Women In Privacy: An Interview With the Women Leading Fastmail

In this article, Helen and Nicola from Fastmail talk to 1Password about their leadership in email privacy.

As 1Password discovered in their Women in Tech panel earlier this year, it’s important to show women succeeding in male-dominated industries, like technology/security, and to talk about how men can help create space for others in the workplace. Check out 1Password’s blog post about their women-led Security team to hear more stories about women in leadership.

In this article, the team at 1Password talk to Helen Horstmann-Allen (Fastmail’s Chief Operating Officer) and Nicola Nye (Fastmail’s Chief of Staff) about their interest in privacy-focused technology, challenges they’ve encountered in the industry, and their advice for women and non-binary folks working in or thinking about joining the tech industry.

What’s your role at Fastmail?

Helen: I came to Fastmail in 2015, when they acquired my email forwarding company, Pobox. As the Chief Operating Officer, I work to bring the best email experience to our customers. I also oversee product, support, and marketing. Internally, I lead business strategy, company culture, and people development, including hiring and onboarding.

Nicola: As Fastmail’s Chief of Staff, I build workplace culture and people development for the Australian team. But much of my time is spent leading projects across two continents, managing our legal and compliance work, and serving as our privacy officer. I wear a lot of hats!

What made you pursue a career in tech?

Helen: Being able to take action and solve problems quickly. If you’re interested in creating something, your ability to build it in tech is unparalleled. The people who use technology, and the impact my work can have on their daily lives, is what keeps me here.

Nicola: I love computer programming! It was a new area of study when I was in school and the possibilities felt endless. Now, my focus has broadened beyond software for its own sake to the social and political implications of technology—I’m fascinated about how people use computers to problem-solve. Technology lets you reach the entire world; it provides replication at scale; it makes things available to an audience of thousands or millions—this gives incredible benefits, but it raises concerns too.

How did you become interested in privacy-focused technology?

Helen: I believe privacy is a basic human right, so when I got into technology it was just a basic assumption for me to protect the data privacy of people who use email. I think privacy drives the best customer experience and when I think about the kind of product I want to use, I want a product that respects me. My data should be for my eyes only. That’s especially true when you talk about email, calendars, and contacts.

Nicola: About 10-15 years ago, I was pretty disillusioned by the tech industry. It seemed that much of the startup era was about building software to solve nonexistent problems—funded either by advertising or burning large piles of investor’s cash. I couldn’t continue to work like that, and I nearly left the industry altogether.

However, the problem wasn’t the industry itself but finding a company that aligned with my values. I realized I had to find a company building products that put people first. I wanted to work somewhere I felt good about my job, somewhere I could help people and make the world a better place.

How has the tech industry changed for women since you started in tech?

Helen: Well, first of all, there are many more of us! I remember going to talks and classes when I was in college where less than 10 percent of the attendees were women.

Before working at Fastmail, I ran my own company. Running my own business protected me from the toxic experiences many of my peers endured. A vast number of women who started when I did have since left tech. It doesn’t matter how many women you bring into tech—when the negative experiences outweigh the positive ones they will leave.

At Fastmail, we’re changing the system, and adding women like me to leadership positions has been crucial. Articulating and sharing our company culture and values have helped us recruit more women and non-binary people, which has brought in more diverse perspectives.

Nicola: People often ask me why I have pink hair. In my career, I’ve worked in predominantly white, male environments. I felt a lot of pressure to fit in, take up less space, and not make waves. In doing so, I gave up some of my own identity. Now that I’m older, wiser, and feeling a responsibility to those who come after me, I dye my hair pink. My hair color reminds me, and everyone around me, that I am proudly a woman in tech, despite the challenges. My pink hair is a celebration of female accomplishments in tech: It’s a bold color and cannot be diminished!

The tech industry has improved over time but still has a long way to go. Women with bright hair are not unusual in our industry and many of us have similar motivations for our coloring: It helps us claim our space.

What challenges have you faced in this profession because of your gender—systemic, or not—and what advice do you have for overcoming it?

Helen: The biggest challenge for me has always been opportunities missed, mentors unmet, connections unmade, the places I don’t go, and the conversations I didn’t join. Whether it’s because of gross behavior on the part of a subset of men, or just the semi-aggressive questioning that implies you need to prove you deserve to be there or that you belong, it was easier to miss out and not fight every single fight. The energy women spend fighting battles is the energy our male peers get to put into networking, chasing opportunities, and opening doors.

Creating your own opportunities can be exhausting. I try to be very mindful of the doors I can open for others now. I now recommend women consider being on boards. I have honed many of my leadership skills in my board work.

Finally, I think we are so vulnerable to the voices that talk us down, including our own! I choose to treat myself the way others see me—intelligent, kind, funny, beautiful, a person who can solve every problem in their world. Don’t do your critics’ work for them—trust the voices of your supporters and people who care about you.

Nicola: I have found that people used to discount my expertise, especially if there was a man nearby. Sometimes this manifests as being mansplained to or being ignored when I’m interviewing with a colleague.

It’s also often seen as the responsibility of a woman, or a minority, to be the vocal advocate for diversity and inclusion initiatives in a workplace. Don’t hire us to fix your culture—you’ve already hired us into a job, now is not the time to lay a second (full-time) job onto us as well!

My number-one tip is to give yourself permission to take up space. You’ve earned it. You do have the expertise. Don’t shrink because you can see it makes others uncomfortable. It’s exhausting to advocate for yourself (and others) constantly, so my second tip is to get allies who know what to look for who can call out poor behavior or assumptions.

Finally, give yourself permission to NOT do the diversity and inclusion work. It’s enough that you’re out there being awesome and handling daily friction without also having to hold others to account.

How has Fastmail been able to build a team with women leaders?

Helen: By promoting more women. We’ve hired terrific women for management positions, and we promote women and non-binary people across our team at all levels. I like to help the people who work for me grow by offering them a job, giving them more responsibility, providing professional development, and being a mentor. Women and other underrepresented groups benefit from enthusiastic sponsors pushing them long before they think to ask!

Nicola: Shout out to Helen, our COO! She’s excellent at lifting people up where she sees capabilities. She also identified that the most powerful force for improving our team’s productivity is core skills (sometimes known as soft skills).

Fastmail has ended up with women in leadership roles because they can bring our team exactly what we need to succeed. Technology can be taught, but communication and people skills are what fosters effective teamwork. Women have had to develop those skills as a survival instinct to influence without authority, to drive consensus, and to deliver in hostile environments.

What should be done to increase the number of women in leadership roles?

Helen: The pathway to leadership is simple—push people towards new opportunities, perhaps before they see themselves as ready. Then, offer them the support they need to succeed in those opportunities. If you give women opportunities, they will succeed.

Nicola: When hiring someone new to your team, ask this question to their references: “In what area would this person undersell their strengths?” I like to ask this question because women, queer folk, and people of color live in a society where they feel like they have to explain themselves constantly. We struggle with imposter syndrome; that’s not our fault.

What advice would you give to women who want to enter the tech industry?

Helen: Don’t be afraid to connect with people and share what you’re going through. Seek out trusted, more seasoned career people in your life who will tell you what’s good, what’s expected, and what’s toxic. I am grateful that people no longer give the advice that you need to stay in a job for two years “or it looks bad.” Don’t waste your life at a workplace that doesn’t value you.

Nicola: Tech is so much fun! There are many women folk in tech and allies—get yourselves established with a network by asking around. Meetups make this a lot easier, along with hackathons or game jams and there are several conferences great for newcomers to tech, many of which will let you attend for free if you work as a volunteer.

Women aren’t the only underrepresented group in tech—what can be done to make tech more diverse across race, class, and gender?

Helen: First, much like poison concentrates up the food chain, privilege concentrates up the opportunity ladder. For example, if you screen applicants based on where they went to school, you’ll overlook qualified people from less privileged backgrounds. It is important to find different mechanisms that are less susceptible to bias.

Second, when interviewing someone I try to create an environment that lets each applicant bring their best selves to the forefront. Some people don’t need any encouragement to brag about themselves—but lots of others do. Creating a welcoming atmosphere in your hiring process is good for everyone.

Nicola: Hire women and other minorities. There’re plenty of perfectly qualified and able women and queer folk out there.

If you’re trying to bring about a change in your culture, you can’t hire someone who is an exact culture fit to what you have now if you don’t already have substantial diversity in your company. These people explicitly don’t look like who you already have in your company.

Finally, make sure you’re prepared to give them the support they’ll need to succeed. Just hiring people isn’t enough; they need a welcoming and understanding environment where they can flourish.

How can men, and those in privileged positions, become better allies to their marginalized co-workers?

Helen: Being an ally often starts with listening to what less-privileged colleagues are telling you about their experience in a team. When you respond, think about whether you’re trying to make them feel better or trying to make yourself feel better. If it feels hard to do or say the right thing, just listen.

Become a better mentor and sponsor—a change that starts by cultivating gratitude. What help have people given you along your journey? Who are the people who gave you the opportunities that changed your life? In viewing your own life with gratitude, think about how you can give that gift to others.

Nicola: Active listening. You’ll hear things that hurt. You’ll want to say, “but I’m not like that,”—remember, it’s not about you. Be prepared to call each other out with key phrases like: “We don’t do that here,” “Would you say that to me/a man,” or even “Why would you say that?”

Active sponsorship. Put your coworkers forward for training/conferences, whether as an attendee or encourage them to speak. Give them stretch projects. Help them find coaching or a mentor who can lift them up.

Active empathy. Make it clear that you care about the users of your tech—“Is this safe for marginalized people?” and “what harm might our tech cause if used improperly or properly?”—and then extend the same degree of thought to your colleagues.

Is there anything we haven’t touched on that you want to share?

Helen: The first time I met someone at Fastmail, it was our CEO, Bron Gondwana. Bron traveled from Melbourne, Australia to Philadelphia to meet me. After our meetings, he asked if I wanted to join him for some sightseeing while he was in town. At the time, I had twin babies, who were just 18-months-old, and a 3-year old. I was nervous to tell him that I have three young children, and I could only meet at the playground or another kids’ activity.

I told him about my family, and he responded with enthusiasm and support that warmed my heart. Bron joined us at our local pumpkin festival, toted one of my twins on his shoulders, and helped our 3-year-old decorate a pumpkin. It’s one of my most favorite memories. It told me a lot about the workplace culture I was joining.

Our teams observe how we behave as leaders, what we share, and the stories we tell. People at your workplace want leaders who authentically embrace them for who they are.

Nicola: To those women currently in technology: Sometimes we get so busy looking up to where we are going, seeking out mentors and colleagues, that we forget to look back to how far we’ve come. You are already a role model to others. Just by working in this industry, you are already making a change. Great work!

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