The Big Picture
Cleveland Water Taxi and its sister company, CLE Tiki Barge, is more than just a growing, dynamic boat tour company—we’re in the business of creating unforgettable experiences in Cleveland! As our CEO’s lead navigator, you’ll be the person who keeps the business (and the CEO’s life) moving forward. You’ll handle the professional, the personal, and the high\-priority daily logistics with a calm head and a positive, flexible attitude.
This role is roughly 75% business administration and 25% personal support. If you have a natural knack for problem\-solving and want to be a key part of our crew as we grow, this is the spot for you. We need someone who thrives in a fast\-paced environment and isn't afraid to take the wheel on new projects.
What You’ll Do:
Executive Operations \& Strategic Support
* Proactive Calendar Logic: Independently manage and optimize calendars for both the CEO and the business. You don't just "schedule" – you must protect the CEO’s time by anticipating conflicts that may arise, accounting for travel buffers, and prep time.
* Travel \& Off\-Site Logistics: Research and book cost\-efficient travel options (flights, hotels, car service) for the CEO and management staff. Build \& maintain detailed itineraries including meeting venues, appointments, and meal reservations. Manage registrations and expense tracking.
* End\-to\-End Project Coordination: Take full lead on administrative projects and company events – from digital organization (Google Drive/Workspace) to managing data entry and clerical systems to managing vendor coordination and on\-site logistics.
* Documentation \& Design: Prepare, proofread, and polish reports, presentations, and marketing materials (Canva), ensuring every outward\-facing document is error\-free.
* Executive Liaison: Serve as the primary point of contact for staff, vendors, and partners, ensuring a seamless and professional flow of information.
Communication \& Inbox Mastery
* Gatekeeping \& Filtering: Manage multiple email inboxes by filtering noise, prioritizing urgent matters, and drafting high\-quality responses.
* Correspondence Management: Screen calls and manage high\-volume correspondence, responding with the appropriate level of urgency and professionalism.
* Internal Task Tracking: Oversee internal communications and task management systems (e.g., Connect Team) to keep the entire crew aligned on the CEO's priorities.
Household \& Family Logistics
* Home Operations Management: Act as the logistical lead for a busy household with two children (11 and 14\) and family dog. This includes tracking inventory, managing grocery/supply replenishment for all family members, monitoring school related deadlines, and ensuring the family schedule remains seamless.
* Vendor \& Maintenance Oversight: Research, schedule, and supervise household vendors (groomers, pet related services, landscapers, deliveries, repairs, etc.) to ensure work meets a high standard.
* Personal Financial Support: Assist with household expense tracking, vendor payments, and simple budgeting for home projects.
* Lifestyle Support: Manage personal appointments for CEO, children and family dog. Execute specialized errands and projects (gift sourcing, seasonal transitions, personal travel arrangements) to keep the CEO’s personal life running as smoothly as the business.
What You Bring To The Crew:
* 3\+ Years of Experience: Background as an executive assistant, administrative assistant, or personal assistant.
* Technical Mastery: Proficient in Google Business Workspace and Canva. Expert at creating, editing, and proofreading documents, as well as architecting organized shared drives, project folders, and inboxes.
* High\-Level Resourcefulness \& Accountability: You are a natural "closer" who takes full responsibility for the finish line. You take pride in independently researching, troubleshooting, and exhausting every possible solution before seeking direction from the CEO.
* Rapid Context\-Switching: The mental agility to thrive when priorities shift instantly. You can pivot between 10 different tasks without losing your grip on details or deadlines.
* Autonomous \& Initiative\-Driven: You don't wait for a to\-do list; you anticipate needs. You are comfortable working independently and taking the lead on projects from start to finish.
* Strategic Prioritization: Exceptional time\-management skills with the judgment to identify which "fire" to put out first when everything feels like a priority.
* Crystal\-Clear Communication: You can distill complex information into brief, actionable updates, ensuring the CEO is informed but never bogged down by unnecessary details.
* Impeccable Discretion: A flawless track record of maintaining strict confidentiality while handling sensitive personal, financial, and proprietary business data.
* Local Logistics: A reliable vehicle and a clean driving record for local errands and household support.
Bonus Points:
- Experience in maritime, hospitality, or tourism
- Knowledgeable about Cleveland’s waterfront attractions and events
- Experience in event planning, HR management, payroll, and booking platforms
- Social media savvy (editing and customer engagement)
- Commission \& bonus opportunities
- Complimentary employee passes
- Discounted cruises
- Flexible hybrid schedule
- Fun and laid\-back (but hard\-working) company culture
- Opportunities for growth as the company expands
- 4 hour shift
- 8 hour shift
- Day shift
- Monday to Friday
- Night shift
- Weekends as needed
Compliance \& Employment Requirements
* Background Verification: Final candidates must successfully complete a comprehensive background check and reference verification.
* Maritime Regulatory Compliance: As a maritime business, this position is safety\-sensitive. Upon hire, the candidate will be enrolled in a USCG\-compliant drug testing consortium. This requires an initial pre\-employment drug screen and adherence to random testing as dictated by the consortium.
* Work\-Style Assessment: As part of our interview process, candidates will be asked to complete a brief professional compatibility profile to provide insight into their preferred work, communication, and problem\-solving styles alongside the executive team.
Seasonal Flow \& Perks
* High Season (March\-October): Expect 30 – 35\+ hours per week during peak season.
* Off Season (November\-February): Hours typically adjust to \~20 hours per week.
* Perks Include:
To Apply:
Send your resume and a short note about why you’d be a great fit!
Job Types: Full\-time, Part\-time
Schedule:
Work Location: Hybrid \- partially from home, at CEO’s personal residence and at business residence (Olmsted Township \& West Bank Flats in Cleveland)
Pay: $20\.00 \- $25\.00 per hour
Work Location: Hybrid remote in Cleveland, OH 44113