🎧 The Education Equation: Dr. Janice Jackson on Scaling Solutions

On this episode of The Education Equation, host Jeremy Singer speaks with Dr. Janice Jackson, former CEO of Chicago Public Schools (CPS) and Executive Director of the Aspen Institute's Education and Society Program.

Dr. Jackson, a CPS alumna, discusses her journey leading one of the nation’s largest school districts. She notes that her time as a principal provided the best preparation for the superintendency. Under her leadership, CPS boosted its graduation rate from 55.8% in 2010 to 82.5% in 2020. This dramatic turnaround was driven by intentional work, including making students take a college entrance exam to graduate and implementing the Freshmen on Track system, which was informed by data from the University of Chicago Consortium on School Research. This success was built on data transparency, accountability, principal empowerment, and strong public-private partnerships.

The conversation moves to Hope Chicago, the two-generation debt-free scholarship model she founded. Hope Chicago provides debt-free support (tuition, books, fees, and a stipend) to students from neighborhood high schools. By reducing financial risk, the model has significantly increased matriculation rates from about 57% to about 85% today. First-year persistence also increased from 61% to about 75%, demonstrating that removing debt and providing one-on-one support boosts college success.

Now at the Aspen Institute, Dr. Jackson is exploring the future of student outcomes on a national level. She emphasizes the need for leadership to address major challenges like economic preparedness, the impact of AI and EdTech, and the rise of alternative schooling models. Her goal is to translate her lessons from Chicago to a national context, advocating for a return to non-political accountability to ensure every child can succeed.

Dr. Jackson's education book recommendation: "It's Being Done": Academic Success in Unexpected Schools

Key Takeaways:

- Principal Power: The principalship is the single best leverage point for large district change.

- Data-Driven Turnaround: CPS used the "Freshmen on Track" indicator to drive a dramatic increase in its graduation rate from 55.8% to 82.5%.

- The Affordability Barrier: Hope Chicago's debt-free scholarship model significantly increases college matriculation and persistence rates for low-income students by eliminating financial risk.

- National Education Gaps: At Aspen, Dr. Jackson is focusing on creating a new course for education that addresses economic preparedness, AI integration, and the regulation of alternative schooling models.

Why You Should Listen:

Dr. Jackson offers a rare perspective, having led one of the country's largest school districts through a period of significant positive change. Her work provides clear, data-backed examples of how systemic improvements can be achieved. Listen for her insights on transforming a large school system and why her work now focuses on setting a new, accountable course for American education.

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Time Stamps

[00:00:54] Introduction to Dr. Janice Jackson's background

[00:05:37] The principalship as the best preparation for CEO

[00:14:15] Achieving CPS’s historic graduation rate increase

[00:29:21] Launching and scaling Hope Chicago

[00:36:06] Setting a new course at the Aspen Institute

In this special live episode, Jeremy Singer interviews Liz Cohen, author and VP of Policy at 50Can, as part of the College Board Forum 2025. Cohen, an expert in K-12 education, discusses her new book, The Future of Tutoring: Lessons from 10.000 School District Tutoring Initiative. She argues convincingly that tutoring is one of the few interventions with clear evidence of improving educational outcomes.

The conversation explores how the COVID-19 pandemic and federal ESSER funds created a unique opportunity for the research and scaling of tutoring, which Cohen refers to as an "accidental experiment". By May 2023, 80% of U.S. school districts were offering some form of tutoring. Cohen shares data on significant academic gains from initiatives in places like Washington D.C. and Guilford County, North Carolina.

Key Takeaways:

Defining High-Impact Tutoring (HIT): Effective elements include tutoring at least three times a week for a minimum of 30 minutes, a student-to-adult ratio of no more than 4:1 (ideal), and the use of a consistent tutor.

Virtual vs. In-Person: The data shows that the modality—virtual or in-person—does not significantly impact outcomes, and virtual tutoring increases access and flexibility.

The Power of Embedding and Alignment: Success is enhanced by integrating tutoring into the regular school day (often via an intervention block) to reduce student stigma, and by aligning the tutoring with the core curriculum.

AI’s Role: Cohen is optimistic about AI's potential to reduce costs and enhance human tutoring, for example, by creating "AI tutor coaches" to provide instant guidance and eliminate the "learning curve" for new tutors.

Navigating Cost and Scale: The discussion addresses how to sustain costly HIT programs after ESSER funds expire, exploring solutions like outcomes-based contracts and increased efficiency.

Why You Should Listen:

Liz Cohen’s insights provide a blueprint for education leaders seeking to implement proven, scalable interventions. She argues that the successful adoption and scaling of tutoring demonstrates the education system can embrace big, hard changes. The episode concludes with thoughtful questions from the live audience on tutor preparation, combating student stigma, and measuring the return on investment by reducing future remediation costs.

Liz’s education book recommendation: The End of Education: Redefining the Value of School by Neil Postman.

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Timestamps:

03:18 The Impact of COVID on Education

06:11 The History and Evolution of Tutoring

13:09 High Impact Tutoring Defined

19:07 Success Stories and Data Insights

20:04 Embedding Tutoring in School Schedules

26:40 Strategies to Reduce Tutoring Costs

31:43 The Role of AI in Tutoring

37:47 Rapid Fire Questions and Audience Q&A

A Reimagined Internship with Dan Gonzalez

Welcome to the Education Equation, a new podcast focused on what the evidence says actually moves the needle in education. In this episode,Jeremy Singer talks with Dan Gonzalez, co-founder and co-CEO of District C, a national nonprofit reimagining the internship experience. Dan's career spans engineering, the classroom, and corporate leadership,

In 2016, Dan and his wife, Ann Jones, launched District C to address a crucial gap between academic learning and the collaborative skills students need for the modern workforce. Their solution, called Teamship, offers a new internship model where student teams solve real-world problems for real businesses.

Referenced in the Episode:

Dan C talking about the "3-point economy" - https://www.districtc.co/point-of-view/

Dan’s Education Book: Savage Inequalities by Jonathan Kozol: https://www.amazon.com/Savage-Inequalities-Children-Americas-Schools/dp/0060974990

Finding Purpose: Dan explains how he found purpose in the "unlikeliest of places"—a crisis at Manhattan Prep—where a team rallied together to protect the company they had built after a major security breach. This experience taught him the importance of a common purpose in professional life.

The Problem with Traditional Education: Dan argues that the education system often prepares "two-point players" for a "three-point economy" by focusing on individual achievement rather than essential collaborative and problem-solving skills. Teamship aims to develop these "three-point skills" that are valued by every employer.

Teamship's Model: The Teamship program involves teams of three to four students who work on a real business problem over four to six weeks. The time commitment for the business partner is intentionally light—just five hours total—with an educator trained by District C serving as the coach. Dan provides examples of typical projects, which fall into categories such as operations, marketing, or human resources.

Challenges of Scaling: The biggest challenge for scaling District C is getting school districts to adopt the program, as it doesn't have an existing "vessel" or a specific class where it easily fits. Dan hopes to solve this by creating a dedicated space for this type of programming within the school day.

This episode is a must-listen for anyone interested in the future of education and workforce development. Dan Gonzalez offers a compelling look at how to bridge the gap between classroom learning and the skills students need to succeed in the real world. He discusses the benefits of Teamship, the power of a shared purpose, the challenges of scaling educational innovation, and the importance of preparing the next generation with essential collaborative skills.

If you enjoyed this episode, be sure to subscribe to the Education Equation podcast wherever you listen to podcasts. Visit us at ⁠TheEducationEquation.org ⁠for more.

Jeremy Singer shares why we're starting The Education Equation and what you can expect in upcoming episodes as we kick things off!

Be sure to like and Follow The Education Equation with Jeremy Singer wherever you get your podcasts.

Education Innovations and The Charter School Impact

In this episode, Jeremy talks with Jim Manly, Chief Schools Officer at the KIPP Foundation, about his over 30-year career in education, his insights on charter schools, and his vision for the future of learning. 

Jim's career spans more than 30 years and includes roles as a teacher, school leader, and system leader at innovative organizations like Teach for America and Success Academy. Jim shares his journey from a struggling teacher to a founding principal of Success Academy Harlem Two, where the school became the top-performing school in its district. 

In talking about evidence of KIPP and charter school impact he highlights this CREDO study: https://ncss3.stanford.edu/wp-content/uploads/2023/06/Credo-NCSS3-Report.pdf 

His favorite Education book: Why Don't Students Like School? by Daniel Willingham

Key Takeaways:

> The Power of High Expectations: we discuss how Success Academy’s early success was driven by an "unwillingness to listen to old conceits of what necessarily had to happen in public schools." Jim notes that when they challenged the notion that students couldn't handle a rigorous curriculum, the kids responded with curiosity and eagerness. He learned that it was the adults, not the students, who were holding back academic achievement.

> The Importance of Systems in Education: Jim highlights the shift at KIPP from relying on individual, dynamic school leaders to implementing strong, consistent systems. Jim explains that the COVID-19 pandemic made it clear that a lack of robust systems meant new staff didn't have the necessary tools to succeed when faced with a major disruption. KIPP's new strategy includes academic progress meetings and a specific coaching model that focuses on intellectual preparation, real-time feedback, and analyzing student work.

> AI's Role in the Classroom: While skeptical of past educational innovations, Jim sees tremendous potential for AI as a productivity tool for teachers. He believes AI can handle tasks like grading papers, freeing up teachers to spend more time working directly with students. This shift allows teachers to focus on "the human relationship" and "real time coaching and feedback," which is where true learning happens.

> A "Devastating Loss of Conversation": Jim laments the current state of education policy, noting that despite proven successes in charter school networks like KIPP, Success Academy, and Uncommon Schools, these models are not being adopted more widely. He believes that we know the answers to improving schools, and the failure to implement them at a larger scale is a "giant win for our country" that is being missed.

Why You Should Listen:

This conversation offers a rare, behind-the-scenes look at the high-stakes world of charter schools and the philosophies that drive their success. Jim provides candid insights into the challenges and opportunities of scaling educational excellence and explains why a focus on foundational skills and data-driven instruction is critical for student success. Jeremy and Jim also delve into criticisms of charter schools.

Don’t miss an episode! Subscribe to The Education Equation with Jeremy Singer wherever you listen to podcasts. Visit us at TheEducationEquation.org for more.

Transforming Education: AI in the Classroom with Dacia Toll

In this episode of The Education Equation, host Jeremy Singer talks with Dacia Toll, the co-founder and co-CEO of Coursemojo, an AI-powered teaching assistant platform. Dacia is also the co-founder of Achievement First, a prominent charter school network with around 40 schools across the Northeast. The discussion focuses on how Coursemojo addresses two critical challenges in education: reading achievement and teacher retention.

Toll explains that the reading data for eighth graders is at a 30-year low, which she describes as a "national emergency." She also emphasizes the urgent need to make teaching a profession that more people want to join and remain in. Coursemojo tackles these issues by making the core English Language Arts (ELA) instruction that teachers are already doing more effective, engaging, and easier. Unlike many other EdTech products, Coursemojo is not a supplemental tool; it integrates directly with schools' existing instructional materials.

Coursemojo’s research referenced in the conversation is available here: https://coursemojo.com/research/

Dacia’s favorite education book is Know Better, Do Better by Meredith and David Liben 

Key Takeaways:

> A New Approach to EdTech: Coursemojo is an AI-powered teaching assistant platform that integrates with a school's existing curriculum rather than being a supplemental product. This approach helps teachers do what they already do more efficiently.

> The Power of AI: The AI frees educators from the limitations of multiple-choice questions, allowing for open-ended questions and the instant analysis of vast amounts of unstructured data. The AI is used to categorize student responses and develop criteria for each question.

> Real-Time Data for Teachers: The platform provides a live dashboard that shows teachers a real-time view of student understanding for every question, enabling them to offer more strategic and effective support. It also identifies the two most common class misconceptions and suggests discussion questions.

> Evidence of Impact: Pilot programs in Texas and Tennessee show that Coursemojo contributes to substantial gains in middle school reading achievement. In Aldine ISD, schools using Coursemojo saw an additional six percentage points in reading gains, while in Sumner County, students using the product had an eight percentage point gain.

> Focus on Foundational Skills: Coursemojo helps students move beyond basic reading skills to think critically about texts and understand complex ideas. It encourages kids to do more thinking, reading, and writing.

> Balancing Pedagogy and Engagement: The product combines an intentional instructional approach with subtle gamification and social elements to keep students engaged and motivated.

Why You Should Listen:

This episode offers a fascinating look at how AI is being used to address some of education's most pressing challenges. It provides a hopeful and realistic perspective on the role of technology in the classroom, emphasizing the importance of a human-centered, values-driven approach. You will learn about a tool that is not just promising but is already showing significant, measurable impact on student outcomes and teacher experience.

We're just getting started! Be sure to subscribe wherever you listen to podcasts so you never miss an episode. Visit us at ⁠TheEducationEquation.org ⁠for more.

The People Systems Behind Educational Change

In this episode, host Jeremy Singer speaks with Sari Factor, Vice Chairman and Chief Strategy Officer at ⁠Imagine Learning⁠, a company dedicated to providing high-quality educational experiences. Factor, who began her career as a math teacher, has over 40 years of experience in the education sector and has held leadership positions at major companies such as Kaplan, McGraw Hill, and Houghton Mifflin.

Sari and Jeremy discuss the significant challenges of implementing change in K–12 education, which Factor describes as "people systems" that are inherently difficult to change. The conversation also touches on the sobering results from the National Assessment of Educational Progress (NAEP), which showed a widening performance gap in both math and reading. Factor shares her insights from ⁠a Forbes piece she wrote in Marc⁠h, where she advocated for rethinking K–12 curricula to improve student outcomes. They also delve into the effectiveness of knowledge-based literacy programs and problem-based math curricula, and the challenges of getting them implemented successfully.

Here’s the link to the research referenced in the episode: https://www.imaginelearning.com/research-library/

Sari mentions that her favorite education book is Disrupting Class by Clay Christensen.

Key Takeaways:

> Curriculum and Pedagogy: Knowledge-building literacy and problem-based mathematics programs are effective because they are based on the evidence that people learn by making connections to what they already know.

> The Challenge of Change: Schools are "people systems" and are difficult to change due to factors like the short tenure of school leaders and high teacher turnover rates. Implementing new curricula can be overwhelming for educators, especially seasoned ones, as it asks them to change their practice.

> The Role of Teachers: Effective educational programs position teachers as facilitators and modelers rather than deliverers of instruction. The learning happens more through student inquiry and peer collaboration.

> The Promise of AI: Artificial intelligence can help reduce teachers' time-consuming tasks, like grading short writing assignments or drafting communications to parents, freeing them up to build more meaningful relationships with students.

> Looking Forward: Factor is hopeful that parental engagement and the school choice movement will drive innovation in education. She also believes AI will enable schools to move beyond traditional assessments and focus more on evaluating students' growth in durable skills like communication, resilience, and problem-solving.

Why You Should Listen:

This episode is for anyone interested in the real-world complexities of education reform. Whether you're a teacher, a school leader, a parent, or simply a curious listener, Sari Factor’s depth of experience provides a clear-eyed view of what works and what doesn't. She offers valuable insights into the "why behind the what" of curriculum design and implementation , highlighting how strong leadership and a focus on evidence can lead to positive change, as seen in the Philadelphia School District and Los Angeles Unified. Factor also shares a compelling personal anecdote about her time at McGraw Hill, demonstrating the courage required to make difficult decisions for long-term success.

We're just getting started! Be sure to subscribe wherever you listen to podcasts so you never miss an episode. Visit us at ⁠TheEducationEquation.org ⁠for more.