Q&A with Rita Chesterton, co-founder and CEO of Skaffl

EdTech Times had the privilege of speaking with Rita Chesterton, co-founder and CEO of Skaffl. Skaffl is a startup company that develops an iPad app allowing teachers to plan, distribute, collect, and assess assignments digitally. Please read below to find out more about Skaffl and the problem they’re addressing.


Company at Glance: 

Rita Chesterton, co-founder and CEO of Skaffl.

Rita Chesterton, co-founder and CEO of Skaffl.

Website:  http://www.skaffl.com

Founders: Rita Chesterton, Matt Smollinger, Mike Hanssen, Angela Moramarco

Founded: 2012

Category: K-12, Teacher Tools, iPad Application

Product stage: Early Stage

Facebook: https://www.facebook.com/braketapp

LinkedIn:  https://www.linkedin.com/company/skaffl-llc

Company twitter: @skaffapp

Founder twitter: @ritachesterton

Other social media:  https://www.youtube.com/channel/UCrZJ6n-GRDIhHI9odmgFrLQ


ETT: How did you identify the problem you’re attempting to address? What was your process?

RC: I was working as the instructional technology specialist at a district that started a 1:1 iPad pilot for our 7th graders. One of the first things that teachers asked was how they could distribute, collect, and assess assignments on their iPads. It was exceedingly difficult. Every file type, and every app required its own workflow. I knew that there had to be an easier way, but I couldn’t find one, so I decided that I would create one.


ETT: How did you develop a solution to this particular problem?

RC: At first I thought about creating an app just to distribute documents back and forth, but then I realized that the problem was actually much larger. I thought about all the technologies that teachers in my district were using to manage their workflows and saw that they included wikis, blogs, our school website, moodle, planners, calendars, and on and on.

I realized that what teachers needed and were looking for wasn’t simply another repository for digital content but an integrated system that could take them from planning through assessment all on their iPads.  So I partnered with Mike, the technology coordinator at my district, made up a couple wireframes and went to a Startup Weekend event where we met Matt, our CTO.


ETT: How would you describe the product/solution opportunity you’re presenting?

RC: Skaffl allows teachers to plan, distribute, collect, and assess assignments in one comprehensive workflow application.  With our built-in editor students can complete many assignments right in Skaffl. Since iPads have many other great creative uses, Skaffl also permits students to submit work created in hundreds of other great Apps.  Teachers can mark-up student work and assign a grade using the built-in editor, which saves them hours every week in their grading.


ETT: Why do you think your product/idea will succeed?

RC: We speak directly to the needs of teachers in the classroom. Having been a teacher myself, and then a technology specialist I’ve seen a lot of really great tech tools for teachers and some really bad ones. Making sure that the details are done correctly makes all the difference. The response to our pilot was overwhelmingly positive, and when we show teachers what we have in the pipeline they get downright giddy.


ETT:  What makes your product/business model different from that of your competitors?

RC: We focus on the details, on the day-to-day use cases that make all the difference. We also see a bigger picture and have created Skaffl with a foundation that will allow it grow to help teachers with their planning and students with their organization, two areas that our competitors ignore.


ETT: How would you define the market segment your company is in?

RC: We’re creating a new market segment somewhere in the general learning management system category, but we really dislike that term, so we’ve coined the phrase “Workflow Management System.” Right now you have just two options, traditional learning management systems like Moodle, Blackboard, and Canvas, or Social Learning Management systems like Edmodo and Schoology. Neither one of these types of systems effectively meets the needs of today’s K-12 classroom, particularly when everyone has iPads.


ETT: What are the unique opportunities in the education technology market, from your particular perspective, and where do you see the education technology market going in the next few years?

RC: Right now we are seeing an explosion of new technologies for teachers, new hardware including tablets and Chromebooks and thousands of new Apps and web tools. What teachers need now more than ever are ways to help them manage all these resources, and help them guide their students in the learning process. As we move from teacher-centered to student-centered classrooms, teachers more than ever need integrated systems that help them in and out of the classroom.


ETT: What advice, if any, do you have for someone thinking about launching a company in the education technology market?

RC: If you aren’t a teacher, find an educator who is willing to be a co-founder or at least an advisor. If you are creating a tool that teachers are going to use, you need to know what it’s like to teach. There is often this assumption that because everyone has been to school that we all know what teachers do. This assumption often leads to products that are great ideas on paper, but just don’t work in a classroom setting.


EdTech Times thanks Rita Chesterton for sitting down with us and speaking with us. We recommend you check out Skaffl at:


Yevgeny Ioffe

Yevgeny Ioffe

Yevgeny Ioffe, or as people call him, Yev, has been working in both the startup world and established companies. His career spans from joining Xplana Learning as it launched to Cengage Learning to MBS Direct when it acquired Xplana in 2009. Yevgeny brings to EdTech Times his passion for start-ups and technology, along with his interest in the ever evolving world of edtech. Yevgeny obtained his BSc and MA from Brandeis University and MBA from Boston College.