Oliver Wreford and Kacie Jester Step into New Leadership Roles

We’re thrilled to announce two well-deserved leadership moves that reflect our deep commitment to the educators and students our EdTech companies support. Oliver Wreford has stepped into the role of Portfolio Leader for EdTech, bringing a wealth of experience to guide our growing group of businesses. Kacie Jester is now CEO of School Pathways and Aequitas, two companies that help K–12 schools streamline operations, support personalized learning, and ensure compliance across traditional and non-traditional education models.

From EdTech CEO to Banyan Portfolio Leader: Oliver Wreford

Oliver has spent his career scaling innovative education technology solutions, including in his former role as CEO of School Pathways and Aequitas. He brings a blend of product development expertise, strategic insight, and deep empathy for those using the technologies represented in our EdTech portfolio.

“It’s not enough to ask what your users want, you have to understand their unique needs and those of the people they serve,” he shared in a recent interview. “In EdTech, that means listening closely to educators, families, and students to ensure we grasp their pain points, needs, and goals.”

In his role, he also mentors our company’s leaders, facilitates cross-team collaboration, and ensures each business grows, while preserving its culture and core mission.

“Banyan Software shares the vision that’s guided me throughout my career, and that’s empowering and elevating companies that put students and educators first. I’m excited to help the dedicated teams across our EdTech portfolio continue building tools that make a meaningful difference in the lives of learners and educators alike.”

Oliver seeks to understand both the teams he leads and the unique needs of those they serve. His guidance and unwavering commitment to truly two-way partnerships, has made a lasting impact, most notably on his successor, Kacie Jester.

A Leader Who Grew with the Company: Kacie Jester

Few CEOs have a more grassroots connection to their company than Kacie Jester. 

Her journey with School Pathways began in high school, when she and her mom were paid per page to digitize curriculum for the company’s founders. In college, she cleaned the offices once a week, and, years later, Kacie returned as an account manager. 

Kacie steadily advanced through customer-facing roles, eventually becoming Director of Customer Success. After the company was acquired, Kacie took on more responsibilities, which would eventually prepare her for leading the company as its CEO. 

“Looking back, I can see that Oliver was mentoring me before I even realized it,” Kacie recalls. “He pulled me into sales calls, budget conversations, and strategic planning. He was establishing those building blocks with me, so by the time this opportunity came up, I was ready to hit the ground running.”

As the CEO of School Pathways and Aequitas, Kacie brings a people-first leadership style rooted in empathy, open dialogue, and collaborative decision-making.

“I didn’t come back to School Pathways thinking I’d become CEO one day. But every step of my journey, from working as an account manager to leading customer success, helped me understand our customer base and how schools, districts, and superintendents approach their EdTech decisions. That experience has truly prepared me for this role.”

Kacie’s path to leadership came full circle when she got to share the news with Amy Gruber, School Pathways’ co-founder and her longtime mentor, shortly before Amy’s passing. 

“It was a great moment, finally getting to tell her.” Kacie said. “She was my hype person, always telling me ‘You can do this.’ She believed I would lead one day.” 

Kacie is focused on School Pathways and Aequitas expanding their reach in K-12, exploring thoughtful innovation driven by AI. She’s committed to building, and maintaining, strong culture in a remote-first world, ensuring that connection, trust, and momentum thrive across both organizations

Their leadership ensures we can keep supporting the people and platforms that help students and educators do their best work, now and in the years ahead.