Student Engagement Specialist

NOTE: The Council is hiring FOUR individuals for this position.

Location: Frankfort, KY. Hybrid position that works primarily remotely. Must have a Kentucky address.
Travel: Frequent in-state and occasional out-of-state travel.
Compensation: $65,000 - $68,000
Retirement: TIAA

Overview

GEAR UP Kentucky is a federal, statewide grant program coordinated by the Council, which works with students, families, and schools in low-income Kentucky communities to support college preparation and success. GEAR UP Kentucky is designed to increase the percentage of students who graduate high school and successfully transition to and through postsecondary education. In October 2025, the Council was awarded a seven-year, $35 million grant to serve at least 10,000 students in eight high-need KY school districts, the fifth GEAR UP state grant for Kentucky that has been administered through the Council. GEAR UP positions are for the term of the grant which is through September 30, 2032.

The Student Engagement Specialist serves as a member of the GEAR UP Kentucky Student Engagement Travel Team, which is responsible for the planning, coordination, facilitation and documentation of student and family workshops in all partner middle and high schools.

The Student Engagement Team will plan, organize, and deliver engaging, interactive workshops that meet the learning objectives and developmental needs of participants. This role combines event planning, public speaking, and hands-on facilitation to ensure high-quality, impactful learning experiences for GEAR UP students and families. The team will deliver a series of high-energy, interactive workshops with entire grade levels of students in multiple rotations throughout the school year, and at summer programs and events. Travel time is estimated at 40-50%.

Each of the four Student Engagement Specialists will have an Area of Specialization where they will serve as the peer expert, providing consultation, training, and resource support to colleagues across the program.

Duties and Responsibilities

Workshop Planning and Coordination

• Communicate GUK vision and mission effectively to all project audiences.
• Work closely with the GEAR UP Student Engagement Travel Team, maintaining open lines of communication and supporting each other in event planning and delivery.
• Collaborate with GEAR UP Kentucky school-based staff and Project Specialist to establish an annual schedule for student workshops across partner schools.
• Coordinate logistics for each scheduled workshop with GEAR UP Kentucky staff, including pre-event communication, volunteer recruitment (when necessary), and dissemination of pre-event materials or assessments.
• Develop structured agendas for each workshop based on GEAR UP Kentucky-approved lesson plans including event set-up and tear-down and roles and responsibilities of each team member.
• Orient and prepare staff and volunteers (if relevant) in advance of events, ensuring clarity of roles and responsibilities for smooth workshop delivery.
• Ensure all materials, supplies, and equipment are prepared, purchased, and available for events, in collaboration with the Project Specialist.

Event Management and Logistics

• Responsible for the seamless operation of events, ensuring that all logistical details are addressed in advance and executed on the day of the event.
• Travel to partner schools for scheduled workshops, ensuring timely arrival and readiness to deliver workshops as planned.
• Effectively manage travel schedules to ensure all event responsibilities are completed without disruption and with respect to travel demands.
• Manage the transportation, set-up and breakdown of event equipment and resources to and from each school location, following provided guidelines.
• Provide event set-up and tear-down, ensuring all materials are handled appropriately, space is left clean, equipment is accounted for, and all tasks are completed within the allocated time.

Event Facilitation

• Lead and facilitate engaging, interactive workshops for students, maintaining a high-energy, student-centered approach that encourages participation and active learning.
• Ensure workshops are delivered according to established timelines, objectives, and guidelines, adapting as needed to meet student age groups and needs.
• Foster a dynamic and respectful learning environment where all students feel comfortable participating and expressing themselves.
• Provide individual or small-group support when necessary, ensuring all students understand and engage with the workshop content.
• Engage with local community partners, business representatives, and school staff to help deliver and reinforce content and enrich the student experience.
• Facilitate workshop sessions at annual student scholarship summer event using provided lesson plans to deliver high-quality content to support students' transition to postsecondary education.

Data, Evaluation, and Continuous Improvement

• Track student participation in workshop activities and ensure timely, accurate entry into GUSS data management system.
• Collect and document participant feedback during and after workshops using provided technology (e.g., student check-ins, surveys).
• Analyze feedback, participation data, and personal observations to generate insights that inform program refinement and continuous improvement of workshops and GEAR UP programming.
• Document suggestions for updates to materials, activities, and processes that contribute to continuous improvement.
• Complete quarterly progress reports, summarizing outcomes, engagement trends, challenges, and recommendations for future development.
• Regularly review, refine, and update workshop content, communications, and planning processes to align with student needs, program objectives, and best practices.
• Maintain accurate inventory records of workshop materials and ensure equipment and supplies are securely stored and well-maintained.

Team Membership

• Serve as a member of the Student Engagement Team
• Serve as a member of the District Implementation Team
• Serve as a member of the Postsecondary Pipeline Team

Professional Development

• Participate in professional development opportunities, seminars, conferences, and networking opportunities as assigned.

Areas of Specialization

• Early Postsecondary Opportunities: The Student Engagement Specialist with this focus area will serve as the peer expert for Early Postsecondary Opportunities (EPOs), providing guidance and support to colleagues across the program. This role emphasizes Dual Credit and Advanced Placement (AP) advising, Kentucky Career Pathways, supporting student and family knowledge of and access to these opportunities, and strengthening connections to postsecondary institutions. The specialist will train and support peers on Kentucky Department of Education (KDE) standards for college and career readiness while promoting effective strategies for student access to EPOs and contributing to the overall success of district and program goals.

• Students with Disabilities: The Student Engagement Specialist with this focus area will serve as the peer expert on supporting students with disabilities and their families. This role emphasizes increasing knowledge of and access to specialized services, supports, and accommodations that promote student success in their postsecondary journey. The specialist will train and support colleagues in identifying resources, fostering self-advocacy, and strengthening advising practices to ensure students with disabilities are equipped to transition and thrive in postsecondary settings.

• First in the Family & Financially Limited students: The Student Engagement Specialist with this focus area will serve as the peer expert on supporting first-generation and financially limited students and families. This role emphasizes increasing access to financial aid knowledge, sources, resources, and support systems that empower students to successfully transition to and persist in postsecondary education. The specialist will guide colleagues in implementing strategies that promote supportive advising practices, strengthen financial literacy, and expand opportunities for student success.

• Highly Mobile Youth: The Student Engagement Specialist with this focus area will serve as the peer expert on supporting students who face systemic barriers to education, with an emphasis on students navigating housing insecurity and the foster care system. The specialist will guide colleagues in understanding the unique challenges these students encounter, ensuring that GEAR UP Kentucky services are responsive and designed to reduce barriers to postsecondary access and success, such as unmet basic needs.

Peer Training & Support

• Design and lead professional development workshops, training sessions, and resource-sharing initiatives for GEAR UP Kentucky staff in area of specialization.
• Provide peers with best practices, tools, and strategies to strengthen advising, implementation, and service delivery.
• Serve as a consultant to staff, offering guidance, troubleshooting support, and recommendations to improve consistency and quality across districts.

Qualifications – Education and Experience

• Bachelor’s degree in a related field.
• Minimum of five years of professional experience.
• Experience working directly with middle and high school students in the area of teaching, guidance counseling, college and career advising, youth development, social work or a related field.
• Experience in event planning or meeting facilitation, including coordinating logistics and managing stakeholder engagement.

Preferred:

• Work experience in a K–12 school setting and/or college access program, with direct interaction supporting students, families, and/or educators.
• Experience designing and delivering student workshops and professional development sessions for peers or colleagues.

Successful Applicants Will Demonstrate the Following:

• Understand and commit to the mission, vision, and goals of GEAR UP Kentucky
• Demonstrate a team-oriented mindset, ability to work collaboratively toward the success of the GEAR UP program.
• Communicate effectively and professionally in interpersonal interactions with students, families, school staff, community organizations, and postsecondary representatives.
• Produce clear, concise, and professional written communications.
• Organize multiple tasks and maintain attention to detail.
• Commit to continuous growth and receive and respond to feedback in a constructive manner.
• Work independently while adhering to established program policies, procedures, and expectations in a hybrid environment.
• Demonstrate dynamic, high-energy facilitation skills to lead engaging, student-centered workshops in large and small group settings.
• Exhibit excellent time management skills and work ethic to balance the planning, deliver, and documentation of multiple events, often with travel involved.
• Be adaptable and flexible. Strong problem-solving skills to quickly address logistical challenges or student needs during workshops.
• Demonstrate leadership skills or orient and prepare staff and volunteers.
• Lift, load, set up and move event equipment and supplies (e.g. sound system, tables, signage, etc.).
• Proficiently use Microsoft Office including Teams and Outlook and manage multiple email accounts and platforms to coordinate communication, scheduling, and documentation.
• Maintain a valid Kentucky driver’s license and fulfill requirements to be authorized to drive a Kentucky Division of Fleet Management vehicle.

Application Information

Interested applicants should send a letter of application specifically addressing the responsibilities and qualifications of the position, a resume, and the names, titles, and contact information for at least three professional references to CPE.HR@ky.gov.