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Featuring CEO Rachel Carlson, Jenny Xia Spradling, and Yidrienne Lai | April 15, 2021

A Conversation on Equitable Entrepreneurship

While fifty percent of entry-level jobs in corporate America are held by women, only 7% of women in Fortune 500 companies hold the title of CEO. The pandemic has created significant setbacks for women — over two million women have left the workforce since the start of the pandemic. To explore this issue, ICONIQ Growth spoke with CEOs Rachel Carlson and Jenny Xia Spradling, two entrepreneurs building companies to amplify positive impact in education and philanthropy and also internally within their organizations.

In 2015, Rachel co-founded Guild Education with the mission to help transform traditional tuition assistance programs into a strategic recruiting and retention tool. They are working with numerous high-profile companies including Walmart, Disney, Discover and Lowe’s to provide education as a benefit to their employee base.

Jenny Xia Spradling is the founder and co-CEO of FreeWill, an estate planning platform that makes it easier to get money to charities by reducing friction in the process. In just 4 years, FreeWill has helped facilitate over two and a half-billion dollars in charitable commitments.

In this conversation, Rachel and Jenny shared their insights on entrepreneurship and how to pave paths toward equity for women in the workplace.

Building for Sustained Progress

After serving in the Obama administration, Rachel launched Guild to close the education gap. Nearly one hundred million Americans have not completed a college degree nor a meaningful education certificate and therefore, may not have access to the skills needed to “future proof” their careers. Guild unites programs offered by higher education institutions with employers that want to in turn offer high impact, scalable, tuition assistance programs. Guild serves a critical role in enabling the upskilling of the workforce, which ultimately creates greater career advancement, retention, and economic opportunities for those who need it most — many of whom are working mothers and women of color.

Jenny conceived of FreeWill when she noticed the inefficiencies of the non-profit sector. She recognized that leaders were spending a disproportionate amount of time on fundraising, in comparison to furthering the main focus of their organization. Jenny has always been passionate about social impact work and saw this opportunity to further the impact potential of non-profits by creating FreeWill, which provides a solution for non-profits to offer a valuable estate planning tool to its donors. FreeWill seamlessly facilitates individuals’ bequests and charitable gifts at scale. In turn, non-profit leaders can focus more on what they are passionate about — creating sustained positive change for communities they are serving.

Hiring for Diversity

In order to build a diverse workforce, Jenny suggests starting early and sticking to a goal without compromise. For FreeWill, that goal was 50% female engineers on the team. Network effects worked in FreeWill’s favor: Women were sharing with other women that the company was hiring female engineers and dedicated to a 50% female engineering team. The result was a surge in female applicants.

Beyond skill assessment, FreeWill hires for attributes including self-awareness and open-mindedness. The company is solving complex problems which require a diversity of insights and perspectives. Therefore, they screen for candidates that can advocate for their own ideas but are open to others’ opinions — in short, individuals with high emotional intelligence.

Jenny believes that building diversity is about cultivating an inclusive environment. While it is difficult for an early start-up to provide three months of maternity or paternity leave, it is crucial to uphold those policies as they solidify company values and establish cultural precedence. Jenny actively creates an inclusive environment and demonstrates her company’s diversity at the very beginning of the interview process by ensuring that the interviewing panel is representative of the company’s commitment to diversity.

Cultivating Collaborative Environments

FreeWill encourages their female leaders to take an entrepreneurial approach to their work by cultivating an environment that embraces and rewards strategic risk and big swings. Research shows that young girls are usually rewarded for “being nice,” and young boys are rewarded for courageously discovering. Given this, women are trained from an early age to be risk-averse, which can cap their growth potential as a leader and idea-maker. Jenny actively coaches the women on her team to pursue ambitious goals and encourages that mentality by celebrating the risk, so long it is supported by a good thesis, no matter the outcome.

Jenny recounted that their first employee was astounded that her male co-founder took notes during the meeting. Jenny shared that flipping the stereotypes and insisting that male counterparts carry 50% of administrative work (a typically female-designated role) created a very equitable and empowering environment.

A Modern Work Culture

To better support the working parents on the team, Guild recently built a daycare center on site, which has improved team retention and overall morale.

FreeWill has instituted flexible hours including six hours of work rather than eight, and blocks of no-meeting time. The company has also prioritized physical health and mental health, offering mental health support and physical co-working spaces for working mothers to escape the house for a few hours.

Both Rachel and Jenny found that the opportunity to work flexible hours and be rewarded for performance instead of face time was crucial for women and mothers. Jenny believes the company is now better at assessing performance than before the pandemic because the playing field has been leveled: Without the physical and visual biases present in the meeting room, performance is measured solely by metrics and things that can be codified and standardized across the company.

Metrics coupled with a safe environment is a recipe for a thriving internal working culture. Leaders at the top taking the initiative to talk about feelings and emotions allow others to do so as well. Jenny shared that her leadership team focuses on regulating their own internal bias, speaking up about mental and physical health, and creating trust to hold one another accountable.

Competency Frameworks

Rachel and the Guild Team use competency frameworks to level the playing field and hold men and women equally accountable across the same expectations. Rachel shared that we are conditioned to apply different competencies and roles to women (e.g. “the note taker”) and to men (e.g. “the idea proposer.”) Therefore, diligence around using the same competency framework for men and women in the same role is systemically consistent.

The women on the Guild team tend to pick up more of the nurturing work, which has led Rachel to wonder how to best measure success on contributions around management, nurturing, and mentoring versus strategic and big picture efforts. Jenny has also been considering ways to recognize the time spent on administration and support, and how to incorporate that into performance reviews. Ultimately, if the direct reports succeed and productivity and retention increase, that is equally as valuable as a big swing move.

Encouraging Vulnerability

When one of Rachel’s team members asked how she is “doing it all,” she responded sincerely that she had help at home, her husband’s support, and more, but often felt guilty and missed bed-time tuck-ins. She believes that the notion that women are supposed to “do it all” perpetuates a false narrative. She stands by the belief that it is her responsibility as a leader to tear down this idea. “It’s okay to take care of your children and you are not responsible for doing every single thing,” she said. “They’re going to turn out great whether or not you read two books or one book [as part of their bed time routine].” Rachel encourages her leadership team to be vocal and share that they are using mental health resources or have support at home. Normalizing vulnerability and forthrightness supports greater empathy in and outside the workplace.

With the implementation of policies and processes, Rachel hopes that we can create more space for prioritizing mental health and work-life balance. For example, in interactions with VCs, Rachel discovered that some firms do not permit a partner to sign on behalf of another partner currently on maternity or paternity leave. This perpetuates a message that work comes before life, and it doesn’t.