Job Description
Job DescriptionJob Title
Executive Assistant to the Chief Advisory Officer (CAO)
Location: Remote (U.S.-based)
Job Type: Full-time
Compensation: $50,000–$65,000 (based on experience) + benefits
About the Role
Pen Pioneer is seeking a highly capable Executive Assistant to the Chief Advisory Officer (CAO) to support a fast-paced professional services environment within tax and advisory services. This role is critical to ensuring the CAO can focus on high-impact work by proactively managing priorities, communications, and day-to-day operations.
The ideal candidate is polished, detail-oriented, and thrives in a deadline-driven setting. This is a high-trust role requiring sound judgment, discretion, and the ability to anticipate needs before they arise.
Key Responsibilities
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Manage the CAO’s calendar end-to-end, including scheduling, prioritization, and conflict resolution
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Prepare meeting agendas, briefs, and supporting materials
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Triage email and messages, handling routine items and escalating matters that require attention
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Track deliverables, action items, and deadlines through completion
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Coordinate with internal teams to ensure work progresses smoothly and on time
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Draft clear, professional communications on behalf of leadership
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Support client meeting logistics and help deliver a high-quality client experience
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Maintain strict confidentiality and handle sensitive information with discretion
Qualifications
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3+ years of experience supporting senior leadership (Executive Assistant or similar role)
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Exceptional organizational skills with the ability to manage multiple priorities simultaneously
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Strong written and verbal communication skills
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High attention to detail with consistent follow-through
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Comfort working in a fast-paced, deadline-driven environment
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Experience in accounting, tax, advisory, legal, consulting, or other professional services is a plus
Preferred Qualifications
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Strong technical proficiency (Microsoft Office, Google Workspace, scheduling tools, CRM or workflow systems)
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Proven ability to anticipate needs, think ahead, and solve problems independently
Benefits
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Competitive salary and comprehensive benefits package
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Paid time off and paid holidays
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Opportunities for professional growth and development
About the Company (Confidential Search)
Our client is a well-established professional services firm specializing in advisory and compliance solutions for businesses and individuals. The firm is known for its client-first approach, high standards of excellence, and a collaborative, high-performance culture. Leadership values efficiency, trust, and continuous improvement, creating an environment where proactive professionals can make a meaningful impact while growing their careers.
Candidate Screener Questions
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Please describe your experience serving as the primary Executive Assistant to a senior leader (VP, Partner, or C-level), including the length of time and scope of your responsibilities.
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Can you walk us through your experience managing and triaging an executive’s inbox? What systems, tools, or approaches have you used to prioritize and escalate messages?
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Tell us about your experience running meetings end-to-end, including preparation, agenda creation, note-taking, tracking action items, and managing follow-ups.
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Are you available for a kickoff call with a human recruiter within the next 48 hours? If so, please share your available dates, times, and time zone.