Overview
Seeking a Chief of Staff and Executive Assistant to Support a Founder Led Portfolio of Companies Based in Illinois
Location: Highland Park, IL | Hybrid 2 Days Onsite
Company: Instant Alliance
Salary Range: $100,000 to $150,000 plus bonus
About the Founder Led Organization
Instant Alliance is a rapidly growing human capital and recruitment firm headquartered in Chicago, IL. With more than 25 years of success and a diverse client portfolio ranging from Fortune 200 companies to innovative start-ups, Instant Alliance has established itself as an industry outlier in professional staffing.
The organization prides itself on delivering customized, high impact talent solutions through a proven recruitment process that consistently stays ahead of industry trends. At Instant Alliance, a deep passion for people and an unwavering commitment to excellence drive everything the organization does.
Role Overview
The Chief of Staff and Executive Assistant serves as a high trust partner to senior leadership, providing comprehensive administrative, operational, and strategic support in a fast paced, complex operating environment. This role is critical to ensuring the executive team operates efficiently and effectively by managing complex workflows, safeguarding confidential information, and supporting both day to day execution and long term priorities.
The ideal candidate brings exceptional organizational skills, sound judgment, discretion, and proactive problem solving capabilities, along with the ability to anticipate needs, operate independently, and adapt to evolving priorities.
Key Responsibilities
Executive and Leadership Support
- Provide high level administrative support to senior executives, including complex calendar management, meeting coordination, and executive communications
- Manage competing priorities across multiple leaders, ensuring schedules, deadlines, and deliverables remain aligned
- Serve as a trusted liaison between executives, internal teams, Board members, vendors, and external stakeholders
- Handle highly sensitive and confidential information with professionalism, discretion, and sound judgment
Operations and Project Support
- Track projects, milestones, deadlines, and deliverables across multiple concurrent initiatives
- Support strategic planning, reporting, and executive level decision making processes
- Implement workflow improvements, documentation standards, and process enhancements to reduce administrative burden
- Maintain well organized executive documentation systems and shared workspaces
Communications and Materials
- Draft, proofread, and format executive facing documents, presentations, and correspondence
- Prepare briefing memos, talking points, leadership updates, and presentation materials
- Support internal communications and cross functional coordination to maintain clarity and momentum
Administrative and Office Management
- Manage expense reporting, budget tracking, bill payment, and HSA administration
- Coordinate vendor relationships and administrative platforms, including QuickBooks, ZoomInfo, Bullhorn, VMS systems, and mail services
- Administer executive tools and systems such as Notion workspaces, password managers including LastPass, and document repositories
- Support website and back office administration, including internal knowledge bases and executive team spaces
Compliance, Governance, and Special Projects
- Support the identification, writing, submission, and portal management of RFPs for government and enterprise contracts
- Ensure compliance with internal policies, governance requirements, and documentation standards
- Assist with Board governance materials, committee coordination, and leadership reporting
- Provide IT and infrastructure support by troubleshooting systems and coordinating with technical teams as needed
Calendar, Meetings, and Travel
- Coordinate internal and external meetings, leadership offsites, and Board or committee sessions
- Prepare agendas, pre reads, briefing materials, and presentation decks
- Capture detailed meeting notes, track action items, and ensure follow through
- Plan and manage domestic and international executive travel, including itineraries, accommodations, and logistics
Qualifications
- Five or more years of experience supporting executives, senior leadership, or Boards in fast paced environments
- Proven ability to manage complex calendars, competing priorities, and confidential information
- Strong organizational, communication, and problem solving skills
- Advanced proficiency in Microsoft Office and Google Workspace, with experience using tools such as Notion, Asana, Canva, Zoom, Slack, and Microsoft Teams preferred
- High level of professionalism, discretion, and executive presence
- Ability to anticipate needs, work independently, and adapt to changing priorities
Success Factors
- Trusted partner to leadership with strong judgment and consistent follow through
- Exceptionally organized and detail oriented, while maintaining a strategic mindset
- Proactive, solutions oriented, and comfortable operating across functions
- Calm, reliable presence in high pressure or time sensitive situations
Benefits
Instant Alliance offers a comprehensive benefits package designed to support both personal well being and professional growth, including:
- Competitive compensation
- Comprehensive health insurance
- 401(k) with employer match
- Paid time off
- Professional development opportunities
- Career growth potential across multiple areas of the business