Executive Assistant

About this role

Who are we?

Howden is a global insurance group with employee ownership at its heart. Together, we have pushed the boundaries of insurance. We are united by a shared passion and no-limits mindset, and our strength lies in our ability to collaborate as a powerful international team comprised of 24,000 employees spanning over 56 countries.

People join Howden for many different reasons, but they stay for the same one: our culture. It’s what sets us apart, and the reason our employees have been turning down headhunters for years. Whatever your priorities – work / life balance, career progression, sustainability, volunteering – you’ll find like-minded people driving change at Howden.

Role: Executive Assistant Location: Chicago (Hybrid)

Who are we?

Howden is a collective – a group of talented and passionate people all around the world. Together, we have pushed the boundaries of insurance. We are united by a shared passion and no-limits mind-set, and our strength lies in our ability to collaborate as a powerful international team comprised of 20,000 employees spanning over 100 countries.

Our people are our biggest asset as well as our largest shareholder group and are everything that makes us unique; our inclusive culture, the quality service we offer our clients, and our continued growth, all come from our people-first approach. There’s no such thing as individual success. We all need to play our part, contributing our skills and experience to make a true difference. That’s Howden.

Why work at Howden?

We have always been employee-owned and driven by entrepreneurial spirit. Right from the beginning, we've focused on employing talented individuals and empowering them to make a real difference to the company, whilst building successful and fulfilling careers at the same time. Simply put, we hire talented specialists and give them what they need to make a difference for clients. Always have, always will.

People join Howden for many different reasons, but they stay for the same one: our culture. It’s what sets us apart, and the reason our employees have been turning down disappointed head- hunters for years. Whatever your priorities – work/life balance, career progression, sustainability, volunteering – you’ll find like-minded people driving change at Howden.

What is the role?

We are seeking an experienced full-time Executive Assistant in Chicago, IL. The ideal candidate will play a key role in managing expense reporting through SAP Concur, ensuring accuracy and compliance with company policies. Strong communication skills are essential, as you will interact with employees and vendors to resolve inquiries and discrepancies. In addition to expense management, you will provide flexible support for ad-hoc administrative tasks, contributing to the smooth operation of the team.

What will you be doing? • Provide high ‑ level support to two vertical leaders, managing complex calendars, coordinating cross ‑ functional priorities, and ensuring seamless operational flow across both business units.

• Review team expense reports, process approvals on behalf of executives, and maintain visibility into monthly and quarterly spend relative to budget. Manage and process expense reports accurately using SAP Concur, ensuring compliance with policies and timelines.

• Monitor and organize the executive’s email inbox, ensuring no critical communication is missed—especially during travel. Provide independent routine responses, triage priorities, and maintain a clean, well ‑ structured inbox.

• Serve as the primary point of contact for expense ‑ related inquiries, offering clear guidance and resolving discrepancies with employees and vendors.

•   Coordinate internal and external meetings, manage logistics, prepare materials, and ensure timely follow ‑ up.

• Handle urgent or unexpected administrative needs with flexibility and a proactive approach, supporting multiple teams as required.

• Demonstrate strong attention to detail and problem ‑ solving skills to identify and correct errors in expense reporting and operational workflows.

• Prepare polished documents, reports, and presentations using Word, Excel, and PowerPoint.

•   Apply AI knowledge to streamline processes, enhance productivity, and support evolving business needs.

What are we looking for?

• 5+ years supporting multiple executives with proven administrative, operational, and logistical coordination in corporate environments.

•   Highly proficient in Word, PowerPoint, Excel, and Outlook, with advanced capabilities in document creation, formatting, presentation building, and data organization.

•   Strong written and verbal communication skills; articulate with excellent grammar; able to interact professionally across teams, executives, and vendors.

• Exceptionally organized with the ability to prioritize competing tasks, resolve conflicts, and maintain a positive, solutions ‑ oriented approach.

•   Hands-on experience with SAP Concur or similar expense management systems, ensuring accurate reporting and compliance.

• High attention to detail in financial, administrative, and document ‑ heavy tasks; consistently produces polished, error ‑ free work.

• Comfortable managing multiple priorities, ad ‑ hoc requests, and shifting deadlines in dynamic environments.

• Strong organizational and problem ‑ solving skills to maintain efficient workflows and ensure timely completion of tasks.

• Willing to work outside standard business hours when urgent needs arise; flexible and dependable, though such requests are infrequent.

• Trusted to handle sensitive information with discretion, professionalism, and a high level of integrity

Compensation

The expected salary range for this role is $90,000 – $110,000+ and will be determined based on factors including candidate experience and work location. This role is classified as non- exempt under the Fair Labor Standards Act (FLSA).

In addition to a competitive base salary, employees are eligible to r

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