For Teacher Transactions, The Devil’s in the Details

Jamie Rosenberg knew that getting funding to teachers and schools and tracking it, was much harder than it should be. Here’s what he did about it.  

INTERVIEW | by Victor Rivero

No stranger to education technology, Jamie Rosenberg has launched two successful technology companies in the space. His journey from mergers and acquisitions lawyer to social entrepreneur is a living example of how one person can change the world. He is the Founder and CEO of ClassWallet, a leading funds management and tracking platform for school systems which boasts some of the largest organizations in the country as customers; it is a platform transforming how education dollars are spent providing more accountability and transparency.

Jamie’s first company,, which he launched in 1998, is one of the first crowd funding sites on the Internet, and the first national online platform for education philanthropy. Through, Jamie partnered donors with classrooms raising over $25M for teachers in 30% of schools in America, and improving the learning environment for 3.5M students.

Jamie (pictured with ClassWallet team, above left) has been featured in numerous publications such as Time and Parade magazines, and newspapers across the country. CBS aired a national program hosted by Vanessa Williams about Jamie’s accomplishments in 2013. He has been a featured speaker or panelist for the Future of Education Finance Summit, Education Industry Association, ASU GSV Conference, Florida International University Center for Social Entrepreneurship, National PTA Conference, National School Boards Association Conference, and Social Venture Capital/Social Enterprise Conference.

“Teachers don’t have the time to manage cash, checks, receipts and forms,” says Jamie. What his platform does is streamlines manual, time-intensive tasks of collecting receipts, reconciling invoices, and making vendor and reimbursement payments by digitizing and automating those processes for you.

“School district and school administrators, education foundations, and PTAs spend a ridiculous amount of time reconciling paperwork and receipts even for the smallest of transactions, and stress about the audit each year,” he says.

“The understanding and obsession with solving this problem is what makes us tick. We know that if we can simplify the incredibly frustrating process of solving for classroom needs, our students will be smarter, and administrators and teachers will all be happier.”

What is your view about the role of technology in education these days?

Jamie: These days technology allows for many things. Where we see it shine is in allowing processes (such as requesting supplies for teachers) to be streamlined and automated.  Educators can then focus on teaching, and what matters instead of wasting time with purchase orders and bureaucratic red tape that can tie educators’ hands.

Up to 50% of teachers leave the profession after five years.  With a 50% churn, what is the cost of training?

Jamie: We hear from schools that retention is all about a culture that supports teachers.  When you feel like a lone soldier fighting the battle alone, without the support that you need, you leave the profession.  I have seen statistics that show the cost of a teacher leaving is as high as $17,000 to the district.

What makes you say that?

Jamie: We recently sat down with teachers, administrators, and district administrators for a Florida Association of School Administrators Focus Group on Teacher Recruitment, Retention, and Absenteeism.  The Focus Group confirmed what is happening nationwide in education. Teachers are fed up with trying to educate the nation’s children with little support and adequate resources to succeed in the classroom.  There is increasing dissatisfaction with working conditions and feelings of lack of support.

What do you believe is the state of education today? 

Jamie: Teachers no longer see the profession as a long-term career choice.  Millennials make up the largest percentage of teachers, yet only 6% of superintendents even understand the needs of millennial teachers according to the latest Gallup poll.  Teachers in five states have walked out of classrooms to protest and strike against the current condition. We need to work to reverse the trend of teacher churn. Teachers want more autonomy and trust and need to easily be able to get the resources that they need to be successful in their classrooms.

Could you address the idea that teachers are paying out of their pockets, that they are personally spending out of their own goodness, but that this is not an ideal scenario – you know, that whole issue?

Jamie: The average teachers spend $600 out of pocket per year.  They are tired of trying to educate students with outdated teaching materials, low teacher pay and poorly funded systems.  They have turned to crowdfunding to try to raise funds that they need for the classroom as well as protesting the current situation.

Switching gears, you raised 30 million dollars for teachers through your first company Adopt-A-Classroom and saw what educators need is the help to get the supplies that they need quicker and with less bureaucratic red tape. How does ClassWallet address this problem?

Jamie: Much of the reason teachers spend their own money is that it’s just easier. There is so much red tape to make any purchase happen within the district processes, teachers would rather do it themselves. Imagine that, the process is so painful, teachers would rather spend their own money.  ClassWallet removes all that pain, makes it very easy for teachers to access district funds and therefore are much less inclined to dig into their pockets.

ClassWallet is in 74,000 classrooms and works with some of the largest school districts in the country. Through this work, what have you learned?

Jamie: ClassWallet allows districts to delegate individual classroom budgets to teachers, allowing for hassle-free reimbursements and online shopping with business login credentials to stores like Amazon, Staples, Scholastic, Home Depot, School Specialty, Really Good Stuff and dozens more.  Teachers reimbursement direct deposit or goods delivered in their name directly to the school in days.

What we have learned is that while change can be difficult, digital processes indeed can improve processes for teachers.  A recent survey we conducted supported this fact. 83% of 9,253 teachers said that having real-time access to their balance and spending reports is useful.  70% of the 9,253 teachers said that ClassWallet is easier and quicker than other processes the district requires for similar tasks.

So how can the finance office help to empower teachers through decentralizing procurement with individual classroom budgets?

Jamie: School leadership needs to empower teachers to make their own purchasing decisions.  One is hard-pressed to find schools where teachers are trusted enough to make instructional or purchasing decisions.  When school districts invest in trust and teacher agency teachers are empowered. Schools enhance morale, improve working conditions, increase teacher retention, and attract the best new teachers, thus improving student achievement.

If you had one message you could pass on to all school districts at once what would it be?

Jamie: The status quo is unsustainable. School districts have to give teachers more autonomy to get the resources quickly and nimbly so students get what they need when they need it, not weeks or months later.

Victor Rivero is the Editor-in-Chief of EdTech Digest. Write to:


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