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Whetstone Education CEO Libby Fischer: “Progress can’t always come from behind a desk”

Progress can’t always come from behind a desk. There’s a time and a place to sit behind your desk and stare at your computer screen. However, it’s impossible to completely understand the needs of your customers when you’re stuck in your office. When I took over as CEO of Whetstone, our product was in bad […]

Progress can’t always come from behind a desk. There’s a time and a place to sit behind your desk and stare at your computer screen. However, it’s impossible to completely understand the needs of your customers when you’re stuck in your office. When I took over as CEO of Whetstone, our product was in bad shape. It wasn’t adding value to our users’ lives and we were getting awful feedback from customers. Rather than tweaking a few lines of code, I knew that a larger shift had to take place in our product and our offerings. Whetstone could not have made this shift without understanding the true needs of our customers. I got out of my office and journeyed to every school I could to shadow principals and administrators to get a better grasp of their needs. The result was a fundamental change in what we delivered to schools and it led to an enormous shift in how school leaders viewed our product. Sometimes, you just have to get out there and talk to your customers to figure out what’s best for your company.


As part of my series on strong female leaders, I had the pleasure of interviewing Libby Fischer. 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). Libby has done more than just turn around a struggling business. She has transformed the way school leaders train teachers across the country and influenced countless teachers and students in the process. Whetstone’s success creates an immeasurable ripple effect that can dramatically reshape the way educators grow and learn.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I got into tech completely by accident. I majored in Spanish, not business or computer science. My first job out of college was teaching in the Mississippi Delta with Teach for America. After a few years, I moved south and started working at Whetstone Education as the Director of Growth. Not too long after that, I was promoted to CEO at the age of 26 because, frankly, nobody else wanted the job. It’s the absolute best thing that’s ever happened to me, and I think this meandering route to the hot seat gives me a different perspective than many people in tech who have worked their way up or are well-studied on The Lean Startup model. I’m not a born entrepreneur, and I’ve never had any ambitions to be in business or tech; but I had to learn to operate both Whetstone and myself as a leader really fast, or else the lights would have gone out. And I fell in love with it. This high stakes, on-the-job training has helped me pivot and navigate the myriad of emergencies that come up in any business, and I think my non-traditional background is what gives me my competitive advantage.

Can you share the most interesting story that happened to you since you began leading your company?

One of the most interesting (and scary) things to happen to me since taking over Whetstone was realizing that our product was not solving our users’ problem. I had just moved across the country to take this job on a whim, and I was fielding a stream of complaints (and rightfully so) that Whetstone was making our users’ lives harder. After a certain point, I got out from behind my laptop and went from school to school, following around dozens of principals as they observed teachers and coached them through feedback. I watched as they used sticky notes, paper forms, and spreadsheets to cobble together a mess of a feedback system rather than using the platform they paid for that promised to organize their work and make the process easier. It was incredibly humbling. After each meeting (and after taking deep breaths in my car wondering if I made the right decision in taking the job), I mocked up a better version of Whetstone based on what I saw the principals doing. I emailed it off to each principal for feedback and went back to the schools to shadow them as they tested our updated software. It took six months, but one day I started receiving “I love Whetstone” emails. That’s when I knew we were on the right path.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I don’t know how funny this is, but in 2015 we attempted a re-brand. For whatever reason, my Director of Marketing and I thought Whetstone’s new logo should be an alligator (It’s a New Orleans thing). We went through 6 or 7 rounds of graphics before deciding on the alligator we thought conveyed a brand that was competent yet fun. After we started showing the new logo to people, quickly heard what we needed to hear. The public reaction was unanimous: an alligator is an aggressive creature! A teacher feedback platform should NOT have a deadly animal as its logo. The lesson we learned is to bring a variety of different viewpoints into decisions like these. This helps us get better-informed ideas and avoid wasting money and time. Maybe someday we’ll use the alligator logo on a t-shirt for April Fool’s Day or something like that.

What do you think makes your company stand out? Can you share a story?

I like to joke that if the founders of Whetstone had done any competitive research before forming the company, Whetstone wouldn’t exist. This is because Whetstone was originally created to manage traditional teacher evaluations, and there was a very crowded field of data management companies already. Where we innovated and pulled ahead of the pack was in the transition from being an evaluation platform to being a feedback and coaching platform. When I took over 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 made monthly visits to schools and shadowed principals and teachers to see where else we could add value to their work lives. We saw a TON of instructional coaching — quick observations where a principal would leave feedback for the teacher on a sticky note, weekly data meetings in which 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, and much more. 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 also analyze each interaction to help school leaders tailor professional development (PD) sessions to teachers’ individual needs better. Unlike the 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.

Are you working on any exciting new projects now? How do you think that will help people?

We are adding video to Whetstone! One of the things we see our most successful partners doing is using video to enhance coaching conversations. Typically, this involves a teacher recording a video of his/her classroom, watching the video afterwards, and going through a self-reflection protocol. They identify one or two things they want to improve, and they meet with their instructional coach to make a plan for how to implement changes. Video can be a really powerful tool for moving the needle on a teacher’s practice, and we are excited to be able to offer it to our clients for the 2019–2020 school year.

What advice would you give to other female leaders to help their team to thrive?

Building a thriving team is one of the most important elements in running a business. One of the best ways to create an effective team is through motivation and a shared company vision. If you don’t have a company or team vision, make that your first priority when you get to work tomorrow morning. A shared vision allows your team members to have a guiding light that all other tasks stem from. Each small assignment you request of your team members needs to somehow ladder up to that ultimate goal. Are you trying to get your software in the hands of every school district in the U.S.? Are you working to launch a new product by the end of the year?

Whatever your vision is, make it clear so that every team member can work toward it independently of outside instruction. To be a leader, you don’t need to micromanage; you simply need to empower those around you to work on a shared mission.

What advice would you give to other female leaders about the best way to manage a large team?

First of all, listen to your staff. They’ll tell you, either in words or by actions, where the biggest problem in your company is. It’s also important to listen to your advisors; if you don’t have a mentor, go find one. Additionally, you should keep a running list of every seemingly unanswerable question you run into as CEO.

For the first two years as CEO, I spent a lot of time wishing someone would just tell me what to do. By my third year, I realized nobody was going to give me all of the answers. I had to find people I trusted to bounce my ideas off of, and I had to ultimately own the success and failures that came from them. Ultimately, you have to listen to your gut. If there’s something 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 grown from a small issue into a big issue because I was scared to tackle it early on.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Martin Roth, the Chief Revenue Officer of LevelSet, has been an invaluable mentor to me. Before I met Martin, I was a sales team of one and I was afraid to call people on the phone. Martin not only helped me get over the mindsets that were holding me back, but he also helped us make our partnerships work more data-driven. When you’re building a business, you can’t waste any time; Martin has helped us make sure we’re spending what little time we have on the right things so that we can expand our impact and make sure more teachers are receiving more feedback.

How have you used your success to bring goodness to the world?

I work with a local New Orleans coding immersion school called Operation Spark. The mission of Operation Spark is to help all underrepresented people (not just women) enter the tech industry as full-stack software developers. One of our developers, Grace, came to us from Operation Spark. She is a fantastic developer and a tremendous asset to our company, and I am committed to giving back to Operation Spark to get more great women in tech, especially in New Orleans!

What are your “5 Leadership Lessons I Learned From My Experience” and why? (Please share a story or example for each.)

  1. Take advantage of critical opportunities. My life before Whetstone didn’t exactly have the defining points of the traditional tech CEO’s CV. As a college student, I majored in Spanish. I didn’t know how to code, and I’d had a love-hate relationship with software platforms in the past. But, I was in the right place at the right time. Most importantly, I had the right attitude for the circumstances that were put in front of me. When you take over a failing company, you can’t linger on the mistakes of the past. You have to stay positive and think outside of the box to achieve success where others failed. My non-traditional background and my willingness to take advantage of this opportunity has turned Whetstone into a multi-million dollar company and impacted thousands of school leaders, teachers, and students across the country.
  2. Progress can’t always come from behind a desk. There’s a time and a place to sit behind your desk and stare at your computer screen. However, it’s impossible to completely understand the needs of your customers when you’re stuck in your office. When I took over as CEO of Whetstone, our product was in bad shape. It wasn’t adding value to our users’ lives and we were getting awful feedback from customers. Rather than tweaking a few lines of code, I knew that a larger shift had to take place in our product and our offerings. Whetstone could not have made this shift without understanding the true needs of our customers. I got out of my office and journeyed to every school I could to shadow principals and administrators to get a better grasp of their needs. The result was a fundamental change in what we delivered to schools and it led to an enormous shift in how school leaders viewed our product. Sometimes, you just have to get out there and talk to your customers to figure out what’s best for your company.
  3. Practice what you preach. Whetstone Education provides a platform for classroom observation and teacher feedback. Our whole value proposition is that we offer a tool to make feedback more approachable. That being said, I knew that I needed to incorporate observation and feedback into our own internal processes as a company. As Whetstone’s CEO, it is my core job responsibility to develop and empower my staff to achieve at their highest possible level so that we can serve our clients effectively and meet our business objectives. I take this part of my role so seriously that I hold weekly one-on-ones with each of my five department heads. This way, we problem-solve, brainstorm, and plan out how they are going to accomplish their objectives and key results (OKRs) — all of which are designed to help the company grow. The frequency of these meetings sometimes gets an eyebrow raise from fellow CEOs who think it’s overkill; but Whetstone’s growth rate, retention rate, and extremely low employee turnover tell me something’s working. Beyond helping my team members accomplish their business objectives, I feel it’s my personal responsibility to help them grow their careers.
  4. Prepare your employees for life after their job. As much as I’d like to believe everyone will be at Whetstone forever, I know that the sad day will come when folks move on. I want to be happy for them when that day comes, and I’ve learned that one thing I can do to help them build strong careers is to give them the opportunity to build relationships across industries. One of the privileges of being CEO is constant invitations to interesting events around the city and country. I bring my team members along with me as much as I can so that they can meet other leaders and learn about other ideas or problems they may be interested in solving. In the meantime, they bring back ideas and energy to make Whetstone stronger, so everybody wins! Employees have a way of circling back to previous roles or previous industries they’ve worked in. I want to make sure that Whetstone is thriving and seen as a place worth coming back to if and when people choose to.
  5. The only way to grow your business is to listen. Leaders who reject feedback or constructive criticism will never advance their businesses. Your customers and staff will inform you of where the market is going and where the rough spots are in your company. Your advisors and mentors will allow you to bounce ideas off them and offer you valuable advice. As I said before, no one will come out of nowhere and tell you how to do everything. Listening is the best way to absorb vital information that will help you create these solutions yourself. As you do this, your confidence in your leadership and decisions will grow, and you’ll get better at following your gut, which is admittedly scary at first. Personally, I’ve found that the best things in life are on the other side of fear, and every big issue I’ve had as a CEO stemmed from a little issue that I was scared to approach earlier. I conquered this (and my imposter syndrome) by listening to the people I chose to surround myself with.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Beyond ensuring that all people have access to a quality education, the movement I would inspire is a movement toward a better work/life balance for all people. Whetstone is based in New Orleans, and because there’s always something fun going on in the city, we had to figure out how to build a high-growth SaaS tech company without working 100 hours a week. It’s really important to me that my team and I can leave the office by 5pm most days to be with our families or enjoy our city. Last year, we noticed that nobody was taking advantage of our unlimited time off policy, so we now REQUIRE that everyone takes 10 days off a year. It’s easy to blame the world’s ills on Silicon Valley, but the “you’re not really working if you’re not sleeping at the office” mentality it has bred is toxic (New York City is to blame for this, too). Whetstone’s bootstrapped growth rate, retention rate, and low turnover are proving that it’s possible to get excellent business outcomes while maintaining a company culture that values people as humans and makes them happy at work. Don’t take my word for it — ask them.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Nelson Mandela once said, “Education is the most powerful weapon which you can use to change the world.” This quote means so much to me and is, in and of itself, a life lesson. It shows that learning and growing within yourself has the potential to create a ripple effect and change the world around you.

This is true in my life, especially in my experience running Whetstone. As a newcomer in both the tech world and the world of business management, I had to learn the ropes very quickly. I’m constantly educating myself in an effort to improve the education of those around me.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I would love to share a meal with Whitney Wolfherd, CEO of Bumble, because I want to learn how she has been able to scale Bumble as quickly as her brilliant vision for the company expands. While most other dating apps build their growth strategy around the lowest common denominator (facilitating casual hook ups), Whitney has taken Bumble to explosive, world-wide growth by thinking about relationships holistically. If you think about a dating company’s business model, a match that results in a relationship is actually a bad thing for the company — they lose two users who no longer have the need for its service. Rather than seeing this as a bad thing, Whitney saw it as an opportunity to leverage Bumble to facilitate other types of relationships: friendships and professional relationships. Not only is she solving a very real need in the market (seriously, how do you make friends after age 25?), but the nature of these relationships is that they’re non-exclusive, so users will keep coming back in perpetuity. It’s brilliant! As a business leader, I’ve learned that the minute you get comfortable is the minute you need to start innovating. This is HARD and Whitney makes it look so easy. I want to learn how she continually pushes herself to take the company to the next level, and never rest on its laurels. Plus, she’s got great style.

How can our readers follow you on social media?

Follow Whetstone Education on Facebook or Twitter for updates, press, and industry-related news. Read our blog for a deeper dive on how school leaders can use instructional coaching to get their teachers better faster.

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