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Sam Weber

EdTech from a unique perspective

After COVID, the growth of streaming platforms was a huge challenge for educators. In this context, investors and EdTech leaders thought about how to bring teaching and learning tools to Zoom. The answer was Class, a software that added not only the best in live digital learning, but a vision of a next generation virtual classroom. From his role as Vice President of International Strategy and Operations at Class, Sam and his team built the go-to-market function at Class to get closer to customers. He shared how his past experiences have led to his current work, what he's learned, and what knowledge and skills he finds most valuable today.

This new venture shared a common history: Blackboard. This interview explores the successes, obstacles and lessons learned. As Sam said: "Blackboard was my transition, using some of these professional skills that I gathered on the technology side. Less pedagogically or as an instructor, but in the business of education and education technology".

Can you please start by telling us a bit about yourself, your family, your origins?

Sam Weber:

I grew up in New England, in Boston, and I generally stayed there through college. But since then, I've lived in a number of different places. I lived in Central America for a few years, I lived in California, in San Francisco, and in Washington, DC. for a while. That's where I started working for Blackboard, and I've lived in London now for 11 years.

I have two small daughters. They're four and a half and two and a half. So, my life has been focused on them the last few years, but we've enjoyed starting to raise them here in the UK. I don't know if we'll live here forever. Maybe here, maybe somewhere else. I definitely consider myself an American. I've lived and traveled a lot. I hope to think that I have perspectives from having lived and worked and met people from all kinds of backgrounds and places throughout the world.

Can you share the journey that led you to work in education and EdTech?

Sam Weber:

The first thing I did after university was teaching English as a second language in Costa Rica, and that was a really impactful experience. Then, I worked for an NGO back in the US for a couple of years, where I was really focused on non-formal education methods for adults across topics like child health and microfinance. The firm was really about using nontraditional education methods to help people.

I went back to grad school and got into the commercial side of technology through business development, sales and some strategy work. Later, I worked at a venture firm for a while, and at a media company, and decided—once I had some skills—that I really wanted to apply to something that was a bit more mission-oriented, that had to do with education.

Blackboard was my transition towards using some of these professional skills that I gathered on the technology side. Less so pedagogically or as an instructor, but still in the business of education and education technology. This interest in education I had acquired being in the technology space for seven or eight years. I started at Blackboard in 2009, so I've been working in EdTech since then. But I think education became something that was really formative and important to me very early in my career. I developed some professional skills and then applied them into EdTech.

What do you like the most about this industry?

Sam Weber:

For me it's two things. One is that it's something that affects everyone, everyone has some form of educational experience and it's very broad. I feel that what we're all working on is relevant in such a broad way. Secondly, I think we're at a point of change where models are changing. Certainly in a lot of western countries the traditional model of education, sort of the post-industrial revolution, hasn't changed that much. But it's starting to change in some ways, it feels revolutionary, it seems like we're just at the tip of the iceberg. The way we assess, the way we recognise how different people learn and the tools we use to get there are changing. We're able to use technology in a very different way that's very different from this much more rote model that was designed for people to come out and be competent to do a very specific job.

Between strategy, marketing, and sales, what do you tend to do the most?

Sam Weber:

I started in a more strategic role and wanted to get closer to the market. So I moved into business development and sales roles. I always wanted to be closer to revenue in a lot of ways, closer to customers and customer acquisition. Literally everything, from things that I think most traditional sales people think are really boring, but are really important if you're going to build a go-to-market function. Not just the where and the what, but the how.

I'm really interested in how you go-to-market, what are the ways you do that.

✨ Pearl of wisdomI'm still the person who gets really excited when we get a $1,000 customer.

But I've expanded as I've matured into understanding the whole go-to-market function.

I need to work with people that I respect and admire for their experience in designing and building. But then the rest is how do you go commercialize it? My interest and to a certain extent, my scope now spans more than just how you make a deal.

How do you go win a customer, what's the positioning? What are the go-to-market activities? What are the capabilities you must have to do that, whether it's direct sales or channel sales? How do you do marketing across a multi-channel strategy? Maybe you don't because you're not sophisticated enough to do that.

What's your greatest challenge today?

Sam Weber:

✨ Pearl of wisdomI think the challenge in a startup is to stay focused. Do we need to focus on affordability because that's the hottest issue in Brazil, for example? The idea is to stay focused on what you're trying to achieve every month, every quarter, every week.

I think that's our challenge right now because our overall strategy is right and I think we've got the next couple of years mapped out in a way that I don't think we need to go back to the whiteboard right now. It really is a game of execution.

What do you do on your day-to-day to stay focused?

Sam Weber:

The number of tools that are available to us to help us do this is now limitless. In one of my last roles, I felt like there's a big difference between being really busy and getting things done right or being effective. I'm a little bit of just a list maker, so it's important to have tools, it's hugely important to be transparent. I'm a big fan of collaborative tools where everyone in your peer group or your team describes their priorities even for the week.

Listing the three things you're going to get done this week forces you to tell everybody else what those things are. And just that itself is a really good exercise because we've all got 300 things to do every week. I like the idea of prioritization and transparency because it holds you accountable. Some of us have that self-discipline but I think it's really helpful to share what your priorities are.

That goes for sales and marketing too. Like you use Airtable to manage all your campaigns and just help you prioritize. On the selling side, especially in a startup, you can get overwhelmed, because you can start chasing anything that sounds like it's interesting to you. You have a whole country or region to sell into structured form.

How do attention and focus fit into content strategy?

Sam Weber:

I think about content in three ways. First, what's most important is that it's direct and deliberate and clear. It doesn't have to look great, it doesn't matter what format it's in. You don't have to have thought about it for a long time.

The second is that I think we don't spend enough time being thoughtful about how we create content. An example is a pitch or an internal presentation, something that has stakes to it. I've had a lot of experience working with folks who are a generation younger than me, probably smarter than me, who are happy to turn around a deliverable in a matter of hours. And in some cases, I've asked them literally "I don't want to see this for two days, but when I see it, I want it to be something that your mother would be proud of". And I typically get the same presentation back 45 minutes later with the three changes that they thought I asked for.

And then I think the third is authenticity and to have a voice, a point of view.

✨ Pearl of wisdomWe're at a point now where businesses are too afraid to write anything that's like anything other than generic. But, is someone going to learn anything when they read what you wrote? You’ve got to have a take.

This is how you can tell the difference between Chat GPT and something else. You’ve got to have a take.

Is there a particular skill set that you feel is more important to have in marketing or sales?

Sam Weber:

On the marketing side, we've split the storytellers from the analytical folks. There’s a performance side, a creative side, and then folks who get stuck in the middle. That's a challenge. I think you find your home in one of those places and start to figure out how to do both.

✨ Pearl of wisdomIf you start as a pure generalist on the marketing side, you want to build skills. Marketing has become so sophisticated and specialized that I think you've got to pick an avenue into the field.

I've got lots of ways to send somebody a million messages about buying my product because they have the right title. And I'll just keep trying whatever it is to get them on the phone.

The idea of picking up the phone has been lost to a certain extent. There's plenty of cold calling that goes on, but a lot of that is just trying to get you to come to a meeting for somebody else.

✨ Pearl of wisdomActually talking to somebody and listening to somebody on the selling side, is what I'm seeing as the big difference between people who are more successful and those who are not.

The last group can manage a groove flow better than anybody you've ever seen, but just struggle to understand who it is they're talking to when they get to somebody on the phone.

What skill do you feel you should have if you like strategy and you're in an early career looking for interesting work?

Sam Weber:

✨ Pearl of wisdomThe most functional skill is analytics. I wish I had a better quantitative background. What I wish I had learned earlier is that the way you get better at strategy in a particular space is to actually go talk to the participants in the market that you're evaluating.

Whether that's customers or suppliers, getting to the primary source is undervalued.

You can now get McKinsey's templates anywhere, so it's just easier to go build a model based on secondary research. The way you get the right inputs into your model to build strategies is to get source material. It's not as fun or as cool to talk to 15 school administrators or 400 teachers or ten procurement officers who often don't really want to talk to you.

Maybe it's harder, it's more work, but what you really want is you want to be unfettered, you want to get away from the translation of what's happening to find out what's really happening. Then you can tell your story and you build your strategy around it. The last bit is like figuring out how to get the right data sets.

Is there something that you need to keep in mind when you're selling to education institutions?

Sam Weber:

✨ Pearl of wisdomI think a lot of people don't really want to hear this, but I do think it's an idiosyncratic industry and you have to meet them the way they like to be sold to. You have to know what their buying cycles are. It's really hard just to throw a standard SAS enterprise sales playbook in the education sector.

There aren't people who are used or are comfortable getting those calls. They go to two conferences a year and that's when they might look at different services or products. You may want to try something that's a little different, but if you don't know how they think, you're going to struggle.

Certain markets tend to be transparent. In the Netherlands you'll find a tendering process that hasn't changed in ten years. In parts of Latin America, for example, there's a really large number of private institutions that have a CEO model, that have a specific hierarchical business decision-making process. Compared to universities in the US, which are much more like state or public universities, the private university in Latin America has committees and cycles and different processes.

✨ Pearl of wisdomWhat I've found is that it's hard to take a tried and tested enterprise software sales model, which means that taking really good tried and tested enterprise sales people and just sticking them in the education space sometimes works, but it's not necessarily an indicator of future success.

Other approaches like the Challenger model are trickier. People love that model, they love coming in and saying: “the reason your students aren't successful is because you haven't bought our software.” It's like: "I know what your problems are, and therefore you're not doing a service to your constituents. Let me show you what I've got.” I don’t think that works in education.

I would say it's much harder to get established in education. But once you get somewhat settled, if you can cultivate your customers, I think this market, more than most, will sell on your behalf.

✨ Pearl of wisdomThis market may hate to use the word "market", but people who work in this space are constantly looking at their peers. So your flagship accounts may have been impossible to get, but they will help you build a community and they will help communicate for you.

If you were to pick one strategy tactic or one activity that might be working for your marketing team, what would it be?

Sam Weber:

It's important to understand where we are. We're relatively new, so your tactics are going to be different depending on where you are in your own lifecycle and awareness amongst your customer base and trying to figure out if there's intent. But we've seen the best results with relatively old school stuff, webinars and events. Branded stuff that's 100% digital proved less effective than I would have expected.

There are some more well-known events, some that, when we went the first time, we thought it was an absolute waste of time because we were relatively unknown. By the time people knew who we were, the second time, it was incredibly useful because it was a validation just to have a presence there. People that don't know who you are, don't talk to you. I think it depends on the market. For us, events are much more of a spear market than a net market and smaller events are better.

What personal advice would you give to your 20-year-old self?

Sam Weber:

My advice for someone that age is to go experience the world. If you haven't found the right career at age 20, I don't think you should worry too much about finding it. By the time you turn 21 you're going to have a long time to figure out what you like to do professionally or maybe what you're good at. But it's an incredibly formative time. My advice to people that age is to step outside what they know. And typically, that means going experiencing a different culture or a different place that could be not that far from where they live.

We tend to live in these little isolated worlds and traveling will serve you to understand how different people live, communicate, and work. Exposure to things that are different is really important, especially for people who are high achievers and are thinking about careers in a university setting.

✨ Pearl of wisdomGo step off that conveyor belt. Study really hard to get into this school to then get this job, which is going to get me another job and then you go see the world when you're 70? That just seems like a shame to me. People who do better tend to be those who have the ability to see things differently.
🔥 Rapid fire questions
Inbound or outbound?
It depends. For our company at this stage, outbound. Totally outbound. Once you've got reference, once you're established, prove inbound.
For sales, direct or through channels?
In an international business with global aspirations, it's channel. You can work with people locally who know what's going on.
Spears, nets or seats?
Depends on the stage.1
Regarding marketing, should you work with an agency or not?
Again, I really think it depends. For sure, it's really important to do your own research to understand your customers yourself; to figure out how to acquire them yourself. If I didn't know how to position and storytell for a certain market, hiring an agency can make sense. In other ways you gotta do it yourself, in my view. It makes no sense to get somebody else to do it; you don't learn enough. The whole point of the exercise is to be agile, to test and learn. If you've given all your testing and learning to somebody else, what's the point of that?
Would you choose volume or key accounts?
Right now, key accounts.
Discipline or talent?
Discipline.
Do you have any inclination for a particular CRM or marketing automation platform? Eloqua, HubSpot, any other?
CRM is pretty crappy, I think there's none that every person loves. HubSpot is good. For email, Survey Monkey is great.

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