Meet a millennial who co-founded a $2 billion company: Scary opportunities are ‘just how great careers are made’ – CNBC | Directory Mayhem

Shadiah Sigala was always a go-getter.

The 38-year-old Mexican immigrant’s mother moved to Southern California with her and her two siblings when Sigala was 7 years old. As a honors student in high school, “My biggest dream in life was to be the most educated person,” she says. But she didn’t know exactly how to get there.

“My mother and all my aunts and uncles never went to college,” she says.

Eventually, with the help of her school’s guidance counselor, Sigala attended Pomona College for Latin American Studies and later Harvard Kennedy School for a Masters in Public Policy. Therefore, setting goals that she wasn’t quite sure how to achieve and figuring out how to achieve them became her MO

“One of my superpowers is being able to wade through uncertainty very comfortably, gathering facts and making decisions,” she says. Ultimately, this superpower led her to co-found HoneyBook, a financial management technology platform for small businesses. HoneyBook was valued at more than $2 billion in 2021.

Here’s how Sigala built her career and her advice for anyone looking to find their own successful career path.

“I am a builder”

After her master’s degree, Sigala was hired as a project manager at the health insurance company Aetna. “I was getting more money a year than any of my family members could ever make,” she says of her $80,000 annual salary.

Still, she adds, within the first week she knew “I’m going to be so depressed here.” She didn’t like feeling like a small cog in a big machine. She stayed with the company for two years, saving all the time and contemplating her next move.

During her time at Aetna, she learned about entrepreneurship and realized, “I’m a builder,” she says. Starting your own company seemed like the best way to go.

Building on her love of cooking, which began with her mother teaching her as a child, Sigala eventually started her own cooking business in 2010 and used her Pomona College alumni network to find wealthy alums willing to hire someone to do the cooking to pay for their meals.

“And I paid my bills that way for about a year,” she says.

“Why not digitize all those crappy tasks?”

As a young business owner, Sigala learned that she could be self-sufficient. But she realized that cooking wasn’t for her. “My time is not scalable,” she says. It was also a low-margin business.

Sigala’s then-husband eventually moved them to San Francisco in 2012, and it was there that she discovered the world of tech. She began arranging briefings with anyone in the industry who wanted to speak to her, asking questions like, “Do you work in a startup? What does that mean? What is technology? What is software? What is hardware? What is consumer? What is marketplace?”

When she learned that Silicon Valley entrepreneurs build technology, in part, to solve problems, she realized that even as a business owner, she had a problem she wanted to solve herself: There was no streamlined way to handle the backend logistics Emails, Payments and Invoices.

Shadiah Sigala and her daughter.

Courtesy of Shadiah Sigala

When she met three Israeli entrepreneurs tackling the same problem, they realized, “Why not digitize all those crappy tasks that micro-enterprises need to get rid of so they can actually focus on what they love?”

That idea became HoneyBook, which was founded in 2013 and where Sigala would spend five years in senior sales and HR roles. According to LinkedIn, the company now has more than 200 employees.

Scary Opportunities are ‘How to Make an Outstanding Career’

In 2018, Sigala co-founded her newest venture, Kinside, a childcare marketplace offered as a benefit to employees. As a mother of two, inspiration for the company came as she attempted to navigate the US’s complicated childcare system on her own. Kinside offers new parents a single place to find childcare near them.

According to Crunchbase, the company has raised more than $16 million. Sigala currently serves as CEO.

When it comes to advice she would give to others navigating the world of work, Sigala suggests letting fear and excitement guide you. As you search for your next role, ask those around you questions and be open to new directions. When a job “feels like it’s above your pay grade, that’s the path to a great career,” she says.


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