In the Room: Women Tech Leaders Drive Community and Progress at

Change has to start somewhere, and at, it’s starting with women in leadership who want to be present as the role models and leaders they wish they had upon joining the tech industry.

Written by Kim Conway
Published on Oct. 12, 2022
In the Room: Women Tech Leaders Drive Community and Progress at
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“It was common for me to be the only woman in the room.”

Emily Massa recalled her new-to-the-industry experience prior to joining’s team, and her statement invoked a resounding feeling of familiarity and discomfort among her fellow women tech leaders. 

“It felt intimidating at times — especially as I had just graduated and I was still evaluating if tech was the right career path for me,” said Massa, who is now a product design manager. 

Chrissy Youker, a senior software engineering manager, thought back to a role where she didn’t have a voice. “There were times where, even as a subject matter expert, I wasn’t listened to,” she said. But well before that, she attended a university where she was one of only four women in a graduating class of 250 students. “I would sit in class and feel like I didn’t belong there,” said Youker. “I struggled with that for years.”

Anne Hickey had a similar experience attending a university where only 24 percent of students were women at the time, only to find that, in a professional setting, the ratio of women in tech roles was equally staggering. Determined to change the landscape, the senior director of business applications set herself on a path dedicated to change. “After joining the workforce, I developed a passion for getting more women into the tech space,” said Hickey, who now leads the still-growing WomeninTech@Care employee resource group. 

In providing a platform for people to find care for their loved ones, not only proudly helps professional caregivers — predominantly women — find work but also has pushed for diversity in its leadership hiring practices. Along with team leaders like Massa, Youker and Hickey, women are largely represented in the company’s senior leadership roles.

While externally building community and connection among its users, has also internally championed the value of connection in the advancement of women in tech. “Mentorship and community are foundational, not only for getting women into the tech industry, but also getting them to stay,” said Hickey. “I’m exceptionally cognizant of that as a leader.”

Like Hickey, Massa wants to be part of the change. “To me, seeing is believing,” she said. “Having women role models to emulate is extremely important, because when I see leaders who look like me, I envision myself in those roles more clearly.” Inspired by her fellow leaders, Massa provides mentorship to the women on her team and helps build on their confidence, encouraging them to aim high, speak up and take on challenges that will push them to see their career goals through. “I made it my goal to be the role model I wish I had,” said Massa.


“I made it my goal to be the role model I wish I had.”


Moved by Massa’s reflection, Youker chimed in: “I couldn’t echo Emily’s sentiment any more. Being the manager or leader I wish I had when I was coming into my career is all I want to be for others.” 

Among her colleagues, Youker is known for closing conversations with a question that opens up space for her team members to confide in her: “Do you have any questions, comments, concerns, thoughts, opinions, feelings?” For Youker, changing how women experience the workplace starts with wiping out the construct of being “too emotional.”

“I want people to have a safe space to talk about how they feel about a solution we’ve proposed or a product we’re trying to build. Because that’s going to give us trust in each other, and it’s going to build communication and collaboration,” Youker explained, adding that it’s also a critical component for women trying to advocate for themselves. “I want you to tell me how you feel and why, so I can go advocate for you and help you advocate for yourself.” 

At, women team members aren’t the only ones in the room — and that’s intentional. If there’s one thing Hickey, Mass and Youker know, it’s that to see the change, they have to be the change. “The people inside this company truly care — not just about the mission, but about one another,” said Hickey. “We work at, and it shows.”


When Women Win, So Does

In September, Hickey’s team launched a year-long project that unified with the recently purchased LifeCare. “We had a large cross-functional team, and amazingly, a large number of women in our ERG participated in it,” she said. Over in engineering, the team built out a reimbursement product and revamped the enterprise enrollment process, leading to a sharp uptick in enrollment numbers. “It’s amazing to see that, in the year I’ve been here, these are the impacts we’ve made,” said Youker.


A event featuring a speaker


An ERG for women, by women

Anne Hickey
Senior Director of Business Applications •

Growing up with parents who studied and worked in the sciences, Anne Hickey was seemingly destined to work in the realm of technology. “They raised me to believe that I could do anything I set my mind to; nothing is too hard or too complex,” she shared, radiating with pride. “I think that was a fundamental belief system — having confidence in myself — that led me to become successful in this field.”

Her connection to began long before she joined the company, as Hickey was applying for business school. “I chose to write one of my admissions essays on Sheila Marcelo — the founder and former CEO of — as an entrepreneur focused on social responsibility, mainly helping women use technology to obtain care for those they love,” she explained. We 

Shortly after her time in business school, Hickey was pointed back in the direction of by a former colleague. 

“It was a no-brainer — I was already sold on the mission a long time ago.”

Combining her passions for technology and empowering women’s success, Hickey leads two groups at the company: the business applications team and the WomeninTech@Care ERG. And to really live by the confidence her parents instilled in her, she is an advocate for one-on-one mentorship as a means of encouraging a thriving technical career. 

“If I can share the lessons I’ve learned along the way and encourage my women colleagues — even if it’s just one person — to keep pushing forward in this field when it gets tough, I know I’ve left a lasting impact on the industry as a whole.”

Here’s what Hickey had to say about building community at …

On the WomeninTech@Care ERG: When we started back in January 2021, we had 38 members, and since then, we’ve grown to 60 members who are all women in STEM and management roles at Care. We meet monthly to create a safe space where we can connect and grow with each other, and we stay connected via our dedicated #WomeninTech Slack channel. I absolutely love that this group was organically formed. There was no edict from the top saying we needed to exist or have a certain mission. We do whatever it is we want, and there is a lot of passion in the group. 

On the ERG’s exciting programming: We’re committed to creating experiences that support our members’ growth and help them identify how to get the opportunities they want. We’ve invited internal and external speakers to present on topics that will help our members grow and gain perspectives. We’ve facilitated breakout sessions to talk through challenging workplace topics, like overcoming workplace bias and managing Zoom fatigue. We also focus on networking and have a virtual water cooler to connect with one another in our remote environment. 


“We’re committed to creating experiences that support our members’ growth and help them identify how to get the opportunities they want.”


Recent WomeninTech@Care Events

After reading “Brave, Not Perfect” by Reshma Saujani this past April, the group came together for a discussion on the impactful topic of taking more risks. Over the summer, members had the opportunity to bond on a more human level, receiving “breakout boxes” that provided materials for activities like building terrariums and making s’mores. The September WomenInTech@Care meeting welcomed executive-level women from a platform that helps entrepreneurs start, run and grow their businesses to talk about the importance of allies.



Persistence in Problem Solving

Emily Massa
Product Design Manager •

Emily Massa’s journey to the technology industry began with her 2010 move from Macau to San Francisco in pursuit of a graphic design degree. Unaware of the tech opportunities that awaited her, something clicked for Massa during an interaction design class.

“I started to understand why people love technology,” she reflected. “It’s a tool that you can do anything and everything with to create innovative solutions to any human problem. I found that really fascinating and decided to switch my major from graphic design to user experience and interaction design.” 

The Bay area’s startup scene, which Massa described as “vibrant,” was home to her first role as a product designer. She then spent 6 years in another role that solidified what her degree switch signaled: “Building products is my true passion.”

With her lengthy tenure came an important lesson in finding purpose. “Product design is basically finding a solution to a problem,” said Massa. “When you love the problem, you will love the journey of finding the solution.”

Massa’s decision to join aligned nicely with the sense of purpose that followed her passion for the company’s mission and product. Today, both passion and purpose inform her decisions as a hiring manager. “Being a product designer, I think you need to love the problem in order to keep exploring until you see success in finding the right solution,” she explained. “That passion, stamina and persistence is what I’m always looking for.”


Here’s what Massa had to say about product design at …

On the consumer side of operations: On the product team, everything we do is for the customers. There are numerous opportunities to improve and innovate the product experience both for families looking for care and caregivers looking for jobs. Depending on where we are in the product development cycle, my day can vary from spending time with the product team to explore new design solutions for user problems; meeting with the engineering team to review feature demos and refine features we have in the works; or connecting with my direct reports to provide support and mentorship. Each day brings new challenges, and that keeps things very exciting and helps me grow.


“This is meaningful work that makes a difference in the world; it is more profound than just a job.”


On what it’s like to work on her team: Product team hires can expect to work on solving cool, important, human problems — helping people find care throughout the ages and stages of life. You will play a part in making that journey much easier. This is meaningful work that makes a difference in the world; it is more profound than just a job. On my team specifically, you’ll work with a very diverse, equitable group of people. It’s also one of the most friendly environments I have experienced in my 10 years in the tech industry. 


Virtual event woman speaking in a room of people on a screen that's next to a stuffed bear


Progress, Not Perfection

Chrissy Youker
Senior Manager, Software Engineering •

On her first day of work with, Chrissy Youker accidentally — but poetically — wore a shirt with a big smiley face that read, “Take care.” With a big smile on her own face, Youker proudly shared that one of the reasons she joined the team was because Care cares. “That resonates throughout the company,” she said.

Of note, Youker appreciates that as an employee and a manager, she has flexibility in how she uses and encourages taking paid time off. “If work gives you the opportunity to live life, you’re going to be able to give back to work,” she said. “I’ve seen that time and again with the developers on our teams. It has made us successful, and it makes our team want to work harder — for Care and for each other.”

In true, mission-driven style, that level of support and thoughtfulness extends outwardly as well. It was another factor that convinced Youker she was in the right place. “The space I work in, Care for Business — our enterprise portion of the organization — is trying to make sure that we give people the ability to take care of their families by putting money back into their pockets with reimbursements for child or adult care,” she explained. 

“I may not be a parent, but there are so many people I care about who are and need that extra support, and I’m impassioned by that.”


Family care for Care families

Putting family first, offers its working parents — both mothers and fathers, no matter if their family is growing by childbirth or adoption — 16 weeks of parental leave. The family-minded benefits go even further, with the inclusion of a membership, which comes complete with access to breastfeeding support, backup care and babysitters. “Care makes that possible, not just for the clients we support but also for our team,” Youker said.


Here’s what Youker had to say about engineering at …

On redefining success: We have to iterate on everything from improving our tech stack and codebase to determining what products we’re going to build. We have to be willing to be flexible and say, “This is better than where we were yesterday. It’s not perfect, but it gets us a little closer.” Success is iterative: When we break the pieces of success down, it becomes a lot more accomplishable. And if every piece is reliable, reusable and easily maintainable, it creates a foundation for us to build on top of and allows us to be more agile.

On what new engineering hires will learn: Engineering tech is changing every single day, and we have to be willing to change with it. I’m working with my devs on building our documentation; it’s not the prettiest part of the job, but it can be the most rewarding. When we document how things work, we allow the person behind or beside us to better understand what they’re working on. I want to make people’s lives easier, and I want them to enjoy their jobs. We are all here to help provide families with the care they need, and the only way we’re going to do that is if we do it together.


Responses have been edited for length and clarity. Images provided by

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