Argo Group and Farm Family are specialty property and casualty insurance brands whose underwriting companies are wholly owned subsidiaries of Brookfield Wealth Solutions, a leading provider of wealth and insurance solutions. Argo and Farm Family partner with agents and brokers to help businesses stay in business, delivering collaborative insurance solutions for niche markets.
Job Description
Title: Executive Assistant (Onsite – NYC or Chicago)
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About the Role
Join a small but mighty administrative team supporting three high‑performing executives across a fast‑moving, growing organization. This role is ideal for a polished professional who thrives in complexity, anticipates needs, and brings solutions—not problems. You will be a critical partner to senior leadership, operating with independence, sound judgment, and the confidence to advise executives when needed.
This is a fully onsite role (5 days/week) based in New York City or Chicago.
What You’ll Do
Executive Partnership & Judgment
Act as the primary point of contact for executives; triage and respond to inquiries independently.
Serve as an extension of executive leadership, ensuring decision readiness and information flow.
Exercise discretion in determining what requires executive attention vs. resolving issues yourself.
Represent executives with professionalism in all meetings, communications, and external interactions.
Build strong relationships with senior leaders, board members, clients, and partners.
Calendar, Scheduling & Time‑Zone Navigation
Own calendar strategy for three executives, balancing shifting priorities, time zones, and business needs.
Make judgment‑based scheduling decisions, negotiate conflicts, and anticipate future needs.
Plan ahead based on travel, organizational priorities, and emerging business demands.
Travel, Expense, and Logistics Management
Independently coordinate complex domestic and international travel, optimizing time and cost.
Manage executive and team expense submissions, ensuring accuracy and policy compliance.
Review invoices, contracts, and documentation for appropriateness before routing.
Create requisitions in Oracle to generate purchase orders.
Meeting Excellence & Operational Leadership
Plan and coordinate offsite meetings, including contract negotiation.
Prepare and distribute meeting minutes; track and drive action‑item completion.
Manage executive projects, timelines, and deliverables; keep stakeholders accountable.
Identify operational risks or inefficiencies and recommend solutions proactively.
Develop, document, and improve administrative processes for better effectiveness.
Provide support to the broader admin team as needed.
Confidentiality & Professionalism
Handle highly sensitive personnel, legal, financial, and strategic information with discretion.
Determine appropriate levels of information-sharing based on audience, context, and risk.
Produce polished, accurate written correspondence and executive communication.
What You Bring
Bachelor’s degree preferred.
5+ years of administrative experience with at least 3 years supporting senior or executive leadership.
Strong business acumen and an ability to understand organizational priorities.
Exceptional organizational, communication, and problem‑solving skills.
Proven experience handling confidential information with professionalism and integrity.
Adaptability in a fast‑changing environment.
Responsiveness after regular business hours, when needed.
A track record of career progression and expanding scope.
A team‑oriented mindset—someone who covers for others and steps up when needed.
A proactive problem‑solver who anticipates needs, thinks strategically, and offers solutions.
Compensation:
• NYC: $73,000–$101,000
• Chicago: $67,000–$93,000
PLEASE NOTE:Â
Applicants must be legally authorized to work in the United States. At this time, we are not able to sponsor or assume sponsorship of employment visas.
If you have a disability under the Americans with Disabilities Act or similar state or local law and you wish to discuss potential reasonable accommodations related to applying for employment with us, please contact our Benefits Department at 210-321-8400.Â
Notice to Recruitment Agencies:
Resumes submitted for this or any other position without prior authorization from Human Resources will be considered unsolicited. BWS and / or its affiliates will not be responsible for any fees associated with unsolicited submissions.
We are an Equal Opportunity Employer. We do not discriminate on the basis of age, ancestry, color, gender, gender expression, gender identity, genetic information, marital status, national origin or citizenship (including language use restrictions), denial of family and medical care leave, disability (mental and physical) , including HIV and AIDS, medical condition (including cancer and genetic characteristics), race, religious creed (including religious dress and grooming practices), sex (including pregnancy, child birth, breastfeeding, and medical conditions related to pregnancy, child birth or breastfeeding), sexual orientation, military or veteran status, or other status protected by laws or regulations in the locations where we operate. We do not tolerate discrimination or harassment based on any of these characteristics.Â
The collection of your personal information is subject to our HR Privacy Notice
Benefits and Compensation
We offer a competitive compensation package, performance-based incentives, and a comprehensive benefits program—including health, dental, vision, 401(k) with company match, paid time off, and professional development opportunities.
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