I started working in my first classroom eight weeks after graduating from college. I was completely unprepared. Three years later, I started at a small educational technology start up. I felt like I was starting from scratch -- and in many ways, definitely was -- but calling on teaching experience helped not only inform my role, but keep me grounded in the people we seek to support, day in and day out.

On the surface, working at a start-up and teaching couldn’t seem further apart. However, the longer I’ve worked at Neverware, the more I’ve seen the overlap between being in a classroom and being in our office.

Here are a few ways I’ve found early stage companies and the classroom to align:

Planning is good but adapting is crucial.

Deep in my Google Drive are videos of my first few months of teaching. They are painful to watch. All you can see are the wheels falling off of every lesson -- what you can’t see in the video are the endless nights of planning and research that went into a meticulously ordered and scripted lesson plan. I was sure that there would be a direct correlation between the time I put into lessons and the learning my students gained, which any teacher can tell you, isn’t strictly true.

It wasn’t until I gained confidence in my own practice that I started to be able to allow for a dynamic learning experience. I could slow down, check for understanding, and switch my method of instruction mid-lesson to account for gaps in background knowledge or an activity that wasn’t engaging (even if I thought it would be!).

It reminds me of the first structure we had at Neverware for classifying customer health and happiness. We were categorizing customers by color (red, orange, yellow and green) based on a series of qualifications (uptime of the server, email communication, etc.). I manually updated each customer’s log daily, dragging and dropping information and writing task lists. I was so proud of the system!

Then, we grew from 19 to 150 customers in six months. The system stopped working at scale. Just as I planned an activity that didn’t work in practice, it was time to forgo fidelity to the script and start getting flexible. It took many iterations (and what I’m sure will be many iterations more) to find a system that allowed us to log client histories and collect feedback data, but there’s now a system in place that helps us care for customers while acknowledging how many of them there are. The initial planning was important -- adaptation to the changing environment was critical.

Be ready to explain things many times, in many ways.

Reflecting back on my best teachers, they structured classes that felt engaging and applicable. After becoming a teacher, the “how” of these kinds of lessons became much more apparent. Often times, it was the ability to explain concepts with different modalities -- first in a lecture, then through a group project, finally through a presentation -- that made the learning enjoyable, and most importantly, simple to retain and apply in different scenarios. Repetition and multiple formats are needed to authentically communicate a concept.

At Neverware, this looks like creating a wide range of resources to help each customer in the way that feels most helpful and accessible to them. We’re currently working on building out our self-service resources so that customers can access support with their products on their own schedule, creating a robust chat mechanism on the website to help answer questions in real time, and make both phone and email support available to our EDU customers whenever they need it. With the launch of our free offering, we tested a forum where CloudReady users could easily find answers to their questions, but also read about the use of CloudReady in new and different applications. Seeing users chatting with other users helps confirm for us that we’re reaching people (and diversifies our ability to explain how the product works!).

Support here means interfacing with a wide range of educators, from individual teachers to school leaders to district and network staff. Each conversation includes a different goal and different level of prior knowledge about our product and about technology in general. It’s critical to meet people where they are at, and have a Plan B and C at the ready.

Within support conversations, it means not assuming anything about the person that you’re speaking with, and being prepared to explain complex technical concepts from the beginning. If the first explanation of why the installation of the product doesn’t work, it means preparing a short screen-cast video, sending a help article on updating the BIOS on their specific machine, or hopping on the phone to walk through creating an installer stick. It’s keeping the goal of communicating knowledge first, and being flexible around what that might look like.

Unless purposefully designed and aligned, data is a distraction.

Both in education and in the start-up world, people are crazy for metrics. Measure all the time! Measure everything! Make a dashboard and email it out every morning, noon, and night! It’s admirable, but in many cases, not particularly effective. Without authentic, thoughtful measures of achievement aligned closely with goals for success, it’s assessment for assessment sake. No one would imagine of quizzing students on material they didn’t learn, or wasn’t relevant to learning goals -- in the same way, keeping metrics precise, consistent and actionable keeps everyone invested in their improvement.

In my experience, meaningful student assessment followed two initial steps. First, there was a clear vision of what it meant for students to be successful; what students were to know and understand at the end of a lesson, unit or year. Crafting these objectives is not simple -- think about the difference between “student will know how bones work” and “student will be able to list three distinct ways bones help the body function.”

Once the objective is clear, the next step is to create a clear idea of how the instructor will know that the student has achieved that goal. That forms the basis of the assessment. Then, when it’s time to execute, there’s no time wasted on teaching extraneous information -- for this objective, understanding how bones are formed is not part of the objective, and would not need to be included in the lesson. Aligned and rigorous assessments prevent wasted energy and can stand as a marker of authentic understanding.

When students are assessed consistently and in a manner aligned with the content, both teacher and student can come to a real understanding of how that student is progressing. If the assessments are truly comprehensive, they will also understand where they are strong and where they are not, and plan targeted interventions.

One measurement that we pay especially close attention to at Neverware is Net Promoter Score (NPS). NPS works for us as a measure of customer satisfaction because of its simplicity, allowing us to track a single number over time to gain insight into how well we are managing expectations about our product as well as incorporating our customers’ needs into the product pipeline. The number gets to the heart of what we care about -- are customers willing to not only maintain a relationship with us, but advocate for us? -- without collecting tons of “customer satisfaction” data that ultimately goes to waste, as it’s not meaningful or aligned with our goals.

We share NPS data on a monthly basis with the organization, and have pegged performance bonuses for the entire company on goals around NPS. The president of the company, the director of engineering, and everyone, on every team, has customer satisfaction as a leading indicator of their job effectiveness, keeping us laser-focused on serving the needs of our customers.

Rather than just having final, monthly measurements (exams), we also have smaller, formative collections of data. We collect data from our chat and from our tickets as well, examining whether the smaller collections inform the larger, and helping give us real-time feedback on what’s working and what isn’t. This data is housed in the Customer Operations team, to prevent data overload, but we do share it in instances where it feels informative.

Having a central mission might not make decisions easier, but it makes them much more clear.


Teaching is hard. There is tremendous pressure in conditions of uncertainty. You have to remain positive, consistent and reach out for help when needed. In this way, most of all, teaching is similar to working at an early stage start-up. It can be grueling, and it’s not for everyone.

In both instances, the thing that has kept me motivated is the idea that there is a central mission the organization I’m part of is striving towards. That mission imbues hard conversations, no-win decisions, and every time the option to push the quality of the work higher arrives. We set very ambitious goals in my classroom around test performance -- so ambitious that at times, they felt impossible -- but communicating about them every day with my class kept us all centered not just on the “I can”, but on the “I want” of success.

As we’ve expanded our product offerings at Neverware to include individuals, and eventually, enterprise clients, we’ve maintained a laser focus on making it simpler to get great computers into people’s hands. We have a set of product principles, agreed upon by the entire company, that are crucially in priority order. When input from customers reaches product, it helps guide where our company’s energy should go and keeps us focused on the end goal.

Ultimately, if you’re fortunate, working in a classroom and working at a start-up both offer a unique opportunity to make change, both in classrooms and out.