Executive Assistant

Digital Executive; Iowa; Remote; USD 15,000 - 18,000; Full time

Job summary

Digital Executive is seeking a full-time Executive Assistant / Personal Assistant to support a busy entrepreneur overseeing a boutique hotel, hospitality company, and a family-owned business. You will handle calendar and inbox management, coordinate meetings, organize documents, and manage personal tasks to free up time for growth and strategy.

The role requires proactive, detail-oriented individuals who can work with minimal supervision and own tasks across two companies.

Qualifications

• 2+ years of experience as an Executive Assistant, Personal Assistant, Virtual Assistant, or similar role.
• Excellent written and verbal English communication.
• Experience managing executive calendars, inboxes, scheduling, and travel arrangements.
• Highly organized and detail-oriented with strong follow-through.
• Proactive and resourceful, able to work independently.

Responsibilities

• Manage the executive's calendar, schedule meetings, coordinate availability and ensure timeliness.
• Oversee inbox management: organize emails, flag important items, draft responses and follow up.
• Coordinate meetings with partners, employees, contractors, vendors, and stakeholders.
• Support administrative operations across both businesses and ensure deadlines and follow-ups are met.
• Assist with document retrieval and organization for contracts, certificates, financials, and lenders' requests.
• Support hospitality property management, acquisitions, and ongoing operations.
• Coordinate communications for short-term rentals and upcoming hotel projects.
• Track and follow up on action items from meetings with teams.

Skills

Executive support

Calendar management

Travel planning

English communication

Tools

Google Workspace

Scheduling software

Job description

We are hiring a full-time Executive Assistant / Personal Assistant to support an entrepreneur who oversees two businesses: a growing boutique hotel and hospitality company and an established family-owned business specializing in window tinting and outdoor living solutions. This role is focused on helping the executive stay organized, managing day-to-day administrative responsibilities, and ensuring things run smoothly across both businesses. You'll be responsible for calendar and inbox management, coordinating meetings, organizing documents, and handling personal tasks that free up the executive's time to focus on growth and strategy. The ideal candidate is proactive, resourceful, detail-oriented, and comfortable taking ownership of tasks with minimal supervision. Full-time. Fully remote. Must be ENGLISH-SPEAKING.

Hours

9am–5pm CST

Salary

$1,500/mo

Key Responsibilities

• Manage the executive's calendar, including scheduling meetings, coordinating availability, and ensuring he is prepared and on time for all commitments.
• Oversee inbox management, including organizing emails, flagging important communications, drafting responses, and following up on outstanding items.
• Coordinate meetings with business partners, employees, contractors, vendors, and other external stakeholders.
• Support administrative operations across both businesses, ensuring important tasks, deadlines, and follow-ups are completed.
• Assist with document retrieval and organization, including gathering contracts, certificates, financial documents, and other paperwork requested by lenders, brokers, contractors, or city officials.
• Support the hospitality business with administrative tasks related to property management, hotel acquisitions, and ongoing operations.
• Assist with coordinating communications and documentation for the company's existing short-term rental properties and upcoming hotel projects.
• Support the executive's responsibilities in the family business, including scheduling strategy sessions, coordinating internal meetings, and tracking follow-ups related to marketing, sales, and business growth initiatives.
• Keep track of action items from meetings and follow up with the appropriate team members to ensure progress.
• Coordinate personal travel arrangements, including booking flights, accommodations, and transportation.
• Handle personal assistant responsibilities such as making dinner reservations, organizing gifts for clients, friends, and family, and coordinating other personal logistics.
• Conduct research and assist with ad hoc projects across both businesses as needed.
• Identify opportunities to improve administrative processes and implement systems that help the executive stay organized and productive.
• Act as the executive's right hand, anticipating needs and proactively handling tasks without requiring constant direction.

Key Qualifications

• 2+ years of experience as an Executive Assistant, Personal Assistant, Virtual Assistant, or similar administrative support role.
• Strong written and verbal English communication skills.
• Experience managing executive calendars, inboxes, scheduling, and travel arrangements.
• Highly organized and detail-oriented, with strong follow-through and the ability to keep the executive accountable to commitments.
• Proactive and resourceful, with the ability to independently research solutions and figure out unfamiliar tasks.
• Comfortable communicating with business partners, vendors, contractors, and other professionals.
• Tech-savvy and comfortable using Google Workspace, scheduling software, and other administrative tools.
• Strong problem-solving skills and the ability to adapt quickly to new responsibilities and industries.
• Comfortable handling both business and personal tasks with professionalism and discretion.
• Willingness to learn new processes and take on additional responsibilities as the businesses grow.
• Must own and be able to use a working computer with high-speed internet.
• Must be ENGLISH-SPEAKING.

Nice to Have

• Previous experience supporting a founder, CEO, or entrepreneur who operates multiple businesses.
• Background in hospitality, real estate, property management, or construction-related industries.
• Experience coordinating documentation with contractors, lenders, brokers, or local government offices.
• Familiarity with project management tools and creating administrative systems or SOPs.
• Experience working in a small business or startup environment where responsibilities evolve over time.