Executive Assistant (Full-Time)

Gulfshore Playhouse, a mission-driven, professional theatre company located in Naples, Florida, is seeking a dynamic, detail-oriented and organized individual to serve as Executive Assistant, providing full administrative support to the CEO & Producing Artistic Director.

Gulfshore Playhouse offers a diverse season of straight plays and musicals ranging from venerated classics and Broadway hits to contemporary works and world premieres. The Playhouse is passionately committed to producing high-quality, professional theatre which exceeds the expectations of the cultured residents and visitors of Naples, FL, many of whom are regular theatre patrons in New York, Chicago, Boston, Philadelphia, and Washington, D.C. 

Gulfshore Playhouse has performed for many years in an intimate 200-seat venue at the Norris Center, a municipal building run by the City of Naples. The Playhouse is in the final phases of a $60M capital campaign and has broken ground on the Baker Theatre and Education Center, a state-of-the-art facility, featuring a 350-seat mainstage with a Broadway-sized stage, a 125-seat flexible space, rehearsal studios, classrooms, and rental space. In 2022, Gulfshore Playhouse became nationally recognized at the 77th member of the League of Resident Theatres (LORT). This is an extraordinarily exciting time for the Playhouse, which is experiencing unprecedented growth, and the Executive Assistant will have the opportunity to participate in everything from production to special events to coordinating daily business affairs.

Status: Full-time, year-round position

Start Date: Available now

Reporting directly to the CEO & Producing Artistic Director, the Executive Assistant will provide executive support in a one-on-one working relationship, serve as the primary point of contact for internal and external constituencies on all matters pertaining to the office of the CEO, serve as a liaison to the board of directors and senior management teams, organize and coordinate executive outreach and external relations efforts, and oversee special projects.  The Executive Assistant must be creative and enjoy working within a small, entrepreneurial environment that is mission-driven, results-driven and community oriented.  

The ideal individual will have a strong drive to provide high-quality work, the ability to exercise good judgment in a variety of situations, with strong written and verbal communication, administrative, and organizational skills, and leadership capabilities.  The Executive Assistant will have the ability to work independently on projects, from conception to completion, handling a wide variety of activities and confidential matters with discretion.  The Playhouse values hard work, kindness, generosity, passion, and grace-under-pressure.  The Executive Assistant will be expected to work extended hours when necessary to meet goals. Some weekend and evening hours are required including attendance at Opening Nights, special events, and/or meetings that may happen outside normal hours.

Representative Duties:

Executive Support

  • Completes a broad variety of administrative tasks for the CEO including managing an extremely active calendar of appointments; composing and preparing correspondence that is sometimes confidential; arranging complex and detailed travel plans, itineraries, and agendas; and compiling documents for meetings, speeches, rehearsals, and donor presentations
  • Plans, coordinates, and ensures the CEO’s schedule is followed and respected.
  • Provides ”gatekeeper” assistance, creating win-win situations for direct access to the CEO’s time and office
  • Communicates directly, and on behalf of the CEO with board members, donors, owner’s reps, members of city government, staff, and others on matters related to the CEO’s strategic and artistic initiatives
  • Researches, prioritizes, and follows up on incoming issues and concerns addressed to the CEO, including those of a sensitive or confidential nature.  Determines appropriate course of action, referral, or response
  • Works closely and effectively with the CEO to keep her well informed of upcoming commitments and responsibilities, following up appropriately.  Acts as ”eyes and ears” when necessary, keeping the CEO updated on issues taking place in the environment.
  • Provides leadership to build relationships crucial to the success of the organization
  • Helps with all tasks that facilitate the CEO’s ability to effectively lead the company
  • Prioritizes conflicting needs; handles matters expeditiously, proactively, and follows-through on projects to successful completion, often with deadline pressures
  • Supporting the budgeting process through compiling information from a variety of departments

Senior Management Support

  • Participates as an adjunct member of the senior team including assisting in scheduling meetings and attending all meetings
  • Assists in coordinating the agenda of senior management team meetings and/or rehearsals which the CEO is directing or attending. 
  • Minutes taking and transcribing for meetings when needed
  • Support of the COO & Managing Director and other senior managers when appropriate


  • Assisting in a variety of projects, such as event brainstorming and preparation, invitation creation and distribution, or solicitation/thank you letters;
  • Researching and otherwise supporting play-reading and preparation as necessary
  • Attending rehearsals; providing email support, communication support; and note-taking as needed
  • Setting up interviews with potential creative members; liaising with the casting director regarding scheduling of auditions, creation of sides, and breakdowns; interacting with directors, designers, and actors as appropriate


  • Strong organizational skills that reflect that ability to perform and prioritize multiple tasks seamlessly and with excellent attention to detail
  • Very strong interpersonal skills, and the ability to build relationships with stakeholders
  • Expert level written and verbal communication skills
  • Demonstrated proactive approaches to problem-solving with strong decision-making capability
  • Emotional maturity
  • Fearlessness, a friendly, outgoing disposition, and a can-do attitude
  • Highly resourceful team-player, with the ability to also be extremely effective independently
  • Proven ability to handle confidential information with discretion, be adaptable to various competing demands, and demonstrate the highest level of customer/client service, and staff responsiveness possible
  • Demonstrated ability to achieve high performance goals and meet deadlines in a fast paced environment
  • Forward looking thinker, who actively seeks opportunities and proposes solutions

Education and Experience

  • Bachelor’s degree required
  • Strong work tenure; 2-5 years of experience supporting C-level executives
  • Experience and interest in internal and external communications
  • Proficient in Microsoft Office (Outlook, Word, Excel, and PowerPoint), Adobe Acrobat, and Social Media web platforms

Our Charter:  https://www.gulfshoreplayhouse.org/wp-content/uploads/2018/11/Charter.pdf

Wage: Salary range: $38,000-$42,000

Gulfshore Playhouse is an equal opportunity employer committed to fostering a diverse staff; we strongly encourage people from underrepresented groups and diverse backgrounds to apply. 

Gulfshore Playhouse offers benefits that increase along with tenure, including health, dental, and vision insurance, a 403(b) retirement plan and paid vacation and sick leave. 

Please send a cover letter, resume, and a list of references to jobs@gulfshoreplayhouse.org.

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