'First' retirement for Dinah Davis

When Dinah Davis announced her retirement from cybersecurity scale-up Arctic Wolf in early February, she did so with a gracious post on LinkedIn.

“I did what I set out to do ­– build a framework and software development team that has been key for Arctic Wolf to scale and execute beyond its wildest dreams,” she wrote. “To all the fantastic people I have worked with over the last 7.5 years at Arctic Wolf, THANK YOU. Working with you has been an absolute privilege and career highlight.”

The post caused a ripple across the Waterloo Region tech community. Only 43, Davis is an accomplished and well-respected cybersecurity leader – one of the few women in the local ecosystem to hold a core-tech executive role.

So, why walk away from a great job – Vice-President of R&D Operations – at one of the region’s most successful tech companies?

“I’m calling it my ‘first’ retirement,” Davis says with a laugh. “There might be many, many more in the years to come.”

In an interview with Tech News, Davis talked about her career, her passion for helping women in tech, what she has learned about scaling development teams and her decision to take a break from full-time work.

“I’ve pretty much been working 20 years straight,” she says. “Other than a mat leave – which, by the way, is not a break at all – I’ve never taken more than three weeks off, I’ve never had more than a week between jobs and, I’ll be quite honest, I got myself good and burned out.”

Davis joined Arctic Wolf in 2015 as Director of R&D. Her mandate at the fast-growing cybersecurity company was to scale the development team, which grew from 15 to more than 400 during her seven and a half years with the company.

For an organization to grow that quickly, she says the team has to work as hard as an Olympic athlete in training – and not just hard enough to win one gold medal, but many.

“That’s how audacious the goal has been, how high the bar has been for what we were trying to, and have, achieved,” she says. “It was glorious and awesome, but you cannot live at that pace, at that intensity, for a super long time.”

Davis’s immediate plan is to decompress for a while. She’s looking forward to spending more time with her 14-year-old daughter and staying involved with a few “side projects.”

Those projects include podcasting, public speaking and serving as a mentor and board member with the Rogers Cybersecure Catalyst, an education and training centre associated with Toronto Metropolitan University (formerly Ryerson).

“I love professional speaking, I love working with startups and I love being a mentor,” she says

Davis’s career journey – more zigzag than linear – began with a passion for mathematics.

“In high school I loved math. And in my last year I took calculus, and I loved that even more.”

It was also in high school that Davis had one of her first experiences with how women are often treated differently than men.

When she asked her high school guidance counsellor about careers, the only thing he suggested was math teacher. Looking back, Davis is pretty sure that if she’d been a boy, the counsellor would have suggested some other options, like engineering or computer science.

“I was 17, I didn’t know what I wanted to do,” she recalls. “So, when he said you should be a math teacher, I was like, OK, that sounds plausible.”

She attended the University of Lethbridge in southern Alberta because of its teaching program and the fact that it was closer to Winnipeg, her hometown, than universities in central and eastern Canada. 

But after spending time at the front of a classroom, Davis discovered that teaching wasn’t for her.

“I felt that to be a good teacher you had to love spending time with the children, you had to love wanting to teach,” she says. “And what I realized was I loved the mathematics, but that other stuff felt really hard and really frustrating.”

Despite growing up in the ’90s, Davis had little experience with computers. Her first real exposure – a mandatory computer science course in third year – was mind-blowing.

“I remember this moment, like a lightbulb going off in my head, and I said, ‘This is just another syntax for how I think! This is just mathematics on a computer!’ I fell in love with computer science in that moment, in that class.”

Davis took as many computer science courses as she could over the next two years. She also landed a summer job as a research assistant to one of her professors who needed help coding a combinatorics algorithm.

They were looking for mathematicians who could code, and I was like 'That's me! That's me!'

– Dinah Davis

That experience helped her land the first of three co-op terms with the Canadian Security Establishment (CSE), the federal digital security and cryptologic agency.

“I saw this posting for mathematicians who could code,” she recalls. “They didn’t even put it out there like a ‘software developer’ or ‘computer scientist’ ­– they were looking for mathematicians who could code, and I was like ‘That’s me! That's me!’”

It was at the CSE that Davis fell in love with cryptography and cybersecurity.

“I loved pure math… and when you look at public-key cryptography and the protocols, it’s a very strong mix of pure mathematics and logical problem-solving,” she says.

With some prompting by a Lethbridge professor, Davis applied to two graduate schools for a master’s degree in math and cryptography. One of the schools, the University of Waterloo, was her “moon shot” application.

“If I got to go to the University of Waterloo, that would be like going to where the crypto gods are,” she recalls thinking, still in awe two decades later. “Wouldn’t that just be so amazing? I’ll never get in (she thought)… but it turns out I got in!”

The UW experience changed the course of her life. Not only did she earn a master’s degree with great employment value, she also met her future husband.

“It’s amazing when you look back over your life,” Davis says. “I don’t know where my life would be (without the UW experience).”

One big learning from her UW days was the power of networking. During a conference, she met several members of the BlackBerry cryptography development team and sat with them at dinner. It was 2003 and BlackBerry was fast becoming the world’s most secure and popular smartphone.

“They were all on their BlackBerrys and I was like, ‘What are they doing?” she recalls with a laugh. “This whole concept (people glued to their phones) was so foreign.”

One of the BlackBerry developers was a co-op student. When Davis was looking for a full-time job a few months later, that student gave her resumé to his boss, the head of BlackBerry’s cryptography development team.

At the time, the tech industry was in one of its periodic downturns (much like today’s slump) and recent grads were having a tough time landing jobs. But thanks to her BlackBerry connection, Davis got an interview and landed a coveted position on the company’s “crypto dev” team.

“I got my dream job right out of school,” she says. “We lived on that bleeding edge of mobile cybersecurity.”

It was a huge opportunity. Not only was she working on cool technology for a fast-scaling company, she also got her name on the first of about 18 patents.

Throughout her schooling and co-op terms, Davis got used to being one of the few women in a male-dominated industry. Her BlackBerry experience was positive: As the only woman in the small crypto dev unit, her male colleagues were “stellar, awesome people” who treated her like just another member of their highly skilled team.

Still, Davis admits that she intentionally downplayed her gender.

“I tried to just act like one of the guys,” she says. “I didn’t want to make waves; I just wanted to have a successful career.”

Davis left BlackBerry in November 2011. Internal strife within the company had grown to the point that she couldn’t see a future for herself at the smartphone maker.

“It was very evident to me from the position that I had that the infighting inside the company was going to take it down.”

An executive search company lured her away to a new position at a small tech company. The environment for women was a stark departure from her positive experience at BlackBerry, prompting Davis to rethink her “don’t make waves” approach.

“(At BlackBerry) I didn’t want to be looked at as one of those ‘feminist women,’” she says. “I realized later that I had been very wrong about that, and if I was going to work at a company, they were going to have to be OK with me talking about women-in-tech issues.”

The overall mission was to change perceptions of women in technology and create a space for women to feel safe and have their voices heard."

– Dinah Davis

The experience led Davis to start Code Like a Girl in 2016. The online publication provides stories intended to help women “navigate the tech world, encourage young women to pursue a career in tech, help parents and teachers get young girls interested in technology, and inform male allies how they can help.”

“The overall mission was to change perceptions of women in technology and create a space for women to feel safe and have their voices heard,” Davis says.

As life and work got busier, Davis took a step back from Code Like a Girl. But the site is still very active, with 42,000 followers and about 1,000 hits per day.

Putting her startup experience behind her, Davis went on to spend a couple of years at edtech company Desire2Learn (now known as D2L) before getting the itch to go back to cybersecurity.

Once again, she invoked the power of networking. Davis was one of a number of women leaders invited by the University of Waterloo to talk to Grade 9 girls about careers in science and technology. One of the other participants was Kim Tremblay, a fellow UW grad and co-founder of Arctic Wolf.

“Right before the event was going to start, I went up to Kim and said, ‘Hi. Please don’t leave right after the event because I want to do (what you do) one day, and I want to learn from you how to do that.”

Her chutzpah earned Davis a lunch meeting with Tremblay. In 2015, she went to work for Arctic Wolf as Director of R&D, later moving up to VP of R&D Operations.

Looking back on her career, Davis says she’s pleased to see that more young women are choosing careers in science, technology, engineering and math (STEM). She credits role models like Tremblay, as well as intentional efforts by universities such as UW to encourage and support young women to enrol in STEM programs.

She also thinks that the #MeToo movement, including the writings of software engineer Susan Fowler, played a role in helping women in tech speak out about biases, harassment and sexual assault.

“I think a lot has changed,” Davis says. “I don’t think enough has changed, but I think in the last seven years we saw more progress than I saw in the first 13 years of my career, and that’s really heartening.”

While there are more women in software development and other tech jobs now, there are still too few women in cybersecurity.

“Cybersecurity is a more closed group,” she says. “It also has a perception that it’s guys in hoodies in the dark, and that you have to live, eat, breathe, and sleep cybersecurity and be a hacker.”

It's a misconception that Davis wants to change.

“There are hundreds of different types of jobs in cybersecurity,” she says.

What’s more, cybersecurity is a booming industry that’s only going to grow.

Davis has urged universities and colleges to develop short cybersecurity programs – a year or two long – to train people from a variety of backgrounds to find entry level jobs in the industry.

Rogers Cybersecure Catalyst, for example, offers a six-month program.

“It’s a perfect industry for a lot of people to retrain into,” she says. “It’s perfect for people who have had some life experience and are wanting to get into a role that has a future.”

Diversity in the workplace is another one of Davis’s passions. Whether it’s diversity of gender, race, culture or where you studied, a variety of outlooks and lived experience strengthens creativity and innovation in the workplace.

“It’s empirically proven that the more diverse your company is, the more likely the company is to do better,” she says

Over the course of her 20-year career, Davis has experienced several downturns in the tech economy. While the current slump is certainly hurting some companies, she is optimistic that things will bounce back.

Noting that tech has been “starved for talent for so long,” she also wonders if some of the bigger companies “are manufacturing a problem” when they lay off staff.

“(I think some of) these big companies are using it as an excuse to take out high salaries to make themselves look good to their investors,” she says.

Downturns can have a silver lining for the ecosystem, she adds. Pointing to BlackBerry’s mass layoffs between 2012 and 2015, she says that many of “those amazingly smart and talented people” went on to start new companies in the region.

“The same thing is going to happen with those Google people and other people who are getting laid off,” she says. “They are either going to start something themselves or they’re going to start supporting a smaller company and help them grow.”

As she takes a pause from full-time paid work, Davis is looking forward to cultivating her “side projects” – public speaking, podcasting and mentoring.

“Yes, I retired, but I want to be able to come back and do something positive, just like Code Like a Girl,” she says. “I always want to be looking for positive outcomes.”