What I’d say to me back then - tech entrepreneur Heather Shoemaker on overcoming sexism in the VC market

In her early career at tech start-ups, Heather Shoemaker flew all over the world helping large companies re-factor their source code so that their applications could support multiple languages. 

With a degree in linguistics and a Masters in telecoms, this seemed the ideal job. Shoemaker was able to combine her love for speaking different languages with coding them, in the field of software internationalization:

What I discovered during that approximately decade of my life was that when companies were going global, the biggest challenge they face isn't what I was doing. What I was doing isn't easy, but once you do it, you just maintain it. It's a pretty straightforward process.

The more complex challenge was providing multilingual customer support. Those same companies were having to figure out how to staff native-speaking teams across the world to translate self-help articles, and maintain chat and other forms of support in multiple languages: 

It's a much messier challenge, it’s an operational challenge. At the time, there was no technology to solve that problem. I started thinking about what I would do to solve that problem from a technology perspective.

By then, Shoemaker had taken a role at eCollege in the Denver Tech Center to lead its globalization efforts, ahead of the company being acquired by Pearson. 

I had negotiated a lot of shares when they recruited me, which set me up pretty nicely to go off and do something on my own. I decided to do what I had been thinking about doing as an internationalization engineer, which was to build the technology that would make the multilingual customer support process easier so you weren't having to staff up these teams of native-speaking folks all over the world.

Sexism

When deciding to and set up her own business, Shoemaker recognized it was going to be more difficult as a woman than if she’d been a man. But she had experienced plenty of sexism in the corporate world anyway.  As the only woman engineer in the start-ups she worked for back in the early 2000s, Shoemaker was greeted as a novelty: 

I would go into these big companies and be leading sessions, training engineers on how to maintain this level of internationalization and their source code, and they would look at me like – ‘Oh, a woman, interesting’. They would listen, they were just surprised that there was a woman in this role. There were a few scenarios where I got some pushback, where the attitude was - what do you know, you're a girl? Though nobody said that at that point.

Shoemaker didn’t experience blatant sexism until she started advancing in her career and got into positions of leadership. 

That's when it really started to kick in, when there was a lot more at stake.

When eCollege got acquired by Pearson, Shoemaker was at senior director level, but it was clear that she would have to make significant sacrifices to ever get to VP or C-level in that world - sacrifices she wasn't willing to make: 

There was a lot of bias, especially for women who have kids. At the time I was at Pearson, I had my second baby, and I remember everything being stacked against me. I had to drive a long distance to get to work with an infant at home. When you're breastfeeding, you have to pump during the day. I was always winding up in these public restrooms, pumping. It's not pleasant.

Trying to climb the corporate ladder, Shoemaker saw men getting the breaks as they didn't have nearly the same obstacles as women, especially those with kids at home. She decided at that point to branch out on her own:

I didn't know I was jumping out of the frying pan into the fire at that point. I just thought, this is stressful, how much more stressful can it be to start my own company? I had no idea.

When Shoemaker started working on Language I/O around 2012-13, the company was able to grow organically. As nobody else was in the space of multi-lingual customer support at that time, there wasn't pressure to grow quickly. Then other start-ups and entrepreneurs started noticing the significant market size, and began entering the space:

Of course, these were men because hardly any women found a start-up as a technical founder.

And those men quickly started to raise VC funding, she recalls: 

I remember seeing an announcement by what is today our chief competitor, that they'd raised a significant amount of money. I realized we can either die this slow painful death while other companies gobble up the market share, or I can raise funds as well. That’s where I really started to notice sexism.

Not part of this world

As a female tech founder asking VCs for money, Shoemaker was treated as though she wasn't and shouldn’t be part of that world: 

I got so many weird comments. One VC said, 'If you were a guy with a beard, this would be a much easier sell'. Another said, 'I like investing in women-founded companies because women are just so much more trainable'. I got comments like that - they're not aggressive, but they're definitely undermining.

After about a year of talking to VCs in Silicon Valley and on the East Coast, Shoemaker gave up. It wasn't working, it was stressful and depressing. At one point she even considered presenting herself as male on the video calls, with voice modulation and putting on a beard and moustache: 

I knew this would go so much faster, but where do I go from there? I raised the money and they discover she's a woman, that's not a good start to a relationship. I abandoned that idea, and I abandoned the whole process at one point.

Shoemaker finally got her break, at a graduation party for a Wyoming tech boot camp in Cheyenne:

I was standing there with a beer in my hand and this guy I didn't know came up to me and said, ‘Hey, are you Heather Shoemaker? I understand you have a SaaS tech start-up here in Wyoming. I'm with an angel group in Casper, Wyoming, and we'd like to invest in your company’.

This was Jerad Stack from angel investment group Breakthrough 307, who helped Shoemaker raise $500,000 in Wyoming. 

So after several years of trying to raise funding unsuccessfully, it was only by being in the right place at the right time that Shoemaker managed to build her idea into a successful business:

If I hadn't been in the weirdest state in the country to start a start-up, he would've never found me. I just got lucky. The beauty of being in Wyoming is it's the least populated state in the country. It doesn't matter if you're a man or a woman, if you're starting a tech firm, the state is thrilled because it's such a non-diversified economy, it runs entirely on oil and gas.

The government and business leaders are looking to create jobs other than oil and gas jobs here for kids to be able to hire into when they graduate from high school. So Jerad was just thrilled that there was a SaaS start-up that was generating money and legitimate.

While it wasn't a huge amount of money, the funding was enough to get some momentum going for Language I/O, as other investors are more likely to be interested in a business if somebody else has already taken the initial risk. 

From there, she was introduced to Bob Davoli in Boston, who has his own VC firm Gutbrain Ventures: 

He's very much a feminist, had invested in woman-founded companies before, he's been in the natural language processing space for a long time. I didn't have to convince him of the size of the market, he wasn't asking me stupid questions, he got straight to the facts.

Davoli led the seed round for $5 million, pulled in some other investors and has been pivotal in helping Shoemaker grow the company ever since. 

Language I/O is also the first recipient of the State of Wyoming’s new WYVC Fund, which was the largest investor in a recent $8 million Series A1 funding round. The company has raised more than $22 million to date and is now on the path to profitability.

Advice

To achieve success as a female tech founder took many years of rejection and frustration, but Shoemaker’s advice for other women following in her wake is simple - don't give up:

It's going to be harder than it is for men. Just accept that, settle in and get ready for a long journey. You might get lucky, and it might not be a long journey, and I hope that, but just settle in because it's going to take a little bit longer.

She also advises women to have a bulletproof pitch, as you can't afford to not know the answers to questions: 

Have a relatively small pitch deck, but have hidden slides for all of the questions that might be asked because they will try to trip you up, especially in technical areas.

Another tip is to find an investor who knows your space. VCs not on the East or West coasts aren’t as narrowly focused on the tech market, which can make the process more challenging. 

It's hard to find somebody in the Mountain West, in a more rural area that gets your market and the value proposition. When I went and found folks who had invested in similar technologies, it makes the whole pitching process a lot easier.