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Wesley Matthews

Scaling EdTech Success: Wesley Matthews Shares an Insiders' View of Entrepreneurship, Teamwork, and Growth

Why did you decide to move to the US?

I came to the United States for two reasons. The first was that I wanted to gain experience working in the US and outside of Chile. And the second was that I came to get an MBA. I had a five-year plan. Twenty years later, I'm still here. 

✨ Pearl of wisdomThe primary challenge in education varies by geography. In the United States, there's concern about the enrollment cliff, with declining enrollments leading institutions to focus on efficiency and cost-effectiveness. Conversely, regions like Latin America are experiencing significant growth, particularly in areas like continuing education and non-traditional education.

What was the career path that led you to EdTech?

I started my career in education in Chile. My first job out of college was working for a university. Then I started a consulting company down in Chile that focused on improving business processes and the use of technology for different industries. But a number of our projects were with universities, and I became very passionate about working in education. When I came to the U.S. in 2005, my first job was at a university, and I've stayed in or near education ever since.

✨ Pearl of wisdomDoctums helps institutions by operationalizing their strategic objectives, connecting current operations, processes, and strategies to organizational goals. Additionally, Doctums identifies opportunities to reduce costs and introduce technology, creating efficiencies for a more streamlined operation.

Why did you choose to stay in EdTech?

I started working with universities right out of college. When I started working in higher education in the US, and I stayed in education, I also worked in K-12. But as I worked more and more in education, the mission of these institutions, the societal benefits, the interactions with students were very rewarding, and it created a lifelong passion, and I don't think I'll ever do anything else.

✨ Pearl of wisdomAt some point during my journey, I recognized that if I wanted to operate my own companies at scale, I needed to learn what scale looks like. I needed to understand how to operate within a much larger company. That's why I worked for very large, global companies—to learn how to properly scale an operation, professionalize the necessary components, and avoid the mistakes that many startups make as they try to grow.

What personal accomplishment are you most proud of?

My greatest personal accomplishment is my family, my close-knit unit of my children and wife, and my extended family. I feel that we have a very close relationship that has allowed us to extend our values to our children, who are both thriving in higher education and pursuing their own careers. And then I think an extension of that is that we've built a company that resonates with those same family values, where people are treated like family members, where there's a shared set of values or morals that makes us work very well and creates a fantastic place to work.

Talk to us about Doctums.

Doctums is a management and technology consulting firm. We started as a US-based company in Chicago, but now we have offices throughout Latin America and Canada, and we serve all 50 states. We focus on providing a set of services that were very much needed in the industry when we started the company. We bridge the gap between high-end, very complex, SI-level consulting and more tactical technical consulting services available in the market. When we looked at the services being provided, we saw a gap between these two ends of the spectrum. There was an opportunity to offer deep expertise, both functional and technical, to help institutions address their challenges. Additionally, we wanted to operate not only at a strategic level but also to operationalize our recommendations. We aimed to actually deliver and help implement those recommendations, rather than leaving clients with just a roadmap. This approach has been very valuable to the industry, not just in the U.S., but in other countries as well.

We've been operating since 2019, so we're in our fifth year. We've grown organically as the business has evolved. We're focused on providing the right services for each market. The services we deliver in the U.S. may be slightly different from those we deliver in Peru, Mexico, Chile, or Canada. We tailor our service offerings to the needs of each market. One of the things we do is take what we learn in each market and use that experience to inform and help institutions in other geographies adopt best practices or technologies that might be beneficial to them.

✨ Pearl of wisdomEntrepreneurship is very difficult and not for everyone. It requires a certain character, tenacity, and a disposition to deal with negatives without being downtrodden by them. It also requires understanding that you can't do this alone. Every successful entrepreneur learns to work with people, to do true teamwork, and ultimately to rely on them.

What is the most pressing challenge in education today?

That's a great question. The biggest challenge facing education depends on which geography or country you are talking about. The challenges in the United States are different from those in Latin America. For example, in the U.S., everybody's talking about the enrollment cliff. There are declining enrollments, and at some point, there's going to be a significant decline, which means that institutions have to become more efficient, more cost-conscious, and be able to do more with less. In other regions, they're seeing tremendous growth, especially in certain service offerings like continuing education or non-traditional education, which is growing rapidly throughout Latin America. In the U.S., I see a shift toward continuing education, and that's where most of the growth is going to be. You see some of the larger institutions like Western Governors, Southern New Hampshire, and Liberty that have grown exponentially over the last decade. I think that's a great indicator of where the market needs to go—where it needs to reinvent itself into more flexible, customized offerings that students can consume the way they want to and not necessarily follow such a traditional track.

How does Doctums help institutions overcome these challenges?

Doctums can help institutions in a number of ways. First, we can look at your strategic objectives and help an institution operationalize those, understanding how they can take their current operations, processes, and strategies and connect them to an organizational strategy to deliver the desired outcomes. Second, we can identify opportunities for reducing costs and introducing technology to create efficiencies that will ultimately result in a more streamlined operation, helping those institutions achieve their goals.

✨ Pearl of wisdomWe have chosen a path without outside investment so we can control our decisions and maintain autonomy. However, that doesn't mean it's the wrong decision for others. It means you need to choose carefully. The best offer from a valuation perspective may not be the best for your company in every scenario. You need to consider that carefully when choosing who you want to invest in your business.

What was the moment you decided to make the jump and commit to entrepreneurship?

Entrepreneurship is in my DNA. I come from a family of entrepreneurs. My grandfather started several companies, and I've always known that this was the path I wanted to follow. I actually started my first company in my early 20s. By now, I’ve started five or six companies. At some point, I recognized that if I wanted to operate my own companies at scale, I needed to learn what scale looks like. I needed to understand how to operate within a much larger company. That's why I worked for very large, global companies—to learn how to properly scale an operation, professionalize the necessary components, and avoid the mistakes that many startups make as they try to grow.

Who do you admire?

I have great admiration for my grandfather, for his achievements as a businessman, especially given the challenges he faced. But I think I admire anyone brave enough to try this. Entrepreneurship is very difficult and not for everyone. It requires a certain character, tenacity, and a disposition to deal with negatives without being downtrodden by them. It also requires understanding that you can't do this alone. Every successful entrepreneur learns to work with people, to do true teamwork, and ultimately to rely on them. These are qualities that not everyone has and many need to develop. Anyone who tries to do this has my respect.

✨ Pearl of wisdomChoosing who to start a business with is key because you're going to be with them for a long time. You have to enjoy working with them. You don't have to be best friends, but you must respect each other and work well together. You need to share a set of values and align on the company's direction.

The way investment in the tech industry works has changed rapidly. How have these changes impacted startups?

Twenty or 30 years ago, most EdTech companies were either self-funded or funded by friends and family, but there wasn't a lot of professional investment in educational technology. That has changed significantly. For any entrepreneur, it is a choice. If you want to grow rapidly, having an influx of cash can be a huge catalyst. It can be very positive. But that money comes with influence, which can be positive, neutral, or negative. If you find the right investment partner, such as a PE firm that brings additional expertise, helps with scaling and growing, and contributes more than just cash, it can be a great experience. However, if you seek an investor who only provides cash without wanting a seat at the table, those are hard to find. Typically, investors will want to influence how their money is used. The worst situation is acquiring a partner that doesn't align with your goals, which can happen.

We have chosen a path without outside investment so we can control our decisions and maintain autonomy. However, that doesn't mean it's the wrong decision for others. It means you need to choose carefully. The best offer from a valuation perspective may not be the best for your company in every scenario. You need to consider that carefully when choosing who you want to invest in your business.

✨ Pearl of wisdomThere are two things I look for in new team members. First, can they significantly contribute to what you're trying to accomplish? Secondly, you need people who are nimble and can think creatively, who are not afraid of wearing multiple hats. You need people who can change with you, evolve as the company evolves.

What do you look for in a business partner?

This is something I learned early on and it has guided my thinking the most. I've started several companies; some have been successful, and some have not. One crucial lesson I learned is that choosing your co-founders and partners determines your path to success. Having the wrong partners is highly detrimental to a company. In my 20s, I started a few companies with no money, so we offered equity to attract people. We offered too much, making them partners and decision-makers. This resulted in too many voices at the table, and they weren't necessarily the right people. We didn't find out until later, and then it's really hard to unravel.

Choosing who to start a business with is key because you're going to be with them for a long time. You have to enjoy working with them. You don't have to be best friends, but you must respect each other and work well together. You need to share a set of values and align on the company's direction. If these things are true, you should move forward. If any of these things aren't true, you should reconsider because you will run into trouble quickly.

✨ Pearl of wisdomFor anyone starting a company, it's crucial to first understand the industry you're entering. Research and grasp the market potential and the specific pain points your product aims to solve. Additionally, consider whether your potential clients will truly value the solution to the identified pain point. While you might see a problem as important, it's essential that the market also agrees and is willing to pay for the solution.

What are the keys to bringing together the right team for a startup?

As you grow your company, starting from just you and your co-founders and beginning to scale, even at a small scale, you start to bring in more employees. There are two things I look for. First, can they significantly contribute to what you're trying to accomplish? Do they have a set of skills that you really need within the company? These could be very specific skills necessary to build a product or deliver a service. That's one criterion.

Secondly, you need people who are nimble and can think creatively, who are not afraid of wearing multiple hats. In a startup, there's no space for people to say, "This is my swim lane. This is what I do. If you ask me to move outside of that swim lane, I will not do it." You need people who can change with you, evolve as the company evolves. When you find those people who can do that every day with a smile, enjoy what they're doing, and make your life and everyone else's life in the company enjoyable, hold on to them.

When you know an industry, you know thousands of problems that a company could solve. How do you choose the problem that you want to solve with your company and that is worth the investment of time, people, money?

The first part of your question, I think, is crucial. The first thing I would recommend for anyone starting a company is to ensure you understand the industry. If you believe you have an idea for a product but are not familiar with the industry, research and understand it, including its market potential and the pain points you aim to solve. Observe the market. If there are glaring, unaddressed pain points that are obvious to you and not being tackled by current service providers, that's a clear indication of a potential opportunity.

The second consideration is whether the identified pain point is one that your potential clients will value if solved. You might be able to solve a problem that you consider important, but if the market doesn't agree, they won't value or pay for the solution. Therefore, you need to determine if your solution is not just viable and valuable, but also if the market will consume it and pay a reasonable price for it, enabling you to continue evolving and growing your business. If these criteria aren't met, you won't have a product that satisfies the market.

✨ Pearl of wisdomAs an entrepreneur, you must be willing to quickly change what you're doing. This doesn't always mean abandoning your company, but it may require a drastic change in direction. For example, with Doctums, when we founded the company, we had a clear vision for its direction. However, when opportunities arose that didn't align with our initial vision but were the right thing to pursue at the time, we chose to explore them. This flexibility allowed us to grow and eventually return to our initial mission.

You've started several companies, some more successful than others. In cases where things haven't gone well and you find yourself needing to stop digging to get out of a hole, how do you know when to put down the shovel?

I think that's a very important point to consider. As a founder, when you're emotionally attached to your business and don't want it to fail, it's crucial to be passionate about what you do without becoming overly emotional. For instance, I believe in higher education and see it as the best industry to work in for the rest of my life. I'm passionate about helping institutions and students. However, I can't allow myself to become emotionally attached to a product or service to the extent that I continue to invest in it despite diminishing returns.

As an entrepreneur, you must be willing to quickly change what you're doing. This doesn't always mean abandoning your company, but it may require a drastic change in direction. For example, with Doctums, when we founded the company, we had a clear vision for its direction. However, when opportunities arose that didn't align with our initial vision but were the right thing to pursue at the time, we chose to explore them. This flexibility allowed us to grow and eventually return to our initial mission. So, knowing when to stop digging may sometimes mean digging in a different direction.

✨ Pearl of wisdomAs a founder, President, or CEO, you'll naturally care deeply about every aspect of your company, from its website and emails to its services and products. However, as your company grows, your hands-on approach can start to impede progress. It's crucial to recognize when this happens and take a step back. Trust in your team's abilities and their shared vision.

A founder always has to wear many hats, especially a serial founder like you. But what's the one hat you can't take off?

I think there are two perspectives on that. One mistake I made was not giving up some of those hats fast enough. I needed to become comfortable delegating to capable people. However, as the founder, as the President or CEO of your company, you're going to care deeply about how everything looks—your website, every email message that goes out, every service that's delivered, or every product that's put out into the market. There's a point in your growth where you're going to start impeding the company from moving forward. You need to realize that as soon as possible and get out of the way. Trust that you've hired the right people and built the right team to deliver on your vision. They may not deliver exactly the way you would do it, but it may still be a great outcome. You need to get comfortable with something that may be great but not what you would have done. That's step one.

Step two is when you asked me about the roles or hats a founder, president, or CEO can never give up. I believe there are two. First, founders, especially in the first few years of the company, are responsible for business development. You need to be involved, ensuring deal closures, supporting your sales team, and presenting the product in the best light possible. Chief Rainmaker is the first hat that is probably the hardest to give up, even if you want to, because some founders aren't comfortable with it. However, doing it well is crucial for entrepreneurial success.

Second, you must always wear the hat of creating a vision and strategy for the company. You need to articulate this clearly, communicate it to all levels of your company, and ensure that it's a vision and mission your team, partners, and stakeholders can align with and share values around. This is something you can never stop doing. You need to continually reinforce it. Sometimes, this vision needs to shift and change as the market, customer demands, and the economy change. You must guide your company through these changes and stay focused.

✨ Pearl of wisdomMy advice for any startup is to scale at a pace you can afford. If you're wondering about the next step in scaling, focus on what your organization needs to look like to handle the challenges ahead. Consider this before it happens, because if you don't, you may miss opportunities.

Let's go from a startup to a scaleup. There's a product-market fit, there's enough demand for what you're offering, and you have customers who are paying for your service. At this stage, what are the key levers to grow your business?

If you have experience operating at scale, perhaps in a large EdTech firm, you understand the level of process and organizational maturity required. If you're new to this and starting a company, seek advice or bring in advisors who can help you grasp what scaling entails. For us at Doctums, this meant establishing early on the procedures of a much larger company. We built our company to operate as we envisioned it would look five years later. We hired a general counsel, set up a Human Resources department, implemented payroll, and put in place all necessary structures, even with just a few employees. This preparation ensured that when growth hit, we were ready to absorb it and demonstrate to the market that we could operate at scale.

My advice for any startup is to scale at a pace you can afford. We were fortunate to afford certain things early on, which proved instrumental to our growth and success. If you're wondering about the next step in scaling, focus on what your organization needs to look like to handle the challenges ahead. Consider this before it happens, because if you don't, you may miss opportunities. You could encounter a deal or a project that requires capabilities you don't yet have, leading potential partners to walk away.

From your experience of leading or observing the construction of products and services, what is essential to keep in mind during the construction process?

In the realm of education, especially for products tailored to college and university administrators, it's crucial to remember that they ultimately serve students. When building products, it's not just about fixing administrative problems; it's about connecting those solutions to an improved student experience. This approach makes the product more valuable, appreciated by the market, and also resonates with employees who are often in the industry because they care about education and student success. At Doctums, many of our team members are former university employees who worked directly with students and are passionate about helping institutions achieve their goals of better serving students, delivering a superior experience, and operating more efficiently and fiscally responsibly. Therefore, when building a product, it's important to connect it with what matters most to the client: the students.

✨ Pearl of wisdomIn the realm of education, especially for products tailored to college and university administrators, it's crucial to remember that they ultimately serve students. When building products, it's not just about fixing administrative problems; it's about connecting those solutions to an improved student experience. This approach makes the product more valuable, appreciated by the market, and also resonates with employees who are often in the industry because they care about education and student success.

Education is transforming in multiple ways. From your perspective, what are the most dramatic changes?

Education is undergoing significant transformation globally. While the traditional four-year undergraduate degree will always have its place in the market, there is a growing recognition that it's not suitable for everyone. Alternative pathways such as short courses, certifications, and competency-based education are gaining acceptance, with many employers no longer requiring a four-year degree but instead valuing specific certifications and a willingness to learn on the job.

This shift is driving growth in continuing education, certificates, and competency-based education models. Institutions that successfully adapt to these changes are experiencing significant growth, while those slower to evolve, especially those without strong reputations like Ivy Leagues or big state schools, are facing enrollment challenges. As students become more discerning, comparing prices and considering online alternatives, institutions must evolve their programs and technology to meet these changing needs.

This evolution presents opportunities for startups offering innovative solutions to help institutions transform and enhance the student experience. For startups entering this space, it's crucial to focus on solving a specific pain point exceptionally well rather than building a broad product. Startups should aim to execute flawlessly and scale their solution effectively before considering diversification into other areas. By maintaining focus and delivering value, startups can capitalize on the evolving education landscape and drive market growth.

✨ Pearl of wisdomSelecting which events to attend and how to allocate the marketing budget is crucial. Seeking advice from an advisor or a company familiar with the EdTech market, like 27zero, can be incredibly valuable. They can recommend events based on your product, market fit, and target audience, which can lead to early success in the market.

What advice would you give to 20-year-old Wes?

I think the best advice for my 20-year-old self is what I said earlier about choosing your partners carefully, understanding that you're in this for the long haul with your partners, and you're better off trying to find money to pay someone a salary than bringing them on as a partner if they don't align with you fully.

How do you choose which events to attend and how to invest that event budget, which is usually a significant portion of the marketing budget?

When it comes to events, you fall into one of two categories. You're either an industry insider, like myself and the people at Doctums who have been in the industry for decades, knowing exactly which events to attend and why. However, if you are an EdTech startup and unsure about which events to attend to represent your product effectively, the choice of events becomes critical, especially with a limited marketing budget. Events range from large ones like EDUCAUSE to smaller regional ones, and attending all of them is not feasible. Therefore, selecting which events to attend and how to allocate the marketing budget is crucial. Seeking advice from an advisor or a company familiar with the EdTech market, like 27zero, can be incredibly valuable. They can recommend events based on your product, market fit, and target audience, which can lead to early success in the market.

✨ Pearl of wisdomWith 27zero, we found two crucial things. Firstly, we found a company that understands educational technology. This is essential in the EdTech space, as working with a partner who can quickly grasp concepts, ideas, and strategies without extensive explanations accelerates our market impact significantly. Secondly, 27zero is a company that values people, which is evident in how they treat their team and, consequently, their customers. Everyone has had nothing but good things to say about the company, and you've delivered on everything we aimed to achieve. I couldn't ask for more.

What has been your experience working with 27zero?

We had a long journey to find the right marketing partner, and we worked with some truly great companies and individuals. I don't want to diminish their contributions; they helped us reach where we were before we met 27zero. However, with 27zero, we found two crucial things. Firstly, we found a company that understands educational technology. This is essential in the EdTech space, as working with a partner who can quickly grasp concepts, ideas, and strategies without extensive explanations accelerates our market impact significantly.

Secondly, 27zero is a company that values people, which is evident in how they treat their team and, consequently, their customers. From myself to everyone in the company who interacted with them, we've all had a positive experience. Everyone has had nothing but good things to say about the company, and you've delivered on everything we aimed to achieve. I couldn't ask for more.

What impact has working with 27zero had on the business?

Working with 27zero has had a significant impact on Doctums. When we began our partnership, we had brand recognition but struggled to effectively communicate our brand message. 27zero helped us align our messaging and develop a comprehensive framework for our marketing efforts. This allowed me to step back from micromanaging marketing tasks and delegate responsibilities to the 27zero team and our internal team members. As a result, our marketing campaigns and branding efforts have been executed more smoothly, leading to tangible results. Our pipeline has grown, and we're attracting new types of clients and expanding into new regions. Our brand recognition has also improved, thanks to 27zero's help in creating a strong and appealing brand image. Overall, working with 27zero has been a positive experience, and I look forward to continuing our partnership as we evolve as a company.

The EdTech Mentor is a 27zero publication. Let’s start a transformative EdTech marketing conversation today.
🔥 Rapid fire questions
Ed or Tech?
The name Doctums comes from "doctum" in Latin, which means educated. We are here to assist in education. We educate. We are educated. It's ingrained in everything we do. It's part of our DNA. However, technology is also fundamental to me. I'm a software engineer by training, and I believe that technology can accelerate the education industry's advancement. I aim to help the industry adopt technology successfully and responsively. At Doctums, we stand at the intersection. While we don't develop technology, we rely on it. We enhance it. We assist the industry in its adoption. But at the core, our focus is on education. We do all these things ultimately to benefit students. So, sorry, but I won't choose between Ed and Tech

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