Position Overview

We are seeking an exceptional Executive Assistant to the CEO to create the structure, discipline, and day-to-day support that enables the CEO to operate at his highest level. The EA will become a trusted partner in managing the CEO's time, attention, logistics, and administrative priorities. The right person will develop a deep understanding of what matters most, anticipate what is coming, and proactively create order around a fast-moving executive and business.

Success in this role means the CEO spends more of his time on vision, strategy, growth, strategic relationships, partnerships, and the future of Choice Digital, and less time managing the mechanics around them.

The Executive Assistant will work closely with the CEO and Chief of Staff as part of Choice Digital's Executive Office. While the Chief of Staff helps translate the CEO's priorities into organizational execution, the Executive Assistant ensures the CEO has the time, organization, information, and logistical support required to lead effectively.

Key Responsibilities

CEO Time and Readiness

• Proactively manage a complex and dynamic executive calendar, including protecting defined blocks of focused, strategic, and preparation time and redirecting or declining requests that don't fit the intended shape of the day.
• Evaluate meeting requests, resolve conflicts, and make thoughtful tradeoffs with increasing independence, distinguishing between what requires the CEO's direct input and what can be handled on his behalf.
• Look ahead across weeks and months to anticipate capacity constraints, preparation needs, and potential conflicts.
• Ensure the CEO has the information, materials, and context needed for key meetings and commitments.
• Coordinate closely with the Chief of Staff to ensure priorities are appropriately scheduled and supported.
• Maintain a fast, reliable response standard for scheduling and logistics requests, even when the CEO's own availability for real-time response is limited.

Travel, Logistics, and Administration

• Coordinate domestic and international travel, including itineraries, accommodations, transportation, changes and preferences.
• Anticipate the work surrounding travel and build appropriate preparation and transition time into schedules.
• Manage recurring executive needs including email and inbox organization, expenses, receipts, documents, signatures, contacts, and appointments.
• Coordinate select personal scheduling or logistics when necessary to protect the CEO's overall capacity.
• Respond quickly and resourcefully when plans change.
• Handle sensitive information with exceptional discretion and judgment.

Executive Office Systems

• Manage the CEO's inbox with delegated authority, including triaging, drafting, and sending correspondence on his behalf when appropriate, while knowing when a matter requires his direct input.
• Communicate professionally and with sound judgment across employees, executives, customers, partners, and investors, including in situations that require significant discretion and confidentiality.
• Develop context around the CEO's key relationships so requests and interactions can be handled with appropriate judgment and urgency.
• Document preferences and establish clear protocols for scheduling, travel, communication, and recurring executive needs.
• Build repeatable workflows that reduce friction and make executive support increasingly proactive.
• Identify administrative work that can be simplified, automated, delegated, or eliminated.
• Create a consistently high-quality experience for people interacting with the CEO and Executive Office.

What Positions You for Success

• Significant experience supporting a CEO, founder, or C-suite executive
• Demonstrated expertise managing complex, dynamic executive calendars
• Experience coordinating domestic and international travel
• Exceptional attention to detail and follow-through
• Strong written and verbal communication skills
• High emotional intelligence and situational awareness
• Excellent judgment regarding priorities, confidentiality, and executive relationships
• The ability to anticipate needs rather than wait for direction
• Confidence making decisions independently within established guardrails
• Experience creating administrative systems and processes from the ground up
• Fluency with modern productivity and collaboration tools, including Google Workspace
• Comfort working across multiple time zones and with changing priorities
• The ability to remain calm, responsive, and resourceful when plans change quickly

What we Offer

• Competitive annual compensation range of $100,000 to $120,000
• Annual bonus linked to company success and your personal performance
• Equity offerings through stock options
• 401(k) retirement savings match (up to 4%)
• Flexible PTO policy
• Company paid holidays
• Medical, Dental, Vision, and Life Insurance

In compliance with Colorado state law, pay for this position is anticipated to be between $100,000 and $120,000. Actual offers will be based on the applicant's skills, experience, and education.

While the anticipated deadline is anticipated to be September 30th, 2026, you are encouraged to submit your application as we may still consider qualified candidates beyond this date.

Candidate profiles and resources from recruiting agencies and vendors are not being considered for this role. Please do not solicit Choice Digital with requests for business.