Senior Executive Assistant Jobs 2026 at Tawani Enterprises Chicago Illinois
Tawani Enterprises is hiring a Senior Executive Assistant to support their Chairwoman in Chicago, Illinois. The position offers competitive compensation along with comprehensive benefits including paid time off, 401K, and full medical, dental, and vision coverage for full-time employees.
This isn’t an entry-level executive assistant role. You’ll serve as the personal assistant to the principal providing highly personalized administrative support requiring discretion, sophistication, and seven-plus years of proven experience supporting senior executives. If you’ve mastered executive support and want a position combining professional administrative work with personal coordination responsibilities, this opportunity offers genuine advancement.
Job Overview
Tawani Enterprises requires an Executive Assistant who can seamlessly manage both business and personal matters for the Chairwoman. The role demands someone who understands that supporting a principal at this level means handling everything from professional correspondence to coordinating personal donations and family communications.
Your responsibilities blend traditional executive support like email management and phone screening with more personalized duties including composing thank you notes to guests, coordinating staff birthday gifts, mailing books to friends and colleagues, and managing annual donation calendars. This combination requires both corporate professionalism and personal touch.
Serving as primary gatekeeper means you control access to the Chairwoman, determining which matters require her direct attention versus what you can handle independently. This level of autonomy and judgment comes only with substantial experience supporting executives who trust your decision-making completely.
Available Positions
Senior Executive Assistant to the Chairwoman
The assistant professionally handles all email correspondence, screens phone calls, and processes incoming mail while responding to routine matters independently. Taking comprehensive messages when the Chairwoman is unavailable ensures nothing important gets missed despite her busy schedule.
Acting as liaison between the Chairwoman, the organization, family members, and household staff requires diplomatic communication skills navigating different relationships and contexts seamlessly. Composing thank you notes to all guests, drafting letters for distribution, and coordinating gift deliveries adds personal touches maintaining relationships.
Managing personal donations involves corresponding with charitable organizations and maintaining the calendar tracking annual giving commitments. Coordinating staff birthday gifts and other internal celebrations builds positive workplace culture.
Contract maintenance ensures all agreements remain organized, current, and accessible when needed. Project oversight and supervisory experience comes into play coordinating initiatives and managing any support staff reporting to this position.
Eligibility Criteria
This senior position requires substantial proven experience and sophisticated capabilities.
Educational Background
A Bachelor’s degree represents the minimum educational credential, with business-related fields preferred though not mandatory. Your degree demonstrates foundational academic achievement while your experience proves practical competency.
Professional Experience
Seven or more years in specific executive administrative support capacity means you’ve supported C-suite or equivalent executives previously, not general office administration. Minimum three years with project oversight or supervisory and personnel management experience demonstrates your capability handling complex initiatives and leading others.
Skills and Competencies
Extremely detail-oriented and organized personality ensures nothing falls through cracks when managing diverse responsibilities. Exceptional organizational abilities, proactive problem-solving, and adaptability enable handling unexpected situations professionally.
Advanced to expert level Microsoft Office abilities mean true mastery beyond basic proficiency. Excellent written and oral communication skills support everything from composing professional correspondence to verbal interactions with high-level contacts.
Age Requirements
No age restrictions apply. Tawani Enterprises evaluates candidates based on experience depth and demonstrated capabilities.
How to Apply
Tawani Enterprises manages recruitment through their dedicated application portal.
Access the official posting at Tawani Enterprises careers portal where the application interface appears.
Review the complete job description carefully, noting the blend of professional and personal support responsibilities distinguishing this from typical corporate executive assistant roles.
Prepare your resume emphasizing your executive support experience with specific examples of principals supported, responsibilities managed, and initiatives you’ve coordinated or supervised.
Highlight your Microsoft Office expertise, project management experience, and any supervisory roles demonstrating your progression beyond entry-level administrative work.
Complete the online application accurately and upload your resume showcasing your seven-plus years supporting senior executives.
Submit your application and monitor email for responses from Tawani Enterprises regarding interview scheduling.
Important Instructions
Senior executive assistant positions supporting principals at Chairwoman level require exceptional discretion handling confidential business and personal matters. Your application should reflect professional maturity and sophistication appropriate to this responsibility level.
The personal coordination aspects including family liaison, gift coordination, and donation management distinguish this from purely corporate executive assistant roles. If you prefer strictly business-focused positions without personal support elements, this role may not align with your preferences.
Chicago residency or willingness to relocate is essential since this is an in-person position requiring daily presence supporting the Chairwoman directly.
Deadline
The posting does not specify an application deadline, suggesting Tawani Enterprises reviews qualified candidates continuously. Given the seniority required, applying promptly ensures consideration for this distinguished executive support position.
Additional Career Resources
While exploring senior executive support opportunities, consider browsing maintenance technician jobs 2026 for diverse career opportunities across different professional fields.
Common Questions
What makes this different from typical executive assistant positions?
This Senior Executive Assistant role combines traditional business support with significant personal assistance responsibilities including family liaison, gift coordination, personal donation management, and correspondence with personal contacts. You’re supporting the Chairwoman holistically rather than just her professional duties. This requires comfort navigating both corporate and personal contexts with equal professionalism, understanding that principals at this level need seamless support across their entire life, not just business hours.
Is the seven years of experience requirement flexible?
The seven-plus years requirement reflects the genuine seniority and autonomy this position demands. Supporting a Chairwoman as her primary gatekeeper and personal assistant requires judgment, discretion, and sophisticated problem-solving developed only through substantial experience. Candidates with five or six years of exceptional executive support might contact Tawani directly to discuss their qualifications, but the requirement exists for valid reasons regarding the responsibility level involved.
What does serving as primary gatekeeper actually involve?
As primary gatekeeper, you control access to the Chairwoman’s time and attention, screening all incoming communications and determining what requires her direct involvement versus what you can handle independently. This means declining meeting requests diplomatically, redirecting inquiries to appropriate parties, and protecting her schedule from non-essential interruptions while ensuring truly important matters reach her promptly. This responsibility requires excellent judgment distinguishing urgent from merely loud, understanding organizational priorities deeply, and maintaining positive relationships even when saying no.
Final Thoughts
Tawani Enterprises’ Senior Executive Assistant position offers sophisticated executive support opportunity in Chicago supporting the Chairwoman with competitive compensation and comprehensive benefits. The role combines professional administrative excellence with personalized service at the highest organizational level.
If you hold a Bachelor’s degree, bring seven-plus years of executive administrative support experience including three years with project oversight or supervisory responsibilities, demonstrate expert Microsoft Office abilities, excel at written and verbal communication, and want to provide seamless support to a senior principal blending business and personal coordination, submit your application through Tawani Enterprises’ careers portal emphasizing your discretion, organizational mastery, and proven executive support track record.
