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3 vie to be Pinellas’ next school superintendent. Which one will prevail?

With a decision coming Tuesday, the School Board considers a homegrown leader and two educators from outside the district.
The entrance to Pinellas County school district headquarters in Largo, where the School Board will meet on May 17, 2022, to choose a new superintendent.
The entrance to Pinellas County school district headquarters in Largo, where the School Board will meet on May 17, 2022, to choose a new superintendent. [ LUIS SANTANA | Times ]
Published May 13

The next leader of Pinellas County Schools will either be a lifelong district educator at the center of an era of improvement, or one of two out-of-towners who have deep roots in Florida and are respected for their interpersonal skills.

Ann Hembrook is praised by colleagues for her ability to listen and reflect before acting. Michael Ramirez exudes so much empathy his current boss said people feel sorry for him after he cuts their jobs.

But Kevin Hendrick enjoys the loyalty of Pinellas staff who have seem him implement programs that are seeing results. He told the School Board on Wednesday not to hire him because he is local, but for “the quality of the work that I’ve done.”

Here is the field that will be narrowed to one on Tuesday:

Ann Hembrook: ‘A real collaborator’

As a child, Ann Hembrook wanted to be a pediatric nurse. Then she had the experience of tutoring her younger brother. She found she had the patience to try different strategies until she saw results. Her brother turned to her one day and said, “You should be a teacher.”

Today — 47 with a husband in education and two adult children — Hembrook is a Marion County area superintendent, known for her collaborative style, solution-driven approach and skill at diffusing difficult, emotional situations.

“I would characterize her as being warm, humble, kind, incredibly knowledgeable, very capable and of leading but also a real team player,” said Nancy Thrower, a Marion County School Board member.

“She doesn’t just listen,” said Debbie Brockett, school superintendent in McMinnville, Ore., who worked with Hembrook in Nevada. “She really hears them, then reflects on what they are saying before she makes her next step.”

Hembrook believes she benefited from her childhood in a U.S. Navy family, stationed in Spain. She was educated in U.S. Department of Defense schools. But the family lived off base, where she could spend free time with her Spanish friends.

Ann Hembrook, left, chats with Ajori Spencer as her husband, Steve Hembrook, looks on during a meet-and-greet event at Pinellas County school district headquarters on Wednesday, May 11, 2022, in Largo.
Ann Hembrook, left, chats with Ajori Spencer as her husband, Steve Hembrook, looks on during a meet-and-greet event at Pinellas County school district headquarters on Wednesday, May 11, 2022, in Largo. [ LUIS SANTANA | Times ]

As a high school student in the United States, she was blocked from taking an advanced English class because of gaps in her vocabulary. Years later that experience pushed to work against barriers for students who need support.

After graduating from the University of Central Florida in 2001, Hembrook taught in Brevard and Orange counties. Diane Gullett, who is now Hembrook’s superintendent in Marion, had moved to Nevada and Hembrook went west to interview for a job there in 2019. Brockett, who was on the interview panel, said Hembrook impressed the group with her depth of knowledge and her ability to differentiate between the needs of various types of students and teachers.

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On the job, Hembrook was not afraid to push back — discreetly — if she believed something was not in the best interest of students or staff. During one situation Brockett described, involving an ambitious school improvement initiative, Hembrook suggested changes that would achieve the same goals but without causing as much burnout among staff.

Brockett was also impressed by the way Hembrook tackled the potentially explosive task of replacing a Native American-themed high school mascot, and her resilience when the superintendent rejected a school principal candidate who had been endorsed in the community.

In 2020, Hembrook moved to Marion County to work for a third time with Gullett, a superintendent she considers a valuable mentor.

There, she earned high marks for helping the schools reopen after the COVID-19 shutdown. “That’s where I saw the team player in her,” Thrower said. “She was a real collaborator. And I know that the schools felt really well-supported.”

During Wednesday’s publicly livestreamed interview session, Hembrook took careful notes on every question and gave detailed, deliberate answers. She was candid when she did not have enough knowledge to give a firm answer. This is the first time she has applied to be a superintendent.

“I will tell you if I don’t know something,” she said. “I’m going to learn it. I’m going to find out.”

Kevin Hendrick: ‘Put to the test’

If there’s a hometown favorite for the job, it’s Kevin Hendrick.

A 46-year-old Largo High graduate, he’s spent all but two years of his 25-year career in the Pinellas school system, rising from a Pinellas Park High math teacher to his current post as chief academic officer.

His wife teaches in the district. His son is in middle school. In a recent district climate survey, Hendrick’s name was mentioned most often as the person they’d like to see replace retiring superintendent Mike Grego. School Board members said they’ve gotten plenty of comments advocating on Hendrick’s behalf, and none against him.

“Kevin knows Pinellas County and would have virtually no learning curve so he would be able to dive in to address the challenges of our community immediately,” local business executive Scott Wagman wrote in an email to board members.

Conservative parent activist Angela Dubach said she didn’t even bother reviewing the other candidates, as she figured Hendrick is a shoo-in for the post.

But Hendrick refused to look at the job as his to lose. “It’s about winning,” said Hendrick, a former Dunedin High basketball coach. “I’m not thinking about it as, ‘don’t mess up.’”

People who know Hendrick have seen big things in his future for a long time.

As Largo High’s top male graduate of 1994, he was voted by his classmates most likely to succeed. Adults figured he’d pursue a high-paying job.

Kevin Hendrick, a veteran school administrator in Pinellas County and a finalist to be the district's next superintendent, speaks to the crowd during a meet-and-greet for the candidates on Wednesday, May 11, 2022, in Largo.
Kevin Hendrick, a veteran school administrator in Pinellas County and a finalist to be the district's next superintendent, speaks to the crowd during a meet-and-greet for the candidates on Wednesday, May 11, 2022, in Largo. [ LUIS SANTANA | Times ]

“I just really believed in the power of education,” said Hendrick, who now has three education degrees. His working-class parents didn’t dissuade him.

Hendrick recalled his father’s advice to wake up every day to do something he will enjoy. “I have done that every day since,” he said.

He’s been Dunedin High’s teacher of the year, a state finalist for principal of the year while at Northeast High, and the district’s administrator of the year in his current role. He’s received consistently strong performance evaluations, with an early supervisor calling him “one of the best teachers I’ve ever seen.” Leaders in the Pinellas Classroom Teachers Association, which has not always appreciated Grego’s administration, had an overall positive view of Hendrick.

Ric Davis, who heads a committee overseeing district efforts to eliminate the achievement gap among races, said the district has made great strides with Hendrick. Longtime parent activist Raegan Miller said, “I have always found him to be very calm and thoughtful. When you are around him, you can tell that people like him and trust him.”

Hendrick said he tries to treat everyone with respect, and that has led to disagreements but rarely dislike. “It doesn’t mean you always tell people what they want to hear,” he said. “But you listen, try to be authentic and genuine, and make the best decision.”

He angered LGBTQ students and their supporters by administratively removing the graphic novel Gender Queer from two high schools, but said the illustrations of sexual activity made the decision clear. He defended the district’s efforts to infuse culturally relevant teaching and social-emotional learning into classrooms, despite opposition from conservative groups.

Hendrick pressed forward with having teachers simultaneously instruct in-person and remotely during the height of the pandemic, despite furious pushback from overwhelmed educators. Although his decision wasn’t popular, Hendrick views it as key to the district’s limited student learning losses during that time.

He said his work during the pandemic boosted his confidence.

“I think that I was able to show district leaders, the School Board and, frankly, myself,” Hendrick said. “I took the lead on that and it went well, and it could have not gone well.

“My readiness for the superintendency was put to the test.”

Michael Ramirez: ‘Leading with love’

By his own description, Michael Ramirez was coasting through high school in Broward County. The family had relocated from Queens for his father’s job as an airline mechanic. His parents valued education but were not adept at navigating the system. “As long as the school wasn’t calling home, all was great,” he said.

As a junior, Ramirez wanted to take Algebra II. The school said he wasn’t ready and put him in a liberal arts math class to prepare. There, teacher Clara Neeck pushed him. ”She challenged me to believe in myself even when I didn’t see what she saw in me,” Ramirez said.

Ramirez worked at a jeans store after graduation, but eventually found his way to Southeastern University, a small Christian college in Lakeland. A professor suggested an education class. During a visit to Lakeland High School, Ramirez said, “I just knew I had found my calling, to connect with students and make a difference for kids.”

Ramirez, 49, with two young daughters, is the third of five children. Both his parents are of Puerto Rican heritage. He described his upbringing as traditional, with his mother devoting most of those years to raising the children.

As a social studies teacher, he appreciated what he calls “the relational” aspect of teaching. Parents would say his class was their children’s favorite. Ramirez never thought it was the subject matter that made them feel that way.

Michael Ramirez, a top school official in Denver and a finalist to lead Pinellas County Schools, speaks during a meet-and-greet event on Wednesday, May 11, 2022, in Largo.
Michael Ramirez, a top school official in Denver and a finalist to lead Pinellas County Schools, speaks during a meet-and-greet event on Wednesday, May 11, 2022, in Largo. [ LUIS SANTANA | Times ]

Neeck, his former math teacher, became a guidance counselor and got to see how Ramirez conducted himself as he rose through the ranks of the Broward district administration. “He always listens,” she said. “He always researches. He has patience. He is still persevering, still dedicated.”

An advancement opportunity, resulting from Ramirez’ membership in an organization for Hispanic school administrators, took Ramirez to Denver in 2019. He was deputy to superintendent Susana Cordova. She remembers how Ramirez smoothed over a rift between a school principal and the security team, and how he worked to make sure classes were covered when the pandemic hit and many teachers opted to work remotely.

“He very quickly finds ways to make a large system feel like a small town, or like a family,” she said. Cordova was replaced in 2021 with Alex Marrero, who called Ramirez “my rock since I’ve been here.”

One story Marrero tells: The district had to cut 80 jobs, and the employees were called to a meeting with four administrators. By Marrero’s description, those in Ramirez’s group ended the session asking whether Ramirez was all right, rather than expressing anger about their own situations.

“That’s a perfect example of who Michael Ramirez is, to the point where I regret not having him do it, one day a week for all 80,” Marrero said.

Ramirez said the Denver experience has been instructive, but the family is determined to return to Florida. He stresses the importance of his faith, but colleagues say he never tests church-state boundaries.

He said he is proud to call himself “a leader of color.” At one point in Wednesday’s session in Pinellas he said, “I don’t use the term ‘sub-groups’ because I don’t think anybody is a sub of anything.”

Addressing the acrimony that is now endemic in public school settings, he said, “I believe it’s about finding common ground in a society where the polarities are so opposite. How do we find common ground and rally around our schools, our public education? How do you find things we agree about and then also establish rules about how we are going to behave when we don’t agree? It sounds simple. but leading with love, right? Loving despite our differences.”

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