Executive Assistant

About SLHeeley Tax SLHeeley Tax provides individuals and businesses with reliable, affordable tax preparation, bookkeeping, and payroll services. We are a close\-knit, highly collaborative team consisting of our President (who leads tax preparation and bookkeeping), our Vice President (who steers our HR, office management, and administrative operations), an additional tax accountant, 4 bookkeepers, 2 dedicated assistants, and a supportive front office receptionist. We are currently hiring for two separate positions: an Executive Assistant to the President and an Executive Assistant to the Vice President. While both roles share the same operational core, one assistant will serve as the right\-hand to our President, and the other will work directly with our Vice President. We pride ourselves on maintaining a low\-key, laid\-back environment with a relaxed, family feel. Our team is a group of sarcastic and snarky people who genuinely enjoy working together. If you prefer a workplace with absolute corporate stiffness, we are probably not the right fit. But if you have thick skin, appreciate good wit, and want an office where you can truly be yourself, you will fit right in. Why Join Us? (The Perks) The "No\-Fridays" Off\-Season: Enjoy incredible work\-life balance! From May through December, our office is completely closed on Fridays. Relaxed Dress Code: We are strictly business\-casual even during the tax rush (jeans paired with a nice top, sweater, or an official SLHeeley sweatshirt). Supportive, Educational Leadership: Our Vice President is a patient, approachable former teacher who loves to guide, answer questions, and help you learn. Management will gradually add new things to your plate as you master tasks. Growth\-Driven, Adaptive Roles: Your compensation and daily focus will scale directly with your capabilities. We start pay on the standard end, but as you master tasks and take more off leadership's plate during your initial 6 months with us, your hourly pay will increase. These positions are built to adapt over time; as we see which high\-level aspects of the President’s and VP’s workloads you can confidently take over, we will reshape the roles to lean into your personal strengths and maximize firm efficiency. Annual July 1st Pay Reviews: Following your initial onboarding period, we provide a yearly pay increase based on overall performance, evaluated every year on July 1st. Annual Performance Bonus: Every February, we award a year\-end bonus based on a percentage of your salary that scales upward based on management evaluation and the unique value you brought to the table throughout the year. Robust Health Benefits: We offer Blue Cross Blue Shield (BCBS) PPO and HMO health insurance plans, and we cover 50% of the employee\-only premium. Generous Paid Time Off: 10 paid days off for scheduled holiday office closures PLUS approximately 66 hours of individual PTO in your first year. Work Schedule Our workflow operates like a pendulum, and you must be comfortable managing both extremes: Tax Season (January – April): It is busy, high\-energy, and non\-stop. You will work 50–60 hours per week (with guaranteed time\-and\-a\-half overtime pay for all hours over 40\). Standard office hours: Monday – Friday, 9:00 AM – 5:00 PM. Extended hours: The office stays open late on Mondays and Tuesdays until 8:00 PM, and is open for six Saturdays total (4 hours each). These shifts are split across our entire 3\-person administrative team, keeping your individual schedule fair. Exact schedule is finalized together as an Admin Team in December to give you time to plan for evening and Saturday hours. Note on Leadership Presence: The VP and President are remote a few days every week, making your role as an on\-site anchor and gatekeeper incredibly important. Off\-Season (Mid\-April – December): The office shifts to a quiet, slow, and relaxed pace. You will work 35–40 hours per week across a highly flexible Monday through Thursday schedule (Closed Fridays). Core Responsibilities Process Improvement \& Workflow Optimization Tax Tracking: Manage and track the internal flow of tax returns using LaCerte and FileShare, ensuring documents move efficiently from intake through final delivery. E\-Filing Coordination: Handle the e\-filing of completed tax returns, ensuring all electronic submissions are accurate and submitted timely. Assist with tax return assembly, including organizing and cleaning up client documents electronically and manually. Check processed Powers of Attorney (POAs) through IRS software and assist with setting up IRS payment plans. Compile tax return folders, handle year\-end mailings (including organizers), and respond to general inquiries regarding past, current, or pending returns. Bring an active eye for optimization; analyze current office flows, brainstorm creative ways to improve existing administrative systems, and help streamline office operations. Executive Support \& Client Relations Serve as the primary communication liaison and professional gatekeeper for your assigned executive, communicating with clients on their behalf regarding tax, administrative, or bookkeeping updates. Screen incoming correspondence, manage executive calendars, and accurately assess leadership availability. Draft memos on business topics and assist with special projects for senior leadership. Handle customer complaints with patience, provide appropriate solutions within time limits, and follow up to ensure total client satisfaction. Monitor office supplies and communicate with vendors on behalf of Executive Team. Office Operations \& Administration Manage incoming/outgoing client documents via the company portal, send out DocuSign requests, and assist with engagement letters. Work directly with our IT department, maintain internal document tracking systems, and monitor the server's back\-up drive. Serve as backup support for the Front Desk receptionist when necessary. Coordinate and schedule office repairs, maintenance, and basic administrative tasks (such as ordering team lunches). Assist with Human Resources (HR) duties and manage the firm's social media presence as needed. Skills and Qualifications Experience: 3\+ years of office administration or professional assistant experience required. Experience working within a CPA, accounting, or tax firm is highly preferred. Software Savvy: Highly computer literate and proficient with Microsoft Office products. Familiarity with LaCerte and FileShare is a major plus, but hands\-on training will be provided. Growth Mindset \& Critical Thinking: A strong desire to learn, expand your skill set, and navigate an evolving environment where your role adapts based on proven performance. We want someone who doesn't just execute tasks but naturally looks for ways to improve them. Work Style: Excessive attention to detail, strong problem\-solving abilities, and outstanding organizational skills. Must be a self\-starter who is comfortable navigating multiple screens and multitasking. Communication \& Personality: Excellent verbal, written, and active listening skills. Expert proofreading skills are essential. A good sense of humor, thick skin, and a collaborative spirit are a must. Education: High School Diploma required; Associate or Bachelor's degree preferred. HR experience is a plus. How to Apply (Crucial Instructions) To be considered for this position, you MUST include both your resume and a well\-written cover letter explaining why you are the perfect fit for our team. Attention to Detail Test: Because we handle sensitive tax documents, attention to detail is our number one priority. To prove you have read this entire description, you must include the phrase "Ready to Take on Tax Season" in the very first sentence of your cover letter. Applications without this exact phrase will not be reviewed. Pay: $23\.50 \- $27\.00 per hour Benefits: Employee discount Health insurance Paid time off Retirement plan Application Question(s): During tax season (January–April), this role requires 50–60 hours per week, including rotating evenings (until 8:00 PM) and six total Saturday shifts (4 hours each), with guaranteed overtime pay. Are you fully available and willing to work this seasonal schedule? How many years of experience do you have managing client portals, sending electronic signature requests (like DocuSign), or organizing electronic files in a professional setting? Experience: Office Administration : 2 years (Required) Ability to Commute: * Naperville, IL 60540 (Preferred) Work Location: In person