Senior Executive Assistant

Who we are

Allwyn is a multi-national lottery operator with leading market positions in Austria, the Czech Republic, Greece, Cyprus, Italy, the United Kingdom, and the United States. Our primary focus is lotteries, helping them raise more for good causes. We drive innovation, efficiency, and safety across our casual gaming entertainment platform in the quest for enhanced player engagement.

Allwyn North America is headquartered in Chicago and currently operates the Illinois Lottery under a private management agreement while seeking other opportunities throughout the U.S. We also provide products and services to lotteries and their players throughout Europe and the United States.

The Senior Executive Assistant is a trusted partner to the CEO and Senior Leadership Team, delivering high-level executive support, strategic coordination, and operational excellence. This role manages executive priorities and calendars, exercises sound judgment and discretion, and serves as a key liaison between executive leadership, employees, board members, external stakeholders, and business partners.

This position primarily supports the CEO, with additional executive support to the Senior Leadership Team as needed.

• Manage complex, dynamic executive calendars, ensuring alignment with business priorities and strategic objectives
• Coordinate domestic and international travel, including itineraries, accommodations, transportation, and meeting logistics, and facilitate cross-divisional travel and outreach plans
• Prepare and process expense reports and other administrative requirements accurately and on time
• Draft, review, and manage confidential correspondence, presentations, reports, and executive communications
• Monitor and prioritize incoming communications and requests, ensuring timely responses and appropriate escalation
• Serve as strategic gatekeeper to the CEO, managing competing priorities and protecting effective use of executive time
• Handle conflicting priorities expeditiously and proactively, driving projects to completion under deadline pressure
• Coordinate Senior Leadership Team meetings, off-sites, strategic planning sessions, and all-staff meetings, including agenda development
• Maintain awareness of organizational priorities and key business developments to anticipate executive needs and proactively address issues
• Participate as an adjunct member of the Senior Leadership Team — scheduling meetings, attending select sessions, and recording and distributing minutes

• 5+ years of experience supporting C-level executives, including complex scheduling, travel coordination, and confidential communications, in a fast-paced corporate environment
• Advanced proficiency in Google Workspace and Microsoft Office Suite, including PowerPoint, Excel, Word, and Outlook
• Strong organizational skills, with the ability to prioritize multiple tasks seamlessly and excellent attention to detail
• Outstanding written, verbal, and interpersonal communication skills, with the ability to build relationships across staff, board members, and external partners
• Proactive, resourceful problem‑solver with strong decision‑making capability and emotional maturity
• Effective both independently and as part of a team, with the ability to work well under pressure
• Proven ability to handle confidential information with discretion, adapt to competing demands, and deliver the highest level of client service
• Demonstrated ability to meet high-performance goals and deadlines in a fast‑paced environment
• Forward‑looking thinker who actively seeks opportunities and proposes solutions
• Self‑motivated, solution‑oriented, and proactive, with strong problem‑solving and critical‑thinking skills
• Operates with purposeful pace, agility, and a strong sense of urgency

• Bachelor's degree or equivalent combination of education and experience
• Experience working in highly regulated, corporate, or publicly-facing environments
• Experience supporting Board of Directors activities and governance processes

Our goal is to create one of North America’s most inclusive organizations – where people can bring the best of themselves to…