Senior Executive Assistant

Allwyn North America•Chicago, IL

23d•Onsite

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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

Benefits

Competitive employee package
Compensation: The expected salary range for this role is $80,000–$100,000 annually.
Comprehensive medical, dental, and vision insurance options, including company contributions to Health Savings Accounts (HSAs).
401(k) plan with a company match of up to 6%.
Employer-sponsored life insurance, short-term disability, and long-term disability plans.
Generous Paid Time Off policy with up to 30 days per year based on tenure, company holidays, paid volunteer days, and paid parental leave.
On-site gym membership
Wellness reimbursement
Student loan repayment
Commuter benefits