Awesome Women in Philly: Managing Teams from Half a World Away

She Steps Up
Oct 20, 2020 · 5 min read
Photo by NASA on Unsplash

Helen Horstmann-Allen is the COO of Fastmail, an email service that allows you to free yourself from big tech and make the independent choice. As COO, Helen provides overall business strategy and product direction for Fastmail and its suite of products. Before Fastmail, she ran her company, Pobox, an email forwarding service, for 20 years before Fastmail acquired it in 2015. Helen graduated from the Wharton School of Business and currently serves on several nonprofit boards in the Philadelphia area.

What makes Fastmail different from Gmail, Outlook, etc? Why would someone consider Fastmail instead of another email?

People have spent the last few years hearing about how Big Tech is using their data, in lots of pretty harmful ways, but it’s so darn convenient. Fastmail lets you take back your privacy for the cost of a cup of coffee a month, without giving up the convenience and features you get from Gmail and Outlook.

Fastmail has offices in both Philly and Australia; how do you manage teams that are so distant from one another?

It’s absolutely a challenge! Before COVID, travel and face-to-face meetings were a huge priority. More than 2/3 of our staff has visited the other location, and I lived there for nine months. But we had a head start on 2020. Zoom has been part of my life for years, we use Topicbox so important conversations are accessible to everyone everywhere, and our team was kitted out with video call tech, home broadband, and WFH as needed.

The time divide also has upsides — your colleagues work while you’re sleeping!

Many times when folks want to make a career change into tech, they think they need to start learning to code. Is this the only way to enter the tech space?

Absolutely not! There are lots of jobs in tech that don’t require the ability to code. I love working in technology, but not because I’m in love with writing code. I studied business at Wharton, and I led my company to be acquired by Fastmail. Now I lead product direction for Fastmail, and design, marketing, finance, and customer support teams report to me. I’ve definitely developed technical skills along the way, but while hitting other goals, like growing our company or solving customers’ problems.

Also, don’t overestimate what “everyone else” knows, or what skills are valuable. I know SQL from a class I took in school, and I still use that all the time (versus what coding I know, which is horribly out of date.) Learning to code isn’t the only way to become part of the tech sector.

As the leader of a company that was acquired, how did you go about incorporating Fastmail’s culture into your team? Were there challenges or big wins?

We had to navigate our team and our national cultures. Australians have both different accents and different assumptions! But that can make it easier to ask a lot of questions and have candid conversations. “Is this how Fastmail does it, or Australians in general?

Now, I have the pleasure of bringing Australian work culture to a US team. Post-acquisition, we expanded our paid time off and sick leave — we’ve even added a sabbatical plan to mirror Australia’s Long Service Leave for employees who work for you for seven or more years. Australia has mandatory voting and Election Day is a public holiday. It was important to me that the US team has Election Day as a holiday too. We’re closed every year so our team can VOTE.

What tips do you have for a leader who needs to grow her team?

Hiring is one of my favorite activities, but it’s also a missed opportunity in many, many teams. Review your pre-hiring activities and staff onboarding as carefully as your new customer funnel.

Ask the newer team members about how you can improve the process, or what they wish they knew or had learned when they started. If you do it every time you consider hiring, you’ll be surprised how quickly it will improve — with better outcomes for you, your team, and your new hire!

If a woman had aspirations to enter the C-suite at some point in her career, what advice would you give her?

Know what drives you — and make sure it’s beyond a particular title. If you are achievement-oriented, it can be hard to stop working towards goals, and realize that you better enjoy the process of the work you’re doing, too.

You also must be a people leader past a certain level. So, especially early in your career, never pass up an opportunity to lead. Volunteer organizations are also a great way to hone your leadership skills — without authority or a title to lean on, you really refine your personal leadership toolkit!

What book or tv show are you loving right now?

I love science fiction, and stories that ask, “What if?” Sarah Pinsker’s book, A Song For A New Day, is about a society that goes entirely online because of a pandemic, and what it costs them when people decide that face-to-face life is too risky.

If you’ve been inspired to learn more about race in the US, I really recommend Caste, by Isabel Wilkerson. It’s a great examination of roles and expectations for people in America, how deeply damaging caste systems are (not just in our own society), and how rigorous the enforcement of social hierarchy still is.

Digital privacy is something I know a lot about, but it can be challenging to explain. Netflix’s documentary, The Social Dilemma, breaks down why digital privacy is important for people who maybe have never thought about it. Stick it out until the end — if the first half made you feel totally freaked out, the second half will give you hope that we can fix it.

If you could go back in time and talk to yourself in college, what would you tell her?

The people who you enjoy knowing, almost always enjoy knowing you. Despite your worries that everyone made all their best friends when they were eight years old, and it’s too late for you to make friends, it is never too late to make another great friend. So if you enjoy someone’s company, don’t worry so much — just ask them to do something!

Also, for the ten bottles of wine, you buy a year, splurge the $8 for a $20 bottle.

Awesome Women in Philly is a monthly Q&A series by She Steps Up, a Philadelphia, PA-based group aimed at empowering women, trans, and non-binary folks professionally and personally. We’re always looking for more awesome women to feature! Reach out to us via our website or our Instagram for details.

She Steps Up

A Philly-based group aimed at empowering women, trans, and…