emotional well-being goals. In addition to paid time off for company holidays, vacation, sick and personal days, Ryan offers paid parental leave, mental health services and more.

The target salary range for this position is $64,750.00 - $75,000.00 annually.

The wage range for this role considers many factors, such as training, transferable skills, work experience, licensure and certification, business needs, and market demands. The pay range is subject to change and may be modified in the future. Full-time roles are eligible for bonuses and benefits. For additional information on Ryan Specialty Total Rewards, visit our website https://benefits.ryansg.com/.

We provide individuals with disabilities reasonable accommodations to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment in accordance with applicable law. Please contact us to request an accommodation at HR@Ryansg.com

The above is intended to describe this job's general requirements. It is not to be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job description restricts management's right to assign or reassign duties and responsibilities to this job at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.