Executive Leadership

Imagine Learning leaders are driven and united by a commitment to empower educators to make student success possible.

jonathan grayer

Jonathan Grayer

Chairman and Chief Executive Officer

Empowering educators with digital curriculum to achieve better student learning outcomes — that’s Jonathan’s vision and the heart of his work at Imagine Learning. He founded the company in 2011 with the purchase of e2020, and it is now the largest digital curriculum provider to K–12 schools in the U.S., serving over 15 million students. The power of data-driven personalization helps teachers better tailor their lessons and lets parents and administrators better understand student progress.

In 2016, Jonathan established the Grayer Family Foundation, whose mission is to help underserved young people gain access to better education, housing, and nutrition. The Foundation has given millions of dollars to social entrepreneurs making the world a better place. In 2022, he founded the Imagine Learning Foundation, created with one principal goal: to foster the well-being of learners and the people who support them at home and in their communities. In addition, he serves on the board of the Memorial Sloan-Kettering Cancer Center, where he is the Chair of the Patient Care Committee.  

Prior to Imagine Learning, Jonathan was Chairman and CEO of Kaplan, Inc., the largest division of the company formerly named the Washington Post Company. He transformed it from an $80 million test preparation business into a $2.3 billion global higher education and professional training leader, supporting learners in pursuit of their academic and career goals.

Jonathan holds an AB and MBA from Harvard University.

Andy Caulo

Executive Vice President & Chief Revenue Officer

Andy is an educational sales leader who develops strong, respectful customer relationships and works to provide the highest quality products and services to meet the needs of districts and schools across the nation. His confident and collaborative management style supports and motivates his Imagine Learning sales team, known for their professionalism and focus on customer success. “Our sales team takes great pride in providing excellent service to educators across the country so that they, in turn, can better serve their students.”

Before joining Imagine Learning in 2008, he worked with Simon and Schuster, Macmillan/McGraw-Hill, and Compass Learning.

andy caulo
Sari Factor

Sari Factor

Vice Chairman and Chief Strategy Officer

Sari began her career as a mathematics teacher but soon thought of much bigger ways to impact students. Recognizing that technology could greatly transform the way students learn, she made a career move into education technology and has been working to leverage technology to help students, teachers, schools, and districts ever since.

Sari joined Imagine Learning in 2011 and has held leadership positions at successful educational publishing and learning technology companies, including Kaplan, McGraw-Hill, Houghton Mifflin, and Everyday Learning Corporation. “I knew that I could fulfill my vision to combine technology with research on learning to make education truly student-centered.” 

John Orsanic

Chief Financial Officer

John brings a wealth of financial expertise to Imagine Learning, having most recently served as the CFO at Fandango, part of NBC Universal, and previously in a series of financial leadership roles at iHeartMedia + Entertainment, and General Electric. He has been responsible for financial planning, asset valuation, M&A, controllership, and financial reporting functions for domestic and international units. Over the last 10 years, John has played key roles in growing digital-first companies to market-leading results.

At Imagine Learning, John is committed to advancing our mission by ensuring financial sustainability and fostering growth opportunities.  “I’m thrilled to join Imagine Learning at such a pivotal point in the industry and for the business, with investments in AI and digital-first curriculum, which have the potential to transform teaching and learning, empowering educators with world-class digital solutions to personalize instruction and improve learning outcomes for every student.”

chris graham
chris graham

Chris Graham

Senior Vice President and General Counsel

Chris is a business lawyer with over 20 years of corporate and transactional experience. As a partner at Verrill Dana, a leading regional law firm, he advised private equity funds and their portfolio companies, including Imagine Learning. Inspired by our commitment to positively impact the future of K–12 education, Chris joined the Imagine Learning team in 2020.

Chris also served for 5 years as General Counsel of a publicly traded technology company where he managed the company’s legal function. Through his involvement with the Connecticut Veterans Legal Center, he has worked on the pro bono representation of veterans.

Michael Humphrey

Executive Vice President, Government Relations

Michael is a veteran of the K–12 industry with over 30 years in the business. He works closely with advocates across the United States to ensure adequate funding for education. 

Michael’s experience outside of education is valuable to Imagine Learning: “Being able to look at something from another perspective can be beneficial… it allows me to see opportunities that may otherwise be overlooked. Sometimes that sparks a transformation, not unlike what our company is doing now with technology and curriculum.”

Before joining Imagine Learning in 2010, he worked for broadcast.com, Yahoo!, Simon and Schuster, and Compass Learning.

mike humphrey
Adam Klaber

Adam Klaber

Vice Chairman and Chief Operating Officer

Adam joined Imagine Learning in 2013, initially to focus on how to use technology to enhance our products and keep our operations running smoothly and efficiently. He led our Performance Matters business which was sold to PowerSchool in 2018. “It is so exciting to explore the ways in which we can advance education with enhanced technologies.”

Before joining the Imagine Learning team, he was a former General Manager at IBM and Senior Partner at PwC Consulting. At I.B.M., he held several senior executive roles, including creating and leading the CRM, Business Analytics and Optimization team as well as leading services in Latin America and Southwest Europe. 

Gautam Parasnis

Executive Vice President and Chief Digital Officer

Gautam’s expertise is in leadership, technology, and customer relationships. He supports Imagine Learning in using technology to transform our products, operations, and customer experience. “When we incorporate technology meaningfully into classrooms, it is remarkable to see the difference in student engagement and outcomes.”

Before joining Imagine Learning in 2014, Gautam was a consulting partner at PricewaterhouseCoopers and I.B.M.’s Global Business Services.  At I.B.M., Gautam held several senior leadership roles, including being the Global Leader of the Customer Relationship Management practice for their consulting business and the Growth Markets Unit Practice Leader for their Oracle business.

gautam parasnis
kinsey rawe

Kinsey Rawe

Senior Vice President & General Manager, Courseware & Instructional Services

Kinsey found his way into online education after developing a learning management system for a financial services company. As he began working in K–12 education, he soon recognized that the tools and technology being developed overlooked a crucial stakeholder in the learning process — teachers. Kinsey promptly began work on an instructional model that leveraged data and features to help teachers become more efficient, effective, and comfortable with online instruction. The response was overwhelming. “When I rolled it out to a group of educators, they said I had given them a ‘magic button’, and actually gave me a standing ovation”, he recalls.

Now, at Imagine Learning, Kinsey continues his passion for creating solutions that make a difference in the day-to-day lives of educators and students.

Leslie Curtis

Chief Experience Officer

A veteran of technology marketing, Leslie was drawn to Imagine Learning by the opportunity to make a real difference within the education industry. “Each day, I am overjoyed to see first-hand how Imagine Learning has helped inspire positive change for teachers, students, and families across the nation.”

Before joining the Imagine Learning team, Leslie spent her career building and invigorating brands, launching products, developing innovative marketing models, and helping to drive growth at Texas Instruments and Dell. As Corporate V.P. of Worldwide Marketing at AMD, Leslie led marketing for their mobile, desktop, and server products.

waseem alam

Waseem Alam

Senior Vice President & Chief Corporate Development Officer

Waseem joined Imagine Learning in 2015 to help identify and acquire the most innovative education technology solutions. “Our goal is to help make the lives of students, parents, teachers and administrators easier with the most impactful and innovative education technology products in the market.”

Previously, Waseem spent several years in various consulting and education strategy roles.

Senior Leadership Team

 nathalie baillet

Nathalie Baillet

Vice President of Financial Planning and Analysis

Nathalie’s 20 years of global experience in healthcare and online media industries, complemented by her Executive MBA, have helped her nurture cross-functional teams that operate strategically and successfully. Nathalie joined Imagine Learning in 2020 and has held managerial positions at various healthcare and online media companies, including IAC, AOL, and Urgo (Paris).

“I am proud to be part of a team that creates value through data insights to empower all of Imagine Learning’s teams in their mission to deliver best-in-class products to students and teachers every day.”

tom dewitt

Tom DeWitt

Senior Vice President, Sales

With more than 25 years of experience in K–12 education sales, Tom brings his expertise in strategic planning, territory and key account management, and revenue growth to the Imagine Learning team. “My goal is to consistently exceed performance and revenue goals by aligning talents and effort with organizational objectives.”  

Tom previously worked at several start-ups and McGraw-Hill, where he transformed their business model from print sales to a subscription-based license. He also successfully brought StudySync to the California ELA market. 

todd ellermann

Todd Ellermann

Senior Vice President, Product Engineering

As a college student, Todd founded a service organization that expanded internet access to small businesses and his alma mater, University of Arizona. He went on to develop a web-based distance learning application for the U.S. Department of Transportation, and eventually became the Director of IT and Web Development at Lynda.com (now LinkedIn Learning).

Todd brings the same grit he had as a student, along with a wealth of software engineering, data science, and technology management experience to Imagine Learning. “Creating new programs for educators is an opportunity I take seriously as we imagine the future of learning.”

terry gilligan

Terry Gilligan

Senior Vice President and General Manager, Core Curriculum

With over 25 years of experience in K–12 publishing, Terry’s work gives him a clear understanding of Imagine Learning’s role as a core curriculum provider. “We are entering into a long-term partnership with school districts,” said Terry, “impacting their teachers and students daily. Our technology, materials, and services must meet the diverse needs of districts from the beginning and effectively adapt during the life of our partnership. We take that responsibility very seriously.”

Terry joined Imagine Learning in 2019 through the acquisition of LearnZillion. Earlier in his career, Terry held sales and sales management roles at Scholastic, followed by various responsibilities at leading education technology start-ups.

Elizabeth Lehnertz

Elizabeth Lehnertz

Vice President, Marketing

Elizabeth brings over 25 years of experience in education, first as a classroom teacher in Texas before moving into educational publishing and technology. She has held leadership roles in product marketing, product management, and corporate marketing at Pearson, Renaissance Learning, and McGraw-Hill.

With the passion to improve education for teachers, students, and families alike, Elizabeth brings the insight and experience to build and lead industry-leading teams to solve complex problems in a dynamic market.

deb rayow

Deborah Rayow

Vice President of Product Management, Courseware

Deborah began her career as a fifth-grade teacher. After several years in the classroom, she shifted to curriculum planning and professional development, eventually focusing on e-learning, instructional design, and product development. “Imagine Learning provides me an opportunity to apply the best of learning science with innovative digital platforms for a transformative educational experience for teachers and students.”

Deborah’s expertise was honed while working with some of the most recognizable names in education including Kaplan and Scholastic.

robert romano

Carin Casso Reinhardt 

Chief People Officer 

Carin leads Imagine Learning’s people strategy and HR team in their efforts to attract, develop, engage, and reward our 3000+ employees. “I’m focused on finding the right talent, transforming culture, and streamlining processes to support our growth objectives and organizational success.” 

Carin brings 20 years of experience in best-in-class HR programming and systems across the U.S. and globally. Previously, she was VP of HR and Labor Relations for ASRC Federal Holding Company, Chief HR Officer for the National Renewable Energy Laboratory, and the EVP, Global Chief People Officer at NewAge, Inc. She enjoys community volunteer work in Denver, CO and serves as an executive board member for several organizations, including Spawn Ideas.

robert romano

Dr. Kimberlin Rivers

Vice President of Instruction, Instructional Services

Over the last ten years at Imagine Learning, Dr. Rivers has successfully grown a dynamic team of high-quality, virtual educators who serve over 100,000 K–12 students nationwide. “Diversity, equity, inclusion, and belonging are an essential part of our culture and how we do work at Imagine Learning. Our teacher-powered technology and curriculum help educators systematize practices to consistently promote access and equity to all learners, any day, anytime, and anywhere.”

Dr. Rivers brings more than 25 years of management experience in both public and private education sectors, in addition to international transport and logistical operations management. Her passion for employee and leadership development resonates throughout her career.

robert romano

Robert Romano

Chief Executive Officer, StudySync

Robert’s passion for taking new ideas from dreams to reality brings entrepreneurial excitement to the Imagine Learning team. His vision and curiosity about “what’s next” help us create student-centered digital learning experiences. “I am excited to work as part of the talented team at Imagine Learning to create new programs that will help shape and define the future of learning.”

Prior to Imagine Learning, Robert combined his love of literature with a formal education in engineering to create StudySync, a market-leading English language arts curriculum.

kelly staniec

Kelly Staniec

Vice President & Controller

Kelly brings over 30 years of experience in accounting with both public and private companies in the real estate, health care, and technology industries. She joined Imagine Learning in 2013 and established the scalable accounting infrastructure that has successfully navigated our growth.

“As Imagine Learning continues to grow in its outstanding service to K–12 educators and students, our team is dedicated to operational excellence in support of our business.”

Natasha Stillwell

Natasha Stillwell

President of Imagine Learning Studios UK 

Drawing on her background as a science journalist and TV producer, Natasha believes that storytelling, real-world connections, and student-centered learning are powerful tools to engage students and deepen their knowledge. “I encourage my team to really think hard about what the student is going to find interesting about the idea they’re exploring and to build on that point of connection, making learning meaningful, memorable, and magical.”

Before leading the team at Imagine Learning Studios UK, Natasha was the creative force behind the ground-breaking science program, Twig Science.

marcia wilson

Marcia Willson

Senior Vice President, Sales

Marcia is an education veteran, with over 25 years in the industry, building strong and collaborative sales teams with a focus on helping districts leverage technology to maximize student learning. “I am so excited to be able to help widen the reach of Imagine Learning’s innovative digital curricula — every student deserves access to a world-class education.”

Marcia’s career prior to Imagine Learning includes classroom teaching, educational publishing, education technology, and most recently, sales and leadership roles at EMG Networks, Jostens Learning, and Compass Learning.