Empowerly’s Lydia Winn on Shaping EdTech One Step at a Time

Please start by sharing some of your background and the journey that led you to the EdTech world.

I’m originally from Seattle, Washington. I attended UCLA with plans to work in traditional media, particularly television. I was fascinated by storytelling and its influence on culture. However, as I progressed in my studies and career, I found myself more drawn to rapidly changing industries. This curiosity led me from traditional media, which was starting to contract, into digital media and eventually software as a service (SaaS).

SaaS was a completely new world for me, even coming from Seattle, a tech hub. My first experience in software was in advertising technology, which felt like a natural extension from digital media but was more complex and offered new challenges. I’ve always had a strong interest in education, but I didn’t see a clear path for myself in that field because I wasn’t a particularly strong student. That changed after attending a transformational workshop called the Landmark Forum, where I realized I could make a difference in education.

I initially planned to join Teach for America, but the head of product at my software company suggested I explore EdTech instead, given my software experience. That advice resonated with me, and it set me on my current path. I spent months looking for the right EdTech opportunity until a friend recruited me to GoGuardian. The company was small at the time, and I was responsible for overseeing the sales team on the West Coast, covering everything from Las Vegas to Alaska. It was my first exposure to the K-12 education sector, and it was incredibly rewarding to see the impact we could make.

Was that your first exposure to sales as well, or did you have an interest in sales before that?

I’ve been involved in sales almost immediately after graduating from college. My first job was at a talent agency, which combined elements of both sales and marketing. I was responsible for promoting talent, building relationships with clients, and placing our talent in the right roles. From there, I moved to a marketing agency, where I was more directly involved in the go-to-market side of the business.

It took me a while to fully understand that what I was doing was indeed sales. Sales encompasses building relationships, understanding your market, and positioning your product or service to meet customer needs. By the time I got to GoGuardian, I was clear that my role was sales. I was responsible for driving new business, which involved a lot of prospecting, attending events, and getting to know our customers. What I loved most was the opportunity to meet new people and build relationships. Sales is so much more than just closing deals; it’s about understanding people’s needs and finding ways to meet them.

When you mention go-to-market, how do you compare it with the sales function? How do they interplay?

Go-to-market is an umbrella that covers both sales and marketing. It’s the entire strategy for bringing a product to market, from research and positioning to sales tactics and customer retention. It’s about how you approach the market as a whole and how you align your sales and marketing efforts to achieve your business goals.

In my career, I started on the sales side, focusing on building relationships, closing deals, and generating revenue. As I moved up in organizations, I took on more marketing responsibilities, particularly at the top of the funnel, where marketing plays a critical role in generating awareness and driving demand. In short, go-to-market is a comprehensive strategy that encompasses both sales and marketing. The two functions need to work closely together to be effective.

What do you consider to be your greatest achievement in your career so far?

One of my greatest achievements is the people I’ve hired and the opportunities I’ve provided for them to grow and develop their skills. I’m incredibly proud of the teams I’ve built and the impact they’ve had in the K-12 education space. Hiring is one of my favorite parts of the job. There’s something special about identifying talent, bringing someone onto your team, and then watching them grow and succeed.

I also love the impact we’ve made in K-12 schools, with students, teachers, and entire communities. It’s fulfilling to know that the work we’re doing is making a difference in people’s lives. Whether it’s helping a school district implement a new technology solution or supporting teachers in their classrooms, I feel like we’re contributing to something bigger than ourselves.

In your opinion, what’s the biggest challenge in K-12 education in North America today?

The main challenge in K-12 education evolves every few years, but some issues persist globally. One of the biggest challenges in the American K-12 system is the sheer scope of responsibilities that schools are expected to take on. It’s not just about educating students; schools also serve as access points for a wide range of services, including healthcare, food assistance, and therapeutic services.

For example, many schools in the U.S. are the primary access point for services like Medi-Cal, a healthcare program for low-income families. Schools are responsible for providing meals to students who might not have enough to eat at home. All these additional responsibilities create a significant burden on school districts and teachers. When people criticize the performance of K-12 schools, especially in the U.S., I think it’s important to consider these other roles that schools play in their communities.

It’s a lot to ask of any institution, and that’s one of the reasons why the K-12 system in the U.S. faces persistent challenges. It’s not just about the quality of education; it’s also about the broader social services that schools are expected to provide. That’s something unique to the U.S., but it resonates globally as well.

For our global audience, could you clarify what K-12 refers to in the United States?

In the U.S., K-12 refers to the entire spectrum of primary and secondary education, from kindergarten through 12th grade. It’s essentially the education system that serves children and teenagers before they go on to higher education or enter the workforce.

Most of the focus in the U.S. is on public schools, which are funded by the government and serve about 90% of the student population. There are also private schools, but the majority of dialogue and policy discussions in the U.S. center around public education.

Let’s talk about your time at GoGuardian. What was the basic value proposition when you started?

When I started at GoGuardian, we were known as the go-to solution for managing Chromebooks in K-12 schools. Chromebooks were just starting to gain significant market share, taking business away from traditional players like Apple and Microsoft. Our main product was a lightweight Chrome extension that allowed teachers to see what students were doing on their devices during class, ensuring they stayed on task. It also included features like tracking lost devices and implementing school-level filtering to block inappropriate content.

At the time, we were really the Chromebook people. Our product was easy to use and implement, which was a huge selling point for schools that were often understaffed in terms of IT support. Over the five years I was there, we expanded from being the go-to solution for Chromebooks to a comprehensive platform for managing any one-to-one program, regardless of the device.

As we continued to grow, we moved more into the curriculum space, which was a significant shift from our original focus on safety and security. We acquired a tutoring company and an assessment company, which allowed us to offer a broader range of educational tools. It was an exciting time of growth and expansion for the company.

With such a huge market, how did you approach the challenge of selling this innovative product?

We approached the market in two main ways. First, we focused on the mechanics of the market itself. GoGuardian was the first mover in the space, and we had the advantage of being the first product of its kind. We rolled it out quickly, and it was an accidental gift to K-12 schools. I don’t think anyone expected it to take off the way it did back in 2014 when the company was founded.

The second key was investing heavily in our engineering team and product development. We always had the best user interface (UI) and some of the strongest engineers in the EdTech space. That gave us a competitive edge because we could deliver a product that was not only effective but also easy to use. However, the challenge was in translating these subtle product features into compelling selling points for a market that is often very cost-conscious and resistant to change. Disrupting teachers’ routines is something you want to avoid as much as possible, so we had to be very strategic in how we presented our product.

The challenge of go-to-market and sales was really about how to pull out these competitive differentiating features and present them to the right person at the right time in the right district. It was a lot of work, but it paid off in the end.

Can you go into some of the specifics of how you approached selling to different districts? Who were the key decision-makers, and how did you reach them?

We thought about our market in terms of different segments: small schools, mid-market districts, and large districts. Each of these segments required a different approach. For small schools, with under 1,500 students, we knew the staff often wore multiple hats. So, we provided a more robust level of onboarding and customer service, charging a premium but also offering premium service.

For mid-market districts, with between 1,500 and 10,000 students, we had the advantage of scale. These were often suburban schools, especially on the coasts. We leveraged channel partnerships with companies like CDW and SHI, already selling Chromebooks to these districts, and became a natural add-on they could easily recommend.

For larger districts, we had to be patient and use a land-and-expand strategy. Large districts like Los Angeles Unified don’t typically buy for all 600,000 students at once. Instead, they give individual schools autonomy, so we had to sell to one middle school or high school at a time, sometimes needing to sell to 60 different schools before we could have a district-level conversation. It required persistence and relationship-building, but it was the only way to penetrate those larger markets.

In hindsight, would you have done anything differently back then?

Looking back, I don’t think I would offer different advice to anyone selling into different-sized K-12 districts. Our overall strategy was sound, but one thing I would say is that we underestimated the challenge of pivoting from a safety and security tool to a curriculum-focused product. We were used to designing, marketing, and selling products that primarily drew from the software budget, not the curriculum budget.

When we started rolling out true curriculum products, it was a whole new world for us. The vocabulary was different, the stakeholders were different, and the buying process was different. It was a steep learning curve, and I think if we had anticipated that challenge earlier, we might have approached the pivot differently. But overall, I think we did a good job of navigating that transition.

You mentioned earlier that one of your greatest achievements was hiring great people. What advice would you give to someone looking to hire top talent?

Hiring is one of the most important things you can do as a leader. Over the years, I’ve developed a pretty clear idea of what makes someone successful in the roles I’m hiring for. I always start by looking at who the top performers are on my current team. What qualities do they have? What do they value? What are their goals? How do they describe themselves and their careers? Once I have a clear picture of what a top performer looks like, I try to pattern match when I’m interviewing new candidates.

People who come from education, especially former teachers, tend to have a very strong work ethic. They’re detail-oriented, smart, and they know how to put in the hours. Teaching is a tough job, requiring a level of dedication and resilience that translates well into other roles. Beyond that, I look for goal orientation, which is even more important than relationship orientation in many cases.

Goal-oriented people are driven. They have a clear sense of what they want to achieve, whether it’s financial success, developing their skills, or creating better processes. They’re always looking for ways to improve and reach their goals. That’s the biggest thing I look for when hiring, and it’s also what I think makes people successful.

How do you evaluate goal orientation during an interview?

I typically ask experience-based questions that force candidates to reflect on their past behavior and decisions. For example, I might ask, “Tell me about a time you made a sacrifice to achieve something that really mattered to you.” Or, “What sacrifices have you made to be successful?” Another question I like to ask is, “Can you describe a time when you had to learn something complex very quickly with very little support?”

The key is to listen to the details in their answers. If someone gives me an example from the distant past or doesn’t provide much detail, I’ll dig deeper until I get a clearer picture. It’s my job as an interviewer to find out if they truly have that goal orientation or if they’re just giving surface-level answers.

Let’s shift gears a bit and talk about marketing. In your career, what marketing tactics have you found particularly effective in EdTech?

K-12 EdTech is unique because it’s inherently non-competitive. In most B2B industries, there’s always some level of competition and reluctance to share information. But in K-12 EdTech, it’s the opposite. People want everyone to be successful because, at the end of the day, it’s about the students and their education. I’ve never seen anyone in this space flex competitive spirit, which is really refreshing.

One of the best marketing channels for GoGuardian was good customer service. When you provide excellent service, your customers become your biggest advocates. They’ll talk about your product when they move to a new school district, and they’ll bring you with them. That word-of-mouth marketing was invaluable for us.

Another important marketing channel for us was events. K-12 teachers and administrators love to gather, share information, and learn from each other. We had a big presence at events, and it was a great way to start conversations and familiarize ourselves with different regions. Every state has its own mandates and conferences, so attending state-level events was crucial for us.

Finally, we invested heavily in the channel. When I started at GoGuardian, channel partners like CDW and SHI made up 70% of our business. We honed those relationships and even had someone in office at CDW to ensure we were always top of mind for their sales reps. That investment in the channel paid off significantly.

What specific investments did you find most effective with those channels?

For the channel, the most effective investment we made was in funded heads. Essentially, we paid the salary of someone who was technically an employee of the channel partner but worked exclusively on our behalf. They were in the office every day, having conversations with reps, resolving issues, and making sure we were always top of mind. It was a significant investment, but it paid off in spades.

At events, we invested in having a big booth at major conferences like ISTE or the Future of Education Technology Conference FETC, but our bread and butter were the state-level events. Those were the events where we met our buyers, developed relationships, and got them familiar with our product. We also had our reps go through the speaker list before each event to identify the most connected people and start conversations with them. It wasn’t about closing deals at the event; it was about building relationships and starting meaningful conversations.

How did you train your reps to execute this strategy?

We trained our reps to be curious and authentic in their interactions. We would encourage them to attend sessions at the events, even if the topics weren’t directly related to our product. For example, if the head of IT at a school district was giving a talk on open-source software, our reps would attend the session, take notes, and then approach the speaker afterward to ask for more resources or share their thoughts. It was about starting a conversation from a place of genuine interest, not just trying to sell them something.

We also encouraged our reps to engage with potential buyers on social media, particularly Twitter, where many educators are active. If a speaker mentioned a thought leader or a book they admired, our reps would buy the book and give it to them after their talk, saying, “I saw on Twitter that you’re a fan of Chris Adams. I thought you might like this book.” It was a small gesture, but it made a big impact.

The key was to build relationships based on mutual respect and curiosity. We weren’t trying to close deals on the spot; we were trying to build a foundation of trust and understanding. That approach paid off in the long run.

What was your biggest lesson from your time at GoGuardian?

The biggest lesson I learned at GoGuardian was the importance of sticking with something and seeing it through. Before GoGuardian, I was a bit of a career jumper, moving from one company to the next in search of new opportunities. But at GoGuardian, I stayed for five years, and that decision paid off exponentially.

There were many times when I could have left for a 10% raise or a new title, but I’m glad I didn’t. Staying with the company through its growth and evolution allowed me to develop as a leader, build strong relationships, and really understand the K-12 market. I also learned the importance of cross-departmental collaboration. Working closely with other teams, like product and customer success, was crucial to our success.

Overall, my experience at GoGuardian taught me the value of patience, persistence, and building a strong foundation for long-term success.

What’s the value proposition at Empowerly and what’s your role there?

I currently work at an amazing company called Empowerly, where I oversee a team of frontline salespeople and sales development representatives. Our mission at Empowerly is to help students navigate the complex college admissions process and get into top-tier universities. We provide access and insight that takes students from good to great in the admissions process.

The college admissions process in the U.S. is incredibly nuanced and competitive, especially for students applying to top 50 institutions or highly competitive majors like computer science at Berkeley. We assess students in a very data-driven way, looking at their grades, extracurriculars, academic profile, and essays. We then compare their profile to what we know about students who have been accepted into similar programs at their target schools.

My team works closely with families to find the right program for their students and ensure they’re well-prepared for the admissions process. We also focus on making sure that our families have a great experience with Empowerly, even if we’re not the right fit for them. It’s about helping families make informed decisions about their child’s future.

What are the main concerns of the families you work with regarding higher education?

The families we work with are typically very focused on getting their kids into top-tier institutions or highly competitive majors. They’re often concerned about the subjectivity of the admissions process and how to position their child to be competitive. The admissions process is incredibly complex, and every year the outcomes can surprise us. There’s a lot of anxiety around making sure their child has the best possible chance of getting into their dream school.

We work with families to assess their child’s profile and provide guidance on how to strengthen their application. Whether it’s improving their essays, finding the right extracurriculars, or identifying target schools that match their interests and abilities, we’re there to support them every step of the way.

Can you share an example of an edge case you’ve worked with?

One of the most interesting cases I’ve worked with was a family from Alabama who had homeschooled their daughter. The mother was living a digital nomad lifestyle, and their daughter was a straight-A student about to graduate with a Bachelor of Arts degree from Excelsior University, an online university in the U.S.

The challenge was that she hadn’t taken any of the standard classes we would expect an American student to have taken, and she didn’t have any typical extracurriculars. Instead, she had learned to speak Gaelic, which isn’t offered at most American high schools. She had a very unusual profile, and we had to work with her to develop her essays and storytelling to ensure that her application would stand out to admissions officers.

Despite the challenges, we were able to help her craft a compelling application that highlighted her unique experiences and strengths. Not only did she get into great schools, but she also received financial aid and scholarships that made her education affordable.

How do you approach working with international students? Are they considered differently in the admissions process?

It depends on the school. For schools outside the top 50, international students and American students are often treated similarly. But for top 50 institutions, the process is a bit different. Generally, there are admissions officers who cover different regions in the U.S., and then there are a few admissions officers who cover the entire rest of the world.

For international students applying to top schools, the competition is incredibly tough. The conversation isn’t just about whether you’re the top student in your school or region, but whether you’re among the top students in your entire country. For example, last year, Princeton accepted only seven students from the People’s Republic of China. Considering the number of students applying from China, that’s an incredibly small number.

It’s a very competitive process, and international students need to be aware of the unique challenges they face when applying to top U.S. universities.

How do families typically find out about Empowerly and the services you offer?

A lot of our business comes from word of mouth. Families talk, especially when it comes to something as important as college admissions. If a family has a great experience with us and their child gets into a top university, they’re likely to share that with their friends and community. We also invest in paid search, so if you Google “college counseling California,” you might see Empowerly in the top results. Webinars are another key channel for us. They allow us to share valuable information with a wider audience and showcase our expertise.

Do you think it’s becoming almost mandatory to use a program like Empowerly to get into top colleges?

It’s hard to say how many students are using college counseling services, but it’s definitely becoming more common. The college admissions process is incredibly complex, and having expert guidance can make a huge difference in your chances of success. I would strongly recommend college counseling to almost every family, especially those aiming for top-tier schools or competitive majors. It’s an investment in your child’s future, and it can help you make more informed decisions about where to apply and how to maximize your opportunities.

It’s about making an informed decision with all the options laid out in front of you. College is a significant investment, not just financially but also in terms of the time and effort your child will spend there. Having the right guidance can ensure that you’re making the best possible choice for your child’s future.