Winward Academy Founder Named a Top 50 Most Influential Business Leader


Winward Academy Founder Named a Top 50 Most Influential Business Leader in San Diego

Dr. Jennifer Winward, the founder of Winward Academy, has been honored as the city’s most influential education leader by the San Diego Daily Transcript.

After privately tutoring students from San Diego’s finest private schools for twenty years, Dr. Winward wanted to find a way to support more students’ academic and professional success. As founder and CEO of Winward Academy, Dr. Winward serves the San Diego community by changing the trajectory of the lives of all students.

“I want the same resource typically only available to students who live in more affluent neighborhoods to also be available to students whose families have fewer resources,” shared Dr. Winward. “That mission drives our one-for-one charitable program. For every program sold, we donate one to a deserving student. If a student at an elite private school uses Winward Academy to grow his ACT score by over 7 points, on average, then a student at an urban public school should have that same opportunity to grow her score by 7 points or more. We see time and time again in schools across America that it is neither demographics nor geography that determines a student’s probability of success. When presented with the same opportunity and tools, it is a student’s attitude when using Winward Academy that is the leading indicator of future long-term success.”

The drive to bridge the opportunity gap is central to Dr. Winward’s mission to promote education equity in San Diego and beyond. Helping all students, including underrepresented youth, grow their test scores and confidence has a positive multi-generational impact, one that also inspires younger siblings and entire communities. Dr. Winward’s ultimate goal is that all students who use Winward Academy, no matter their zip codes, gain the skills and content knowledge that develop a passion for life-long learning, build confidence, and contribute to continued academic, professional, and personal success.

To achieve this philanthropic mission, Dr. Winward seeks out and nurtures partnerships with local community groups and after-school programs including Barrio Logan College Institute, Price Philanthropies, Promises 2 Kids, and Ronald McDonald House Charities. “At Winward Academy, we want to support amazing programs that serve youth facing challenges of frequent moves, illness, foster care, trauma, and poverty by contributing to their missions to transform students’ academic and professional development,” shared Dr. Winward.

Underserved students who receive access to Winward Academy are 3.5x more likely to be college ready in English, 4.0x more likely in Math, 3.6x more likely in Reading, and 4.0x more likely in Science. “These drastic increases open doors to college and full-ride scholarships that would never be possible otherwise,” shared Barbara Ybarra, Chief Advancement Officer at Barrio Logan College Institute. “Our students LOVE using Winward Academy and are so appreciative to have access to the same resources typically reserved for their peers from higher earning families.”


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About Winward Academy – Winward Academy is one of the world’s leading innovators in the online education space, providing web-based academic support that enhances students’ knowledge, confidence, and competitiveness in middle and high school academics and in college applications. We help thousands of students every year by providing personalized, comprehensive ACT and SAT test preparation and extensive math curriculum support. The Winward Academy learning platform honors over 40 years of education and cognitive psychology research, incorporating proven techniques that promote effective learning.

Winward Academy’s unmatched reputation is wholly attributable to our students’ exceptional success and to the trust earned among students, parents, and schools around the world.

Willy Avery

As the Founder and CEO of Avery Ventures, Mr. Avery provides invaluable consultation on all matters pertaining to the growth and future success of businesses. He earned his B.S. in Business Administration and Management with an emphasis in Entrepreneurial Studies from the Marshall School at University of Southern California (USC). He was invited to join the Alpha Lambda Delta National Honor Society at USC and is frequently called the Wizard of the Impossible by his clients.