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“I probably wouldn’t have taken that interview,” says Rebecca Weekly about the role she currently has – that of VP Hardware Systems at Cloudflare.
During a recent conversation Rebecca was asked to tell the story of how she got her current role, and she was able to share interesting advice for other women in tech as she did so. She revealed that, under normal circumstances, she probably never would have ended up working at Cloudflare at all. The reason?
“I would have looked at the job spec and thought to myself: here’s a company that runs WAF [web application firewalls] and DDoS [distributed denial- of-service attacks] and CDN [content delivery network], and I’m a hardware geek,” she explains. “I’m not saying I would have ruled myself out, but…”
To get to the point in Rebecca’s story to where an impromptu video call turned into one of the most exciting – and unexpected – job offers of her career, we have to go back to the Covid lockdowns. Suddenly unable to travel, Rebecca came to realise just how much travelling she’d been doing for work prior to Covid in her job at Intel.
She enjoyed working at Intel, and she was particularly fond of her team. She’d spent almost seven years working her way from Cloud Strategic Planner to Senior Principal Engineer to VP and General Manager of Hyperscale Strategy and Execution. That was six months before Covid hit.
Covid helped her see she wanted more
“In some ways Covid gave me a stay of execution,” Rebecca says. “I was travelling so much for work that I found it tough to balance the needs of my kids (who at the time were just shy of two and four) and my work life.”
In fact, Rebecca had already experienced a kind of epiphany during her first six months as VP, as she explains:
“The telling moment for me was I came home and in the first 21 days of November I’d been to Taiwan and back, Taiwan to Shanghai and back, London and back, all within those 21 days. There was a 36- hour period between two of my trips and I’d come in when my two-year-old was still asleep and in the morning, he said ‘No hugs for mommy. Mommy’s never home!’”
With Covid, Rebecca was able to restructure her team to make them more effective so she wouldn’t have to do so much travelling. She used the lockdown period to think and reorganise and achieve more balance. Yet even after all that, something still wasn’t right.
“As we started coming out of Covid, I had this thought of ‘Am I learning everything I want to learn? Am I moving forward in my career?’” she says. Having had the chance to sit back and think about her career, Rebecca decided to parley the skills she’d developed into what she calls “the next phase of learning.”
The importance of knowing what you want
Rebecca presents as a structured and considered thinker – the sort of person to carefully weigh up options before making decisions. What’s interesting about her recent career development, however, is that once she began to expand her network and meet more people, opportunity came looking for her.
Here is where Rebecca’s first golden nuggets of advice emerges as she talks about her experience: be clear about what’s important to you in your career. She explains her thought process like this:
“It was that combination of what do I want in my life that makes me happy with myself at the end of every day, plus what do I want to accomplish in work, and will I be on a path to continue learning staying here where I am, versus looking at something new?”
Expanding her network led to unexpected opportunity
What did Rebecca do next? In September 2020 she joined the board of OCP (the Open Compute Project) and was elected their chairperson a few months later. OCP is a non-profit organisation, and Rebecca was clear that she recommends that women join non-profit boards as a first step towards Board participation, because “by doing that you’re able to expand your contacts and expand the different entities you will be able to access.” Moreover “you will find doing board work is incredibly rewarding and very good for your career.”
As to how good, it was through the process of joining the OCP board that her current company Cloudflare reached out to her.
As Rebecca tells it: “It was a very interesting outreach. They said, we see you work with hyperscalers. We know you work with OCP that sets the standard for systems across the world. We’d love to pick your brain, buy you lunch and understand more about what you’ve observed, what best practices are, as we up our game.”
After several exploratory and energetic discussions about the industry, the team at Cloudfare simply asked ”Have you thought about doing this at a place like Cloudflare?’”
Imposter syndrome rears its head
This, for Rebecca, is where this casual conversation created a life changing opportunity. As she relates the experience, she was not expecting a job offer. Indeed, when she talks about her usual process of switching firms, she has a very analytical, logical process that she follows:
“I generally prefer to decide when I’m ready to make a career change, then think through what I’m looking for in the process and then run a process.”
Rebecca’s surprise at being offered a job seemingly “out of the blue” is interesting. Often women are more cautious than men when it comes to taking career risks or trying new jobs. How Rebecca describes her response to the job offer could be seen to support that impression; it took her almost half a year to weigh up the pros and cons and make the leap.
“I got on a spreadsheet and looked at every job I had interviewed for over the previous five-six years in this kind of ad hoc fashion against this one. I tried to grade it based on things I was interested in, and against the growth opportunities in my previous role, management experiences, the opportunities to be influential in changing something, and the opportunities for learning.”
Maybe this was Rebecca’s MIT training and background coming out, but to many of us, this does not sound like an ad hoc process! What Rebecca said next might be even more revealing, though:
“I agonised so much because I wasn’t ready, and I had to do a lot of soul searching to really feel confident in my selection in ways that I don’t like to do normally.”
It seems like it was that stepping outside of her comfort zone, taking a leap of faith from an organisation she enjoyed working at to one she didn’t yet know. She described how important the importance of feeling some confidence is, as you take a risk.
How do you calculate risk vs reward?
Rebecca even puts a figure on it – at least when it comes to her own piece of mind: “I always have a bias towards 60% I know I can do this, 40% I feel like I’m holding to the ledge by my fingernails. I need to bias a little more towards ‘I got this’.”
Does this always have to be a 60-40 split, I asked? Maybe it was ok to take more of a risk and go 50- 50? I asked her if she thought that would create more risk or more opportunity. Partly, this is because, in my experience in the talent consulting business, I have often encouraged female candidates to take more risks in search of more opportunity. I was also curious partly because it struck me how taken aback Rebecca had been at being approached casually by Cloudflare when she was not actively looking.
In executive recruitment, this is a common approach, as we know that the best candidates are happy and successful in their current role, and only if they’re presented with a compelling opportunity will they consider a change.
In the end, Rebecca concluded by reflecting on her reasons for considering a new opportunity:
“Besides pay, there are lots of other things that make work interesting, and you will be more excited about your work if you are excited by the mission or the company or the job that you’re getting to do, or the learning that will be there. But ignoring your skillset, how it applies to that company, and if you’re going to be any good at it, is a recipe for failure. So, you do have to weigh up whether you can technically do the job as well.”
In closing
“Today, we are more empowered to make decisions that are good for us and good for our families and our careers. This pandemic has empowered us to say we have the right to make these decisions. We’ve made things that seemed impossible two years ago work, and work effectively, and so with that we can take bolder, more confident steps forward, and support other women in doing that as well.”
Since this article was written
Rebecca Weekly is now Vice President of Infrastructure at GEICO, joined Feb 2024
