Executive Operations Assistant Jobs in Chicago, IL

About Everspring

Everspring is a leading provider of education technology and service solutions. Our advanced technology, proven marketing approach, research-based instructional design services, and robust faculty support deliver outstanding outcomes for our university partners, powering their success online.

About the Role

Everspring is seeking an exceptional Executive Assistant & Operations Partner to the CEO. This is not your typical Executive Assistant role. You'll become a trusted partner, acting as the right hand to the CEO and partner to the senior leadership team, ensuring operational efficiency and clear communication across the team and with stakeholders. The role involves managing multiple priorities, coordinating projects, and streamlining communications and requires strong organizational skills, great communications abilities, a love for taking ownerships, and an enthusiastic and professional presence.

As the right hand to the CEO and a partner to the senior leadership team, the ideal candidate possesses expertise in the following domains:

• Calendar Management & Time Optimization: Proactively manage complex calendars, mitigating scheduling conflicts and balancing executive priorities
• Project & Document Management: Draft professional correspondence, assemble board packs, track project deliverables, and synthesize information for strategic reports
• Meeting & Travel Coordination: Organize company and executive events and offsites, facilitate virtual meetings, and coordinate complex travel logistics
• Confidentiality & Discretion: Handle sensitive HR, legal, and operational information with absolute confidentiality
• Executive Presence: Warm and outgoing, but with the ability to command a room, communicate eloquently, and lead by influence. Maintain poise under pressure, with the capacity to shift between administrative and strategic tasks
• Stakeholder Relations: Act as a gatekeeper and primary liaison between executive leadership, internal staff, and external partners (Board and University leadership)

This role reports to the Chief Executive Officer and is located in Chicago, offering a hybrid work environment with a minimum of 3 days required in the office every week and additional days as business needs arise.

If the idea of playing an important role in a growing company with a great team and strong mission excites you, we'd love to meet you.

What You'll Do

Executive Support

• Manage the CEO's complex and dynamic calendar, balancing competing priorities and ensuring optimal use of time.
• Coordinate internal and external meetings, including executive leadership meetings, board meetings, investor meetings, and university partner engagements.
• Arrange travel, including detailed itineraries and logistics.
• Prepare, submit, and reconcile executive expense reports.
• Draft, proofread, and edit executive correspondence, presentations, reports, and other communications.
• Serve as a trusted liaison between the CEO and internal and external stakeholders.
• Anticipate executive needs and proactively solve problems with minimal direction.
• Support strategic initiatives and special projects on behalf of the CEO and executive leadership team.
• Adapt to evolving business needs and take ownership of new responsibilities as they arise.
• Support special projects, company initiatives, and ad hoc requests on behalf of the CEO and leadership team.

Board & Executive Event Coordination

• Coordinate all logistics for Board of Directors meetings, including scheduling, meeting materials, catering, travel arrangements, and on-site execution.
• Support executive leadership meetings, offsites, and strategic planning sessions.
• Manage logistics for executive and VIP visits, partner meetings, and special leadership events.
• Partner with executive leadership to ensure seamless planning and execution of high-profile internal and external events.

Office Management

• Oversee the day-to-day operations of Everspring's Chicago office, ensuring a professional, organized, and welcoming environment.
• Identify and implement process improvements that enhance office operations and efficiency.
• Handle ad hoc operational projects and requests as needed.

Employee Experience & Engagement

• Lead the planning and coordination of company-wide events, including All Hands meetings, employee engagement activities, and celebrations.
• Partner with leadership, People Operations, and internal stakeholders to create meaningful employee experiences that reinforce company culture.
• Coordinate employee appreciation events, holiday celebrations, team-building activities, and other engagement initiatives.
• Serve as a cultural ambassador, helping create a positive and connected workplace environment.

Requirements

• Bachelor's degree
• 3-5 years of executive assistant, project management, office management, or related experience supporting senior executives.
• Experience supporting senior or C-level leadership, and/or leading complex projects
• Proven ability to manage multiple priorities in a fast-paced environment.
• Strong organizational and project management skills with exceptional attention to detail.
• Outstanding written and verbal communication skills.
• Ability to exercise sound judgment and maintain strict confidentiality.
• Professional presence and strong interpersonal skills with employees at all levels.
• Self-starter mentality with the ability to work independently and anticipate needs.
• Proficiency with AI, Microsoft Office Suite, including Outlook, PowerPoint, Excel, and Word.

About Everspring

Everspring is a leading provider of education technology and service solutions. Our advanced technology, proven marketing approach, research-based instructional design services, and robust faculty support deliver outstanding outcomes for our university partners, powering their success online. Everspring offers a range of full-service turnkey solutions, as well as standalone single service offerings, and innovative self-service products that enable universities to establish and maintain themselves as leaders in the digital delivery of education.

Based in Chicago, Everspring serves a growing number of colleges and universities. Built In Chicago has named us one of the "Best Places to Work" since 2021 and we were also certified as a Great Place To Work for four consecutive years, including 2025-2026.

Compensation offered at Everspring will be determined by factors such as location, level, job-related knowledge, skills, and experience.

Position Location: Illinois

The annual base salary range for this position is: $70,000 to $100,000.

We offer benefits that include hybrid work arrangement, paid parental leave, medical, dental and vision insurance, FSA, HSA, employer-paid short-term and optional long-term disability, 401k with an employer match vested immediately, a generous PTO plan that accrues with tenure, professional development, tuition reimbursement program, discounted onsite gym, optional pet insurance and more!

If you need a reasonable accommodation during the application or recruiting process, please reach out to HR @ everspringpartners.com

EEO Note:

Everspring is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws. This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, recall, leave of absence, compensation, benefits, training, and apprenticeship. Everspring makes hiring decisions based solely on qualifications, merit, and business needs at the time.