Leaping In

In her blockbuster book Lean In, Sheryl Sandberg implores women to seek out new career challenges and opportunities, rather than shy away from them, even as they juggle work with marriage and motherhood. Few career decisions offer as much challenge and opportunity as the decision to found a company. Entrepreneurs don’t just lean in, they leap in — and for their extraordinary efforts they sometimes not only reap great financial rewards but also succeed in fundamentally changing our world for the better. As a venture capitalist, I have been honored to work with several remarkable women who have taken the leap into entrepreneurship, including Sheila Marcelo, founder and CEO of Care.com, Anna Zornosa, founder and CEO of Ruby Ribbon, and Ilana Stern, founder and CEO of Weddington Way.

Partnering with these women as they build their businesses, I have observed three shared aspects of their “Leap In” leadership styles that I believe led them to embrace entrepreneurship and today help drive their success:

Leap with Purpose. Often an entrepreneur’s decision to start a company is rooted in a pivotal personal experience. In the case of Care.com, Sheila Marcelo became pregnant as a sophomore in college, and she and her husband struggled to find high quality child care as she finished school and started her career; later her father, living with her at the time, suffered from a heart attack, and she scrambled to find care solutions for both her father and her children. Sheila founded Care.com to provide families affordable, convenient access to high quality care options, so that others would not experience the challenges she did, and she screens all hires to ensure they believe in this mission. When she was recruiting for a CFO, John Leahy won her over not only because he had strong public company CFO experience but also because his first comment upon meeting her was, “I love the mission of Care.com.” When Care.com acquired Betreut in Germany, Sheila made multiple trips to Berlin to meet with employees to share and discuss the company’s mission and culture. She is deeply driven to deliver on the mission of Care.com, and to succeed she knows that her whole team must embrace it.

Leap for Learning. When Anna Zornosa conceived of Ruby Ribbon, a company that sells a unique line of shapewear apparel through technology-leveraged direct sales, she recognized that she had little experience in either apparel or direct sales (though she had led large sales teams within technology companies). Yet she dove right in, networking aggressively to build her contacts and setting herself on a steep learning curve. Three months later, when she made her pitch for series A funding, she was authoritative on the opportunity, and was surrounded by respected advisors who complemented her skills and experience, had bought into her vision and were committed to helping her succeed. And though she is a seasoned Silicon Valley executive, Anna has engaged for many years with a coach to help her continue to grow as a leader. As she embarked on building Ruby Ribbon, she called upon her coach to help her navigate some thorny personnel issues and to help improve communication and collaboration on her team. Anna is unafraid to acknowledge and tackle new challenges and welcomes the opportunity to invest in herself as a leader.

Leap Through Walls. Entrepreneurs rarely get venture funding without articulating a big vision, and these women are no exception. But what sets them apart is that they also think big in terms of what they can accomplish with limited resources in tight timeframes. They set aggressive goals and then they stop at nothing until they’ve achieved them. Care.com started with a matching platform for consumers to hire babysitters and nannies, and has rapidly expanded into other verticals, such as pet care and tutoring, while also adding other services such as mobile payments, payroll, and care solutions for employers. I recently heard a quote from Nelson Mandela that reminded me of how I have often felt about Sheila and her team’s accomplishments at Care.com: “It seems impossible until it’s done.” Similarly Ilana Stern, the founder and CEO of Weddington Way, has set out to re-invent commerce around weddings, building an online collaboration engine that enables brides to consult with others in the wedding party on purchases. The Weddington Way team started with the sale of bridesmaids dresses, and is rapidly expanding into other categories.

Writing this on the eve of the Care.com IPO (but not published until now due to quiet period restrictions), I salute women entrepreneurs everywhere, and especially Sheila, Anna, and Ilana, who have provided the inspiration for this post. They are my Leap In heroines.