An interview with Tasha Drew, Senior Director, xLabs, Office of the Chief Technology Officer (OCTO).
Tasha discusses her remarkable upbringing in tech, not letting sexism get in the way of her aspirations, her career to date, and advice for all on how to find mentors and support in their journeys.
[Lisa] Hi Tasha, good morning. In the spirit of celebrating women who are making a tremendous impact in the tech community at VMware, and beyond, thank you for taking the time to talk to me today.
[Tasha] Hi Lisa. Great to be here with you.
[Lisa] I’m excited to discuss your tech journey and your current role at VMware, where you balance strategic vision, execution, and team management to build projects from research and incubation to getting fully realized technology into customers hands. But first, please indulge me with the details of your upbringing. To say you grew up around computers and the computer industry is quite an understatement.
[Tasha] Yes, that’s certainly true! My dad, Rob Drew, worked at IBM and focused on creating a messaging technology, MQSeries. The project followed a familiar pattern, where internal funding was flaky, but customers had a huge demand for it, and when it finally got full backing we moved our family from Los Angeles to Hursley, England to build it at the IBM research lab there. He later faced many typical big enterprise challenges in getting it to market, but once it shipped in 1993, it became a billion dollar toolset for IBM.
[Lisa] That’s amazing! Is MQSeries, or a derivative, still in production today?
[Tasha] It is in production around the globe. For example, it handles credit card transactions between large enterprises like Gap and Visa. My dad is incredibly proud because in the history of MQSeries, it’s never lost a message. The technology also provided the underpinnings for what became the WebSphere product suite, which was very successful and only recently EOL’d.
[Lisa] What a treasure trove of how-to and hands-on experience in the world of software development at your feet! Could you shed some light on lessons and observations you picked up as a kid at the dinner table concerning your dad’s experience in managing people in dev teams—qualities that are inherent in your job today? You know, along the lines of timeless mantras from fellow IBM’r Frederick Brook, like “adding manpower to a late software project makes it later,” and the positives and negatives of working for an enormous organization.
[Tasha] I’ve heard stories my entire life, from my dad and beyond, of project successes and failures and how teams work together to ship awesome new things. The Mythical Man-Month has been quoted to me my entire life, in various forms, which even today, is why I smirk when people ask me if I’ve ever read the book. I grew up hearing about the high stakes court intrigue of a massive corporation. My dad’s favorite business lesson growing up was “Take the money! Figure out how to spend it later!” For anyone who’s run a program in a large company, this makes a lot of sense. For people in startups or small orgs, it probably sounds a bit strange.
[Lisa] Let’s talk about how your dad rubbed off on you in your early work experience. In high school, you had an internship at Clorox working with a robot, and you and the robot had “forged a relationship that shall last for the ages.” What was that all about?
[Tasha] Ah, yes. My boss tasked me with fixing her chemical sampling robot, which was constantly malfunctioning and shooting pipette chemicals off the trays and onto the floor. It was like Short Circuit, revisited. I played around with it and changed all its buffers manually to get it to land in the right spots. Took me forever. Then, the day I left Clorox, my boss finally hired a vendor to calibrate it, and it turned out that was a thing she could’ve done the whole time I was messing around with it. It was a hilariously humbling experience.
[Lisa] Huh. I wouldn’t have known the first thing about calibrating a robot when I was in high school, Tasha. Just saying.
[Tasha] Arguably, I didn’t either. Haha.
[Lisa] So tell me. Did you encounter any obstacles being a woman interested in tech in college or shortly thereafter? And if you did, could you briefly describe the situation and how you went about overcoming it?
[Tasha] In college, I had some positive experiences, but a lot of negative ones as well. Lecture halls for classes of 200 often only had 2 or 3 women in them. A lot of my classmates would try to get me to do their lab work for them, or copy my work, but there wasn’t a lot of inclusion. One particularly crushing time, I worked for four straight days on a project and then gave my piece to a classmate. Without talking to me or reaching out to me at all, he rewrote everything, turned it in, and then told my professor I hadn’t done anything, so my grade was lowered. I never knew how to stand up for myself in those situations.
[Lisa] Making universities and the tech industry a place where women feel safe and welcome at that time must have seemed insurmountable. I recently watched an interview with Bloomberg Technologies’ Emily Chang, where she spoke about her book “Brotopia” and an occasion when she had asked a former Silicon Valley CEO why there weren’t any women in his firm and he had answered candidly, “because we didn’t want to lower our standard.”
Obviously, that sort of experience stayed with you, no?
[Tasha] Actually, the scope of the sexism I survived in undergrad only became obvious years after I left. I found out, for example, that a professor publicly prided himself in never giving women students higher grades than a C- and that’s the only class I’ve ever gotten a C in. There were just constant failures that were hard to understand as I was someone who was very used to being able to outwork or outsmart everyone. I entered college as a high school valedictorian with a full academic scholarship, and left determined to have nothing to do with academia again.
[Lisa] What about your mom, Tasha? Could you tell us a bit about her and the ways she influenced your aspirations? Did she also suffer sexism?
[Tasha] The sexism my mom faced was even worse. She graduated in 1965 as one of the first class of women admitted into Emory. At that time, no one would offer her any job, despite the fact she’d graduated Phi Beta Kappa, telling her in her interviews that she “would just quit and get married, so why would we hire you.” When I started in the work force and began sharing stories with them, I think both my parents were disappointed that so little had changed since they were young.
When my sister and I were growing up, my mom was determined that we wouldn’t have the same crushing lack of self-confidence she had been raised to have, so she always very deliberately built us up to have strong confidence in our abilities.
Some people would probably argue she was too effective (haha), but we’re both highly successful professionals, so maybe she should write a parenting book or something.
One thing she always did was give us a “guts award,” when we put ourselves out there or tried something new. Like trying out for a play or a solo in a band, or giving a presentation that we were nervous about. She would also always tell us that feeling nervous and being excited are basically the same feeling, so we might as well tell ourselves that we’re excited.
[Lisa] Getting back to your early work experience. When you graduated from college, which direction did you take, knowing you would best succeed in a leadership role?
[Tasha] When I was interviewing for jobs out of school, I let interviewers know I wanted to move into the business side of technology. I didn’t mean that I didn’t want to program, but for some reason that’s what people heard, and I was offered roles in consulting until I accepted a leadership development opportunity at Lockheed Martin. From there, I received a lot of opportunities to grow, rotating through the different business units while earning a master’s at Rensselaer.
[Lisa] That’s incredibly impressive, especially just out of undergrad. And this is when your career really picked up speed. In fact, while working as a systems analyst and later a systems engineer at Lockheed Martin, you discovered your passion and ability for designing customer solution architecture and as one of your peers has remarked, “an opportunistic, adaptable knack for sniffing out opportunities for product innovation.” You eventually left Lockheed for the startup Engine Yard and joined as the first customer success manager the company ever had. How did that go on all fronts?
[Tasha] It turned out to be a big opportunity for me. I developed strong relationships with Engine Yard’s top 20 accounts—I was technical enough to understand what we were building, which was one of the first PaaS products and a direct competitor with platforms like Heroku, in addition to grasping our customers’ technical needs and businesses. The COO recognized my capabilities early on and decided to move me into product management. R&D was where I really belonged in the first place, but I had had a tough time getting into that space, despite my background.
[Lisa] How essential, would you say, is having experience at a tech startup?
[Tasha] Startups can be a fantastic place to really grow early in your career. While I have been consistently underpaid in startups – and that’s always a bummer to find out, usually from DMs on Twitter from co-workers who feel bad on Equal Pay Day – they’re also the place where I got a bunch of opportunities to try my hand at product management, to build teams, and to learn new technologies. There are never enough people at startups, so if you follow your interests and make sure the work you do is aligned with where you want to go in your career, huge opportunities can open up.
[Lisa] Engine Yard already had a big open source ethos when you were there, right?
[Tasha] It did and it’s part of the reason I got the customer success manager role. I had gone to a RailsBridge course, learned Ruby on Rails, and briefly managed a little startup with friends in my free time. This introduced me to the Ruby and Rails community, and GitHub and social coding. Engine Yard contributed back to Ruby, Rails, and a lot of other tools and services they used to build their platform (Unicorn, Redis, MongoDB, Chef). So, I *got* open source.
[Lisa] You accepted a role at Chef next, which also has a huge open source community.
[Tasha] Yes, and speaking of ‘huge,’ ChefConf 2013 was the first conference I had ever gone to that had a t-shirt that fit me.
Nowadays it’s more normal to have fitted styles, but at the time my mind was blown because I’d always had to buy my own t-shirts, or re-do them on my mom’s sewing machine so they’d fit. I still have that t-shirt because it meant so much to me. And then a few years later, that warm memory was still with me, and I decided to go work there.
[Lisa] At Chef, you were asked to be product lead for Habitat, an open source technology platform for distributed systems lifecycle and management, and got to be part of building it out. You learned a great deal from the brilliant engineers in the community, and how to build an inclusive and dynamic group of contributors. This is when you started looking into the Kubernetes community, right?
[Tasha] Yes, I did, as I was building that project, and serving as part of the core team. I joined SIG Apps, to see how people in the Kubernetes space were thinking about application automation and lifecycle. I dragged my team to KubeCon and had them give talks about our technology and solicit interest to start a collaboration, because I thought we needed to have a strong Kubernetes story to be relevant as the world shifted away from OpenShift, Mesos DC/OS, and Swarm.
[Lisa] And here you were about to experience quite a transition, work-wise and personally.
[Tasha] Indeed. I took maternity leave, and while I was away, I realized that the project and leadership at Chef were taking turns I wasn’t invested in, and it would take me a long time to roll back if I returned. It was then that Jared Rosoff, former Senior Director of Product Management at VMware, reached out to me. He had followed my career at Chef and was very interested and aware of Habitat. He and I started chatting, and he shared with me his vision for using Kubernetes and vSphere together for a modern workload, API-driven platform experience. I was hooked!
[Lisa] When you came into VMware to interview in June 2018, you were a few weeks postpartum, and it was the first time you’d been away from your baby. What were the thoughts going through your head?
[Tasha] I didn’t tell anyone who I met about the baby because I worried about maternal discrimination. But everyone was lovely, and I ended up accepting the job offer. Over time I came to realize that VMware is very family-friendly, and also that I need to set clear boundaries so I can balance work and family life.
[Lisa] So within the Kubernetes community, one of your tasks was to figure out how multi-tenancy was working in upstream?
[Tasha] That’s right. I showed up at a couple meetings to better understand how folks were thinking about multi-tenant Kubernetes, to see how we could collaborate with our vSphere and Kubernetes efforts. After a little bit I ended up getting asked to be a Chair. Since then, we’ve created space for some very cool projects: Virtual Cluster Project out of Alibaba, the Hierarchical Namespace Controller from a team at Google, and the Multi-Tenancy Secure Benchmarks Project, led by the Nirmata team. You can check them out here.
[Lisa] There’s a bit of an interesting story that goes along with how you became the Chair of SIG Usability.
[Tasha] Yes! I had been trying to figure out how to share our Kubernetes icons—or change them if there was a different standard—so that we could all agree on what a “container” or “cluster” etc. “looks” like. It turned out there was no group for that, so Brendan Burns, a Corporate VP at Microsoft responsible for Azure management and governance, suggested (and the community agreed) I start a SIG. And by the way, since folks always ask: I never resolved the iconography question! But we are doing a very cool “jobs to be done” study of users of Kubernetes, the first study of its kind done in open source rather than for a single corporation.
[Lisa] Sounds a bit like you’re downplaying your role as Chair, Tasha. Fact is as the co-chair for the Kubernetes multi-tenancy working group and SIG usability, you help others who’d like to contribute to the upstream Kubernetes community by connecting them with opportunities to share their ideas via regular SIG meetings. And, and, you received the Chop Wood Carry Water Award for your efforts last year at KubeCon + CloudNativeCon North America. That’s quite an accomplishment and well-deserved recognition!
You’ve come a long way, baby!
[Tasha] Indeed.
[Lisa] But there’s more that you’ve accomplished in your three-year tenure at VMware and the first out of the two is focused on Kubernetes and building TKG.
[Tasha] In 2019, I had the opportunity to build the first VMware Kubernetes Service, to launch as part of the Project Pacific project, which became vSphere with Tanzu and the Tanzu Kubernetes Grid (TKG) service. This was a massive multi-business group project, especially at the time, since it required all elements of a stack to work in harmony to deliver the service: vSphere, vSAN, NSX, Tanzu. As a result, I developed a really strong cross-company network. Jared would later tease me that I thought of the company’s mantra “One VMware” in a way that no one else did, because I’m one of the few people to manage to ship a cross-BU product.
[Lisa] And what about Bedazzle, the new project you started?
[Tasha] Ah, yes, Bedazzle! It’s my favorite product name because folks have to talk about ‘Bedazzling vSphere’ in strategy conversations. This project is still on-going, but in the meantime, Chris Wolf, Chief Research and Innovation Officer, had reached out and suggested that I join his xLabs team. xLabs is a group in VMware that’s an “agile incubation lab” for all kinds of ideas. He was very convincing, and the team is very cool, so I made the leap!
[Lisa] I must say that ‘problem solver’ is your middle name, for it certainly appears that over the course of your dynamic career, you’ve been the person asked to go and figure out the next new thing that no one’s quite sure about—again, quoting one of your peers—“with the ability, if need be, to handle an unruly engineering team with grace and humor.” Moving to an agile incubation lab where they’re taking the latest ideas from industry, partners, customers, and internal employees, and productizing them for delivery is sort of your sweet spot.
[Tasha] It has turned out that way, yes! In xLabs, we focus on what we call “advanced development,” which is technically validated concepts 1-3 years ahead of our business units’ roadmap. We have a portfolio of investments, and when we pick up a new concept, our pre-launch team of product managers, product designers, and launch engineers work together with the submitters and stakeholders across the company to develop a product-market fit and MVP proposal. From there, if we decide to move forward, we pull a cross-functional team together, hire the folks we need, and start building. We’re an agile development team, and we focus on learning fast, pivoting fast, and failing fast – and sharing the lessons we learn along the way broadly.
[Lisa] I’d like to close with getting your advice for individuals who want to pursue a career track like yours or break into open source, or tech in general. What are your recommendations?
[Tasha] Be patient (i.e., try not to rage-quit even though things feel terrible sometimes), find supporters who will help build you up and give you energy and joy when you desperately need it, set sensible work/life boundaries, and make sure you’re putting your time and energy on work that gets you where you want to go.
[Lisa] In terms of the latter, you’re a real advocate for keeping a narrow focus on only doing the tasks that align with career goals.
[Tasha] I often refer to it as “building your craft.” I’ve observed that many junior people – especially women – will take care of tasks (organize devrel meetups, order the pizza, get birthday cakes, organize the social gathering) that keep them from investing the time needed to hone where they want to go in their career. My advice is always:
Your time and energy are limited, so make sure you’re using them strategically to build the craft you need to get to the place you want to go. Once people put their labor in this frame, I find they find saying “no” easier. It’s not being irresponsible or unkind: it’s focusing on building your craft.
[Lisa] How do individuals find mentors or the help they need when looking for sponsorship, getting advice on a given topic, learning about someone’s journey, or establishing themselves in a community?
[Tasha] That’s a great question. When you find someone you really respect, or think is cool, don’t be intimidated to reach out. But when you do reach out, have a clear ask. Senior people usually love helping people: it’s how they got promoted in the first place. And if they’re too busy, they can often connect you with the right person via email if they understand the help you’re looking for. So, in a nutshell:
- Make a list of people you think might have a perspective you could benefit from.
- Have a concrete ask.
- Reach out to them.
- Don’t be afraid to reach out to folks you know even if you haven’t connected in a while.
It is important to remember everyone’s time and energy is limited, so not hearing back isn’t rejection. They may just not have bandwidth. Think of other ways you can find the support you need, and keep trucking! For example, some folks who are more famous have written blogs with pointers or a reading list you can follow, so do your homework up front before you ask a question that’s already been answered.
[Lisa] Great advice that I’m taking to heart, Tasha, thank you. It’s been an immense pleasure talking to you today and learning about your dad and his influence on you, your mom’s steady support, your tech journey, the obstacles you’ve overcome, and your many achievements in the open source community. You truly are a formidable engine of change and innovation. And thanks for being one of the talented women in tech who is pushing the envelope and encouraging others to break the bias.
[Tasha] Aww, thank you Lisa, and thanks for all that you do.
You can follow Tasha on Twitter, LinkedIn, and GitHub.
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