Connections + vulnerability = boosted productivity + retention

Sierra Quiros of Betterment explains the vast benefits of DEIB programs and learning together

Sierra Quiros, Senior Manager of Talent and DEIB Programs at Betterment, recently sat down with Jason Lavender of Electives for a People Developing People interview.

During their conversation, they discussed:

1. How to create a learning culture
2. The benefit of leading by example
3. The importance of vulnerability
4. How connections improve productivity and retention
5. The benefit of strong DEIB programs
6. How storytelling brings people together

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Jason Lavender, Co-Founder + CEO of Electives: Sierra, please start by sharing your background and how you got to your current role at Betterment.

Sierra Quiros, Senior Manager of Talent + DEIB Programs at Betterment: Absolutely. I'm a believer in non-traditional work trajectories. And I have one myself. 

I interned for a nonprofit when I was in school, and then afterward, I committed back to that organization and worked on event coordination and management for their largest fundraising events of the year. I always had a knack for event management, but I also really loved working for a mission-driven organization. In that case, the mission was serving under-represented communities in New York City, creating programming for their parks and leveraging green spaces within the boroughs of New York. It’s a super awesome organization.

After that, while I found my footing, I was a server. I’ve always had a service-focused career.

I felt very lucky when I got the role at Squarespace, where I became the campus recruiting coordinator. I was given the opportunity to work on building out their first-ever intern program. It was the first time that the program had any structure, and it was my first foray into program management. I grew it into a scalable, sustainable program.

During my time at Squarespace, I noticed the gap between our ERGs and our recruiting team. I wanted to deepen the relationship and make sure that our recruiting team was being well understood by our employee resource groups (ERGs). In the same regard, I wanted to ensure that our ERGs were supported and understood by our recruiting team and the People team as a whole. Ultimately, I became the Co-Chair of the Latine ERG at Squarespace. 

I joined Betterment as a Talent Development Coordinator in December 2020. We had an ERG program at the time, but it had been built by an external consultant and didn't really speak to the Betterment culture. 

Working on the ERG program at Betterment complemented the work in company-wide community building that I was already doing in talent development. Our ERG program is now a well-oiled machine, and I have really enjoyed iterating on and evolving it over the last few years.

I've been at Betterment for about 3 ½ years, and I'm now the Senior Program Manager for Talent Development and our DEIB programs.

Jason: I love that. In every People Developing People interview I do, it feels like the guest starts off with, “My career path is a bit windy…” I think there's something really special about that, particularly in the People space, because there are so many different perspectives that go into your role. 

At Electives, we're always thinking about the difference between companies that develop people and build learning cultures well and those that struggle. What do you believe are the variables that contribute to the difference?

Learning must be prioritized by everyone to create a learning culture.

Sierra: Three things come to mind. 

First, I'm extremely fortunate to have a supportive senior leadership and executive team. All of our leaders are very involved in making sure that their teams are being developed. They see the benefit, and they make it a top priority for their employees and their teams to be involved in our talent development initiatives.

Secondly, grassroots initiatives are just as important as top-down. It has to be a mutual investment.

Our senior leadership enables employees to build and create spaces for their voices to be heard, and in turn, it is up to our employees to take initiative and make the most of that space. 

For example, one of our ERG program pillars is education. We rely on our ERG leadership teams to be the voices of our underrepresented communities and to inform our workshop and training decisions. We also ask for feedback after every workshop to collect information on what is and isn’t working for our learners. 

Lastly, we have a dedicated team focused solely on talent development. Betterment embedded talent development into what we do from the beginning.

When I joined the team, we already had robust leadership programs. We were already investing in cohort learning and making sure peers could get to know each other. We built the learning foundation early, and that makes it part of everything that we’ve built since.

Jason: The combination of initiatives you described feels so perfect. 

Sometimes there is a tension between capital investments in people versus capital investments in other places of the business. Why do you believe the importance of investing in people is sometimes overlooked?

Leaders need to lead by example.

Sierra: The things that come naturally to folks are usually more business-oriented and tactical. It's more difficult to zoom out and see the whole person and know that if you're nourishing the entire person, you're also creating growth.

What's often overlooked is the power of supporting your direct report to block the time to actually do those things that you're encouraging them to do. We always want to be like, “Yeah, do more… Do this… Do that….” But when do they find the time? And how are we empowering them to take that time?

Sometimes that looks like leading by example and taking that time for yourself each week. For example, if you leave early from work because you have something that you need to do for your family, and you show that that's okay for your direct reports to do as well (without needing to explicitly say it), they feel that safety.

The benefits are immeasurable when you create psychological safety and the ability for people to invest in themselves and take time to do the course or do the certificate or do the networking.

Jason: Within talent development, what are you most passionate about?

We need to help people be comfortable being vulnerable.

Sierra: I am extremely passionate about diversity, equity, inclusion and belonging.

DEIB relates very well to talent development. It's really important that our content speaks to a diverse audience and grounds itself in the understanding that everyone is having a completely different experience and is coming to those courses or learning opportunities with completely different energies.

Secondarily, I’m passionate about supporting vulnerability in the workplace.

For so long, people were afraid of being their full selves at work. We heard a lot about compartmentalizing your experiences at work and at home. But now, we've seen those things exist together. Especially when you work remotely. I'm quite passionate about finding balance and figuring out the right way to get our folks comfortable with that balance in a place where it might feel unfamiliar.

Jason: How do you help Betterment employees connect with each other?

Connections create happiness. Happiness boosts productivity and retention.

Sierra: Learning is a great way to create connections. 

As I mentioned, our ERGs dig into the educational component of their roles within the company and see so much success from it. People participate actively in those sessions because it really speaks to them.

We hear a lot that employees don't quit their jobs; they quit their managers. I think it extends beyond that.

You're not just leaving your role. It extends to your peers and company culture. If we create a work environment where people feel genuinely supported, seen and understood, where empathy exists, we're building a supportive cloth. It doesn't feel like you're part of a cog in the machine or you're just checking in and checking out. You're part of a larger vision.

Building mutual respect and accountability to each other through community building and showing up for each other day to day makes our day jobs feel better. Areas of opportunity can feel more approachable, and vulnerability can become intuitive and a little bit less scary.

According to research from Oxford University, a happy workplace leads to higher productivity - about 13% higher. Building connections is a great way to ensure people feel happier at work.

How many times have you felt excited to go to work just to see the people you work with? It has so much to do with who you're interacting with and who you know has your back at the end of the day.

Jason: That is such a great perspective. I’m curious, what skills do you think people will need more than ever in the coming years?

DEI programs enhance connections.

Sierra: As the lines between work and home have become blurred, folks need support navigating that, which means investing in  training or deeper conversations around identity in the workplace, enhanced self-awareness, and extended kindness.

We're all having our own experiences; DEIB is constantly evolving to reflect that. It doesn't just include culture and race and gender. DEIB, as it exists now, is digging a lot deeper than that. And it's important to continue building learning programs that reflect it.

Cohort-based learning with your peers at your company helps you speak the same language and have a shared understanding of certain topics. That is going to be really important.

Jason: Final question: What advice do you have for folks in similar shoes (or soon to be similar shoes)?

Help your people tell their stories.

Sierra: People want to connect and learn from each other. 

There's a huge amount of power in creating opportunities for organic connection. And power in providing your employees with the tools to build a culture that encourages folks to feel empowered. And to reach out to each other within the culture that your workplace has built.

My second bit of advice is to leverage storytelling as a major player in learning.

Our Women+ ERG has hosted regular chats with women in leadership, and hearing the paths of these leaders within Betterment who are further along in their journey is really inspirational. It adds that human component to learning and to the community at work. When you see that person, you know a little bit more about them. You may have found something in their story to relate to.

We try to reflect our employee experience beyond the workplace in all of our offerings beyond traditional core skill development. We've hosted sessions on caring for LGBTQ youth and applications of positive psychology, and we also regularly work with our financial planning team and head of tax to bring forward offerings on financial literacy.

We leverage our internal resources to build offerings for our community. And that's created some really powerful connections and learning opportunities for us. So my advice is to look inward and see what you’ve already got in your toolbox.

Jason: Amazing! Learning through storytelling is speaking our language. That was the original inspiration for Electives. Everybody has their own story, and when we get those stories out in the world we are learning from so many different people. Thanks so much for sharing your stories and expertise with us, Sierra.

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About Sierra Quiros

Sierra Quiros is a seasoned program manager with a rich background in the tech industry. With a Bachelor of Arts in Communication and a minor in Spanish from SUNY Oswego, Sierra has a strong foundation in building community and fostering connections.

As the Senior Manager of Talent and DEIB Programs at Betterment, Sierra is at the forefront of developing talent programs and driving the DEIB curriculum, managing and supporting seven employee resource groups (ERGs) to execute impactful programming. 

In addition to her corporate role, Sierra is the founder of Hamov Eh, an Armenian-inspired food business that reflects her entrepreneurial spirit and commitment to sharing her heritage. The brand has been growing since 2021 across Westchester, Rockland and NYC. 

Previously, Sierra made significant contributions at Squarespace, where she co-chaired the Somos Squarespace ERG and was a Program Specialist. Her career also includes meaningful experiences outside the tech sector, with deep roots in non-profit efforts. Sierra is a certified ERG Leader, L&D Pro and Health Coach, showcasing her dedication to continuous learning and professional development.

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