Sivan Whiteley, Square courtesy photo

Sivan Whiteley, associate general counsel of Square Inc., helped close a convertible debt offering that is expected to net nearly $390 million in proceeds for the company.

The No. 1 issue that keeps me and my clients up at night is …

Data security. You mess that up in a major way and so much of what you spent years building can be damaged overnight. We’re going to look back on this time 10 years from now and it’s going to seem like the Wild West in terms of the infrastructure, systems and processes in place to protect data. I think data privacy and security is going to keep a lot of people up at night for some time to come.

Who’s the best leader you’ve seen in action and why?

I haven’t seen her in action per se, but I’ve been following the story of Lynn Perkins. Lynn is the founder and CEO of UrbanSitter, a company that helps parents find babysitters and nannies, a must-have service for many women, including me. She is one of the most successful fundraisers in the Silicon Valley. There are a lot of data points on this, but last year less than 3 percent of the total dollars raised by startups were by female-founded companies. Not only has she raised $23 million to date, but more importantly, she is working to educate and mentor future female leaders on the art of raising capital in today’s tech economy.

If I could change one thing about working in tech, it would be …

More balance. I love my career and want to put everything into it. But I also have a family, a commute, and personal pursuits. It’s often a challenge to find the right balance between work and the rest of life. I’m not sure there is a silver bullet, but nobody should underestimate how important it is to find the right balance, as it’s likely to help you excel in every area given the right mix.

After the events that have rocked Silicon Valley this year, are you more or less hopeful about the prospects for women in the tech industry?

I think I’m more hopeful given the recent momentum and open dialogue in the tech industry. It’s great to see industry leaders doing their part, but we still have a long way to go. I think it’s more important now than ever for Silicon Valley companies to lead the charge in creating and validating awareness efforts around equality in the workplace.

Do lawyers bear any special responsibility in addressing gender stereotyping and discrimination in tech?

We all bear this responsibility equally and I fear that creating the belief that lawyers or regulators will take care of it may lead some people to think that means it’s not their responsibility to effect change.

—Ross Todd