Libby Fischer

Tackle your biggest problems first: Whatever is scaring you needs to be thing number one on your to-do list…identify the big ticket items on your to-do list is helpful in giving you a little push.


As an emerging leader in the education technology industry, Libby Fischer is already making a name for herself both nationally and in New Orleans, where she leads Whetstone Education.

In 2014, Libby, a Teach For America alumna, took the helm of Whetstone Education, a then-struggling technology company with a clunky teacher evaluation platform used by 30 schools. Within 9 months, Libby led her two-person team to turn the company around by evolving the product with tools for daily teacher coaching, fast-tracking a UI/UX overhaul that led to a 90% user retention rate, and securing a 50-school contract with the pioneers of instructional coaching, Uncommon Schools in New York City. Since then, Whetstone has grown from 30 schools to over 950 schools worldwide, with flagship partnerships at Denver Public Schools, DC Public Schools, Tulsa Public Schools, and over half of all public schools in New Orleans. Libby has firsthand knowledge, both as a former educator and current leader in the education field, about the power that proper teaching can bring to a school and its community. Whetstone’s revenue has grown beyond $2 million annually — a difference of 28x from 2014 — and Whetstone has created 10 new jobs in New Orleans. All of this was accomplished while bootstrapped.

Libby’s ability to lead Whetstone through uncertain waters with no business background led to her being named one of Forbes’ 30 under 30 in Education in both 2016 and 2017 as well as a Silicon Bayou Top 100 in Tech and Entrepreneurship. Libby was a founding member of the governing board of Elan Elementary in New Orleans, and she currently sits on the regional council of STAR (Sexual Trauma Awareness and Response).

Where did the idea for your company come from?

Whetstone was founded by Ron Gubitz, a principal in New Orleans who needed a better way to keep track of his classroom observations, meeting notes, and teacher feedback. Ron had built an excellent culture of coaching in his school, but emails kept getting lost and there was no way to pull all of the data together. So, Ron went to his friend Andrew Cox, who was a hobby coder and the data guy at the school. Ron told Andrew about his problem and together they built the first version of Whetstone in 2011.

What does your typical day look like and how do you make it productive?

As the CEO of Whetstone, I wear a lot of hats. I oversee every department, making sure that our customers are getting the support they need and that our tech team is continually enhancing our product to support innovative teacher coaching techniques. In addition to this, I spend the majority of my time with our Partnerships Team to increase our impact by building relationships with school districts that can benefit from Whetstone. To make my days as productive as they can be, I’ve joined the cult of Michael Hyatt’s Full Focus Planner (Google it!). It has revolutionized how I structure my time during the day and made me far more productive. Beyond that, I’ve developed a leadership team of highly capable, reliable department heads that ensure our day-to-day operations run smoothly. A key part of our culture is carving out a few times during each week to spend time together as a team away from our laptops, including our 4-year tradition of “La Croix Happy Hour,” where we celebrate our small victories by sipping La Croix out of champagne glasses.

How do you bring ideas to life?

For me, I listen to everyone around me. Customers, staff, and advisors. They always inspire me to come up with great ideas for Whetstone. Also getting out and visiting schools where our platform is being used helps me observe and sparks new ideas on what I can improve or enhance. Here’s a good example of this: When I came on in 2014, I noticed that we had a product that our clients only used once or twice a year — when it was teacher evaluation time. Though I had barely any business or tech experience at the time, common sense told me that if your clients aren’t using your platform every day, or at least every week, they’re probably not getting a lot of value from it and they’re probably going to leave you. So, I knew we had to innovate. We went out to schools and followed principals and teachers around monthly, to see where else we could add value to their work lives. What we saw was a TON of instructional coaching — quick observations where a principal would leave feedback for the teacher on a sticky note; weekly data meetings where teachers and coaches would analyze student data together and plan reteach sessions; teachers observing their peers in classrooms and across schools to learn how to improve their student engagement strategies. Seeing all of this was a lightbulb moment for me — coaching is happening in schools every day. I saw that we had the opportunity to create a platform that could not only track all of these things, but analyze each interaction to help school leaders better tailor professional development (PD) sessions to teachers’ individual needs. Unlike the sit and get faculty meetings I attended once a week when I was teaching, Whetstone schools now provide personalized PD to teachers the same way they provide personalized instruction to students. We didn’t invent personalized PD, but Whetstone enables it in a way that wasn’t previously possible or manageable without a huge internal data team at a school.

What’s one trend that excites you?

More women becoming involved in tech is very inspiring. When I started out, I ended up in the tech industry by accident. I majored in Spanish in college and was teaching in Mississippi after I graduated. Now that I’m in this industry, I love it. I work with a local New Orleans coding school called Operation Spark. Their mission is to help all underrepresented people (including women) enter the tech industry. One of our developers came from Operation Spark and she’s a fantastic asset to our company. I’m committed to giving back to Operation Spark to get great women in the tech industry.

What’s one habit of yours that makes your more productive as an entrepreneur?

I LOVE my Full Focus Planner by Michael Hyatt. Before getting this planner, my day was dictated by my inbox. Whatever the most urgent email was before me, that’s what I focused on. Now, I’m back in charge of my day. It forces me section out my to do list into two categories: “top 3 things that are going to move my objectives forward” and “everything else.” It’s not rocket science, but my carving out time to connect my daily work to my quarterly or annual goals, it helps me focus on what’s truly important. Time management and learning how to fit our software into users’ daily lives is a huge focus of ours.

What advice would you give your younger self?

I would tell my younger self to listen. Listen to your customers because they’re the ones that are going to tell you where the market is going. Listen to your staff because they know where the biggest problems in your company are. Listen to your advisors — if you don’t have a mentor, make sure and find one. And keep a running list of every seemingly unanswerable question you run into as CEO. For the first two years, I spent a lot of time wishing that someone would just tell me what to do. By year three, I realized nobody was coming to give me all of the answers, and I had to find people I trusted to bounce my ideas off of, and ultimately own the success and failures that came from them. Ultimately, you have to listen to your gut. If there is something that you’re avoiding thinking about because it’s scaring you, you need to stop what you’re doing and start working on that thing. Every major issue I’ve had as a leader has been a small issue that turned into a big issue because I was scared to tackle it early on.

Tell us something that’s true that almost nobody agrees with you on.

You don’t have to start out working your way up in a certain industry to excel at the top. Having no experience in the tech industry, only a background in education, I got promoted to CEO of Whetstone because no one at the time wanted to take on this difficult position. It’s the best thing that has ever happened to me and has given me a unique perspective that many people in the tech industry that have worked their way up just don’t have. Because of the situation Whetstone was in at the time, and my inexperience in the tech world, I had to learn how to build both Whetstone and myself up quickly. With the high stakes and on the job training I went through, this has helped me pivot and learn how to handle all kinds of emergencies that are thrown my way, and how to best evolve the business from an “outsider’s” perspective. I feel that my non-traditional background is what gives me a competitive advantage.
I also believe that the Nebraska Cornhuskers will return to football dominance in the next 10 years.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I’ve mentioned the Full Focus Planner enough, so I would say, having weekly 1:1s with each of my department heads is what is making our company successful as we scale. Communication is key when you’re growing, and my department heads are now in the habit of constantly communicating with each other about what advice or decisions they need from me, what’s keeping them up at night, and what’s going well in their departments, so that there are no surprises and no delays in moving forward on the things that will help us accomplish our objectives.

What is one strategy that has helped you grow your business?

One strategy that has helped our business grow is our focus on customer retention. I didn’t know much about business when I took over Whetstone, but common sense told me that if your customers don’t like your product, they are going to leave you, and you’re not going to have a business for very long. So, in addition to responding to customer inquiries within 24 hours (with a lot of exclamation points and GIFs, I might add), we also made it a point to bring our customers into our product development process. If they were frustrated with how something worked, I would ask them to tell me how to make it better. And then we would make it better and ask them to test it and give us more feedback. This built an enormous amount of trust with our early users, and ultimately helped us build a product that users love and get a ton of value from, which helps us bring on new clients.

What is one failure you had as an entrepreneur, and how did you overcome it?

The biggest obstacle I’ve overcome was, in 2014, when I realized our product wasn’t solving users’ problems as we had intended. After getting many complaints from users, I got out from behind my laptop and began visiting the schools in person. Here I followed around dozens of principals as they observed teachers and gave them feedback. Instead of using our platform, they were using sticky notes and spreadsheets to put together their own feedback system. This was incredibly humbling. After each meeting, I went back and worked on a better version of Whetstone based on what I saw the principals and teachers doing. It took six months, but I began to receive positive reviews and feedback and knew we were on the right path. Now, we’re much more responsive to our clients’ needs and have even turned our website into a resource they can use to get coaching ideas.

What is one business idea that you’re willing to give away to our readers?

I want someone to disrupt dry-cleaning. I know that’s not a clear business idea, but it’s a super old-school business model that I think could be improved.

What is the best $100 you recently spent? What and why?

I was going to say my Full Focus Planner (it’s $49.99), but actually, I spent $100 on colorful beads and gems to make my Mardi Gras outfit. This may seem frivolous, but if you’re from New Orleans, this is par for the course (or way less than par for the course). Part of why we’ve chosen not to relocate Whetstone to a tech hub like Denver or Silicon Valley is that we LOVE New Orleans. There is no place like it on earth, and I think the personal joy, value, and satisfaction I get from living here — including Mardi Gras and the fact that people go all out for costumes — makes me a better CEO.

What is one piece of software or a web service that helps you be productive?

We use Ally to track our Objectives and Key Results (OKRs). OKRs have transformed our approach to getting our work done and growing as a business, and Ally is an awesome tool to manage it.

What is the one book that you recommend our community should read and why?

Measure What Matters by John Doerr. It is the OKR bible.

What is your favorite quote?

Laissez les bon temps rouler.

Key Learnings:

  • Tackle your biggest problems first: Whatever is scaring you needs to be thing number one on your to-do list. This is hard to force yourself to do, so some sort of tool (like the Full Focus Planner — I promise they are not paying me for this) that makes you identify the big ticket items on your to-do list is helpful in giving you a little push.
  • Listen to your customers: By bringing your customers into your product development process, you will (i) ensure that your product solves a real problem and (ii) build a level of trust that makes them keep coming back and recommend your company to their friends.
  • Focus on customer retention as much as you focus on customer acquisition: A focus on customer retention will ensure that you’re constantly ensuring your product adds value, which will in turn make it easier to sell to new customers
  • Strategy doesn’t just happen: You must be intentional about it. OKRs have worked for us and I recommend them to anyone trying to grow a company