Women in Edtech: A Q&A with LearnLaunch Co-Founders Jean Hammond and Eileen Rudden

In honor of Women’s History Month, we sat down with two of the women who are LearnLaunch’s Co-Founders: Jean Hammond and Eileen Rudden. In this interview, Jean and Eileen share their stories, including their roles in the start of LearnLaunch, Boston’s education innovation hub. They discuss the significance of finding and forming great teams, the importance of hard work, and the value of being comfortable with taking risks.

*This interview has been lightly edited for clarity.

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What inspired you to pursue entrepreneurship?

Jean Hammond: Back when I went to business school at MIT, there was much less buzz about starting a company than there is now. In fact, there were zero courses in entrepreneurship during my time there. But entrepreneurship always seemed like something that would be interesting or possible to me.

About a year out of business school, my husband’s career took us to Edinburgh, Scotland. I eventually came in as a product line manager for Spyder Systems, an extremely high growth computer network company that grew from 30 to 350 people. At Spyder Systems, I got to try all the different parts of running a company. It was really a great experience for learning.

I then came back to the States and co-founded a company, Axon, with some people from Spyder Systems based on a business plan that I had written. When the company was about four years old, we sold it to 3Com, another networking company. I then stayed on with 3Com for a while and did some really interesting things.

During that time a business school friend came to me and said, hey you’ve had a successful exit, can you invest in my company? That resulted in me being the first investor in ZipCar and started me on the path of angel investing. For a long time, I was mostly advising, investing, or consulting with early stage companies in a lot of different ways.  

I finally decided that I wasn’t always seeing companies that I cared much about and eventually, started spending more and more time around education companies. In fact, I used to have a program called Kids Club where about 25 companies would come together and do little projects that they could work together on. At the same time, Marissa Lowman started having monthly meetups of edtech startups and was soon aided by Eileen. Hakan Satiroglu, who founded the education start-up Xplana Learning, linked up with Mark Miller who had a long track record of founding and advising education-oriented startups. The two later met up with Vinit Nijhawan, serial entrepreneur, venture capitalist. It wasn’t very long after that when Marissa, Hakan, Mark, Vinit, Eileen, and I got together and started the operations that lead to LearnLaunch.

Eileen Rudden: The first organization I started was right after I graduated from college. I co-founded a weekly community newspaper and I ran that for 18 months until we ran out of money. At that point I thought, maybe there was more that I had to learn. I then went to business school. From business school I went into consulting, high tech, and education.The work just kept changing and I had much more opportunity.

Jean Hammond and Eileen Rudden speaking at LearnLaunch 2019 Across Boundaries

I didn’t really come back to entrepreneurship until almost thirty years later, when I believed that the education sector really needed to be transformed, I thought I uniquely had the passion and the skills to help make that happen. It seemed as though there was no appropriate organization to bring the power and potential of digital transformation into education. So I became a founder and an entrepreneur. I felt there was no alternative.

“When I believed that the education sector really needed to be transformed, I thought I uniquely had the passion and the skills to help make that happen.”

What led you to get involved in the edtech sector specifically?

Hammond: Many people in education have some kind of personal story. In my case it’s my grandmother. At 19, my grandmother had already finished teacher’s college, left Missouri, and had traveled to Arizona when it was still a territory. She later became the head of schools for middle school. It took a tough lady to do that. My aunt was also sort of a rebel even though she was a school teacher. I always felt like I had a strong connection to both of them.

I also realized that I had a phenomenal advantage in life. I received an exceptional education, which, in combination with my career experience, equipped me with the knowledge and skill set to start and run companies. I felt like we were never going to level the playing field if we didn’t get out there, start unleashing entrepreneurial energy, and start fixing all aspects of education – especially since entrepreneurship is such an unstoppable force for change.

In education, I came to realize that just like women entrepreneurs in general, edtech entrepreneurs were having an incredibly hard time convincing investors that their products were a safe enough investment and had a high enough odds of success. Of course, investors don’t need your idea to be perfect because it’s all risky out there, but it seemed like it was being a difficult sale and edtech entrepreneurs weren’t getting a fair shake at the money. And that probably continues to be true today. Education as an industry is on the order of about 8% of the GDP in the US, and yet the percent of venture capital that’s invested in edtech at all times is definitely less than 2%. So there is this mismatch between the amount of funding that should be there based on the industry size.

“I felt like we were never going to level the playing field if we didn’t get out there, start unleashing entrepreneurial energy, and start fixing all aspects of education – especially since entrepreneurship is such an unstoppable force for change.”

Rudden: When I was at the Chief Officer of College and Career Prep at Chicago Public Schools, I felt it was like business 30 years before. The principals and teachers are the people that are educating the next generation, and yet everything felt so behind. It was a jarring transition for someone who had been in the technology industry to go into schools.

Although my role wasn’t focused as much on technology, I just couldn’t leave my tremendous background of 25 years in making and marketing technical solutions. I had also been on four public boards of companies that were involved in bringing new technologies to different industry sectors, like in finance or hospitality. I felt that if I wanted to do something in education, I had to combine it with technology. It was really needed and there didn’t seem to be any other people that were focused on this in the same way. That’s what drew me back to entrepreneurship.

What challenges did you experience in your entrepreneurship journey? How did you/what motivated you to tackle them?

Hammond: Some people don’t get into entrepreneurship because it feels very risky to them, but it doesn’t feel risky to me at all. I don’t experience risk as a scary thing, I experience it as a fun and exciting challenge that can be overcome with hard work. There’s a personality aspect of people who are comfortable around a lot of early-stage companies. If there’s a good idea, I’ll say let’s go get the funding and go for it. Or if the product’s not quite right for the users we thought were going to use it, I’ll say let’s fix it and keep going. That personality trait is often indicative of success in both entrepreneurship and also in early-stage investing that helps push entrepreneurs.

As investors, we push, steer, and suggest methods to help startups build stronger and stronger teams. Right now, I’d say that in edtech, some of the teams will have to become stronger to scale to their total potential. Team building is a real challenge and all startups. It’s particularly hard in edtech, because selling to schools, higher education or workplace edtech are all really hard to do. You need to combine a lot of knowledge of the industry, connections, and persistence to make it through.

Jean Hammond moderating a pitch competition at LearnLaunch Across Boundaries

Rudden: I actually didn’t see starting LearnLaunch as much of a risk. I had already established myself in my career and was financially able to make the investment, including the investment of time. Sometimes women don’t have the confidence to start something, and that’s an issue for many women. At that point late in my career, I had the confidence. Earlier in my career, I might not have.

Having good partners in entrepreneurship is really important. When I started a business right after college, I had a collaboration of partners and it didn’t feel like much of a risk. We put ourselves out there and took initiative. So what I lacked in confidence myself, I was able to surround myself with other people as part of a well-rounded and talented team. I felt really happy to have participated with a great team and to have created something on my own, even though it only lasted 18 months.

“The more you put yourself out there and receive positive feedback, the more confidence you build in yourself.”

For the rest of my career, I grew with very large companies and was very successful in technology. That built my confidence over time. I also had a wide range of business and education experience. The more you put yourself out there and receive positive feedback, the more confidence you build in yourself. I’ve probably faced a lot of challenges within my career in technology. There were promotions that I didn’t get it, when my middle son had asthma it was hard trying to balance everything, and there were times when I couldn’t get revenue growing fast enough in a certain role. Throughout my business career, I’ve also seen many other people put themselves forward to take on risks, bold assignments, or major turnaround situations, and that really made a difference for them and their careers.

Are there specific challenges a woman might face in starting her own company? How would you recommend overcoming these challenges?

Hammond: In edtech, we actually have a higher than average percentage of female founders and co-founders. The investing community for women in edtech is better than out there in the venture community at large, but it’s not great. Women edtech entrepreneurs face the same challenges in securing funding that women in any industry do. In 2008, the percentage of women angel investors was around 3%, while the percentage of women-founded companies who received venture capital investment funding was less than 3%. Women definitely have more than 3% of the good ideas, so the fact that they get only 3% of the funding seems moderately weird. Golden Seeds came together with the thesis that there needed to be a senior woman in every management team. The idea was that diverse teams make better decisions. I wanted to be a part of that movement so I founded the Golden Seeds effort for Boston. Since then, there has been significant improvement. In 2013, the percentage of women who were in Angel Investment Groups grew to 33%, and the percentage of women-founded companies who received Angel investment funding grew to 36%.

We don’t think that it’s hugely worse for women-led companies in edtech. In general, investors like to take a risk with people that they can look across the table and say, “That person is a bit like me.” With a heavy concentration of males in all aspects of venture, it continues to perpetuate this problem. Many of the larger edtech venture capitalist firms have decent women representation, so the odds are a little better for women edtech entrepreneurs. That doesn’t mean there’s a ton of money flowing around or that fundraising is easy. It just means there’s a little less bias.

Jean Hammond mentoring a founder from a LearnLaunch Accelerator cohort Company

Rudden: Now that there is a broader community of women entrepreneurs, they have the opportunity to learn from each other. Many women entrepreneurs are now starting businesses where the value is apparent to other women but might not have been apparent to other men.

As a female executive or entrepreneur, you recognize that you might have to work harder or be more persistent to get your point across. There are all kinds of implicit biases that we all have. Rather than letting it get you down, you face it head on with your uniqueness, enthusiasm, and a positive attitude. Hopefully, the world will come around to your vision. And if it doesn’t, as in the case with my newspaper company, the Brockton Examiner, you will still learn a tremendous amount.

What advice would you give to your young female entrepreneurs who are just starting out?

Hammond: There’s really two pieces of advice that I would give: Remember that it’s going to be hard work. You can only do it if you’re willing to do all of the different pieces of the work, so be ready for that. It’s not magic and it won’t be easy. But if you’re willing to do the work, you’ll find there are people around trying to help and tell you what would make a difference. You should also be seeking honest feedback that is to the point, truthful, and not sugar-coated. Ask questions like: How good is this idea? How likely is that to get funding? Great honest feedback is the single best thing for young entrepreneurs, and that is particularly true for women.

When you’re telling a story, tell all of the story. Don’t just give us the first or second phase of the vision. Also, remember to think big enough. Instead of limiting yourself, think: This is what I know I can do, and when we get to that point, we will be able to add on other product features and that will take us even further.

Of note, over 41 percent of the companies who participated in the LearnLaunch Accelerator program were either founded or co-founded by women.

Rudden: It’s important that you connect with a support network of mentors and a team in the venture itself. There are so many platforms that are for bringing people together. Not only are there a lot of startup accelerators and incubators like LearnLaunch, but a lot of colleges and universities are also now providing platforms for their women entrepreneurs. You have to make the decision to put forth an effort, and then you can connect with people.

George Moore, CTO of Cengage, said this to me when we first met: “I would much rather hire a failed entrepreneur than someone who hadn’t put himself out there.” It’s good to be nervous. Starting your entrepreneurship journey involves making big decisions. But even if you try something and it doesn’t work, you just have to realize that if you can recognize why it didn’t work and what you learned from it, other employers will see that as a positive. That can help you understand the risk isn’t as scary as you initially think.

For more information on Jean Hammond, check out this podcast interview from Angel Invest Boston

You can follow both Jean Hammond and Eileen Rudden on Twitter and LinkedIn:

Jean Hammond: Twitter | LinkedIn

Eileen Rudden: Twitter | LinkedIn

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Jamal Merritt is an intern at LearnLaunch.