Engagement Specialist

Turners Falls, Massachusetts
Fly Five Programs

DEPARTMENT: Fly Five Programs 

SUPERVISED BY: Director of Professional Development and Engagement 


The Engagement Specialist is responsible for coordinating internal and external resources, ensuring projects remain within scope and on schedule while maintaining, monitoring, and reporting projections and actuals from the budget outline by the Chief for Fly Five programs and initiatives. They must be eager to learn, flexible, and work cooperatively with others to meet shared objectives. They should seek ways to improve the processes necessary to get work done with outside resources, including third-party vendors, researchers, and Fly Five practitioners. They readily learn and adopt new technologies, and scan the environment for new skills, knowledge, or capabilities that can benefit the business or personal performance. The Engagement Specialist relates comfortably with diverse groups of people, prioritizes multiple projects, has strong organizational skills, and can coordinate workflows to meet deadlines. 

The Engagement Specialist is responsible for initiating, maintaining, and improving the relationship between Fly Five program development and Fly Five practitioners. The Engagement Specialist will create opportunities through an engagement plan to understand the unique perspective of Fly Five practitioners and their wants, needs, and priorities in order to improve their interaction with Fly Five. This engagement plan will also bring real-world implementation examples from teachers and classrooms to the collective knowledge of the Fly Five program and content designers. The Engagement Specialist will work to actively promote the intended use of the Fly Five curriculum in school communities in various ways, including through the Fly Five Ambassador Program. 

The Engagement Specialist must be well organized, enthusiastic, and passionate about promoting the mission of Fly Five through various means, including functions and events. This is a full-time, remote position. This work requires some travel, and it requires customer-facing meetings and in-person classroom visits. This position requires frequent background checks. 

Teacher and School Leader Engagement 

  • Engages with teachers and practitioners as they navigate Fly Five implementation and works with matrix team members to troubleshoot customer challenges 
  • Organizes, maintains, and supports professional learning communities with a focus on implementation success and networking through collaboration with Professional Development Designers
  • Establishes and maintains relationships with Fly Five stakeholders and provides effective communication, including emails, video messages, virtual meetings, in-person trainings, and networking events and recruitment efforts 
  • Demonstrates innovation and competence in building partnerships between Fly Five program development and Fly Five ambassadors and practitioners through virtual and in-person events, including but not limited to training, networking, and recruitment 
  • Collaborates with the Director of Professional Development and Engagement to convey a unified and agreed-upon message for content marketing to maintain educator engagement
  •  Collaborates with internal team members and external vendors to promote and support engagement with Fly Five practitioners and to further their investment and connection with the Fly Five community, including conferences, virtual events, monthly communication, newsletters, and networking events 
  • Conducts focus groups, data collection, in-person and virtual classroom and school observations, and other duties related to Fly Five implementation, with the purpose of sharing real-world classroom experiences to inform curriculum updates and expansion 
  • Collaborates with Professional Development Designers, Writers, and the Project Coordinator to ensure that the professional development and external communication with educators regarding the curriculum implementation is accurately aligned to the Fly Five program C.A.R.E.S. standards 

Ambassador Program 

  • Stays abreast of Fly Five practitioners’ needs and priorities to effectively recruit and engage them in the Ambassador Program 
  • Attracts talent for Ambassador Program and recruits current Ambassadors for specific opportunities to grow and highlight their expertise areas, including through email communication, virtual information sessions, and in-person events 
  • Collects scheduled data related to the Ambassador Program and processes, tools, and resources to ensure that there is a continuous enrollment of highly engaged candidates 
  • Creates communication plans to disseminate information for Fly Five Ambassadors, including implementation sessions, recruitment efforts, development opportunities, and professional networking 
  • Collaborates with the Director of Professional Development and Engagement to create project and budget forecasts and assist in research to identify viable vendors, contractors, speakers, and presenters for Fly Five functions and events 
  • Contributes to budgetary planning and spending for such events and functions, including venue research, securing keynote speakers and supporting the events’ social and educational goals
  • Develops, coordinates, plans, and completes planning and execution of functions and events, which could be social or educational 
  • Stays apprised of institutional promotions, events, and marketing efforts to coordinate external messaging 
  • Scouts venues and performs cost-benefit comparisons to help select the best venue and negotiate with vendors for Fly Five functions and events
  • Facilitates Ambassador meetings for recruitment as well as to maintain current Ambassador networking and training opportunities 

Communication and Organization 

  • Creates and manages digital organizational tools, including but not limited to collaborative documents and project management software, like Monday.com, to support a variety of project needs 
  • Communicates progress of project deliverables, adherence to budget forecasts, potential staffing, and production needs to the Directors through a weekly status report of all current projects 
  • Builds, creates, monitors, and reports on deliverables for internal and external teams based on agreed-upon timelines 
  • Maintains digital files, transmittals, and deadlines for all projects including those with outside vendors 
  • Maintains notes for all meetings as a form of record keeping and communication
  • Monitors and communicates deliverables for all timelines, frameworks, protocols, and processes for producing, designing, and editing curriculum-related products and content 
  • Maintains outside vendor relationships to ensure communication and clarity of project deliverables, budget, bids, and contracts 
  • Works closely with Directors to facilitate and organize virtual and in-person events such as trade shows, expert panels, webinars, seminars, focus groups, discussion boards, cultural centers, Q&A sessions, large-scale conferences, etc. 
  • Maintains communication with contractual staff to ensure prompt payroll and onboarding
  • Provides a regular status update and on an as-needed basis to keep the Directors informed of the status of all projects 
  • Sets up meetings and agendas with internal and external teams 
  • Documents and follows up on essential actions and decisions from meetings
  • Maintains organization of work-for-hire contracts and transmits contractual invoices (okay to pay) from all vendors to Finance in a succinct template that reflects the guidelines set by the Finance department 

Technology and Logistics 

  • Creates and maintains organization of Google Suite drives and files, maintains registration of and communication with participants in online courses, and monitors and updates required items on the Learning Management System (LMS) 
  • Monitors the functionality of the LMS and the Fly Five website from a user perspective on a regular basis 
  • Manages development passes and print production of materials necessary for professional development coursework 
  • Is willing to learn new technologies to streamline organizational and departmental processes with a sense of urgency, high energy, and enthusiasm 
  • Coordinates logistics for Fly Five staff to present and participate in a variety of events, including mini-courses, conferences, and other large-scale events 
  • Manages digital information concerning focus group participants, in-person and virtual classroom observations, and a variety of logistical and filing needs concerning the research for

curriculum updates and expansion 

  • Follows through on internal training to stay current with curriculum updates
  • Communicates openly about potential improvements to team communication, processes, and logistics between teams, departments, contractors, and outside vendors 
  • Maintains relevant knowledge of current organizational software and programs to automate and make departmental systems more efficient 


  • Meets regularly throughout the workweek via video conference to provide status updates, communicate roles and responsibilities for the workload, strategically plan tasks to meet deliverables, and discuss challenges that need problem-solving 
  • Works with matrix teams, including the CRS Publications department, Marketing department, Educational Partnerships department, and with outside vendors in a collaborative and positive way 
  • Takes initiative to adhere to deliverable dates and implement feedback to elevate work 


  • Demonstrates an interest in learning new things 
  • Is flexible, dynamic, and engaging, with strong interpersonal skills 
  • Is a team player with the ability to forge new partnerships that bridge people and organizations
  • Is able to prioritize under deadline pressure 
  • Engages effectively and builds relationships with educational practitioners, school leaders, internal staff, and leadership 
  • Delivers in achieving outcomes, goals, and solving problems 
  • Has strong communication skills, including writing and public speaking 
  • Possesses excellent time management skills and is highly organized 
  • Is able to work independently as well as on matrix teams 
  • Demonstrates the ability to manage multiple projects and tasks simultaneously
  • Engages well with others, having a natural like of people, a knack for leading, and sales skills that help engage others in goals 
  • Assists in building a support network between the individual and the community
  • Researches topics, develops programs, and secures high-level speakers 
  • Promotes and represents the program and sponsor in a positive way at all times
  • Is a professional at all times with demonstrated business acumen

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