Executive Assistant

DescriptionExecutive AssistantOld Republic Surety Company - Brookfield, WI Old Republic Surety Company is seeking a highly organized, proactive Executive Assistant to serve as a trusted partner to our President and executive leadership team. This role plays a critical part in ensuring leadership priorities, communications, and meetings run smoothly across the organization. This position supports the President and select members of the executive leadership team, helping manage complex schedules, coordinate leadership meetings and events, and ensure the efficient flow of information throughout the organization. The ideal candidate is a career Executive Assistant who thrives in a fast-paced environment, anticipates needs before they arise, and takes pride in delivering polished, accurate, and highly confidential support to senior leaders. If you are someone who naturally brings organization, calm, and efficiency to executive environments, we invite you to explore this opportunity. What You'll Do In this trusted role, you will help keep senior leadership organized, prepared, and focused on strategic priorities. Key responsibilities include: Provide high-level, confidential administrative support to the President and executive leadership team, including preparation of correspondence, reports, presentations, and other business materials. Manage and optimize complex executive calendars by balancing priorities, scheduling meetings, coordinating logistics, and ensuring leaders are prepared for upcoming commitments. Maintain the Senior Leadership and OCEO Teams channel, ensuring meeting agendas and materials are completed and distributed in accordance with leadership meeting cadence. Coordinate logistics and materials for senior leadership meetings, town halls, and leadership events. Schedule travel arrangements and prepare expense reimbursement reports in accordance with company policy. Establish and maintain centralized files for key organizational policies, procedures, and guidelines, including claims authority, underwriting authority, and HR compensation structures. Serve as a liaison between executives, employees, clients, and external partners to ensure timely and effective communication. Prepare and distribute recurring and ad hoc reports, communications, and presentations. Partner with internal teams such as Marketing to coordinate executive meetings and special events. You Might Be a Great Fit If You enjoy anticipating what leaders need before they ask You naturally bring structure and organization to complex schedules You are known for your precision, attention to detail, and polished communication You take pride in delivering accurate, error-free materials You are comfortable managing highly confidential information You are able to balance multiple priorities while remaining calm and professional You are confident enough to manage executive calendars thoughtfully and diplomatically You are curious, proactive, and enjoy finding answers independently You thrive in environments where leaders rely on you as a trusted extension of their team What Makes Someone Successful in This Role Successful candidates in this role demonstrate: Exceptional organizational and prioritization skills Strong attention to detail and proofreading ability Professional confidence and executive presence Ability to manage confidential matters with discretion and sound judgment A customer-service mindset when supporting leaders and colleagues Comfort working both digitally and with traditional documentation and files Ability to adapt to changing priorities in a dynamic organization Qualifications Associate's or Bachelor's degree in Business Administration, Communications, or a related field preferred, or equivalent professional experience 5-8 years of executive or senior administrative support experience, preferably supporting senior leadership or C-suite executives Demonstrated experience managing complex executive calendars and coordinating leadership meetings Experience handlingconfidential business communications and documents Proficiency with Microsoft Office 365, including Outlook, Excel, PowerPoint, and Teams Excellent written and verbal communication skills Work Schedule This position is based at our Brookfield, Wisconsin headquarters. 37.5-hour work week Typical schedule 8:00 AM - 4:00 PM Flexibility to start between 7:00 AM and 9:00 AM Hybrid work opportunities may be available upon completion of training Who Are We? Old Republic Surety Company underwrites contract, fidelity, and commercial bonds through a strong network of independent insurance agencies. Our solutions include bid bonds, performance and payment bonds, and maintenance bonds for large, middle market, and growing contractors. Headquartered in Brookfield, Wisconsin, ORSC consistently delivers superior service and creative underwriting solutions across all 50 states and U.S. territories. The company continues to expand its geographic footprint and product offerings while maintaining market-leading growth and strong underwriting performance. Why Old Republic Surety Company? Old Republic Surety Company offers employees meaningful opportunities to grow and succeed. We have a strong culture of promoting from within and support employees who want to advance their careers. Our workplace is collaborative and open, encouraging both teamwork and individual contributions. We seek bright, motivated professionals who share our values and commitment to excellence. Company Benefits Financial Competitive salary: $75,000 - $88,000, commensurate with experience 401(k) Savings & Profit-Sharing Plan with company match Roth investment options 529 Education Savings Plan Employee Referral Bonus Program Health Medical Insurance Dental Insurance Vision Insurance Flexible Spending Account (FSA) & Health Savings Account (HSA) options Life Insurance Supplemental Life Insurance Long-Term Disability Insurance Paid Leave of Absence Benefits Accident & Critical Illness Insurance Pet Insurance Work-Life Balance 37.5-hour standard work week Hybrid work opportunities upon completion of training Casual business attire Generous Paid Time Off (PTO) Paid holidays Volunteer opportunities Company-sponsored events and outings Join Our Team If you are a detail-oriented professional who takes pride in helping leaders operate at their best, we invite you to apply and become a trusted partner to the leadership team at Old Republic Surety Company. To learn more about our company culture and our outstanding benefits, please visit our website. #LI-EA Old Republic Surety Company is an Equal Opportunity Employer and is committed to maintaining a diverse workplace.

Created: 2026-03-12