After almost a decade in university IT and tech sales, Abby Carrales took a two-year break to care for her three children. After deciding to return to work, she spent two years intensely interviewing and networking at tech companies all over the Bay Area before getting a returnship in security compliance at Cloudflare, where she now works as a Security Compliance Specialist. She talks to us about her return to work, fighting impostor syndrome, becoming a rockstar multitasker after having kids, and the importance of finding a supportive community.
How many years of experience did you have before you took a career break?
I had over ten years of experience, including nine years working at the University of California, San Francisco (UCSF). I started working my way through college in Michigan, managing computer labs and classrooms, then graduated into a job at the State of Michigan data center. I moved to San Francisco to work in tech sales during the dot com boom, and I was doing so well in tech sales that I took a year off to travel. When I came back, I found a job at UCSF managing computer labs and classrooms again, until I was poached by another group within the university to do more technical stuff. For the last ten months before I took a break, I worked within the larger UCSF IT department.
What prompted your career break? How long were you out of the workforce?
I was officially off for about two years, then looked for work for another two years. After I had each of my kids—a daughter, followed by a son—I returned to work when each was five months old. But while I was pregnant with my third child, I had complications, so I left work before she was born. I then decided to stay home and focus on my family. When the youngest was less than a year old, I did go back to work for a few months in a contract position at Stanford. But at that time, my youngest daughter was still so young, and my son was also experiencing some medical issues. That, in combination with the long commute, propelled me to end the contract, even though I loved the people I was working with.
How long were you actively looking for work before applying for a Path Forward return-to-work program? What was that experience like?
Once I decided to start to look in earnest for a position, it took me about two years to land a job. I started applying for security-related roles that were more inline with what I had done at UCSF, and came close to getting jobs at a number of startups and big tech companies. I passed personal interviews, technical interviews, and personality tests with flying colors, but it would often come down to me and someone else, and the job would go to the other person. I was asked questions about how old I was, how many kids I had, how old my kids were. The companies outside of San Francisco would even ask me where I lived.
Interviewers were curious about my personal life and how it would affect my commitment to the role. It was soul-crushing to be examined so deeply, in a way that I had never experienced before. When I was younger, I had always been known as a kind of cool chick, a bit tomboyish, and no one ever questioned my career commitment, even though they would question whether I had the technical chops to do the job. Imposter syndrome was something I’d been facing working in tech.
I went to a lot of events. I attended every affinity-group summit and networking after-hours event I could find—from women in tech, to Latinas in tech. I think I’ve been inside almost every tech office in San Francisco! These were all great networking opportunities. I met a lot of individuals and recruiters, had many resume reviews, and practiced my elevator pitch. It’s really helpful to take part in all those activities when you’re looking for work. But you really have to keep at it, and not let rejections get you down.
What type of work was your returnship in?
My returnship was in security compliance at Cloudflare, and that is now what I’m doing full-time. I had the opportunity to rewrite the company’s compliance and security policies, worked on their security frameworks, and am now focusing on risk management and engagement with sales. I’m looking forward to taking on more responsibilities, as I’m one of those people constantly searching for the next challenge to take on. There’s plenty of work to be done here, and it’s encouraged, which is all so heartening.
Are there any skills from your previous experience that you use in your new position?
Definitely. For instance, one of my projects as a returnee was within internal audits. I met with people I had never spoken to before, whose responsibilities within Cloudflare I didn’t know much about. I had to assess whether what they did at the company, and whether the policies they were following, needed to be changed. That was a skill I used a lot at UCSF while working cross-functionally and asking those deep, difficult questions about what they did. Working across fields is something I do really well: I have a Bachelor of Arts degree in Journalism with minors in Photojournalism and Mathematics. There’s also a skill to understanding people and giving them a sense that we’re on the same side. That’s something I have a lot of experience in (due to my experience working in tech sales)—achieving a “yes” and communicating fully.
What are some skills you gained while you were on a break?
I’m just crazy productive now. There’s something that happens when you have children—your brain rewires. I’ve always been good at multitasking and thinking ahead, but when you have a kid, the repercussions to not doing something important are so much worse and immediate than at work. I’ve become incredibly good at prioritizing, managing my time, and avoiding time-wasting activities. I’m always thinking, “What can I do now?” Having kids teaches you that if you don’t take care of something right now, it’s never gonna happen! Procrastination is just no longer a thing for me.
Asking for help is also something I’ve learned to do. It’s not easy for me, because I used to be very independent. But when you have kids, you realize that you just can’t do everything alone.
What has been one of the more challenging parts of returning to work?
The first was negotiating the division of labor with my partner. He’s very involved already, but we have to reconnect each weekend to look at what’s coming up in the next week. Another challenge was just proving myself in the workplace as someone with vast experience, rather than entry-level. It’s still something I’m trying to figure out. The impostor syndrome does get bad, especially as an older woman at a young company. I’ve been in super technical roles, but there’s constantly something new to learn, especially at a tech company like Cloudflare that’s constantly innovating. My team here really supports and values me. It’s just making sure you’re confident and comfortable in understanding the products. I’ve been doing webinars on impostor syndrome and reading up on it to have a more positive internal voice. And my husband and family have been so supportive, and have completely stepped up to the plate.
Has returning to work helped ease some of the impostor syndrome?
Getting the returnship was such a vindication for me, especially in the face of all the rejections. And receiving a full-time offer to continue on at Cloudflare after the returnship—that had me floating.
Did anything surprise you about your return to work experience?
In some ways, how easy it was. Especially with all the support I received. I actually surprised myself too, in how I was able to just slip right back into work. It was comforting—it made me feel like I’ve got this, and I never lost it.
What are you most proud of accomplishing during your return to work experience?
I’ve reached out to other returnees and started a communication channel amongst us. I’ve been participating in the active Cloudflare parents group, which has been encouraging. I’m proud of being able to put time into participating and becoming part of a community here. Cloudflare has been incredibly supportive of Path Forward and all of our ventures. They fully welcome and encourage affinity groups.
Are you part of any other professional or networking groups?
I’m in a group called the CRU, run by Tiffany Dufu. It’s a hand-selected peer networking and mentoring group of women, and the San Francisco group includes ten women. It’s been very cathartic for me and a huge source of personal strength, to be a member of that group and be able to connect with these other women who have varying experience and ages. Even though I’m the only returnee in my group, everyone is so supportive and encouraging—which is not something I’ve always had.
What did you find most helpful about being part of a Path Forward program at your company?
The workshops were so valuable. Meeting Tami and listening to her talk‚ it was like she knew exactly what was going on in my brain: all of my concerns were surfaced and addressed before I even had an opportunity to question them. She knew exactly what to say, and exactly what the return to work process entailed. You can tell that a lot of research and feedback has gone into designing the workshops to ensure that all the most common issues are addressed head-on. This program is so valuable, for anyone trying to get back into work. Knowing that you have a crew and support system, that somebody is there to help—is game changing. I would not have been able to make it through without those workshops.
I really do believe that programs like Path Forward and their partnerships with companies like Cloudflare, can solve the gender gap in leadership. We have years of professional experience, and are coming back with so much more applicable experience, too. It is the diverse set of skills and experiences that companies need right now, and I can see returnships creating that path and more.
You took part in January Career Restart Seminar as a Cloudflare representative. What is the experience of being on the other side of the table, as a recruiter/employer?
I felt their frustration and I could completely empathize with them. I had a true feeling of what to say to them to help make them feel better. I was able to give them action points, which is all that I wanted in their situation—for someone to point me in the right direction. Speaking with these women directly, and being able to speak to their insecurities, was really gratifying in a sense. This brought it full circle for me. It’s good to reconnect with people who are in that place, and to recognize how far I’ve come since then, especially how much I’ve grown recently in the last five to six months. I was grateful to have the opportunity to encourage them—and based on my own experience, let them know that they are going to get there too. Anyone providing them with advice is great, but I think giving them the chance to speak to someone who has gone through the same situation, was really valuable.
Thanks for sharing your story, Abby! We are so happy you’ve found success and balance in your career. Learn more about Abby on her LinkedIn page. – The Path Forward Team