Deadline to apply for 2 management-level openings is Oct. 25
Posted: September 25, 2025
The Hawaiʻi State Teachers Association is seeking applicants for two management-level positions: deputy executive director and chief negotiator.
Andrea Eshelman previously held both positions for the past decade before being selected as HSTA’s executive director earlier this month.
For both posts, HSTA is looking for articulate and dynamic leaders who believe in public education, employee rights, and are skilled in organizing workers.
HSTA deputy director job duties
HSTA’s deputy executive director must be a strong advocate and will represent the Hawaiʻi State Department of Education and public charter school K-12 teachers. The ideal candidate will be a proven leader with the ability to provide supervision, guidance and support to staff, while effectively managing programs and initiatives that advance the union’s mission. If you are a professional with an understanding of labor union operations and direct experience working with Hawaiʻi public school teachers, union advocacy, representation, organizing, coordinating programs and bargaining, we’d like to talk to you.
The deputy will serve as HSTA’s UniServ Manager and provide leadership for field operations throughout the state. This position supervises UniServ Directors, leads HSTA’s organizing programs, oversees contract enforcement, and shares responsibility with the chief negotiator on matters before the Hawaiʻi Labor Relations Board. This role advises and counsels association leadership and may serve as acting executive director in the event of the executive director’s absence.
HSTA chief negotiator job description
HSTA’s chief negotiator will lead and direct collective bargaining efforts on behalf of HSTA, representing the interests of public and charter school educators. This role requires a strategic and skilled communicator who can analyze proposals, develop negotiation strategies, and advocate effectively for members while maintaining positive labor-management relationships. The chief negotiator provides leadership and supervision to negotiation teams and support staff, coordinates internal committees, and collaborates with union leadership to set bargaining priorities. Additionally, the chief negotiator ensures compliance with labor law, interprets contract provisions, and guides the union toward agreements that align with its mission and long-term objectives.
Both positions require a baccalaureate degree, as well as experience in supervision and labor relations. They both require out-of-state travel and are exempt, management-level full-time positions located on Oʻahu. Experience fostering collaboration with staff and working effectively with labor unions is highly desirable.
The deadline to apply for both jobs is Oct. 25.