HSTA board selects Andrea Eshelman as next executive director

The Hawaiʻi State Teachers Association Board of Directors has appointed Andrea Eshelman as HSTA’s next executive director. She brings nearly three decades of experience as a public school teacher, union leader, manager and chief negotiator to her new position.

HSTA President Osa Tui, Jr., said, “As a negotiations committee member since 2011, I was impressed when Andrea was brought in as negotiations support, leading to our 2013 contract settlement. Soon thereafter, I was able to see her elevated to chief negotiator in my role as the negotiations committee chairperson.”

“In all of these years, I have seen Andrea dedicate her life to both the vigorous defense of our members as well as the powerful advocacy for their improved working conditions and compensation. It’s been my pleasure to see her grow in her experience and expertise and I look forward to her leadership at HSTA,” Tui added.

Eshelman said, “I believe that HSTA plays a unique and important role in strengthening public education in Hawaiʻi. Many other nonprofits care deeply about children and education, but what sets us apart is the collective strength of more than 13,000 members and a seat at the table to influence things in a positive way.”

Being appointed HSTA’s executive director “feels like a continuation and natural evolution of my time at HSTA. I have had the good fortune of learning and working along with many dedicated educators and leaders,” said Eshelman.

“I hope to lead us forward as we expand the scope of our work, but also continue to build that power and influence in our core areas. I bring not only a deep institutional knowledge, but the legal expertise gained over many years, and I want to use it in support of our members as we continue to innovate and change,” she added.

The HSTA board appointed Eshelman as interim executive director effective Aug. 1, following the retirement of Ann Mahi at the end of July and appointed her the permanent executive director effective Sept. 1.

Eshelman will oversee HSTA’s staff of 45 employees on four islands.

Eshelman graduated from, taught in Hawaiʻi public schools

Eshelman arrived in the islands in 1986 as a 12-year-old 7th grader when her father transferred to Schofield Barracks in the U.S. Army. She attended Wahiawā Middle (then known as Wahiawā Intermediate) and graduated from Leilehua High.

Eshelman earned a bachelor’s degree in social science history from Fayetteville State University in Fayetteville, North Carolina, where she was class valedictorian.

Upon graduating from college, she returned to Hawaiʻi and began her career as a social studies teacher at Pearl City High. During her eight years in the classroom, she served as an HSTA school-level and chapter leader.

She then joined the staff of HSTA in 2004, where she spent a decade as a UniServ Director, serving as a field agent representing teachers in the Honolulu and Leeward districts.

In January of 2015, Eshelman became HSTA’s deputy executive director and chief negotiator. In that management position, she led HSTA’s organizational strategy, collective bargaining, operations, and assisted in governance for the 13,500-member union.

In collaboration with elected officers and board members, Eshelman provided leadership across legal, policy, field operations, and membership functions. She supervised the union’s 14 field staff and negotiations specialist.

Teacher leader calls Eshelman a natural-born advocate

In 1996, Joan Lewis, currently an instructional coach at Kapolei High, first met Eshelman as a new teacher at Pearl City High while Lewis was president of HSTA’s Leeward Chapter.

“With Andrea’s natural intellectual curiosity, you talk about natural-born advocacy. She was all of that. If I’m being perfectly honest, as her chapter president, there were days when she was a lot to handle. Because she was always trying to push for something more or something new,” Lewis recalled.

“She always wanted to make sure that we were aware of this potential issue, this potential solution, these kinds of options,” Lewis added.

Lewis, who served three terms as HSTA state vice president, calls Eshelman “very systematic, very organized. She helped the people she worked with grow in that kind of systems thinking. And then as she continued to move through HSTA, you could see more and more of the systems coming into play.”

Lewis said she is “ecstatic” at hearing about Eshelman’s appointment, and added, “She is poised to be the executive director who can link HSTA’s history with HSTA’s future in a very thoughtful and seamless manner, and I am so grateful that she is going to be leading HSTA as our executive director.”

Eshelman marshaled HSTA staff and resources to help our members in need when wildfires destroyed Lahaina in 2023, and more than 100 teachers and retirees lost their homes to the flames, which also destroyed an elementary school.

Lahainaluna High social studies teacher Mike Landes, who was then president of HSTA’s Maui Chapter, said, “Andrea helped to coordinate the statewide effort to support our chapter members who lost their homes and classrooms after the Maui fires, including distributing relief checks, sending supplies from Oʻahu, getting access to legal support, hosting informational and support sessions, providing internet hotspots, and just being there for our members in their greatest time of need.”

“Our members expressed how thankful they were for all the help and support HSTA provided, and I’m not sure that it could have happened without Andrea,” Landes added.

Eshelman: ‘I was always somebody who would volunteer to help’

Eshelman recalls wanting to be a teacher since she was a kid.

“I was very stereotypical. I was the bossy oldest child, and we played school, and I was always the teacher with my siblings. We moved around a lot when I was really young, a different place every year until we landed in Hawaiʻi. Teachers were always the people I looked to for helping me adjust,” she said.

Her first exposure to HSTA came when, as a first-year teacher, she attended Teacher Institute in the fall of 1996 at Nānākuli High and Intermediate, not long after the school year started that year.

“And I remember seeing our chapter president, Joan Lewis, on the stage and just being intrigued about the issues that she was addressing, just being very intrigued by what’s this union thing?” Eshelman said.

A couple of years later, she became an HSTA faculty representative.

“Our head faculty rep stood up in May at a faculty meeting and said that she was stepping down. And someone needed to step up in her place, there was this long uncomfortable silence as no one stepped forward. I finally raised my hand and said, ‘I’ll help.’ And then I became a faculty rep,” Eshelman said.

“I was always somebody who tries to step up when help is needed. Acts of service have always mattered to me, and I always want to help other people,” she said.

She held other union and teacher leadership roles in the years that followed, serving as a school community-based management (SCBM) council representative for bargaining unit members, an HSTA grievance representative, and a representative on the HSTA Association Policy Committee at Pearl City High. She also represented the union’s Leeward Chapter on HSTA’s Government Relations Committee and served as secretary on its executive board.

Eshelman also volunteered as a strike captain when teachers across the state went on strike in 2001. She remembers walking the picket lines daily when she was “very pregnant” with her first son.

When she became a UniServ director and joined the staff of HSTA a few years later, “I really enjoyed solving problems and trying to help advocate for people, and finding ways to address the systemic issues impacting educators.”

Eshelman: ‘It’s always been important to me that we stand behind and invest in our public schools’

Eshelman and her husband have two grown sons who both graduated from Mililani High, and the value of a strong public education system has been central to their family.

She recalls a moment early in her career at HSTA, when her eye doctor assumed that leaving the classroom meant she would now be able to send her children to private school. “He was excited for me because he thought I would make more money and could now choose private education for my kids. But that assumption upset me,” Eshelman said.

“For me, private school was never the plan, even if it had been financially possible. Public education was where I wanted my children to be, and it’s always been important to me that we stand behind and invest in our public schools,” she added.

In her free time, she likes to bake, quilt, travel, and “I’m trying to learn how to garden, but I don’t have much of a green thumb,” she said with a laugh.

In her first week as the interim executive director, Eshelman resurrected the popular “Know Your Rights” column that her predecessor, Joan Husted, started decades ago. We invite you to read the latest installment of her column here.