Executive Personal Assistant

Executive Personal Assistant

Cuddy Financial Services
Auburn, NY | Full-Time | Non‑Exempt (35 hours/week)

About Cuddy Financial Services

Cuddy Financial Services is a boutique financial planning and tax firm serving over 700 affluent households with more than $300 million in assets under management. Founded in 1992, we combine deep experience with a modern operating mindset.

We believe the best executive support roles are force multipliers—where judgment, anticipation, systems thinking, and technology come together to create leverage. We actively use modern tools (including AI and automation), but we value clarity, trust, and follow‑through above everything else.

The Role: Executive Personal Assistant (Next‑Gen EA)

This role is designed for a next‑generation Executive Personal Assistant—someone who is operationally excellent, technologically fluent, and capable of supporting a business owner at a high level.

You will act as a trusted extension of the Firm Owner, managing priorities, communication flow, administrative complexity, and day‑to‑day execution. Your success will be measured not by activity, but by clarity, reliability, and leverage created.

This is not a junior admin role—and not an AI‑specialist role. It is a judgment‑driven executive support position, enhanced by modern tools.

What Success Looks Like (First 6–12 Months)

• The Firm Owner’s calendar, inbox, and administrative workload feel calm, organized, and under control
• Important items don’t fall through the cracks—even when priorities shift
• Communication is professional, timely, and appropriately filtered
• Systems are organized, documented, and improving over time
• Repetitive work is reduced through better processes and smart tool usage
• The Firm Owner trusts you to handle sensitive matters independently

Core Responsibilities (What You’ll Actually Do)

Executive & Personal Support

• Manage calendars, scheduling, confirmations, and time‑blocking
• Anticipate needs, deadlines, and follow‑ups before being asked
• Assist with personal and business tasks as delegated
• Handle confidential information with discretion and sound judgment

Inbox, Communication & Information Flow

• Manage and triage the Firm Owner’s email inbox
• Draft, respond to, file, and link emails appropriately
• Ensure important messages are surfaced and noise is filtered
• Prepare professional correspondence and internal communications

Administrative & Financial Operations

• Manage company bills, vendor payments, subscriptions, and accounts payable
• Track expenses, receipts, and supporting documentation
• Prepare summaries (credit cards, subscriptions, vendors, etc.)
• Maintain clean digital and physical filing systems

Client & Firm Support

• Assist with client coordination and document delivery
• Download, organize, and file client investment and tax records
• Maintain internal spreadsheets, lists, and reference materials
• Serve as backup to reception and assist with errands as needed

Technology & AI Expectations (How We Think About It)

You are not expected to be an “AI expert.” You are expected to be:

• Comfortable learning new tools quickly
• Willing to use AI to draft, summarize, organize, and streamline work
• Curious about better ways to do repetitive or manual tasks
• Thoughtful about when technology helps—and when judgment matters more

AI is a productivity amplifier, not a replacement for accountability or discretion.

Required Qualifications

• High school diploma (Associate degree preferred)
• 1+ year of administrative or executive support experience
• Strong Microsoft Office / Microsoft 365 proficiency
• Excellent written and verbal communication skills
• High attention to detail and follow‑through
• Ability to manage multiple priorities calmly and accurately
• Professional presence and strong interpersonal skills
• Absolute discretion with sensitive information
• Comfort using AI tools for productivity

Preferred (Not Required)

• Experience supporting a business owner or senior executive
• Familiarity with CRM systems, document management, or automation tools
• Experience in a professional services environment

Compensation & Benefits

• Pay: $21–$25/hour (based on experience)
• Hours: 35 hours/week, Monday–Friday
• Benefits: Medical, Dental, Vision, Life Insurance (after 90 days)
• Retirement: 401(k) with company match (after 1 year)
• Environment: Professional, stable, modern firm with long‑term growth mindset

Equal Opportunity Employer

Cuddy Financial Services is an equal opportunity employer and participates in E‑Verify.

Pay: $21.00 - $25.00 per hour

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Employee discount
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Work Location: In person