Executive Assistant

CastleOak Securities, L.P. (“CastleOak”) is a premier boutique investment bank focused on providing capital markets services to a broad array of corporate, governmental and institutional clients. Headquartered in New York City, the firm specializes in primary and secondary sales and trading of fixed income, equity, and money market securities, as well as financial advisory (including M&A and private placements). Since its founding in 2006, CastleOak has assisted its clients on public offerings totaling over $4 trillion. CastleOak's professionals average 20 years of successful Wall Street experience and ongoing working relationships with some of the largest global corporations. We offer a competitive total rewards package including: Health insurance: competitive medical, dental, and vision programs 401(k) with a company match Charitable contribution match program for employees Hybrid Workplace Company-paid life insurance, short-term and long-term disability insurance Paid time off: vacation, personal days, sick leave, etc. Role Overview We are seeking a professional, and highly capable Executive Administrative Assistant to provide high-touch support some of our most senior executives. This role is ideal for an experienced administrative professional who is technologically savvy, exceptionally organized, and comfortable managing multiple complex calendars, shifting priorities, and planning activities at the same time. This individual will operate as a trusted partner to senior leadership, helping executives stay organized, prepared, and focused. The successful candidate will bring sound judgment, strong follow-through, discretion, and a proactive mindset. In a lean firm environment, this person must be comfortable taking ownership, anticipating needs, improving processes, and managing a wide range of administrative, scheduling, travel, event, communication, and project-related responsibilities with professionalism and urgency. Key Responsibilities: Provide high-level administrative support to two to three senior executives, serving as a reliable point of contact for internal and external stakeholders. Manage multiple complex and frequently changing calendars, using strong judgment to prioritize meetings, resolve conflicts, protect executive time, and ensure each day is organized efficiently. Coordinate meetings, video conferences, town halls, management sessions, and events, including agendas, materials, room setup, technology, catering, and participant logistics. Anticipate scheduling needs and proactively look ahead to identify conflicts, preparation gaps, travel considerations, stakeholder dependencies, and potential issues requiring a thoughtful pivot to a pre-planned backup approach. Keep executives on track throughout the day by preparing materials, setting up calls or meetings in advance, communicating delays or changes, and rescheduling as needed. Coordinate domestic travel arrangements, itineraries, transportation, and related logistics. Prepare, submit, and reconcile complex expense reports with accuracy and timeliness. Draft, edit, and format emails, documents, presentations, reports, and other written communications with strong attention to tone, accuracy, and detail. Use Microsoft Outlook, Word, Excel, PowerPoint, Teams, and other productivity tools to manage information, track priorities, create materials, and improve administrative workflows. Maintain organized files, contact lists, records, approvals, signatures, and confidential information. Lead firm-wide event planning from concept to execution. Events will include both internal culture building and client-facing events. Take ownership of special projects and process improvements that help senior leaders operate more effectively. Apply strong project management discipline to executive initiatives, meetings, events, and follow-up items by clarifying objectives, tracking timelines, coordinating stakeholders, managing dependencies, and ensuring details are advanced with minimal direction. Exercise intuitive judgment to recognize when priorities, logistics, or stakeholder needs are shifting, and proactively recommend adjustments or contingency plans before issues affect senior leadership or business outcomes. Handle sensitive and confidential information with the highest level of discretion, professionalism, and integrity. Complete additional administrative, planning, and project-related tasks as requested by senior leadership. Required Qualifications: Administrative or executive support experience, preferably supporting senior leaders in financial services, professional services, banking, consulting, or another fast-paced corporate environment. Demonstrated ability to manage multiple executive calendars, competing priorities, and planning activities with confidence and sound judgment. Strong technology skills, including proficiency with Microsoft Outlook, Word, Excel, PowerPoint, Teams, and comfort learning new tools or improving existing processes. Experience with expense management tools (i.e., Concur, Expensify, etc.) Exceptional organizational skills, attention to detail, follow-through, and ability to prioritize effectively in real time. Excellent written and verbal communication skills, with the ability to interact professionally with senior executives, employees, clients, vendors, and external partners. High level of discretion, integrity, and professionalism especially when handling confidential/sensitive information. Proactive, resourceful, and solutions-oriented, with the ability to anticipate needs before being asked. Demonstrated ability to think several steps ahead, identify risk points early, and activate appropriate backup plans with professionalism, discretion, and sound judgment. Strong sense of urgency and ownership, with the ability to work independently while staying closely aligned with leadership priorities. Strong project management capability, including the ability to organize workstreams, manage timelines, follow up on deliverables, coordinate across stakeholders, and keep complex planning efforts moving forward. Flexible and adaptable, with the confidence to navigate changing priorities, last-minute requests, and a fast-paced executive environment. Positive, polished, and service-oriented presence with a practical “can-do” approach. Preferred Qualifications: Experience supporting senior-level executives. Comfort using AI-enabled tools, to draft communications, summarize information, organize priorities, and improve administrative workflows while maintaining accuracy, discretion, and confidentiality. Financial services, investment banking, consulting, or professional services experience. Event planning, project coordination, or office-of-the-executive experience, including comfort helping organize events or initiatives from initial planning through completion. Interest in improving processes, organizing information, and using technology to make work more efficient. Location: New York, NY Work Type: Full-time, Hybrid (3 days in-office, 2 days remote) Compensation: $70,000 - $95,000 base salary, eligible for a performance-based discretionary bonus Core Benefits: Company-paid $300,000 life insurance policy, alongside comprehensive health and retirement packages. NYC Pay Range $80,000 - $120,000 USD All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, citizenship, age, marital status, medical condition (including pregnancy and related conditions), physical or mental disability, protected veteran status, and/or any other characteristic protected by law. Please do not solicit employees of the firm directly regarding open positions. #J-18808-Ljbffr